Quotes for your weekend (pt. 2)

“It’s not men against women. It’s good men and women against bad men and women.”

Whitney Cummings

“No job is worth being miserable for.”

Jackie Fitzkee

“Everyone has an invisible sign hanging from their neck saying, ‘Make me feel important.’ Never forget that when working with people.”

Mary Kay Ash

Quotes for your weekend (pt. 1)

“It’s OK to wing it. Just get on the plane and go. You can pick up a nicer shirt, shaving cream, and a toothbrush once you get there.”

Jason Fried

“Unfortunately, letting your emotions get the best of you in an argument is only good for entertaining the people who already agree with you.”

Sam Harris

“The world needs you at the party starting real conversations, saying, ‘I don’t know,’ and being kind.”

Charlie Kaufman

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.

My work playlist

When I’m working, studying, or reading, here’s my playlist I listen to.

It’s perfect for deep work and getting in the zone.

My 10 Commandments

The front lawn of a courthouse

I’m not the least bit religious, but I do advocate for living a principled and value-driven life.

Here are my 10 Commandments.

Thou shalt…

  1. Pursue a Growth Mindset—seeing everything as a lesson and a chance to improve.
  2. Never be uncomfortable with your shirt off—remaining fit and active.
  3. Treat every human being with the same amount of humor and respect—be they a CEO or a gardner.
  4. Pick your battles, but be confident when expressing your ideas and opinions.
  5. Cherish every minute of quality time you get with close friends and family.
  6. Never order food or watch a show unless with another person.
  7. Never take anything personally—especially rejection.
  8. Go to the gym at least three times per week.
  9. Never text while driving a car—even at a red light.
  10. Spend more time in a day reading or having a conversation than staring at a screen.

Being human, I don’t stick to these perfectly. But having these guidelines has moved me drastically closer to the person I aim to be.

What are your commandments?

I asked my doctor friends about vaccines

Three doctors looking at

This is NOT a post trying to convince someone to get vaccinated. It’s a blog about humility.

How it started

A few months ago, I had a warm debate with a friend about the COVID vaccine. I found her arguments to be shaky and without much reassuring evidence to support them.

But it wasn’t what we were arguing about that struck me. It was the level of certainty she had about her opinions while clearly being nothing close to an expert herself.

Certainty that the counter-evidence was likely bullshit. Certainty that the 1% of medical doctors against vaccines are in the right. Certainty that the virus is being propped up so the government and big pharma may gain control over citizens.

In general, I’m less interested in what a person thinks and care way more about how they think.

The conversation with my friend eventually fizzled out, but I couldn’t help but think: Have you had this debate with any real medical experts?

This was my first dose of humility…because I hadn’t spoken to anyone in that field either. So I decided to change that.

I’m lucky to have friends and folks in my life who are either medical doctors or are surrounded by them. I reached out to each of them and asked for their expert opinions in a neutral way.

I didn’t state my thoughts and then ask for validation. I simply said: “I’m trying to get a clearer picture here. As a medical professional, would you be willing to share your thoughts on the COVID vaccine?”

Every single doctor I reached out to sent me paragraphs in response.

Here are the notable takeaways:

• “I’m extremely confident in my ability to read and dissect medical literature surrounding this topic. I think a lot of people who “do their own research” don’t know the first thing about how to conduct, analyze, or determine the relevancy of medical studies. A Google search is not even remotely the same thing.”

• “One of the reasons mankind is still alive is the existence of vaccines. Polio, Measles, Mumps, Varicella, Meningitis, Influenza, and more…would ravage us if we didn’t have vaccines. I think people have become more skeptical in the world today compared to 20 years ago about nearly everything and essentially with this first new vaccine coming in that time, it’s a perfect target for controversy.”

• “As far as reasons I support it? It’s literally the answer to this problem we are all dealing with. It is safe, it’s well researched, the studies are all massively in favor of it, and it’s the fastest and likely the only way to go back to our normal lives.”

• “After these years of education and practical training, I think vaccines are one those things that have received unnecessary negativity towards.”

• “I know there are people who can’t get it, and that is okay. I also know that people who chose not to get it aren’t necessarily selfish people, they are normally just extremely uninformed or misinformed. Everybody acts in a way that they think is best. But just because you think you’re right, doesn’t mean you are. And in this case, it is causing harm to other people. It’s everyone else’s job to protect those of us who are more vulnerable. It’s part of our societal duties.”

• “I understand people want to be wary about side effects which is absolutely fine, but everything we do in medicine is evidence-based practice. We all take the Hippocratic Oath and essentially we try to do no harm while doing what is right for patients.”

• “I would understand the resistance to the vaccine if there was legitimate cause for concern, but there isn’t. Every single time I see a new BS conspiracy theory pop up, I take a week or two to look at the research and listen to the various experts that I know personally or follow on various forms of media. Without fail, every concern has been comprehensively debunked.”

• “It baffles and frustrates me that people are so resistant to entertaining the possibility that they may be wrong. It’s led to so much vaccine resistance and done so much harm. It’s the reason we are still in this mess, the reason the delta variant is such a problem, and the reason so many people are dying unnecessarily.”

What to do with all this?

To be clear, if any of these doctors said something like: “I actually warn people against the vaccine because of x, y, and z…” I would’ve included that too.

These just happen to be all the major points made by the five people I reached out to. I’m also aware that five people isn’t a great sample size.

The point of all of this is highlighted in the first takeaway I listed: I don’t have the slightest clue of how to read and dissect medical studies. Likewise, my friends who think they can in a matter of minutes seem foolish to me.

I think in the world of the internet—where we can find anyone articulating any opinion—it behooves us to practice more humility.

When did experts become morons? Corruption is real and people make mistakes, yes. But what allows someone to feel certain they know more than someone who’s been studying that thing for decades?

We’re experiencing a strange death of expertise.

Which makes me eternally grateful to have people in my life I can turn to who know way more than I do.

If I were thinking of getting spinal surgery, and I had a friend—who’s a server in a restaurant, say—tell me they actually did some research and thought I shouldn’t because it could damage my vertebrae…my response would be: “What the fuck do you know about spinal surgery??”

Vaccines and spinal surgeries are obviously different things in scope and scale. But what I’m trying to hammer home is the ridiculous nature of listening to people who certainly don’t know what they’re talking about.

This goes for my friends who are for the vaccines as well.

In summary:

1) I don’t know shit. Neither do most of us…so we should turn to the people who do know shit before cementing our own ideas.

2) Skepticism is healthy, but the point of expertise is to have people we can trust to take care of the wildly complex things which keep our lives going.

3) The next time we feel certain about an opinion, we must ask: How much time have I spent challenging this opinion? Who can I talk to in order to challenge these thoughts?

Mindfulness isn’t enough

A guy in a hat closing his eyes and practicing mindfulness

I got coached yesterday on some habits I’ve been slipping into which I’m unhappy about.

DoorDashing food, staying up late on my phone, eating junk.

As I talked it all out, I had an insight. It was a simple one (they usually are).

I said: “I’ve been complaining about these bad habits for months. I’ve been reflecting on them and writing about them. What I haven’t done is create a plan for actually doing something about them.”

Being mindful, having an awareness of what’s going on…it’s vital. But it’s not enough.

A person who knows they’re an asshole is still an asshole.

I had a friend once tell me she was aware that she was a shitty friend. I thought, Yeah…but fix that though.

Awareness is the first step, but it doesn’t build the result we’re looking for. So I wrote down the habits I wanted to minimize and then wrote a plan for how I would change my actions to do so.

Examples:

• I can’t DoorDash food unless it’s with another person
• I got an app that turns my internet off at 9:30pm
• If I eat junk then I can’t have it the following day

These are tangible and doable. Battling with my thoughts has been intangible and chaotic.

When mindfulness isn’t enough, create a plan of action.

3 rules for disagreeing with someone

In the past four years, I’ve had debates, discourse, and disagreements about politics, feminism, religion, race, transgenderism, vaccines, and more.

Some were heated and aggressive. Some were fun and fruitful.

I handled myself quite well during some. I sounded like an ass during others.

It doesn’t matter how much we connect or get along with someone else. We’ll never agree with 100% of what they believe. Disagreeing is a natural part of the human experience.

Through my conversational struggles and from the many mistakes I’ve made, I’ve learned three helpful (yet difficult) rules for having more productive disagreements.

Feel free to disagree with them (get it?).

1) Come to terms with this truth: We can never force someone to think, feel, or believe something. They have to get there on their own.

We are not creatures of logic. We make decisions based on emotion and then justify those decisions with logic.

In countless disagreements, I foolishly thought that if I just brought up another point of juicy rationale, I’d crack the other person and they’d see things the way I saw them.

Confirmation bias plagues us all. It will always be easy for us to pick and choose the (supposed) evidence which fits our narrative. We decide what we want to be true and identify with that belief. Then, if someone disagrees with that belief, it feels like they’re disagreeing with who we are as a person.

Yesterday, my friend told me about a heated debate between his two friends regarding the COVID vaccine.

One friend was arguing that the vaccines are probably not safe. He sent a screenshot of a well-sourced article listing the possible negative side effects.

The other friend then went to that same article and screenshotted a paragraph that was conveniently left out: the conclusion which said that the vaccine was ultimately proven to be safe.

I heard this part and thought that would be the shutting of the door to their argument. But the friend merely brushed it off and continued with his disputes.

With the power of the internet, we can find millions of people who agree with every possible opinion known to man. There are people with PhDs who believe the earth is flat. There are intelligent people who think the planet is 6000 years old.

Whether it’s opinions about vaccines or about our favorite athletes…our default is to cling to evidence that supports how we already feel and to shy away from evidence that challenges our beliefs.

Since that’s the case, we cannot ‘logic’ our way through a disagreement.

2) Ask way more questions.

There are several reasons for this.

Firstly, it’s crucial to understand fully what we’re arguing against. The last thing we want to do is misrepresent someone and challenge ideas they don’t actually hold.

We ask questions to paint a crystal clear picture of what they’re actually thinking.

A strawman is a fallacy in which we argue against the worst possible representation of someone’s point.

Example: “Oh, we need to do something about climate change? So you just want us to stop driving cars and stop having kids, huh?”

No…that’s not what they’re saying. That’s a strawman.

By asking curious and clarifying questions (not leading questions meant to achieve a ‘gotcha’ moment), we’re able to steelman. This is the opposite of a strawman, in which we’re able to articulate someone’s opinions perfectly.

A steelman would have us say: “So just to be clear, you believe…” Then they would say: “Yes.”

That has to be our starting point.

The second reason asking questions is so effective is it demonstrates to the other person that we’re not here to attack them. The more curious we are, the more we show we just want to understand them, the more their guard will drop.

This isn’t a trick. We want everyone involved to lower their guard and feel safe to express themselves without reacting in a defensive manner.

Curious questions make it a conversation, not a debate. This is ideal. Debates have winners and losers. But in great conversations, everybody wins.

The final benefit of asking questions is it adds scrutiny to the conversation, exposing the true strength of the person’s argument.

While this should never be the goal of asking questions, it’s possible that the person “defeats” themselves with their own words. It’s a great way to see if this person has given thought and research into this thing they believe or if they just want to believe this thing.

I recently had a disagreement over the COVID vaccines myself. (To be clear, I’m not super passionate about vaccines. It’s just come up a ton in recent months so it’s fresh on my mind.)

My friend who was super wary of the vaccines was sharing his opinions. I did my best to just ask questions. As I did, I felt that their answers were on shaky ground and I found many holes in their arguments.

There were a lot of “I don’t know’s” and “I don’t remember’s.”

Again, I wasn’t trying to slam dunk this person I have a ton of love for. I just wanted to get a clear picture of their beliefs.

Asking questions is hard, especially when we don’t feel curious at all. Curiosity is tough to fake. But it’s the only way to ensure nothing gets lost in translation.

3) Separate the person from the argument.

We’re not arguing with people; we’re arguing with ideas.

I could go on for hours about how much I hated having Donald Trump as our president. But I’m also super close with people who absolutely loved him.

That doesn’t mean I actually hate these people. It just means I don’t connect with their ideas. We don’t need to agree with someone to hug them or to have a beer with them.

So in a disagreement, it’s powerful to avoid saying things like:

• “Where you’re wrong is…”
• “What you don’t see is…”
• “I disagree with you on…”

With phrases like these, it sounds again like we’re disagreeing with them as a person.

It’s better to say things like:

• “My problem with that perspective is…”
• “That argument to me is…”
• “The way I see things is…”

With phrases like these, we make it apparent that we’re just discussing ideas. It’s not a battle over who’s more righteous, more intelligent, or more sophisticated.

Conclusion

We have to pick our battles. I’ve ruined social events because I thought it was the perfect time to argue against Catholicism.

But we should also feel safe and free enough to express ourselves. This can best be done if we change our goals for disagreement.

Instead of wanting to win, we should want to collaborate and learn.

“Seek out people, books or ideas that contradict your current beliefs and one of two things will happen…A) you will discover that you are wrong or B) you will improve your arguments for your own ideas.”

-Mark Manson

I really don’t feel like writing this blog today

There are many days where even the thought of putting together a few sentences is exhausting.

But doing the things we care about doesn’t always mean we’re having a blast.

Most days, I don’t feel like:

• working out
• reaching out to prospective clients
• writing
• practicing/studying chess

But putting in those groggy hours makes the times I do feel like doing them so much easier and more rewarding.

If I can do this shit when I’d rather do anything else…then I can probably do anything.

3 questions to ask your best friend

Two puppies who are friends

I’ve talked about a feedback exercise we can do with those around us—friends, family, and colleagues. It’s wildly helpful in pinpointing our strengths and weaknesses.

But here are three questions we can ask those we hold dearest.

1) What is your favorite memory—or top three memories—of our time together?

2) When have I hurt you?

3) What have I done that you respect/admire most?

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.

Talk to your friends

Two friends laughing together while sitting on a bench

I had an incredible phone conversation with one of my best friends yesterday.

They’re usually great, but this one really hit all the nails: a ton of laughter, business updates, and vulnerability.

One of the silver linings of the pandemic has been the multiplication of how much I value my friendships. I find it vital to go out of our way to visit and maintain communication with the people we share our lives with.

We all have those friends with whom we can go a year without talking to and then just pick right back up where we left off. That’s lovely…but if it’s a close friend, I see that as an utter waste.

Let me explain.

I’m 27. I started my own business this year, am single, and have no kids. I’ve never been more career-focused than I am right now.

All this to say I’m hyper-aware that we’re all living our own lives. We’re stressed. Many of us are still figuring out who we are and what we want. Some of us have families. It’s not like high school where we can spend every weeknight and weekend having fun with our buddies.

However, since that’s the case, there’s never been a better time than right now to sustain healthy and fulfilling friendships.

I’ve had…

• one of my best friends ghost me out of his life with no explanation to this day
• friends get arrested
• friends have quarter-life crises

It’s when we’re the most anxious, the busiest, and most overwhelmed that we need our friends the most.

If we let a year go by without any communication…yes, maybe we can pick right back up. That’s fine. But how many total hours of laughter, connection, and memories did we miss out on?

I love knowing what my friends are working on, are afraid of, and are thinking about on a consistent basis. I’m not saying I need to talk to them every single week, but more than twice a year is preferable.

We can start small. That friend we see once a year…we can bump that up to twice a year. We can set up a monthly call with our busy friends with kids.

It feels like work. Because it fucking is.

Let’s assume the major facets of life are health, wealth, and relationships (broadly speaking). I’ve noticed we put a ton of effort into working on our physical health, our mental health, and our careers, but we sort of expect our relationships to just take care of themselves.

When really they’re just like anything else important to us. They require effort, practice, and collaboration to figure out what works and what doesn’t.

When I’m an old ass man, I want to look back and think I’m glad I did…as opposed to I wish I had…

Right now, I’m so glad I had that phone call with my buddy. And I’m looking forward to visiting him in two weekends.

I forgot to write this blog

I thought today was Sunday. I don’t write blogs on Sundays.

After more in-depth research, I discovered that it is, in fact, Saturday.

I do write blogs on Saturdays.

This is one of them.

Sober October begins

A pumpkin and a fall leaf during October

For the fourth year in a row, I will not be drinking a sip of alcohol during the month of October.

There are a few reasons for this:

  1. It’s refreshing to take a break from putting poison in my body.
  2. It makes it easier to crush it in my other health arenas: diet, exercise, sleep.
  3. Waking up well-rested and without a hangover is one of my passions.
  4. Even though I don’t drink all the time, it’s nice to prove to myself I truly don’t need or crave it.

I’m always excited to start.

And now, each year I’m adding an extra month of no drinking. This year it was January. Next year, it’ll be three months.

Let us begin.

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.

Todo

Everything we’ve ever done and not done has led us to wherever we are and whatever we’re doing right now.

Every conversation, challenge, and action…

Everything we’ve ever purchased or saved has led our bank account to have whatever number it has at this moment.

Likewise, everything we are currently doing will lead to the person we will become.

So perhaps better than asking What am I doing right now? is to ask:

Who am I becoming?

Are you defective?

Almost everyone is screwed up, broken, clingy, scared, and yet designed for joy. Even (or especially) people who seem to have it more or less together are more like the rest of us than you would believe. I try not to compare my insides to their outsides, because this makes me much worse than I already am, and if I get to know them, they turn out to have plenty of irritability and shadow of their own. Besides, those few people who aren’t a mess are probably good for about twenty minutes of dinner conversation.

Anne Lamott

One thing I’ve learned through coaching so many people is that every single one of us feels like we have a deficiency in some way shape or form.

I’m too x. I always do y. I can never do z.

It reminds me of social media. With today’s technology, we can advertise whatever kind of life we want people to see. The same is true for any sort of image we have.

We can look at someone’s LinkedIn and feel envy. But what we don’t see is them fighting with their spouse, having panic attacks, or consolidating their debt.

Everyone has their shit. Even the ones with their “shit together.”

The thing is, we’re not defective. We each have wildly different strengths, weaknesses, and tendencies. We’re all capable of learning and growing.

If we were a car, we have the ability to take it into the shop, repair it, and spruce it up. Not everybody takes advantage of that truth, but it is true nonetheless.

I’m just a reject

A girl getting rejected

I’ve been rejected a lot this year.

This was to be expected as I launched my coaching career, but reflecting back on the number of No’s I’ve received is insightful.

Byron Katie said: “You can have whatever you want in this life if you’re willing to ask 1000 people for it.”

That’s damn true. However, it also means most of those thousand people will not “give us what we want.”

The cool thing is, with practice and repetitions, we can become incredibly skilled at not giving a shit about a certain outcome.

I’ve invited hundreds of people to connect calls, coaching sessions, or long-term contracts.

The majority of people do one of these things:

• leave me on ‘read’
• say they’ll think about it and never get back to me
• stop responding
• never read the message
• cancel the call and ghost
• say No thank you

In the early days, it was hard to not get emotional when one of these would happen…especially getting ghosted. I would get in my head and question my abilities and motives.

But over time, I became desensitized and learned how to truly take nothing personally. The key lesson from Jia Jiang’s book Rejection Proof got etched into my brain:

When we get rejected, it says nothing about us and everything about the person doing the rejecting. It’s just proof that they don’t feel it’s the right fit right now.

Two weeks ago, I invited one of my best friends to the group coaching program I just created. He politely walked me through why he felt he didn’t have demand for what the program offered. Being wary of my feelings, he asked, “Is that okay?”

I laughed. “No,” I replied. “This program isn’t optional.”

This is the perfect example of this rejection truth.

My best friend said No thanks to me. I know for a fact that he loves and supports me and thinks I have good ideas. So it had nothing to do with me and everything to do with the fact that right now, the program just isn’t a good fit for him.

This can be applied to dating, event invites, or anything else where we put ourselves out there.

Rejection isn’t a bad thing. It’s a process for sifting through and finding the right people at the right time.

Up since 5am

I woke up this morning to someone banging on my door. It was my downstairs neighbor.

He said there was a ton of water coming into his apartment from the ceiling. We inspected my water heater and the entire thing was flooding.

We unscrewed the wall unit and saw it was in fact coming from above. So I walked upstairs and did exactly what he did to me. I knocked on their door about ten times until an exhausted mother asked what I wanted. Rinse and repeat.

Her pipe had burst. We called the emergency number, she took down my phone number, and we laughed about our unique way to begin the Saturday.

In the past, this might’ve set me up for a shitty day. But right now, I’m just stoked I know two more of my neighbors. Plus Hank got an earlier and longer walk this morning.

And seeing the sunrise in its entirety wasn’t bad either…Today is a good day.

A secret skill

A woman skilled at knitting

There’s something one of my best friends does that pisses me off in a delightful way.

She’s infuriatingly good at asking follow-up questions. We can be on the phone for an hour and I’ll realize we’ve been talking about me the whole time.

Two things happen when I come to:

  1. I feel like the most interesting person in the world, and
  2. I feel awful for hogging up the entire conversation

When I voice this, she makes it clear she just wants to know what’s going on in my life. But I still find I have to do a full stop and shift our chat to what’s going on in hers.

One of the biggest insights I’ve experienced this year is this:

Curiosity is a skill. It can be practiced and improved.

Before I started coaching, I felt like a sociopath because I wasn’t super interested in other people. But after months of pursuing conversations and asking follow-up questions, I felt a genuine increase in fascination. Now I think, Every human being is an anomaly.

There’s a cliche which states that the most interesting people are those who are most interested in people. I’ve seen this pan out.

Not that I’m curious to curry favor or trick others into liking me. But I’ve seen firsthand that people are more willing to spend time and money with me when I make them feel like the most interesting person on the planet.

Now, my friend and I have a secret battle to be the first to dive into the other person’s life. We’ll exchange deets for two hours, and I’ll think: Damn…WE’RE the most interesting people alive.

Practicing curiosity will improve our relationships, conversations, and overall worldview.

“If you could choose to be fascinated by the world around you, wouldn’t you?”

Dammit, our parents were right

Parents helping their daughter learn to ride a bike

I’m almost the same age my mom was when she had me.

As my friends and I approach the ripe age of 30, I’m realizing more and more that the cliches of getting older are cliches for a reason.

There are the funnier ones, like:

• hangovers get worse
• it’s easier to build fat
• we enjoy quiet alone time more

But in this blog, I’d like to briefly discuss a recent shift in my perspective. Let me explain.

Until now, I’ve relished a fairly obligation-free life. I’ve been single most years. I have no kids or pets. I’ve never owned any real estate.

But something struck me the other day as I was laying on the couch with Hank—my friends’ dog I’m pet-sitting.

Hank the dog laying on the couch
Sorry for the crouch-shot.

I’ve spent the last two weeks walking, feeding, and playing with this other living creature. Here’s what I’ve realized.

We may begrudge adding more responsibility to our plates, but it makes our lives more fulfilling and purposeful.

When I wake up at 6:30 and can’t see straight, I hear a rhythmic thumping as Hank’s tail wags and slams against my wall. It doesn’t matter how many times we do it; he’s elated to get up, eat breakfast, and go for a stroll around my apartment complex.

Every morning.

If that doesn’t motivate someone to get their day started I don’t know what would.

Parents might roll their eyes reading this. I’m aware I’m just watching a dog here.

But this is my first true experience of another living being depending on me to survive and live an enjoyable life. It’s been a real jolt of energy to add some responsibility to my life.

One of my best friends, for example, just had a baby. Even being ‘Crazy Uncle Dill’ has added some meaning to my days.

Her first words were: “Dillan is hilarious.”

I’m not saying I’m trying to have kids tomorrow. I’m saying I’ll remember this as a pivotal mindset shift as I become…dare I say it…an adult.

How to not be nervous around women

A man and a woman holding hands

There’s a video of Craig Ferguson I’ve been thinking about a lot lately.

It’s his answer to: “How can I as a young man be better at talking to women?”

But I think it applies to all facets of life: making friends, being a great communicator, or building relationships in general.

His answer?

Treat every single human being with the same amount of love, respect, and honesty. It doesn’t matter what their sex, race, job, weight, or age is.

Be curious about people. Exchange stories. Ask questions. Try to build something together.

“Friendship happens on the way to something else. If you “try to meet new people” it feels weird and forced. The more you aim for friendship, the more it eludes you. But if you aim to learn or achieve something with others, friendship happens naturally during the shared pursuit.”

James Clear

Is people-pleasing so bad? (pt. 2)

People shaking hands during a meeting in a conference room

Last week, I wrote about how my mind has recently changed on the topics of people-pleasing, saying No, and protecting our time.

These are all things I’ve been working on for the past year as I run my own business. In order to sustain my health, wealth, and relationships, I have to set boundaries for how I expend my energy.

But where did this all begin for me?

In April. Here’s what happened.

After joining my online coaching program in March, in the span of one month, I was called out by four different colleagues for needlessly apologizing for things. I learned how hesitant I was to stand up for myself.

One of those colleagues was a woman who told me she decided to stop saying “Sorry” the month before.

I was struck by this. But it took me several months to understand how I felt about this philosophy. Well…here’s how I feel about it.

I tried it out for a month or two. To be honest, it felt fucking great.

The first thing I noticed was how automatic saying Sorry was. I would open my mouth to apologize for something I didn’t do or something I had no control over—a dog barking, a broken appliance, the fact that I wasn’t available for something. Catching myself, I would promptly close my mouth and that would be that.

No one got mad. No one seemed to be waiting for some sort of justification.

But then something happened which made me question the whole experiment: I fucked up.

I did something that made a friend upset and I felt awful about it. This highlighted my issue with the whole “I don’t say Sorry” thing…Humans make mistakes.

What happens when we do something worthy of an apology? Saying we don’t apologize is to assume we’re perfect creatures. I’m happy to have the words “I’m sorry” in my toolbelt.

So where’s the middle here?

For me, it’s not about not saying Sorry. It’s about not always saying Sorry.

If Sorry is our default then it means nothing. If we say Sorry five times in one minute then it means nothing. If we apologize for things we had no control over then what does it accomplish?

But if we instead save it for things that truly matter, our words and actions have more impact on the people around us. Now, my friends know I feel deeply sorry when I say so.

We don’t have to apologize for everything. We just have to be willing to apologize.

Doing shrooms in NYC

In March, I joined an online coaching program and met Tomas, a guy who would soon become a close friend.

This weekend, seven months later…I met him in real life.

He’s been sober for six years, so before the trip, I was boasting to my friends that I would save money this weekend by not buying any booze and by going to bed early each night. That didn’t happen.

It turned out that even though Tomas doesn’t drink or do drugs, he’s an incredible host and wingman who loves to have a good time. I felt like I was in college again, a man-sized child lost in the largest city in the country.

I…

• stayed out until 4am each night
• played chess hustlers in Washington Square Park
• befriended strangers when we were out and about
• set up coaching sessions with those strangers
• ate mushroom chocolate and woke up tripping with no idea where in Brooklyn I was
• got late-night tacos both evenings
• left my credit card at the last bar we went to
• saw Seth Meyers walking with his son five feet from me in the park
• got offered blow by the CFO of VICE
• decided I would move to the city about ten times and changed my mind each time

Can I do this every weekend? Absolutely not.

But it’s times like these I never want to give up. I’ll gladly sacrifice my comfort for a day or two for memories and moments like I just had.

This weekend was…fun.

Dillan Taylor playing a chess hustler in Washington Square Park

Simple lesson (pt. 3)

A simple lesson I learned this year:

It’s lovely to craft a successful career for ourselves. But what is twenty times more important is sustaining fulfilling relationships with other people—friends, family, and colleagues.

Simple lesson (pt. 2)

A simple lesson I learned this year:

“Working harder” is almost never the solution. Nine times out of ten, it’s more effective and peaceful to cut out all the nonessentials first.

Simple lesson (pt. 1)

A simple lesson I learned this year:

Rejection is always good news. It’s the best possible proof to show this isn’t a good fit right now.

How to beat confirmation bias

Confirmation bias:

“The tendency to interpret new evidence as confirmation of one’s existing beliefs or theories.”

No matter how objective or reasonable we feel our opinions are, this psychological fallacy plagues every single one of us. From our sociopolitical opinions on down, we will always find it easy to find evidence which agrees with us and difficult to stomach evidence which disagrees with us.

With the power of the internet, one is guaranteed to find something somewhere (or a lot of things in a lot of places) that confirms what they already believe.

There are entire flat-earth communities. Q-Anon has over 10,000,000 members.

Mark Manson said:

“You used to have to go to medical school for two years to have an opinion on a vaccine. Now you just scroll through Facebook for 20 minutes.”

He’s right. Today, a person can decide what their opinion is, look at their phone, and find millions of people around the world who support and agree with them.

I hear people spouting their opinions with the confidence of a seasoned expert. Then, after a few questions, I see how shaky their arguments are.

So how do we combat this? The answer isn’t super fun.

It’s exposure.

The healthiest and most challenging thing we can do is spend intentional time researching the other side…

• Google “{my opinion} debunked”
• Have curious conversations with people we disagree with—for the sake of hearing new perspectives, NOT with the goal of changing minds
• Listen to podcasts/read books that challenge our beliefs

I’ve spent many hours doing all of this in 2021. This shit is hard.

It’s not mentally or emotionally enjoyable to pursue ideas which disagree with the ways we see the world. But it sure is healthy. It:

• strengthens our curiosity muscle
• lessens our tendency to be triggered by those we disagree with
• shifts our value of “being right” toward learning new things

Try it out. What are some opinions you would be uncomfortable putting to the test?

Is people-pleasing so bad? (pt. 1)

A young couple looking at menus in a restaurant

Two weeks ago, I ran a workshop on people-pleasing, saying No, and protecting our time and energy.

It was lovely to hear a group of friends, family, and colleagues collaborate and share stories and ideas.

The underlying notion of the conversation was that people-pleasing is bad and should be avoided. But then one of my coaching friends posed a challenge.

“I think people-pleasing gets a bad rep,” she said. “Sometimes it’s totally justified to do something we don’t feel like doing for the benefit of ourselves and especially others.”

I needed to hear this.

In the self-improvement and entrepreneurship worlds, it’s normal to hear things like:

If it’s not a Hell Yes, it’s a No.
No is a complete sentence.
Say No to most things.

What I realized as my friend was sharing her thoughts was that all these ideas are contextual. If we’re running a business, these rules are quite helpful. We can’t say Yes to every opportunity. We’d get distracted and pulled in too many directions.

But part of having healthy and fruitful relationships is being selfless for those we care about. Again, my friend made an excellent point:

“If you say No to five invites in a row, don’t get upset when your friends stop inviting you to things. Plus, how many times have you gone to something you didn’t want to go to…and you ended up having a lovely time?”

I love when I have my mind changed. Since this discussion, I’ve been more cognizant of saying Yes to things which would bring me closer to people…without burning myself out.