29 life tips on my 29th birthday

No, I don’t feel older. But I do feel wiser.

Here are some things I’ve learned in these 29 years. Hope you find one of them valuable.

1) Learn the names of employees at restaurants you frequent.

Find great servers, build relationships with them, and ask for them every time. It makes them feel validated to have a regular who prefers them, you can tip them well, and you know you’ll always be taken care of.

Ask them about their life. No one does that. 99% of customers don’t even know their name or they forget it after a night.

I went to the Chipotle near my apartment one to three times per week for two years. There was this quiet dude who was always working. His name is Mike and he was taking on extra shifts to take care of his mother who was sick.

Every time I went in there, I said, “What’s up Mike! How are you man? How’s your mom doing?” He’d give me updates and then pile two enormous piles of steak onto my burrito bowl, free of charge.

All it takes is spending five seconds to treat someone like a human being for them to want to go out of their way for you.

2) Ask 3 questions before stating your opinion.

When someone says something you disagree with, hold off on your counterarguments and rebuttals. It’s more important to ensure you know exactly where they’re coming from and why they believe what they believe.

Steelman their argument. Articulate their opinion so that they’re pleased with your summary.

This has three useful effects:

  1. It makes them less combative and defensive.
  2. You avoid arguing with things they don’t believe.
  3. It slows things down and gives you time to decide whether or not you even want to pursue a disagreement.

A simple rule to build this habit is to force yourself to ask three clarifying questions before giving your thoughts. So you believe x because y?

3) In a group of friends, ask: “What impresses you most about every other person?”

When you’re hanging out with two to five people, this is a fun and wholesome game to play. Everyone takes a turn going from person to person and saying what they most admire about them.

No matter how close you are to these people, you’re bound to hear and say things you’ve never heard or said before.

Everyone feels more connected and heartwarming conversation ensues.

4) When you feel the urge to send an emotional text, wait 24 hours.

No one’s ever been told to “stay awake on it.” Get a night’s sleep and see if you want to send that same text tomorrow. You probably won’t.

I’ve saved myself from sending countless passive-aggressive or annoyed one-liners and paragraphs. These kinds of messages never lead to fruitful solutions. They never make the recipient go, “Oh you’re frustrated? I’m so sorry. Here’s why I was wrong and I’ll never do it again.”

All context is lost over text. If it’s that important and the feelings are still there the next day, call the person.

Don’t hit “send” when you’re in a state. That state will pass, but the message can’t be unsent.

5) Have your phone out of sight when watching movies or TV.

Two screens are too many. Just sit and enjoy the story.

Especially if you’re watching with someone else. It’s meant to be a shared experience.

Too much dopamine-searching weakens attention span and makes us less present. Do what you’re doing. If you’re watching a film, watch the damn film.

6) Know what success actually is.

What we think it is: Someone who is really good at something, doing things we could never figure out.

What it actually is: Someone who worked on something for years and years until we all see their polished results.

Just keep at your thing and eventually you’ll be amazing at it.

7) Buy expensive noise-canceling headphones.

Use them for work, to listen to music or podcasts while you cook, or just to quiet the world around you.

It’s one of the best purchases you can make. I suggest Bose.

8) If a book is bringing you zero value or entertainment, just put it down.

I used to have this rule that I had to finish every book I started. Slogging through boring pages was torture. All that rule did was take weeks (sometimes months) away from me reading something I might’ve actually enjoyed.

If it felt like a chore or a battle to get through the last three chapters, stop reading it. There are too many phenomenal books out there for you to be wasting your time on one that sucks to you.

You might hate a book but love it five years from now. But do your present self a favor and spend time diving into writing that fills you up.

9) Status is fun, but it’s a mirage.

Money. Clout. Reputation.

These things aren’t meaningless. I love making great money. I love building relationships with people who have wealth and power.

But these things will never complete us.

How many times do we have to hear rich and famous celebrities tell us being rich and famous does nothing for our happiness and fulfillment? Status can be fun but it will never be the final piece of the puzzle.

If your basic needs are met, if you’re healthy, and if you have loving relationships…and you’re still waiting on more status or success to be fulfilled, you will remain empty.

There’s nothing wrong with wanting to make more money or wanting a more interesting life. But real fulfillment comes from spending quality time with great friends and family, learning hard and rewarding skills, and being a grateful and healthy human being.

10) If you hate cooking, pick an easy and healthy meal to make every day.

It doesn’t have to be every day. Most days will do.

I love cooking…for other people. But when I’m home alone, I feel zero motivation to experiment or spend more than 20 minutes preparing a meal for myself. I just don’t care.

So, rather than wishing for more invisible willpower, I just choose a simple and nutritious meal I could make basically every day.

For a while, it was scrambled eggs with black beans and salsa. Protein. Carbs. Tasty.

Sometimes I’d use peri sauce instead of salsa. Sometimes I’d cook sausage instead of beans. Make it flexible and repeatable. This removes the headache of figuring out what to eat for at least one meal per day.

11) Frequently ask, “If I knew I’d die 10 years from now, how would I be living my life differently?”

Then do those things.

12) Set up regular hangouts centered around activities.

An easy way to consistently spend quality time with people and get out of the house.

Love knitting, board games, or walking? Find a friend or a group of people who enjoy it too. Then pick a day to regularly meet with them and do that thing.

Some examples from my life:

Thursday morning swims with a bestie.
Tuesday night chess club.
Sunday rock climbing with the bros.
Biweekly phone calls with my friend living in Rwanda.

We expect our relationships to take care of themselves. Proactively scheduling things is a lovely and efficient way to ensure we actually tend to them.

13) Run errands without your phone.

When was the last time you left the house without your phone?

Next time you have stuff to do out and about, leave the black rectangle at home. You won’t be on-call. You’ll have no choice but to be present and engaged with your surroundings. You’re more likely to spark conversation with strangers.

Feel the peace that comes from spending an hour or two completely unreachable and offline. Nothing to compulsively check. Nothing to experience other than the world around you.

14) Write letters, not cards, as gifts.

Giving a $5 card with a sentence on it is such a common tradition and it has always seemed odd to me.

People do it for “the thought.” But there are so many other, more personal and meaningful ways, to express that sentiment. Namely, taking 5-10 minutes to write a letter.

Outline plainly what this person means to you, what you love and appreciate about them, and how they’ve helped you and made your life better. Then read it to them.

It doesn’t matter if this is on printer paper or on a notecard. It’ll mean so much more to them than a funny card with your signature on it. They’ll remember how it made them feel for years.

15) No one is thinking about you as much as you are.

From your perspective, you’re the main character in the movie. But for everyone else, you’re a supporting character at best and a background extra to most.

Stop obsessing over everything you do and say. Not a single person is thinking about you even 1/10th as much as you are. They’re just worried about being the main characters in their movies.

Go to the gym. Share your opinions. Apologize and improve when you make mistakes and get feedback.

Because no one cares as much as you do.

16) Take month-long breaks from booze and sugar.

Pick a month. I typically do January and October.

You’ll get excellent sleep, eat better, and have more energy and willpower.

Can’t do this? You might have a problem.

It’s crucial to prove to yourself you don’t need something like alcohol to have fun, be fun, or live an interesting life.

17) Keep a list of your friends’ goals.

What they’re working on. What they want most. Their latest wins.

Check in on them and see how these things are going. It takes minimal time on your end and they’ll feel seen and supported.

18) When you’re feeling stuck, answer these 3 questions:

  1. What do you want most right now?
  2. What’s in the way of that?
  3. What’s step 1?

19) No one has ever been rejected into a coma or black hole.

The fear of being rejected is 100x worse than actually being rejected.

Ask that person out. Give that sales pitch. Ask for help.

The absolute worst thing that can happen is they say no. Now you’ve gone from not having that thing to not having that thing. You’ve lost nothing.

20) They’re not texting you back because…

They don’t want to.

People who are excited to converse and engage with us will prove it by continuing to converse and engage with us.

Short texts. No response. Never calling back.

These don’t necessarily mean this person hates you. You’re just not a priority to them right now. That’s okay. It doesn’t make them bad people. It just means you shouldn’t keep exhausting yourself to keep the conversation alive.

The number of times in high school and college I kept texting a girl who clearly wasn’t interested in me…I thought, Maybe if I just send the right text, if I just send the perfect joke…she’ll want to get with me.

Never happened. People who want to talk to you will talk to you. If they put in zero effort, stop being needy and move on.

21) The 10/80/10 rule.

10% of people will dislike you no matter what.

10% of people will love you no matter what.

The other 80% will decide based on how skilled you are, how fun you are, and how delightful you are to talk to.

22) Be an ESPN sportscaster.

Bring up the accomplishments and highlights of your friends and partners. Hype them up. Show them off. Congratulate them in front of other people and on your own.

“Look at this! Let’s see that again! Isn’t that incredible?”

They may seem embarrassed but underneath that, they’ll feel super supported and respected.

23) Never set a secret expectation for someone.

If you want something from someone, tell them. No matter how overt or passive-aggressive you are, they can’t read your mind.

Quiet expectations are a one-way road to resentment, disappointment, and unspoken tension.

Be clear and direct about what you want.

24) Be on time.

It’s the easiest way to show respect for others and yourself. It also relieves the constant burden of feeling rushed and frantic.

Being the person who’s always late to things is a childish reputation to have.

25) Download ‘News Feed Eradicator.’

Hate scrolling on Facebook but don’t want to delete it?

Download this browser extension. It hides your Facebook news feed. No more being hypnotized by the algorithm.

26) Keep a list of your biggest insights.

Realizations, discoveries, mindset shifts. What have you changed your mind about lately?

It’s like finding old photos of who you were and what you were working on in the past.

27) Tell your friends “I love you.”

Especially guys. You’ll wish you said it more when you die.

28) Under 50 and don’t like what you look like shirtless? Prioritize exercise and diet.

It’ll only get harder. Now’s the time.

Hire a trainer. Get someone to help you figure out what to eat.

Give yourself more energy, confidence, and brain power by taking care of your body. If you were responsible for taking care of someone else’s body, would you fill it with sugar, simple carbs, and processed foods? Would you make sure that that body was never active?

Be kind to your future self and take care of your present self.

29) The quickest way to earn someone’s respect is to be able to take a joke.

There’s a difference between bullying and poking fun.

If someone is messing around with you, laugh. Join in on the joke.

This shows people you don’t take yourself so seriously and that you’re secure with yourself. I struggled to take jokes when I was younger because I was wildly insecure. Every jab felt like a missile.

Now, I make fun of myself more than anyone else. Life’s short. Be less serious and more silly. You’re no God.

Final thoughts:

Hope you enjoyed some of these. Hope you disagreed with some of them. Email me and let me know what you think.

See you next year for my 30th!

2023 feedback review: my results (part 2)

Connor Russo's bachelor party in the mountains with the bros
Connor’s bachelor party in the mountains, April 2022.

Earlier this week I shared the biggest criticisms I took away from my annual feedback review with my buddy. I’ve already been utilizing the changes I wanted to make and it’s been cathartic.

I didn’t want to do this but I feel it’s only natural I share the more tender and positive stuff. One of my biggest insecurities is coming off as arrogant or self-important…but here goes.

Biggest positives:

1) I practice a growth mindset.

Growth mindset: understanding that skill and talent come from consistent time, effort, and repetition.

Fixed mindset: the false belief that skill and talent are innate and unmovable—you either have it, or you don’t.

It’s the difference between, “I’m just not a musical person,” and “If I sit down and practice piano for 10 minutes a day, I could get pretty good.”

Connor, the guy I do this feedback exercise with, has commented on my lack of perfectionism before. I love to just dive into new projects or crafts, know I’ll be garbage at them, then break through that initial brick wall until I’m actually kind of good.

Theatre, chess, jiujitsu, rock climbing, coaching, content creation…

All these things were pretty painful at the start. I was either cringing at my lack of ability or getting humiliated in one way or another.

In those moments, our 100,000-year-old survival systems kick in. We feel anxious and want to give up. But that’s just a wall to get over.

And once we crawl up and over to the other side (after a few weeks or a few months), that awkwardness and clunkiness turns to fluidity. The problem is that a lot of people simply give up before getting over the wall.

2) I’ve built a life around only doing the things I want to do.

This one really hit when he said it. It’s my central operating system: creating the life I want by helping others do the same.

Joe Rogan is undoubtedly my biggest inspiration in how to live. Let me explain.

Love him or hate him, he lives an incredible life. He was pivotal in me taking control of my life back in 2017. For two reasons…

  1. He was the first real masculine male figure who made being disciplined look really cool to me. Listening to his podcasts and YouTube clips gave an energy of, “Hey man. I love you, but you have got to get your shit together! You could be so much better than you are, and you owe it to yourself to start moving in that direction.”
  2. His career was the first crystal clear example I’d seen of only doing the things you love and making great money from that. He’s a podcaster, comedian, and UFC commentator…and he has worked at these for decades and figured out a way to become rich from each passion.

In short, Joe’s work ethic and results made me think I could get good enough at the stuff I enjoy to make a decent living. I particularly loved his career trio: three different pursuits which offer tons of overlap and variety at the same time.

I’m actively trying to model that myself. My trio is:

  1. life coaching
  2. writing
  3. podcasting

If I just do these things for the next 30+ years, that would be my dream career.

Anyway, it sounds almost childish. I just want to do the things I want to do, get better at those things, and repeat that process until I die.

I don’t really set goals. I don’t care about getting a certain amount of money or subscribers or clients. I just want to keep podcasting, writing, and coaching.

If something changes, I’ll pivot. But until then, the train keeps moving.

3) I’m an active listener.

Connor said, “When you listen to people, you make them feel seen and understood, never judged…which is sadly super rare in people today.”

I make a lot of eye contact and often reflect people’s words back to them. What’s funny is I don’t really notice any of that in myself. It must be programmed into me from 1300+ coaching sessions and hundreds of hours of interviewing people.

The biggest gift we can give people is curiosity. Asking people questions and follow-up questions is one of the best ways to make them feel good when they speak with you. It’s a heart-warming way to connect with other human beings.

Connor had a lot of other insanely kind things to say. But these were the three that meant the most to me.

We do this kind of feedback review each year. I’d highly recommend you do something similar with your friends. It can be as simple as two questions:

  1. What’s something I can improve?
  2. What impresses you about me?

What do you want feedback on? What answers are you scared to hear?

Let me know your thoughts.

2023 feedback review: my results (part 1)

Bro love. ❤️

This is Connor. He hated me in middle school, is the reason I run my own business, and has been one of my best friends for 15 years. He and his wife run a kick-ass climate tech studio and startup.

Each year, we do a feedback review where we answer deep and critical questions about one another. (Here were my biggest takeaways from last year’s review.)

2023’s questions:

  1. What’s something you haven’t told me for fear it might hurt my feelings?
  2. How do you wish I was more like you?
  3. How do you wish you were more like me?
  4. What impresses you most about me?
  5. What would you say at my funeral/eulogy?

No feedback is complete without an action item. So for each critique, I came up with ways to change. Here’s how it went…

Biggest criticisms:

1) I’m ugly.

Just kidding.

*1) I send people sociopolitical links they’re not interested in.

I don’t feel identified with the conservative label. But most of my close friends are more liberal or left-leaning than I am, so it makes me feel like I stick out a bit.

And since I rarely seek confrontation and am rather agreeable, I tend to avoid potentially tense or divisive discussions.

But sometimes I let my opinions peep through. And when Connor brought up the fact that I have sent some podcasts and clips or made some brief comments, I realized something about myself.

I have a habit of sending people links. I tell myself and the person I’m sending them to, “Hey, I think you’d find this fascinating.”

But I discovered what I really meant was, “Hey, here’s something I wish you understood and internalized. Hope ya like it!”

It’s been my cowardly way of indirectly debating and making arguments. As though watching a 40-second YouTube short and avoiding any sort of long-form conversation would bring insight to my friends.

Worse yet, I’ve been coming to conclusions about what I think my friends’ opinions are. I thought, I have liberal friends. They must be blue-haired, mega-woke granola people.

But I have zero evidence to even begin to back that claim.

Change #1:

I called a few friends to apologize for hiding behind links, promising that if I had anything to say I’d just say it myself. I don’t have to have someone else make an argument for me in a podcast or YouTube video. I can construct my own opinions.

Furthermore, I realized I crave two contradictory things at the same time:

  1. I want to have open and honest discussions and debates with my close friends about divisive topics.
  2. I absolutely don’t want to have those conversations. I just want to chill with my friends.

One friend made a great suggestion while I was on my apology phone tour. I can pursue conversations like those by simply stating, “Here’s something I’ve been thinking about lately. Can I get your thoughts on it? I’d love to workshop it because it’s something I feel super passionate about.”

Respectful. Light. Welcoming…Instead of, Hey watch this clip, it’ll expose how stupid you are! Lmk what ya think. 😉

2) I hold people to the high standards I hold myself to.

In terms of honesty, communication, and discourse. And well, they don’t feel like high standards to me. They just feel normal and reasonable.

Firstly, I refuse to lie in any way.

I was basically a compulsive liar when I was younger—lying even about small and insignificant things—and it created a world of chaos for me. I had to remember what I said to each person in my life. And worse yet, when you lie all the time, you slowly begin to believe the lies you tell others, building a false world for yourself.

On top of that, one of my most significant life principles is open and candid truth-telling.

I will always tell my friends, family, and colleagues what is on my mind—so long as I can do so in a respectful and valuable way. I don’t just blurt out every thought that pops into my head.

I tell my close friends what they’ve done to make me feel hurt. I tell my family what they mean to me. I give brutally honest feedback to my fellow coaches (with their permission).

And I want others to do the same for me. Hence this entire feedback review.

Lastly, I try to remain kind and compassionate toward people even when they’re not in the room.

One thing I pick up on quickly is how often someone talks about others who aren’t currently present. Gossip is an enormous turnoff for me. It drains me and it makes me question how often the gossiper talks about me when I’m not around.

My goal is to praise others when they aren’t in the room. I’m not naive, but I try to remain positive and grateful basically 100% of the time.

All this is to say…I often expect these same values and practices from other people.

When one of my friends suggests I lie, I’m shocked. When I learn someone feels a certain way about me, I get frustrated that they haven’t brought it up to me yet. When I hear someone gossip, I think less about them.

I’m proud of these values but I don’t want them to make me feel disgusted toward the people in my life.

Change #2:

First, be mindful. Remind myself that my principles are mine and I’m not in charge of other people.

Second, continue being the change I want to see in the world. When someone lies, ghosts, or gossips…don’t judge or shame them in any way. But instead advertise what you would prefer: uncomfortable honesty, candid conversation, and praise. Lead by example.

In other words: make these boring and wholesome alternatives sexy again. It won’t guarantee people will become more like you, but it will continue to create a more positive atmosphere.

3) I don’t collaborate enough in disagreements.

This last one combines #1 and #2.

Not completely understanding the other person’s beliefs + feeling my way of thinking is supreme = subpar debates and discussions.

I love diving into potentially divisive and radioactive topics: race, gender ideology, sexism, etc.

But I have only been able to do so consistently with friends I already agree with. That makes me sad because I want to be able to talk about anything with anyone. It also means I stay in my bubble: not having my ideas challenged enough and not considering opposing opinions.

Part of this is due to the naturally uncomfortable nature of having these conversations…especially with friends. If you’re at a dinner party with four buddies, would you rather play CatchPhrase or debate police brutality in America?

But a huge component is my own lack of collaboration and questioning. I want to dive headfirst into my thoughts and point out other people’s errors. Folks love that.

When someone says something I disagree with, my internal emotional reaction is, That’s ridiculous, let me set this person straight. Turns out no one is interested in being “set straight” or educated.

People just want to be heard and understood. So…

Change #3:

First and foremost, I need to make it clear to people that they are completely free to share their thoughts and opinions without my judgment or condescension.

I can ask way more questions before I share any of my own ideas or counterarguments. Above all, I can find common ground.

Where do we completely agree? Where do our perspectives divert? What values and desires do we share?

I need to address these things before turning into a professor. No one wants to be lectured at. No one wants to attend a TED Talk against their will.

Finally, I have to get better at steelmanning.

Strawman fallacy: attacking a weak or incorrect version of someone’s argument, often straying from the actual points the person is making.

examples:

  • “You care about climate change? So you just want us to stop driving cars and having babies?”
  • “You’re pro-law enforcement? So you think cops should just be able to do and say what they want to innocent civilians?”
  • “You think pornography is bad for society? So you think we should shame women in the industry?”

Steelman argument: debating with the best possible interpretation of someone’s argument.

When you steelman someone, you articulate their opinions to the point that they agree with you. “Yes, that’s exactly what I’m saying.”

It’s hard to do this, especially when we vehemently disagree with someone. But it’s the best way to have a fruitful conversation.

I’m going to practice doing this. I can’t unload my thoughts before steelmanning the person I’m speaking with.

It took a few days for these criticisms to really sink in and for my defensive nature to fade. But I’m excited to put these changes into practice.

Later this week, I’ll share the positive feedback I received in part 2.

10 lessons learned in 2022

A 2022 calendar on a desk

They are:

1) Labels are limits.

We give ourselves disempowering labels and attributes all the time. Here are a few I heard from some of my coaching clients this year:

  • “I’m a chaotic person.”
  • “If I’m not certain I can do something, I can’t do it.
  • “All I need is more confidence…I’m just unconfident.”

None of these are true.

They’re just excuses meant to justify why we haven’t been living the life we truly want. If we’re chaotic, it makes sense that our physical and digital lives aren’t organized. If we’re uncertain, it makes sense that we haven’t put ourselves out there to try something new and scary. If we’re unconfident, it makes sense that we’re waiting and putting things off.

In my coaching experience, I’ve seen people of all ages and careers drastically change their personalities, habits, and values.

Nothing is fixed. Nothing is set in stone. The only thing keeping us from doing what we want is whatever fear, story, or label we tell ourselves to keep us from taking scary action.

2) Men and women are different.

Wooden cutouts of a man and a woman

And that’s okay. Actually, it’s necessary.

There are noticeable, meaningful, and beautiful differences between males and females. That is true of all animals. And what blows my mind most is that that is considered a controversial statement in 2022.

We can start with physicality and work our way down. Height. Weight. Muscle mass. Bone density. Fist size. Hip width. Fat distribution.

These are all averages, of course. I know women taller than most guys I know. And I know men who are more feminine than some women I know.

Which is a great segue from hardware to software.

Anyone who thinks gender is entirely a social construct has never taken testosterone or estrogen.

In Carole Hooven’s book T, she points to research done on men and women transitioning. Without fail, the women who began taking testosterone reported heightened levels of sex drive and decreased levels of empathy and emotionality. And men who started estrogen therapy reported increased compassion and emotional connection to others. I doubt society was telling these people to change in this way.

And no, that’s not to say women are too emotional or that it’s okay for men to be sexual deviants. It’s just useful to look at what makes us different from one another.

We can also observe the spectrum of masculinity and femininity:

Masculine energy: logical, assertive, resilient, seeking discomfort, conquering, direct.

Feminine energy: nurturing, intuitive, allowing, creative, gentle, accepting, indirect.

This can explain why men and women choose different professions, are often confused by the other sex, and are attracted to different characteristics. We’ll end #2 with that last point.

I’ve been single most of my life. So this year I became fascinated by what men and women are looking for on the dating market.

On dating apps, for example, men swipe right on (say yes to) 65% of women. Women swipe right on 3% of men.

That actually makes sense when we realize that women have way more to lose when pursuing a sexual relationship. They could get assaulted. They might get pregnant. They should be pickier than men.

Most women: “I want a guy who I connect with emotionally, who makes me feel safe, and who I can envision having a child and a ton of fun with.”

Most men: “See hot girl. Want hot girl.”

Moving on before I get canceled.

3) Porn is sexual junk food for the brain.

A man with glasses staring at his phone

For the vast majority of heterosexual men, porn is not a good thing.

It weakens sex drive, makes men ashamed of themselves, increases the risk of erectile dysfunction and premature ejaculation, raises our tolerance so we crave more intense porn, makes talking to women even more terrifying, devastates men’s body standards and sexual expectations for women, and decreases motivation and willpower in other areas of our lives.

Quitting porn has been one of the best things I’ve ever done for my sex life and health. But it’s hard. Reading Brett McKay’s How to Quit Porn was super helpful.

A 10-year-old boy with an iPhone will see more gorgeous naked women in five minutes than a man 100 years ago would see in his lifetime. Our brains are not evolved to handle that kind of stimulus.

On the flip side, I don’t think porn is empowering to women.

People say, “sex work is work.” Sure, I think if you’re a consenting adult, you should be able to choose whatever life path you want. But if the goal is to get men to stop objectifying women, making more porn seems like an odd approach.

Banning porn would be wildly impractical and downright impossible. But I don’t think it should be free. I dread the day my son gets internet access and can find whatever he wants at any time.

For anyone who wants to learn more, but doesn’t want to read a whole book, I’d suggest one of these resources explaining your brain on porn:

4) Anyone can, but most people won’t.

Can anyone get in great shape? Can anyone pack up and move to Australia? Could anyone really go downtown and ask out 20 people?

Yes.

But most people won’t. Most people (including myself) have a plethora of fears and stories stopping them from doing the things they’d actually love to do.

Different people have different starting lines, of course. It’s a lot easier for me to be moving to Argentina in a few months than it would be for my friend who has a one-year-old, two dogs, and a home to look after.

But if you live in the western world and are above the poverty line, you can really do anything you want.

One of my clients recently shared her fear of staying productive and healthy over the holidays. “I want to,” she said. “I really want to work out, eat well, and read over these next two weeks. But it’s impossible when you’re traveling and spending time with family.”

Then I asked, “If I said I’d give you a million dollars to have a super healthy and productive couple of weeks, what would you do?”

She smiled and told me working out, eating clean, and finding time to open a book would be effortless.

So again, we can do anything we want. The question is not: Are you able to do this thing? The question is really: How incentivized are you to make this thing happen?

One helpful model I like is asking myself, “If I knew I was going to die five years from today, what would I do?”

My answers to that question always lead me to do scary and fulfilling things. Flying to Vancouver to pursue a woman. Starting a coaching business from scratch with no experience. Moving to Buenos Aires. Spending quality time with the people I love.

In my experience, the people who do cool shit aren’t fearless; they’re courageous. Courage is being afraid but doing the thing anyway. Unfortunately, so many people wait until the fear goes away to live the lives they want. Then they wake up at 50 and wonder what they’ve been doing all this time.

5) Getting in great physical shape is the best thing you can do for yourself and your future family.

I got pretty cut this year. (Bragging? Maybe.)

And I’ve gotten to experience many short-term, superficial benefits.

First, I feel super confident with my shirt off. At the beach, on a summer run, changing in the locker room.

It’s not like women come sprinting out of the woodwork once I peel my v-neck off. But the internal peace I feel knowing that I’m good under the hood is hard to put into words. (The funny thing no one tells you is that when you start to get jacked, 95% of the compliments you get come from other guys.)

Second, I’m mentally sharper.

Many of us have experienced feeling like crap, then forcing ourselves to work out, and all of a sudden we feel awake and ready to go. Aside from the endorphins putting us in a better mood, we also know we just did something difficult and worthwhile. This makes us proud of ourselves and puts us in a more grateful headspace.

The actions needed to get in shape are actually pretty easy. It’s the patience and consistency that’s hard.

Here’s all I’ve done this past year to get a body I’m immensely proud of:

  • go to the gym 1 to 3 times per week
  • use the Fitbod app as a personal trainer to tell me what exercises to do when I’m there
  • eat well more often than not (avoiding sugar, refined carbs, and processed foods)
  • work out with my PT buddy twice a month
  • drink supplements like Creatine and Aminos (These are both legal, over-the-counter substances lol.)

That’s it. I just did these things almost every week.

None of them are difficult. It’s the “almost every week” part that’s difficult.

I hated going to the gym for an entire year. I needed my friend to go with me otherwise I’d leave after one set of one exercise. But once I started feeling and seeing real changes in my muscles and body fat…and once I got more familiar with all the machines and equipment and knew what I was doing, I was hooked.

The last superficial plus I’ll share is an example.

I had a lovely evening with a lady friend earlier this year. The morning after, she told me she really enjoyed grabbing my arms and feeling a good bit of muscle on them.

Is getting jacked necessary for being attractive? Absolutely not.

But in general, people are more sexually attracted to folks who are fit. We’re wired to think they’d make healthier offspring and it signals to us that they are disciplined enough to take care of themselves.

I’ll end this point with something more long-term. Here’s a quote from Dr. Peter Attia:

“If you’re over 40 and don’t smoke, there’s about a 70 to 80% chance you’ll die from one of four diseases: heart disease, cerebrovascular disease [stroke], cancer, or neurodegenerative disease [Alzheimer’s, dementia].”

As more of my friends have children, as I just spent two weeks in Virginia watching my grandpa die, and as another year comes to a close…I’m seeing more and more that my health isn’t just for me.

It’s for my future wife, my future kids, and everyone else. If working out and eating well today means I get one more year with the people I love most, it’ll be worth it. I want to be a 60-year-old man who can pick up his grandkids and play with them.

Freak things happen, but an unfortunate number of early deaths are simply because someone didn’t take good care of themselves.

That wasn’t my grandpa, and it won’t be me.

6) When you start something, it never ends up being what you think it’s gonna be.

I started this blog in 2019. It was meant to teach people about habits and self-improvement.

I avoided talking about myself because I was certain nothing about me was interesting. There was also a fear that people would think, who the hell cares about you and your experiences?

The opposite turned out to be true. The most successful pieces I’ve written have reliably been about my own travels, anxieties, and insights. I go back and read my early stuff and it’s like reading a crappy A.I. who copied other personal development creators.

I’ve also tried my hand at several YouTube channels. Vlogging. Sketch comedy. Mindset tips.

None of them stuck.

I even had two podcasts. One with just my friends and me BSing and one where I’d interview guests on their specific passions.

They both faded out because I didn’t really know what my message was or who the shows were for. All these things combined made me feel like I was a guy who could never finish anything. I couldn’t see things through. I feared I lacked enough grit and resilience to create something worthwhile.

Then this year, as I was interviewing creators for my book, I got an idea.

What if I took my favorite medium, YouTube, and my favorite thing, interviewing awesome people, and combined them? Enter: The YouTuber’s Guide to the Galaxy.

Now, I get to learn from some of my favorite creators in the space—how they started, what their systems are, and everything in between.

Little did I know, I’ve been building all the skills needed to do this all along. Interviewing, editing, uploading, recording myself, listening to my own voice, working with designers and engineers, sharing my opinions…

The next job you take, the next business you start, the next door you open…It probably won’t be the thing you take to your grave. But it will get you closer to whatever the next door is.

You just have to choose.

When you do, one of two things happens.

  1. You love it, and now you know what you want to lean into.
  2. You hate it, and now you know what you want to avoid.

Sitting around and strategizing over the perfect podcast idea is the best way to never start a podcast. But sitting down, hitting the record button, and uploading shitty conversations is the first step to having the podcast of your dreams five years from now.

Don’t worry about what it could be. Just choose something that sounds fun and start. You’ll learn what it’s meant to be along the way.

7) We can double our quality of life by prioritizing our sleep.

Another health one.

I’ve doubled down on my sleep this year and I feel like a God. Late nights and partying are still fun from time to time. But the benefits I get from consistent 8 hours blows everything else out of the water.

Being well-rested makes us more creative, motivated, and happy. Being stricter about bedtime, getting right out of bed in the morning, drinking way less alcohol…These simple acts have a compounding effect.

(image from Deepstash)

Here are easy ways to get much better sleep:

  • go to bed and wake up at the same times as much as you can (including weekends)
  • track your sleep (I use the free app SleepCycle)
  • give yourself an extra hour in bed (if you want 8 hours of sleep, go to bed 9 hours before you wake up)
  • keep it dark before bed, and make it bright when you wake up
  • wear a sleep mask or use blackout curtains
  • avoid drinking anything before bed so as not to wake up to pee
  • keep your phone away during the first and last hours of the day
  • dial down caffeine and alcohol use

8) Dating apps suck.

I have several friends who have met awesome people on dating apps like Bumble and Hinge. I’m even going to be the best man at a bestie’s wedding this spring and they met on Tinder.

Whenever and however two people meet each other and fall in love, that makes me happy. But these are the exceptions, not the rule. And there’s a darker side to dating apps I wish more people would talk about.

Firstly, the experience is quite different for men and women.

Women get way more matches. This means they get more oddball dudes in their inboxes that they have to sift through. It also means they’re able to ghost several guys with ease.

I spent two months on the apps and it was terrible for my mental health.

I’m a fairly confident young lad. I like who I am. But after just a few days on one of these services, I felt as though I was an ugly and useless trash monster not fit for this world.

Above all, I’m afraid of what it’s doing for future generations. Dating apps, along with all other social media, are slowly destroying the need for a very important skill…

The ability to go out into the world and talk to people.

I mean really talk. Sit down face to face and have a conversation. Be able to debate, ask curious questions, look people in the eye, and share personalities and stories.

Teenagers today have higher levels of anxiety, depression, and anti-social behavior than we’ve ever seen. And I don’t think the remedy to that is to disincentivize them from going out and meeting people. Staying inside and staring at our phones just doesn’t seem to be the way.

Since the popularization of dating apps, fewer and fewer men are meeting women and having sex. That’s because we’ve created a “Facebook Marketplace” for dating. People scroll through, see if someone is hot or not, maybe get some idea of their hobbies or interests, and swipe yes or no.

Whereas meeting someone in person makes us much more likely to find them attractive. A picture tells us nothing about what it’s like to be in a room with them. I bet countless people have said no to a guy or gal on an app that they’d absolutely love if they met at a party.

I met some cool women on these apps. While it never blossomed into anything, I don’t regret my time with them. But the mental strain of the dating app rat race wasn’t worth it to me.

That’s why in 2023, I’ve set a goal to ask out 100 women. Face to face. Out and about.

The idea is to eliminate my fear of rejection through pure exposure. And obviously, it’d be great if I met someone awesome before getting to 100 invites.

9) Who’s in your hospital room?

Lake Gaston, 2009.

My grandpa died last week. Prior to, I spent a week down in Virginia with my family to be with them and be by his bedside during his final days.

I’ll write more about him and that time in another blog. But this part is actually about something I learned from Kevin Hart.

My company got to see him speak in Philadelphia right before COVID hit. It was more of a self-improvement talk than comedy.

He told the story of his brutal 2019 car accident.

“Man,” he said. “They told me I might be paralyzed for the rest of my life. When I couldn’t eat or go to the bathroom on my own…you know what I had in that room with me? It wasn’t my fame, my house, or my Instagram following. The only thing in that hospital room with me were all the relationships I built over the years. My team, my friends, my family…”

Since then, I’ve used this as a model for living my life.

If I got in a horrible car accident today who would be there in my hospital room when I woke up? Those people have to be prioritized now.

While it was quite an emotional time, I could smile looking around grandpa’s hospital room. Seeing my dad, my aunts, my grandma, my stepmom, my half-brother…This group of people was just a representation of the life this man created and the lives he touched. He made every single one of us feel special.

That’s what I want to do: make the people in my life feel special.

10) I have no choice but to live a fantastic life.

Manhattan, 2022.

Before my grandpa went, he told us all, one by one, what we meant to him and how much he loved us. He said he lived a great life and had no regrets.

And as I spent those days there, I would look at my grandpa while he was sleeping in that bed. My old man’s old man.

It didn’t take long for it to really sink in. That will be me one day.

A long long time from now, after Elon has taken us all to Mars…I’ll be an old man dying in a hospital bed. That inevitable fate is coming for me and every other person I’ve ever known, loved, and laughed with. I’ve known that and I write about it often. But seeing a physical manifestation of it was 10 times more powerful.

By truly understanding that certainty—that I will die one day, I felt only one thing.

I have no excuse.

Between now and whenever that day is, I have absolutely no excuse but to live a phenomenal life. How can I be rude to a friend, get pissed if a waiter gets my order wrong, or sit around wasting a day…knowing that it’s all going to end someday?

I feel so empowered to sit at this desk and work on projects I love, to charge more money in my business, to travel to other countries, to call my friends and family more, to stay in great shape, to learn more about the world and the people in it. There’s a fire under my ass.

This year, I’ve learned the importance of spending more time around birth and death. Playing with my friends’ kids brings an energy to the room that’s not possible otherwise. It makes me feel lighter and more joyful. It makes me imagine the kind of father I’m going to be.

Thinking and talking about death and dying makes me feel so present and appreciative of the people and opportunities I have at my disposal.

Some might think us all dying one day means none of this matters. I like to use that to my advantage.

Since none of this will really matter 500 years from now, why wouldn’t I go after what I want? Why shouldn’t I ask out a beautiful woman at a coffee shop? What’s stopping me from charging the kind of money I want to charge? Who cares?

Most of us go around waiting for permission to live the lives we truly want. But sometimes certain events can wake us up.

Thanks for waking me up, gramps.

Fin.

Hope you got something out of that!

Please, dear reader, do me a favor. I’d love to know the biggest lesson you learned this year. Please email it to me.

Thanks for your support. Here’s to another year. 🥳

One question: the best feedback you’ve ever gotten

Two men giving feedback to one another at a conference table

Receiving feedback from our friends, family, and colleagues is one of the quickest ways we can improve ourselves.

It can also be extremely painful.

Our egos can get hurt. Not everyone’s opinions are valid. We see what people really think about us.

But building thicker skin and understanding we’re far from perfect are some of the most valuable things we can do. I ask for suggestions for this blog. I do regular improvement sessions with my closest friends. It can be uncomfortable but it always leads to something better.

If none of that interests you but you want to make improvements in your relationships, health, or work…ask this question to the people closest to you.

What’s something you’re afraid to tell me because you think it would hurt my feelings?

The answers you hear may sting in the short term. But you’ll start being more mindful, improving skills, and seeing reality for what it is.

Try it out. Let me know how it goes.

4 questions to avoid repeating mistakes

A table full of writing utensils

It’s been a while since I emailed you guys a blog. 11 days to be exact.

While I’m sure some of you are delighted by this, it’s left me feeling guilty. When you subscribe to something, you do so because you expect value from it.

Some of you support the blog financially. Some of you neglect your children and careers just to read what I write. I’m so grateful.

The truth is, I put too much creative work on my plate at once. Here’s my to-do list from the last 30 days:

  • finish rough draft of Do The Thing!
  • restructure my community’s website
  • write 2-3 blogs per week
  • edit YouTube videos, podcasts, and TikToks for YGG
  • manage new clients in my coaching business
  • go on three vacations with my friends and family

Too much.

But now that I’ve crossed off a few of these items, I’m ready to clean up, reflect, and make sure this doesn’t happen again. I thought today’s post would be a good time to do an exercise I found on Instagram.

It’s called the AAR Method (after-action review) and it’s used by the Navy Seals. It’s a four-question framework. In sharing the model with you all, I’ll give my answers for each step.

1. What did I intend to accomplish?

I tried to move in the direction of what I want my work life to look like.

It’s threefold:

  1. writing blogs and books
  2. running a podcast/YouTube channel
  3. having my one-on-one coaching business

To me, it’s a fulfilling cocktail of conversations and deep work.

2. What happened?

I started sprinting in this direction with no real plan and with little help. My schedule and timelines were up in the air. I got to things when I could get to them.

Problem was, I often felt creatively empty after spending hours of bandwidth on one or two things. I also felt the effects of task-switching. After hours of writing in the morning, coaching in the afternoon, and editing in the early evening, I’d be absolutely drained by 5pm.

3. Why did it happen that way?

I didn’t create any organized systems for keeping everything on track. With everything left to chance, my days were cluttered and sporadic.

I also just expected myself to be able to handle all this. There are these sexy Instagram-worthy archetypes of entrepreneurs doing a thousand things and working 12-hour days.

In reality, most of us have about four to five hours of deep, undistracted work in us each day. So putting eight hours of writing and editing on the calendar was destined to fail.

In summary: unrealistic expectations and a lack of organization.

4. What will I do next time for a better outcome?

Give each day of the week a theme. On these days, I write. On those days, I edit.

Some sort of digital system would also be useful for deadlines. I’m working on that with services like Evernote and Trello.

Finally, next time new projects present themselves, I’ll ask myself: “How much harder will this make things for me?”

I usually go to great lengths to keep from being busy or overloaded. I’d like to never get there again.

I think these questions will help.

The 2 options for learning something

A girl in a kimono karate kicking in mid air

Last week, I took my friend to her first jiujitsu class. She’s athletic and open-minded so I thought I’d show her the misery I put myself through on weeknights.

While she enjoyed it, she said it was…a lot.

I remember when I first started in 2020. For about three months, I reluctantly went to class only to flail around and have someone control my every move. It was demoralizing.

But slowly, I began to defend myself. I got submitted less and less. Eventually, I even beat a few teammates.

The learning curve was steep. Going from total noob to slightly less of a noob was quite a journey.

My face just about every class.

So while learning a move in class last week, I looked over at my friend choking her partner. Her eyes were as wide as they could stretch. Most people aren’t used to bending and suffocating other people for fun. It can be overwhelming.

She took it easy and only sparred with a few people. They took it slow with her and talked her through everything. I’m lucky to be at a super welcoming and friendly gym.

Afterward, she wasn’t entirely sure if it was something she’d want to commit to. I completely understood. It’s hard to market.

“Hey, would you like to try something really really uncomfortable and grueling, that will take you a pretty long time to get even remotely good at, while you roll around in a puddle of other people’s sweat night after night?”

Jiujitsu, everybody.

Whatever she chooses to do, I was quite proud of my friend for giving it a go. It made me realize that we really only have two choices when learning, pursuing, or attempting something new.

Option 1: “One day…”

Option 2: Day 1.

Getting in shape. Learning an instrument or foreign language. Starting a business. We can either start these things or wait.

Starting is exhilarating, ungraceful, and often discouraging. When we begin to climb the mountain, we see how tall it actually is. We can also imagine the downsides pretty easily. It’ll be scary. We could fail. We might look stupid.

But waiting can be an unfulfilling trap. When we create all these conditions that have to be met before diving into something, years can go by and we realize we’re standing in the same (or in a worse) spot. These downsides are usually more long-term and therefore are harder to anticipate until a ton of time has gone by. It’s tough to imagine the regret you’ll feel ten years from now.

An example of this difference is building an exercise habit.

The cons of going to the gym are simple. You don’t know how to use certain equipment. You’re out of shape. You’re not sure which exercises to do. It’ll be unfamiliar and tricky before any results are had.

But the cons of not exercising regularly are cloudier and easier to ignore. It’s hard to motivate ourselves with the possibility of being deeply disappointed by our bodies years down the line. But that’s exactly what happens to many of us. We look at ourselves and wished we started working out a while ago.

That’s because we’re so afraid of Day 1. But it all starts there.

What are you avoiding? What’s Day 1 look like for you?

5 things I’d tell my 18-year-old self

Dillan Taylor at Kings Dominion in 2012
Kings Dominion, fall 2012.

My 10-year high school reunion is tonight. I’m thrilled.

I can’t believe it’s already been a decade. I remember wearing the tye die tank top in the photo above, walking through the neighborhood near our freshman dorm, and smoking a joint with my roommate.

“Dude,” I coughed. “When my sister is a freshman in college, we’ll be 30.”

“Whoa,” he retorted.

At the time, that idea seemed so far away that it would never actually come true. But now it’s less than two years away.

Before I take tequila shots with a bunch of people who didn’t know my name in high school, I’d like to reflect on who I was when I graduated. In the moment, I’m sure I felt like I had finally grown up. In reality, I was just an insecure teenager with a driver’s license.

If I had an hour with that 18-year-old doofus, what would we talk about? Would he be impressed by me? Would he judge my mustache? What would I say to him?

Probably these things…

1) You’re supposed to feel confused, self-conscious, and clueless.

No one has their shit figured out, especially at 18. We’re all just dumpster fires hiding behind beautiful Instagram photos and Facebook posts.

It felt like you were the only insecure kid in high school. But you’ll soon realize that everyone else was just really good at hiding it. I didn’t start feeling truly confident in life until I was 23. And that was after failing college and trying to kill myself.

As a life coach, I work with people of all age brackets. I know 50-year-olds who are still figuring out what they want to be when they grow up. You’ve got plenty of time.

You’ll never “arrive.” There is no solution or formula to life that makes the rest of it smooth sailing.

So just keep putting yourself out there and trying new things. Your values and interests will change as you do. But you have to take action and go out and explore.

2) Don’t go to college until you can specifically state what you want to work on and why school is the best choice for that.

You were a trash student, dude. A 2.2 GPA in high school.

Why do you think putting tens of thousands of fake future dollars on the line would make things easier for you? On top of that, you’d have no supervision and access to all the booze, drugs, and women you could imagine. Does that sound like it would produce high levels of commitment and productivity?

Swallow your pride and stay home for now. Get a job at a restaurant, start saving money, and build creative skills. It will suck to see your friends go off to four-year universities. But you’ll be grateful in four years when you’re not paying $1000 a month for a piece of paper you’re not using.

3) You’re not really valuable right now, but you absolutely will be.

I don’t mean you’re useless as a human being. But at this time, in both the dating market and the general economy, you don’t have much to offer.

It sucks to hear, but if you start slowly building your skills, you’ll be super attractive years from now. That goes for women, businesses, and collaborators.

Right now, girls tend to be attracted to fun. You’ll see that when you go out drinking.

But as you go deeper into your 20s, they tend to be attracted to confidence, drive, and security.

So, if you start working out, developing skills you can sell, and treating yourself and others with respect…you’ll be unstoppable.

4) Be as kind as you can as quickly as you can.

The phrase “Nice guys finish last” is bullshit.

What it actually means is don’t sacrifice your values to make others happy. But do care about the happiness of others.

The more you make people feel welcomed, heard, and cared for…the more they will want to be around you and take care of you too. The most important thing in life (aside from your physical health) will be the relationships you build over the years.

Stop talking shit about people. Stop complaining about things you can’t control. Always seek the lesson and value in every situation.

That is the ultimate kindness: seeing life as something happening for you and not to you.

5) Don’t listen to me.

I can talk for hours about all the things I wish I did more of and less of.

I could tell you to take great care of your body, become financially literate, ask out more women, start playing chess or doing jiujitsu, build a writing habit, and never make a Twitter or Instagram…

But you’ll figure all of these things out from sheer necessity.

The best way to learn how to do something is to learn how not to do it. I can give you all these insights because I’ve done so many things poorly.

And to deprive you of mistakes and regrets you’ll experience would be to limit your ability to grow and learn.

Go out and do stupid stuff. Create cringe memories. Overdraft your checking account.

The people who know the most are typically the ones who have been through the most. Put yourself through the wringer and you’ll have no choice but to be the best version of yourself.

Now go, my son. Smoke a bowl and play guitar for four hours.

You’ll find your way eventually.

How to send a cold email to someone you respect

An iPhone with email apps on the home screen

I’m writing a book on creating. Over the past six months, I’ve been interviewing creators and entrepreneurs of all shapes and sizes.

Many of my friends have asked me how I got into contact with some of these big names—folks like Eric Rosen, Derek Sivers, Courtland Allen, and Steph Smith.

The answer is intricate and complex…

I emailed them.

Around 30% of those I reached out to, all of whom I genuinely adore, responded to my message. Then, shockingly, they agreed to share their time and energy with me. But why?

Well, there are a few basic principles every cold email should have. There’s also a simple formula to make structuring this outreach fun and easy. I’ll share both in this post. Then, I’ll share the exact email I sent to Steph Smith, a badass content writer.

Caveat: There is no way to guarantee that someone will respond. Most people simply won’t and that’s okay! You’ve gone from not talking to them at all…to not talking to them at all.

Let’s start with the step-by-step formula.

Cold Email Must-Haves

1) A personal and human intro.

Anyone can tell when they’ve been spammed a copy and pasted message. It’s impersonal and robotic. It invokes zero motivation in the recipient because they know the sender doesn’t actually care—they’re clearly just sending that same message to the masses.

So right out the gate, it’s vital to convey that you genuinely know who this person is, that you’re familiar with their work, and that you respect them for it.

That way, they know they’ve just been emailed by a human being who is actually interested in their time or resources.

2) Why you’re writing to them.

Cut to the chase.

Who are you and why are you sending them this email?

3) A clear and simple call to action.

What specifically are you asking for?

Would you like their time? Their feedback? A reference?

Make the ask so understandable that they’ll have to say either yes or no. A great finisher question is: Is that something you’d like to do?

Highlight the value they’d be getting out of it. They need to know what’s in it or them.

Also, paint the full picture of exactly what it is they’d be saying yes to. How long would it take? How much effort would be required on their end?

Answer any possible questions or objections before they think of them themselves. Not only does this put them at ease and make it more likely that they’ll agree to the thing, but it also shows them they’re dealing with a professional who is prepared and organized.

4) Give them an out.

Most people, especially those of higher status or prestige, will have no problem saying no to a stranger. Again, they’ll likely just not respond. Which makes sense; they’re busy!

But, a subtle yet impactful thing to end on is something that gives them permission to say no. It can be as simple as: It’s totally okay if you don’t have the time or interest for this right now. Just thought I’d shoot my shot!

Never, ever say something assumptive like: Looking forward to speaking with you soon.

That comes off as passive-aggressive. The person will think, “Huh? I haven’t agreed to speak with you soon.”

Keep it light. It takes the pressure off them and shows them you’re not some needy person begging for their time.

Now that we have the structure, let’s move on to the most important concepts to keep in mind.

Key Principles of a Cold Email

1) Keep it short.

Less is more. No one wants to read a bunch of long paragraphs with no spaces in between. Would you be pumped to read a poorly-typed novel from a stranger when you have a million other things to do?

If a word, sentence, or paragraph can be deleted and have the email still make sense, scrap it.

If reading your message feels like a chore, they’ll likely just chuck it in the Trash bin.

2) Care.

While there’s a ton of psychology involved here, I’m not advocating for manipulating people.

Everything in your email should come from the heart. Remember, these are for people we genuinely respect and value. That also makes it easier when they don’t reply. It’s probably because they’re doing the work that we cherish. And if they do reply, it’s just an unexpected bonus.

3) Be persistent but not annoying.

Most of the time (but not always), I’ll send a follow-up.

I call it being “lovingly persistent.” Not pushy. Not needy. But staying true to asking for what I want.

At some point last year, Lynne Tye—founder of Key Values, stopped responding to my emails. I sent her a follow-up because I really wanted to talk with her. Not only did she respond and set up an interview, but she told me she massively respected my “persistence and hustle.”

To drive this home, here’s a real-life example.

Steph Smith wrote the book Doing Content Right. It’s helped me tremendously with the structuring and planning of my blog and book.

Here’s the word-for-word message I sent Steph:

“Hey Steph!

Got introduced to your book/Gumroad course and I’ve been tearing through it. I’m stunned by the level of detail you put into everything you do. Thanks for helping me grow my blog! 😎

In short: I’m writing a book on creating. 

I’m about halfway done and have a few interviews left to do. It comes out this summer and I’d love to write a chapter on you. Would you like to contribute?

It would be no more than an hour of your time for a video call. Plus, I can send you the questions beforehand to speed things along. What do you say?

No worries if you don’t have the time or interest. I’m sure you have to say no to most things!

Dillan ✌️😇”

That’s it. She got back to me a few days ago and we’re in talks of setting something up next month.

If you want to reach out to someone you dig, do it. You have nothing to lose. Just know that you most likely won’t get a response and that’s totally fine.

But the answer’s always no when you don’t ask for what you want.

Doing so has allowed me to talk to some incredible people. It can help you do the same.

A simple trick for learning things faster

A young boy at a laptop trying to learn something

I’ve been keeping a ‘Get Better’ list ever since I read Ultralearning by Scott H. Young.

While it’s wildly effective to hone in on our strengths, it’s good to balance that out by improving our weaknesses. If we only did the things we were naturally gifted at, our capacities to grow and experience life would be severely limited.

I sucked at chess when I first started playing. But after playing and studying consistently for almost two years, I can now play in tournaments and enjoy beating my friends.

Fortunately (or unfortunately) for me, I have a handful of hobbies and passions. Chess is one. But I also love rock climbing, writing, and Brazilian jiu-jitsu.

The goal is to get pretty damn good at each of these things I spend my time doing. And the main way I stay up to date on what to focus on is with my ‘Get Better’ list.

Simply put, it’s my list of weaknesses in each of my favorite activities. It includes my coaching business, friendships, and even my dating life.

Whatever makes the list, I know I need to find a way to drill it. Obviously, things like chess or jiu-jitsu are easier to practice because there are specific exercises or puzzles I can chip away at.

But there are more ambiguous weaknesses like: “Holding space for friends instead of giving advice.” How does one drill that?

Well, the next time one of my close friends is going through something, I can make an effort to listen twice as well and acknowledge that I see and hear them. No suggestions. No problem-solving.

It’s like working out a muscle that doesn’t get a ton of action. I did the same thing with curiosity.

Last year, in building my business, I had to reach out to a ton of people. This was super tough because I wasn’t naturally curious about others. But after five or ten connect calls with people from my past, I found myself genuinely wanting to learn more about whomever I was speaking with.

The muscle was getting stronger.

We can do this with anything. So if you made a ‘Get Better’ list, what would you want to improve specifically?

Do tell. I’d love to hear about it.

Time doesn’t fly; you’re just not paying attention

People say: “When you’re 10 years old, a year is 10% of your life. But when you’re 50 years old, a year is only 2%. That’s why time speeds up when we get older.”

I think that’s bullshit.

When we’re young, everything is a novelty. We’re learning about the world, about our environments, and about ourselves. We try new things: activities, styles, hobbies. We know very little.

Then as we get older, for better or worse, most of what we do becomes routine. We pick the things we like and we do them over and over again. Or, unfortunately, some of us become akin to factory workers; we wake up, go to work, come home, watch TV, wait until the weekend to have fun, and repeat. Our lives become familiar.

I do the same thing. Although I have the freedom of running my own business and creating my own schedule, I still have my own version of clocking in during the week.

So what’s wrong with this?

Well, nothing’s wrong with it per se. But it does allow our minds to shut off. Let me explain.

Habits are great because they let us go on autopilot for things we want to do (or don’t want to do). I’ve gone to the gym so consistently that sometimes it feels like I just wake up there.

And that’s my point.

You ever drive to work (or somewhere you go often), and when you get there you realize you don’t remember the journey? It’s because you’ve done it so many times your brain doesn’t have to be on guard. Meanwhile, if you took a different route to that same place, you’d be much more alert and mindful because you’d have to make new decisions.

That’s what happens to us in our week-to-week lives. When there’s no newness, when we’re doing the same things over and over again, we wake up one morning and realize it’s already May.

“Where the hell did four months go?”

Nowhere. Time moves at the same rate for each of us. Some just pay attention better than others.

So how can we be more mindful? How can we slow down time? Two ways.

  1. Newness
  2. Gratitude

We’ve covered newness a bit. In this lies adventure, spontaneity, and curiosity.

This is something I could use way more of. I’m a super scheduled person. So I’ve been trying to leave more unstructured time in my calendar.

Trips also help—especially last-minute trips. Surprise your partner. Surprise yourself. Take a weekend off, go to the airport, and take the cheapest flight to somewhere random.

Constantly change things. Keep doing the things you love but find different ways to do them. Do them with different people. Try activities that scare you.

I have a phobia of heights. Right now, I’m slowly using rock climbing to squash that fear through exposure.

As for gratitude, this is a habit that can be built quickly.

Not only can we begin our day by writing or saying three things we’re grateful for. But we can also just start telling the people in our lives why we love them and what they mean to us.

It only takes a sentence.

I try to do this frequently. They don’t always respond with the same sentiment. But that’s not because they don’t feel the same way. It’s because they haven’t built that habit yet.

Want to make a good friend uncomfortable? Tell them how they’ve positively impacted your life. Watch them scramble for words. It’s lovely.

Anyway, my two questions for you are:

  1. How can you add more newness to your weekly life?
  2. Where can you express more appreciation?

Answering these questions will help you create your own time machine.

Sick thoughts

I’m sick. It’s not COVID.

This usually happens twice a year when the temperature changes. Cold symptoms. Cough. Congestion. Sore throat. It’s not fun but I tend to survive.

One thing that the pandemic has taught me is how often I used to go out into the world while sick. I’d go to work, hang out with friends, or go to the gym.

My Ph.D. in Bro Science tells me that coughing in the same room as others is a great way to spread whatever it is. I feel a refreshed sense of courtesy.

On Friday, when things felt super mild, I called my friends before going over to their place for dinner. I explained exactly how I felt and they told me to come on over.

But for the rest of the weekend, I canceled all plans. I’m coughing up a storm. My head feels like it’s full of mucus. The only plus is that my voice is twice as deep from the sore throat.

This is starting to sound like, “Look at how virtuous and ethical I am for canceling events while I’m ill.” But I seriously used to push through stuff like this in the past. It’s crazy to me now.

Once when I was quite sick, I showed up for my shift at the restaurant I used to work. The GM took one look at me and asked, “Are you sick, dude?” I said yeah and he promptly told me to go the fuck home.

Who would’ve known it would take a global pandemic for me to see that being around others while sick isn’t a great idea?

Not me.

On confidence

Confidence is not a necessity. It’s a reward.

I’ve had nearly a thousand coaching conversations with people. I’ve heard it every week for over a year.

“I just need more confidence.”

In other words: “I must first have this internal emotional change. Then and only then will I be physically able to do what I want to do.”

It’s totally understandable. But it’s nonsense.

If confidence is the belief in oneself, how can we have such faith when we’re unskilled and inexperienced in a thing? Unless we’re full of ourselves, we’ll naturally be nervous and unclear. That’s okay.

Being scared has nothing to do with us being able to do something. We do scary stuff all the time. If we don’t, it’s not because of inability; it’s because we choose not to.

Running a business. Talking to people we’re attracted to. Improving a skill.

We often think: “I need to learn X so I can do Y.”

When in reality, it’s: “I need to do Y and then I’ll learn X.”

Do first. Then feel confident as a reward for doing.

Don’t wait for it to fall into your lap.

Next level

A man playing a virtual realty video game

I’m shifting my business. It’s scary.

2021 was the year of building my one-on-one coaching practice from scratch. Mission accomplished. It had grown to the point where I had to stop pursuing new clients in December.

So I spent this winter focused on my current clients, writing my book, and learning how to slow down. The last time I created new income was at the beginning of January. I’ve been living off a decent cushion for myself, but I can’t move to Brooklyn in October if I don’t build something new beforehand.

In my community, we say: “What got you to this level is what will keep you from getting to the next level.”

What got me to the level I’m at was my client-creation process:

  1. Reaching out to people individually, connecting with them, and building a relationship.
  2. Inviting everyone I talked with to a coaching session. Coaching as many of them as I possibly could and seeing if it was a good fit.
  3. Making it easy for them to work with me (financially and schedule-wise).

I loved it. I still do. My one-on-one clients are some of my favorite people on the planet.

But there are only so many hours in a day, week, and month. Rather, I only have so much energy. I’m not some super-entrepreneur who can put in 10-hour days. Even if I could, I don’t want to.

First of all, people don’t actually work 10-hour days. We can’t even work for eight hours. Sure, we can be in the office for that long. But we only have about three to four hours of genuine focused attention at our disposal.

Secondly, with what I do, I get drained pretty fast.

My job consists of listening deeply to a person, being wildly curious about them, and challenging them. Doing this with multiple people for multiple hours would make anyone tired.

That said, I can’t keep doing the 3-step system I mentioned above. It got me here, and it’ll keep me from getting to where I want to go.

So what will get me to the next level?

Something scaleable. A service where I’m not trading my time for money. Here’s what I’m thinking:

  • A group program for entrepreneurs.
  • Only high-paying referrals for one-on-one clients.
  • A content marketing strategy.

In the first sentence of this blog, I said I was scared. That’s not quite true. I’m unclear. And that can often be mistaken for fear.

At this stage, I’m interviewing startup founders to hear about their stories and challenges. It’s already giving me a clearer picture of what I can help folks with. But I don’t quite know what service I want to provide yet.

Luckily for me, I learned a valuable lesson last year: We don’t have to know how to do something in order to do it.

On top of that, we don’t have to be fearless in order to do what we want.

I don’t exactly know what I’m doing yet. But I know I’ll do it.

And when I do, I’ll tell you all about it.

(PS—Connect with me on Twitter for more regular updates and insights! @DillTho)

Done, or perfect?

My friend and I are recording a podcast episode today. Our first one didn’t go so well.

It wasn’t absolutely cringe, as the kids say. But it was tough to listen back to.

We gave too much backstory. We didn’t interrupt each other enough. It felt like we were taking turns giving TED Talks.

But we wanted to start a podcast simply because we enjoy our conversations and hope others would too. Something happens when you hit “record,” though. When you see that blinking red light, the butterflies settle in. It’s easy to feel like everything spoken must be funny or groundbreaking.

I’m so glad we had a mediocre first recording. We can’t grow or improve until we run a test and gather data.

We could’ve prepped and planned for months, trying to create the perfect conversation. But what we did was so much more efficient.

We said fuck it, let’s just do it and see what happens.

Done is better than perfect. Because perfect usually means doing nothing.

A weekend of nothing

“Take a picture of us taking a picture of us.”

Readers of this blog know last week was an impactful one for me.

An intense level of burnout led me to change my entire workflow moving forward. That began this weekend.

Minus any trips, vacations, or special events…this Saturday and Sunday mark the first weekend in a year I didn’t work at all. No sessions, no planning, no creating.

I hiked with my buddy. We played chess. My friends took me rock climbing. Two besties are in town from Rwanda and Philadelphia (two equally foreign and exotic lands). We all got brunch in DC Sunday morning.

It was lovely, to say the least. There was no optimization, no brainstorming, no building. Just stories, laughter, and quality time with close peeps.

I love worky-type stuff. But space away from anything (and anyone) is essential. I forget that sometimes.

To “regular” people who enjoy their weekends, this may sound odd. But these past two days have quite literally felt like a vacation to me. I have to learn how to do nothing once or twice a week. Like anything, I’m assuming it’ll come with practice.

Days one and two are checked off. I’ve already begun the process of maneuvering my time slots with my weekend clients.

It turns out most people are accommodating when we simply ask for what we want.

I could get used to this.

The future of this blog

My backyard.

I don’t believe in having idols.

Taking inspiration from people we admire is great. But seeing someone as God-like or more than human seems creepy to me.

That said, one of the people I look up to most is Derek Sivers.

His book Anything You Want is the reason I wanted to start my own business. He’s given several TED Talks. And last month, I interviewed him for my book on creating.

I’d like to share an answer of his and how it inspired my newest creative endeavor.

Dill:

“Why is absolute control over what you create so important to you? Self-publishing (and printing) your books, coding your website in HTML, building things with your hands, etc.”

Derek:

“I hate bloat. It feels like pollution.

Quick-publish tools are filled with bloat because they have to cover every scenario.

Install WordPress and publish the word “Hello!”, and you’ve installed 884 PHP files, 602 Javascript files, 19 database tables, and hundreds of thousands of lines of code that are filled with bugs and security holes.

Or just type “<html><h1>Hello!</h1></html>” and save it as index.html, uploaded to a simple Linux server, and voilà. You now have a website with only one file and one line of code.  No security holes.  No problem to maintain it.

I hate dependencies. I have no subscriptions. Well-meaning companies say, “Oh don’t you worry about that, we’ll take care of it for you for only $10/month!” I think long-term so $10/month is $6000. And now you’re dependent on this company. If they raise their rates or go out of business, you’re screwed because you made yourself dependent on them.

So for each of these situations, I’d rather avoid the bloat, save the $6000, be un-dependent on any company, and just figure out how to do it myself.

That said, for the book publishing, I just wanted the highest possible quality, and I wanted to keep the rights so that I could do whatever I want with the books in the future. I could license them, translate them, rename them, give them away for free, or whatever I want. When you sign your rights away to a publishing company, the copyright is no longer yours to do what you want with.”


My first thought was, Shit, I use WordPress for my blog. Am I a loser?

While I might in fact be, I got an idea. In the next year, I’m going to transfer this blog over to a website that I code entirely by myself.

I’ve tried my hand at learning to code before. I got the fundamentals of HTML and CSS down. But I’ve always stopped short because I never really had anything to work on. There are only so many sample cat websites I can make until I get bored.

WordPress is easy and convenient. I don’t mind that. But creating my own site from scratch just sounds fun. I can already feel my future headaches as I try to learn Python or Javascript.

This won’t happen this month. It’ll be a slow and steady process. And I’m excited.

As I do with my book, I’ll keep you updated with every step along the way. Stay tuned.

Quantity over quality

Here’s an excerpt from Atomic Habits by James Clear:

On the first day of class, Jerry Uelsmann, a professor at the University of Florida, divided his film photography students into two groups.

Everyone on the left side of the classroom, he explained, would be in the “quantity” group. They would be graded solely on the amount of work they produced. On the final day of class, he would tally the number of photos submitted by each student. One hundred photos would rate an A, ninety photos a B, eighty photos a C, and so on.

Meanwhile, everyone on the right side of the room would be in the “quality” group. They would be graded only on the excellence of their work. They would only need to produce one photo during the semester, but to get an A, it had to be a nearly perfect image.

At the end of the term, he was surprised to find that all the best photos were produced by the quantity group. During the semester, these students were busy taking photos, experimenting with composition and lighting, testing out various methods in the darkroom, and learning from their mistakes. In the process of creating hundreds of photos, they honed their skills. Meanwhile, the quality group sat around speculating about perfection. In the end, they had little to show for their efforts other than unverified theories and one mediocre photo.

TL;DR: Experience and action-taking beat pondering and planning any day.

More feedback

I’m in Philadelphia visiting two of my best friends.

Connor, Laura, Dill.

(This picture was taken last year.)

They hosted me yet again for a lovely weekend of fruitful conversation, laughs, and suburban Philly walks.

One of the things my buddy and I did was a feedback exchange.

These can be tough. He even told me he was uncomfortable before he started diving into the things he wrote for me.

But I’ve done several of these now, and they have only led to…

• both parties growing/improving
• deeper connection
• intense gratitude

We had to answer these questions:

1) When have I hurt you?

2) What do you think would be most beneficial for me to improve?

3) What’s something you’d like me to know?

4) When have you been impressed by me?

5) What do you think I do better than most people?

On Monday, I’ll write about how it went and what I got out of it.

Another trip to Brooklyn (pt. 3)

Yesterday, I gave a synopsis of my weekend in NYC. Give that a read before reading this blog.

Here are my takeaways:

1) Getting sexually harrassed is surprisingly not fun.

It’s kind of a funny story, and I’m willing to joke about it…but having a guy look over the urinal at me peeing was mildly traumatic.

I’ve thought about it every time I’ve used the restroom since it happened.

And I’m a tall, fairly in-shape guy who can defend himself. I can’t imagine what those situations are like for, say, women who don’t have these physical advantages.

2) More venues and events should prohibit cell phones.

They did this at the comedy show. But I would love to go to a restaurant where this was the rule as well.

When we don’t have anything to distract us, we’re forced to be present with the people we’re with. We can genuinely take in our surroundings.

On many occasions, I like to leave my phone in the car. That’s when I truly feel like I’m part of the world.

3) I don’t think I want to live in Williamsburg.

That’s the “wealthy, hip, and yuppy” neighborhood in Brooklyn.

My buddy and I walked through it and the vibe just didn’t land with me. Many people looked as though they had a stick up their asses. They seemed calculated.

This is all just a generalization. We stopped to talk with one dude who was super kind and helpful. But he was Australian so that doesn’t count.

We’ll see. I have ten months to narrow things down.

A weird key to success

A man wearing a snorkel and flippers in the middle of a crosswalk

It’s strange to claim that I’m successful. But I certainly feel like I am.

As we’ve heard many times before, the word “success” means something different to everybody. It’ll mean something different to me even three months from now.

But for now, I can pay my monthly expenses comfortably, I have an amazing tribe of people in my life, and I use my time exactly how I want. Success.

I’ve read tons of self-improvement books and watched just about every motivational video on YouTube. There are loads of tips and strategies successful people teach us.

Having a routine, practicing mindfulness, failing often.

But I’d like to reword that last one.

Whether we’re developing our careers, our passions, or our relationships, I’ve discovered this truth:

In order to be successful we must be willing to look like a fool.

A healthy business comes from the willingness to put ourselves out there. I’ve messaged people asking to connect and they’ve ghosted me with a wide birth—probably thinking I’m selling something or working for a pyramid scheme. (Four people this year have straight up asked me, “Is this an MLM?”)

No, this is Patrick.

Early in my coaching career, I was terrified to reach out to others. My fear was that everyone would see me as a salesman when I just wanted to talk or reconnect.

Would I invite them to a session? Yes, maybe. But if they declined I didn’t care at all. I just love talking to people.

These fears were beaten out of me as I continued to reach out to people every single week. Now when someone doesn’t respond or ghosts me, I couldn’t care less. Who’s next?

As far as my passion for chess…

I started playing consistently during lockdown last year. One of my best friends said we should play.

It was something we could do online together. And we’re both competitive so I had the drive to improve. My sole purpose for several months was just to beat him. He was better than I was and each time he beat me it stung.

But I kept coming back for more. I started studying and practicing each day. Here’s my rating over the past 12 months.

Dillan Taylor's chess rating

Notice the dips and plateaus. Those periods were not fun. They were discouraging.

But like the stock market, if we zoom out and look at the big picture, the long term, we can see that I’ve only gotten better as I’ve stuck with it.

Chess, like many things, goes like this:

Step 1: “I’m getting pretty good! I feel like I could beat anyone….”
Step 2: “I’m not sure I even know the rules. I suck. Maybe I should switch to checkers.”

And the cycle repeats. At every level.

The point is, when I’m not feeling on top of the world, I play with less confidence. But I play nonetheless. I may get destroyed and that always hurts…but if I just keep at it, the graph will continue to go up.

And finally, relationships.

A turning point in the health of my friendships came when I decided to be completely candid with my thoughts and feelings. In other words, I became good at having difficult conversations.

Speaking my mind. Setting boundaries. Being vulnerable.

I’m lucky to have a phenomenal group of friends, and it has been through my willingness to be open that these relationships have grown even stronger.

TL; DR

It can be quite scary, but if we are willing to risk foolishness, we’ll get good at just about anything.

It’s not a “gift”

A mom and dad giving their daughter presents for Christmas

During Thanksgiving lunch this week, one of my family members complimented me when asking about my business.

The past three months have been quite good for me. After a little over a year, my coaching business is established, profitable, and sustainable.

After hinting at all that, someone said, “I’m not surprised. You’re a natural.”

It was an incredibly kind gesture, but I thought to myself, What the hell are you talking about?

With anything I’ve ever gotten good at, the only thing “natural” has been my level of interest in it. That’s the one thing that feels totally out of my control.

I wasn’t interested in school, so I skipped and failed classes until they kicked me out. I wasn’t interested in my full-time sales job last year, so I quit and started my own thing.

But when I’m into something, it gets all of my time, love, and attention.

Before, it was acting. Now, it’s coaching and chess. In the future, it’ll be something else.

Anyway, I know this sounds ungrateful, but when someone labels skill as a “natural” thing, I feel like it discounts all the difficult hours that went into developing it.

I’m not a natural business owner.

In the last year…I’ve had three-week runs of pure terror, worried that I can’t make this work. I’ve spent hours on LinkedIn and Indeed looking at more secure full-time gigs. In June, I was at lunch with my mom physically shaking from anxiety that I wouldn’t be able to make my next rent payment.

Thankfully, I’m not in that place anymore. But none of this was natural.

It came from consistent practice. $12,000 in coaching programs. Hundreds of hours honing the craft of coaching. Countless awkward and uncomfortable conversations. Over a thousand rejections. Doubt. Fear. Stress.

But to be fair, it’s hard to see these things.

It’s like Instagram. We see the finished product but not what led to it.

We see the success but not the hours behind it.

Obviously, I didn’t say any of this to my aunt. I’m not that much of a douche.

I smiled and said thank you. And now I’m back to work, putting in more hours so next year I can look like a prodigy.

No one cares where I went to school

Two students sitting down on the grass at university while doing their homework

In early 2020, I wrote a shitty blog ranting about college.

I still hold all the same opinions. But today I’d like to briefly discuss one aspect.

The fact that I run a profitable business that sustains my life and fulfills me at the highest level. I help people create the lives they want, get organized, and even grow their own businesses.

And in the last four years, not a single person has asked if I went to school.

Not where I went to school. If.

I’m not saying any of this to brag. I’m a college dropout who spent most of those four years living with his mom because he couldn’t afford anything else. (To which I’m incredibly grateful. Thanks, mom!)

The point is this.

In the past, people cared about where we got our credentials. Today, most people just want to know if we’re useful.

“Where did you graduate?” is now “Can you help us?”

I have friends making six figures because they taught themselves how to code. I know folks with great jobs because they’re great people who learn well and have strong interpersonal skills. I do well because I’ve developed the skill of coaching and curiosity.

All of which is possible without paying $80,000.

The caveat here is that of course there are professions where schooling is entirely necessary. I don’t want a surgeon who taught herself how to cut people open.

I don’t think college is a bad idea. It’s just not the only idea. There are many other ways to do interesting things and make money.

Many companies would ask me: What are your credentials?
“Alcoholism,” I would say. “Bankruptcy and divorce.”

Steve Chandler

I went too far

A little girl wearing a mask and holding a teddy bear also wearing a mask

I like to create rules.

Boundaries and guidelines for living a healthy and principled life.

In the past couple of weeks, I’ve added two rules to my chart:

  1. I can only drink alcohol twice a month.
  2. I can’t give unsolicited advice.

I’ve changed my mind on both of these. Let me explain.

Let’s start with the second one: giving advice.

I recently read The Advice Trap: Be Humble, Stay Curious, and Change the Way You Lead Forever. (Here’s my review of the book if you want my quick summary.)

In short, giving advice isn’t always the best way to help someone. We usually provide solutions to the wrong problem and, while we don’t like to admit it, our solutions aren’t always that good.

I soaked this in. The last chapter is a reassurance that giving advice isn’t evil, it’s just not always the most effective option.

Despite this, I processed the whole thing as: I must never give advice.

So, when I inevitably did, I felt gross. I felt like a bad person who was hurting my friends and colleagues.

It didn’t take long for me to go, Yeah…I don’t think I’m supposed to feel this way.

As for my drinking, that rule came from puking two nights in a row while on vacation. Naturally, I woke up that second morning certain I would never drink again. I’m sure I’m the only person who has ever pretended to decide that.

But this weekend, I went to DC to have dinner at my friends’ apartment. They cooked a delicious meal and offered me a glass of wine.

I thought, You know what, I DO want one glass of wine. Maybe even two.

And that’s what happened. The three of us finished a bottle then drank water and played games for the remainder of the night.

I said out loud, “Ah. This isn’t the problem. Getting fucked up is the problem.”

Believe it or not, I just don’t enjoy getting wasted as much as I did when I was 20 years old. Go figure.

The next night, I got dinner at my other friends’ house and we each had one hard Kombucha (I know, we’re tanks). It turns out that when I only have one or two drinks I tend to not make shitty decisions.

Conclusion

I erased both of those rules from my whiteboard.

The lesson?

It’s a great thing to notice areas of improvement in our lives. We have the power to make changes in our habits and tendencies to create something better.

But it’s even more healthy to reassess those changes and course-correct if they’re not fully meeting our needs. We can ask: Is this really a problem? If so, is this the best way to address the problem?

Then when our needs shift we can adjust again. And so on.

I don’t really drink unless it’s a social event and I’m not rushing to preach my worldviews to people. But I will have a beer here and I’ll share some opinions there…

All I can do is try to be healthy and helpful and apologize when I overstep.

That’s the new rule.

The value of heartache

A woman holding a neon heart against her chest

Life can fucking hurt.

Between people dying, hearts breaking, and a million other things which make us physically ill…we’re guaranteed to feel powerful negative emotions at times.

Yesterday, my coach told me, “There’s no system for grief.”

In other words, sometimes we’re sad and we don’t fully know why and there’s no formula to make it go away right now.

We have to just sit in it. And learn from it.

As readers of this blog know, I try to find the lesson in everything I do. After a painful experience, I allow myself to feel my feelings, and then I’ll ask things like:

What was the value in this?
What have I learned?
How can I use this as an opportunity to grow?

It doesn’t make shitty circumstances and more pleasant. But it is a long-term strategy for drastically improving as a person.

I handle myself with grace and respect when it comes to breakups, tough conversations with friends, and uncomfortable business dealings. I don’t take things personally and I never lose my temper.

How have I gotten so good at these things?

Because I was shit at them in the past.

I’ve tried to shame women into being with me (oh, to be 20). I’ve treated friends like garbage until they did what I wanted (sorry, Phil). And I’ve been stunned and speechless on the phone when a potential client told me “No thanks” (this year lol).

It’s through moments like these—memories that make us cringe—where the real growth happens. If someone doesn’t have any cringy memories, I assume they’re the same person they were in high school.

I treat women with respect because I know from experience how awful it is when I don’t. I’m open and honest with my friends because I’ve seen how sustainable and fulfilling that is over being passive-aggressive. And I’m detached from outcomes in my business because I’ve felt the agony of obsessing over a result and it not going my way.

It sounds David Goggins-y, but we learn from pain. Only if we let ourselves, though. Only if we seek the lessons.

We all want wisdom. But we don’t want the thing that brings us wisdom.

Feel…but learn as you do so.

I really don’t want to have a baby this week, but I’d be fine if I did

A baby smiling in the grass next to her teddy bear

Whenever we want to do something cool or useful—travel to a new country, create a business or a piece of content, or have a difficult conversation with someone…

We come up with aggravatingly reasonable justifications to not do that thing.

It’s not in the budget. I don’t know how. The timing isn’t right.

But the timing will never be right.

I look to my mom’s advice on not being ready to have kids. She says…

“I hear so many young people say, ‘Ugh, I absolutely can’t have a kid right now. I can barely take care of myself…’ I said the same thing when I was 29. I was a waitress who partied all the time. But you figure it out. You just do. You have no choice. I had my son and was like…Oh, well, this little boy is my life now. I finished school and started my career. I did all the things I was sure I wasn’t ‘ready’ for.”

My mom obviously doesn’t advocate for shitty parents. She’s commenting on our human ability to adapt and figure things out, especially for the hard stuff.

I don’t want to have a child today or this year. But if I did, I wouldn’t just throw it in the dumpster. I’d do everything I could to make it work! I’d change my budget, adjust my values, and make new decisions for the long term.

Having a baby is a huge example, but we can apply this truth to anything else.

In starting a business or an organization, say, we may feel unqualified to do so. But when we just do it and create clients, customers, and members…we become qualified through practice. Again, we figure it out.

I didn’t know how to run a blog when I started this one two years ago. I had a clunky Squarespace website that was difficult to maneuver around. My writing was meh.

But after posting every day since then, I’ve developed a rhythm and an audience for my ideas. It feels like second nature at this point. Again…I figured it out.

My mom was absolutely not ready to have me at 29. Now I’m about to be 29.

She’s still alive. I’m still alive. So her not being ready was a reasonable fear-based illusion.

What do you not feel ready for?

How good am I at chess?

A little girl sitting in a park next to a chess set

The answer: I am both an expert and have no idea what I’m doing. It just depends on who we ask.

Last week, I was playing and tutoring my younger brother and cousin. We were playing online on a Zoom call.

They’re both newer at the game and aren’t too familiar with fundamental chess tactics and strategies. They were mostly winging it. It was a bloodbath.

As I was mopping the floor with them, I would explain why I was doing what I was doing. Each move I made, each idea I had…I would articulate it.

My cousin said, “How are you able to think so many moves ahead?”

This is one of the most common questions people ask about chess. The answer is: I’m not. It’s just pattern recognition. In some way, shape, or form, I’ve seen that series of moves before. It simply comes with practice.

But what struck me as I was giving two teenagers an instructive beating was something my entrepreneur friend told me last year: Everyone is an expert to someone.

They were listening to me as if I were a Grandmaster. When really, I’m not that good at chess. Again, it depends on who we ask.

Last month, I played a couple chess hustlers in Washington Square Park in NYC. I won a game, felt enlightened, and then played a Master. Him playing me was as easy as me playing my younger relatives. Easier, actually. He didn’t even have to think.

The same is true for any skill. It doesn’t take long for us to get into the top percentile. Understanding the basics puts us miles above someone who has never taken the first step.

Dillan Taylor's chess rating in 2021

I started playing chess because it was something I could do with my friend over quarantine. Like many, my interest became an obsession after watching Queen’s Gambit in the winter.

But I’ve only been playing consistently for about nine months…and I’m in the 96th percentile of chess players.

Of course, the road to 97th, 98th, and so on will be quite the battle. But I show this to emphasize the power of two things: starting and consistency.

It’s easy to compare ourselves to people who have started and have been doing a thing consistently. But that just means if we start and do that thing consistently we’ll be in a much better spot.

Nine months ago, I could’ve compared myself to players at my level now (and I did). But I just focused on what I was doing that day or that week and tried to inch my way forward.

“After one jiujitsu class, you’re better than 99% of people who’ve never taken one.”

Start. Then get a little better each week. It won’t take long to become an ‘expert.’

But never forget that you also have no idea what you’re doing.

How this daily blog saved my life

A little boy with glasses reading a book

I was a fairly negative person until I was 23.

People did shitty things and it felt as though life was happening to me, not for me. I blamed others—or, even more vaguely, “society”—for my shortcomings.

It couldn’t have possibly been my lack of work ethic or my non-existent skills. No, clearly the universe was out to get me.

A big part of changing those thoughts was actually brought on by starting this blog.

For two and a half years, I’ve been typing my thoughts out every morning at this desk. The big fear I had when starting was that I would quickly run out of things to write about. I mean, a fresh blog every day? How interesting do I think my life is?

It turns out, our lives are quite fascinating…if we allow them to be. It’s a choice.

We can choose to go through our days as curious observers. I call this the Researcher Mindset. In other words:

Every single conversation, event, or mishap has value. There’s a lesson in everything. If there isn’t, that’s only because we’ve chosen not to look for it.

I’m not a “Everything happens for a reason” guy. I think things just happen…and we have the awesome power to derive meaning and wisdom from those things.

Let’s go through two examples—one small-stakes and one high-stakes.

1) A potential client says No to my business proposal.

No matter how smoothly the process goes up until the sales conversation, I have no control over how a person reacts when I say the dollar amount.

I’ve said a number and had people calmly say, “Oh, that’s it? Cool!” And I’ve said that same number and seen people baffled and think I’m joking.

People have ghosted me, dodged my messages because the money aspect scared them away, and flat-out asked to end communication with me. Needless to say, for a person running a business and trying to help people, this can be wildly frustrating.

In the early days, it was easy to take rejection personally. I would think…

How could they do this to me?
People suck.
• I can’t catch a break.

Shockingly, feeling that way and giving off that energy never made anyone change their mind and sign up with me. It just made it harder to be present and loving with the next person I was talking to.

So I began using my Researcher Mindset.

With every proposal conversation, I ask: What did I learn from this? What can I take away from this?

By asking these questions, I’ve improved as a business owner tremendously. People get back to me quicker, they’re more comfortable negotiating, and things are just clearer in the conversation overall.

2) My mom dies.

I’m well aware that my mother’s passing will be the worst day of my life.

But I actually don’t even have to wait for that day to use the lesson I’ll learn from it. Let me explain.

What I assume will smack me in the face will be the full understanding that no matter how much we care about a person, our time with them is limited. We will all fade.

The lesson here is simple. The only thing we can control is how much we cherish and utilize our time with these people while we have it.

When my mom invites me to something, I say yes. When she tells stories, I listen.

Conclusion

It can be hard at times, sometimes it may feel impossible.

But the most powerful question we can ask on a consistent basis is: How can I use this?

It’ll make us more resilient, more positive, and more appreciative.

it certainly has for me. Be a Researcher.

Things I never learned in school

  1. What “work hard” actually means and how to do it.
  2. How to build strong habits and break bad ones.
  3. How to seek failure, mistakes, and lessons.
  4. How to be open and vulnerable.
  5. Strategies for romance.
  6. Time management.
  7. What to do when drugs or violence are present.
  8. How to solve complex problems.
  9. The importance of defining my values.
  10. That it’s perfectly normal to hate school.

Strengths or weaknesses?

A strong man working out in a Superman tank top
An older picture of me.

I’ve heard people say it’s vital to improve one’s weaknesses. I’ve also heard people argue we must instead build up our strengths.

I disagree with the notion that it must be one or the other. We can do both. Here’s how.

1) The Feedback exercise

This is a sobering and healthy activity to do with the people who know us best—friends, family, and trusted colleagues.

We ask them:

“Hey! I’m doing a research project and was wondering if you could help me out.

What do you think my biggest strengths are? My biggest weaknesses or blind spots?

What can I improve? What can I do more or less of?

What should I prioritize?

Let’s set up a call to go over all this if you’re down!”

This accomplishes several things. It…

• helps one see the lens with which others see them
• points out things a person isn’t aware of—the good and the bad
• provides a solid picture of one’s strengths to exploit and weaknesses to work on

2) Build on strengths

With a list of strengths, we can simply ask:

How can I use these on a more consistent basis?

How can I do what I’m really good at all the time?

3) Fill in the gaps

Here’s a lovely practice from the book Ultralearning:

Keep a running list of each weak spot for what we do. Examples for me include: chess, fitness, coaching, business management.

With my list of weak points (e.g. finding checkmates in chess, extra belly fat, inviting people to sessions) I now know what to practice so I can become more comfortable with them.

TL; DR

We can use our strengths more and work on our weaknesses.