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.

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.

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?”

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?

An important skill

Most people are willing to have difficult conversations, be vulnerable, and put themselves out there.

The problem is, most people are unwilling to be the initiator of these things.

A powerful skill I’ve developed this year is that of being the initiator.

• Asking for the things I want.
• Setting up plans and events.
• Being active, not passive.

So many of us choose our path out of fear disguised as practicality. What we really want seems impossibly out of reach and ridiculous to expect, so we never dare to ask the universe for it.

Jim Carrey

Asking for feedback

Two men giving each other feedback

This week, my best buddy and I did a feedback exercise.

It’s where we send something like this to the people—friends, family, colleagues—who know us best:

Hey! I’m doing a research project and could really use your help. Would you mind answering these questions…
What do you think my biggest strengths are? What do you respect/admire about me?
What do you think my biggest blind spots are?
What can I be doing more/less of?
If you were me, what would you make a priority?

Seeking constructive criticism accomplishes a few things. All great.

1) It helps us grow as people—personally and professionally.

2) It gives us a clearer picture of the lens with which the people around us view us.

3) It can solidify the things we already know to be true.

4) It really highlights our strengths.

Naturally, this should be done with folks we trust to have our best interests at heart.

When he dove into my strengths and blind spots, much of what he said surprised me. Things like:

• Great at first impressions
• Excellent teacher
• Should surround yourself with more people who take initiative
• Should prioritize paying off debt sooner

We’re cursed with only having one set of eyes to look down upon our lives. Getting other perspectives from the people who care about us is a powerful thing.

Who would you do this exercise with?

Running group calls

I held a workshop last night open to a bunch of my friends, family, and colleagues.

Few things delight me more than connecting people who otherwise would’ve never met.

Hearing one of my coaching friends say, “I loved what Karen said…” made me smile. I was like, That’s my aunt!

I’ve learned a few things from running group calls:

1) People love talking and engaging, even if they think they don’t. It makes the time pass quickly and people enjoy gaining different perspectives on the same topic.

2) The worst thing a curator can do is ask the group: “Does anybody have any thoughts?” Just fucking call on someone. They will share their thoughts. Don’t give them a choice. The six seconds of silence after that question is asked is valuable collaboration time. I call on folks at random every time and no one has ever said, “I actually don’t have anything to say.”

3) The more I prep and plan a group call, the more flat and robotic it sounds. My best calls have been where I’ve let the momentum of the conversation take the wheel. It may be slow at the start, but once people begin sharing, it becomes a flywheel that spins itself.

Thursday swims

My best buddy and I did a triathlon a few months ago.

Prior to that, I could barely swim a single lap without gasping for air.

Since then, he and I have swam every Thursday morning at our local center.

It’s been a slow progression, but each week I find myself swimming more and more laps without having to stop for a break.

With practice, we have no choice but to get better at something. We inevitably begin to flow and figure shit out.

If I keep swimming, I’ll get better. If I stop, I won’t.

Why you don’t need confidence

A confident woman looking in the mirror

I coached a fellow coach yesterday who said she wanted to leave the session with enough confidence to do x, y, and of course…z.

We started exploring.

What’s your definition of confidence? What does it look/sound/feel like?

When in your life have you been truly confident?

How much confidence have you decided you need before you can take action? On a scale from 1 to 10?

She told me about her career as a teacher. She studied education for seven years and then jumped into teaching kids, year after year after year. She said when she stood up and taught a classroom she knew who she was and what she was doing.

I reflected back: “It sounds like you gained tremendous confidence after learning and practicing something for many years…And now you’d like that same level of confidence with something you’ve only just started.”

We explored further.

She explained that as a teacher, she could provide the answers, but as coaches our job isn’t to give away solutions but to help others discover the solutions they already have access to.

She had an insight: “When I’m coaching, I’m not the teacher. Life is the teacher. I’m just supposed to be with them in that space where they can learn their own lessons.”

“Holy fuck,” I said. “That’s awesome!”

When I asked her what her biggest takeaway was, she responded without pause: “I don’t need to worry about confidence. I need to focus on authenticity. I’ll show up as me and practice until I get really good at everything I want to do. The confidence will come.”

Sheeeeesh. I wanted to her hug through my laptop screen.

This was such a lovely example of overcoming one of the most powerful stories we tell ourselves: I need more confidence so that I can…

Don’t get me wrong, confidence is amazing. The flow that comes from a belief in oneself can be euphoric. But it’s not a prerequisite for taking action, it’s a byproduct.

Natural talent is fun, but most of our confidence comes from doing something a lot and getting better at it. When we think we need more confidence what we really need is more practice.

Just jump in. The confidence will come.

Fulfillment formula

A woman in front of a chalkboard with formulas written on it

Here’s an overly-simple formula to ensure a level of fulfillment in our lives:

Step 1: Find something we like to do that’s difficult

Step 2: Do it all the time

Step 3: Get better at it

Step 4: Repeat steps 2 and 3

Be it an instrument, a sport, or a craft…having an activity we look forward to or something that challenges us is crucial—especially if it has nothing to do with our work.

When it comes to this, I’ve found that “Find your passion” is shitty advice.

Every now and then, someone finds something they are obsessed with immediately and that’s lovely. But for the other 99% of us, passions are developed…not found. They are grown like a plant, not discovered like pirate’s treasure.

In his book So Good They Can’t Ignore You, Cal Newport proves that the number one factor in how passionate a person is with something is their amount of experience/skill level in it.

We’ve all felt this. As we get better at something, we have more freedom to play around and do cooler shit, which tends to make us enjoy it more.

I’ve felt this with soccer, chess, tennis, jiujitsu, and writing.

Not that I’m particularly good at any of these things…but I have gotten better at them and have subsequently felt an increase in how much I enjoy doing them.

What do you like doing? What would you love to do consistently until you get pretty damn good at it?

Am I getting worse at chess?

A woman playing chess and holding up the king

The other day I was playing chess against a friend.

The week before, I had beaten him three times in a row. Naturally, I concluded that I would ride that momentum forever and never lose to him again.

When we played next, he beat me three times in a row. I considered quitting chess altogether…

Jokes aside, I must admit there was an emotional toll those three losses took on me. My thoughts were:

• Have I gotten worse?
• How has he gotten so much better?
• What did I do right last week that I didn’t do this week?

Then I heard about a psychological experiment that was conducted in the Air Force. They wanted to prove which method of feedback was more effective in impacting an officer’s performance—positive reinforcement or negative reinforcement.

Generals boasted as they pointed to clear evidence that punishing pilots for mistakes almost always led to improvements on their following flight. Likewise, praise tended to lead to worse results on their next go.

But there was a glaring issue with their testing.

When they were challenged to create a control group, they found that no matter what, soldiers who did super well one week tended to do worse the next week…and soldiers who did super shitty one week tended to do much better the next.

This highlights a popular statistical phenomenon: Regression to the Mean.

Basically in everything we do, there’s a natural variation—ups and downs, push and pull, give and take.

If we have an amazing week at work, things will likely even out the following week to bring us closer to our average. But it’ll feel like we’re regressing.

The same is true for any skill or activity—chess, business, exercise…

As of writing this, my ELO (number rating) in chess is 1420. Sometimes I play like a 1600 and sometimes I play like a 1200…but 1420 is about my average.

Nothing guarantees absolute consistency. In other words, sometimes we’re awesome, sometimes we suck, and both are fine. The more we do something, the more we move toward whatever our average is. When we’re on a low, it doesn’t mean we’re getting worse…and it probably means we’re about to experience a high.

The goal is to improve our mean so we can experience higher highs.

Two people learning piano

Two people playing piano together

There are two people who both want to become amazing piano players.

Person 1 spends weeks researching and buys one of the nicest keyboards they could find. Person 2 buys a cheap one on Facebook Marketplace in a day.

Person 1 is amped to sit down and play, but at random times. When they practice they play for hours, but then go days without touching their keyboard. Person 2 practices for 10 minutes each day no matter what. Person 1 plays when they are motivated. Person 2 builds a system where they play no matter how they’re feeling.

Person 1 jumps around to learn all the songs they love most. Person 2 spends most of their time practicing the fundamentals—scales and chords.

Person 1 talks about playing piano a ton and posts about it on social media. Person 2 actually plays piano a ton and doesn’t talk about it much.

Person 1 takes long breaks from playing when they hit a wall or lose interest. Person 2 pushes through these ruts and improves drastically each time they do.

Person 1 is intimidated by others who are much better than they are. Person 2 finds friends and strangers alike to learn from and be inspired by.

After one year, Person 1 has spent an enormous amount of time thinking about being a great piano player…while Person 2 is actually becoming quite good.

Person 1 has built a gorgeous-looking blueprint. Person 2 got right into the muddy trenches and went to work—making mistakes every single day until things began to flow.

Whether it’s learning an instrument, starting a business, or creating anything, we all want to be more like Person 2.

The E-Myth

I just finished The E-Myth Revisited by Michael Gerber.

It was a super helpful, albeit cheesy book on running a business.

Here are my two biggest takeaways:

1) Being a Technician—i.e. being skilled at your craft/service—does not qualify you to be a business owner.

Great bakers, coaches, or carpenters don’t necessarily make folks who are great at running bakeries, practices, or home remodeling companies. Running the back end of a business is a completely different ball game.

In short, there’s a huge difference between working in your business and working on your business.

2) Your business is not your life; it should fuel your life.

I needed to hear this.

For the past year, I’ve been growing my first ever business and have become more and more passionate about it as it grows each month. Thinking about my business—creating clients, scheduling calls, inviting people to coaching sessions….I would be focusing on this stuff almost 24/7.

I wore that like a badge of honor, but I had to be reminded that that wasn’t my life. My life is my friends, my family, my health. My life is the freedom I enjoy with the people I love. I want my work to give me more freedom, not chip away at it.

If anyone owns any kind of business, or is at least considering it (no matter how big or small), I would consider this book mandatory reading.

What’s your system?

A bunch of electronic chords plugged into a system
The inside of my brain.

We all have a system for doing things.

Some of us reject the the word system. That’s fine, but we all have a series of actions we take or don’t take with everything we do. Habits are just a form of systems.

“You do not rise to the level of your goals. You fall to the level of your systems.”
― James Clear, Atomic Habits: An Easy & Proven Way to Build Good Habits & Break Bad Ones

Our bank accounts are the sum total of our financial habits. The way we look and feel is the sum total of our diet and exercise habits. How messy or tidy our space is is the sum total of our cleanliness habits.

Last month, I got terrible sleep. Since my sleep quality is the sum total of my sleeping habits, I did some investigation.

I noticed I was:

• on my phone a lot right before bed
• eating later in the day
• drinking more alcohol than usual

So I improved the system. No phone after 10pm. Not eating past 8pm. No alcohol on weekdays.

After just one week, my sleep quality has improved drastically and I feel ten times more refreshed and energetic.

Dillan Taylor's sleep report
My sleep data from Sleep Cycle.

In a recent conversation with a coaching friend, she told me, “It’s impressive to me how you set a goal and just attack it.” I was truly touched by her compliment, but right away I explained that that’s not how I approach things.

In the self-help world, we’re told to set SMART goals. Specific, Measurable, Achievable, Realistic, Timely.
e.g. “I’m going to lose 15 pounds by August 2nd.”

I understand the utility of setting such specific goals, but they don’t light me up at all. I usually change my mind halfway through working toward them or if I do accomplish them, I’m left with this empty feeling and simply ask, “Now what?”

I much prefer systems.

To be more clear: I prefer designing systems which allow me to consistently doing the things I enjoy and get better at them. Here are a few of them…

Coaching:

I reach out to a certain number of people each week and update my client notes every Monday. I’m not working toward a defined number of clients or a specific dollar amount. I just love coaching and growing my business, so I have a system in place which lets me do those things well every single week.

Exercise:

I’ve never set an exercise goal. I couldn’t care less about how much I can bench or squat. But I love exercise, so I make sure I go to the gym three to four times each week. The cycle: push muscles (chest and triceps), core, pull muscles (back and biceps), and legs.

This blog:

I look at the analytics of this blog about once a year. I’m eternally grateful for how the number of readers has increased, but I don’t do it to raise traffic. I write this blog each morning because it helps me shape and get clarity on my thoughts on things. I’ve become more articulate and I get to share stories and ideas with friends and people outside my circle. So I’ve made it part of my morning routine.

Conclusion

So I’ll ask you: How can you create a system for the things you enjoy so you can do them more and do them better?

Do you reject systems? If so, why? And does rejecting systems lead you to take more action or less?

Losing power

For the first time in my adult life, we lost power at my place.

We lit candles and reminisced over the good days when we could sit on our phones with the lights on. Instead, we had to sit on our phones with the lights off.

It got me thinking…what else do we constantly have at our disposal that we totally take for granted? It didn’t take me long to realize the answer: everything.

The fact that I…

• can see and hear
• have all four of my limbs
• don’t have any major disease
• have friends
• have parents and grandparents who are alive

The list could literally go on forever.

One day, these things will be taken from me. The only thing I can do is cherish them in the present.

We’re talking about practice, man

A chess board on a bed

I started playing chess last summer. Since then, I’ve played almost every day.

One of the main reasons I got into it was because one of my close friends played as well. He would destroy me, and we’re both quite competitive so that was all the drive I needed to want to improve. I had a worthy rival: Someone just ahead of me to push and challenge my skills.

I read books, got a chess tutor for a month, and have watched mountains of chess content on YouTube.

After about a year of playing consistently, I finally feel like I’m at the point where I can play my friend and confidently beat him most of the time. (Sorry, Andrew!)

This makes me happy for a number of reasons:

1) Feeling our skills improve is one of the best experiences in the world.

Seeing our muscles get bigger, or timing sharpen, our understanding flow better…There is a motivating excitement that comes with any sort of visible growth.

What we’re trying to improve becomes more fun since we can simply do more things.

2) Competition is fun.

For many of us, that competitive drive will never leave. But as we get older, the hope is that we channel it in more productive ways.

Winning in chess is obviously more fun than losing (especially against a good friend), but what’s more fun is competing against my past self.

Dillan's chess rating

Seeing my ELO increase is jubilating. (An ELO is the number that rates a player’s skill level.)

It took me a while to break 1300. Now I’m trying to break 1400. And so on.

3) The Growth Mindset is real.

The Fixed Mindset is the idea that every skill falls into having natural ability or not. Some people can and some people can’t.

People with a Fixed Mindset say things like:

• “I’m just not a musical person.”
• “I suck at this.”
• “This just isn’t something I can do.”

Of course, we all have certain strengths and weak spots. But the Growth Mindset states that if we just put enough time and energy into something, we can improve at it.

Example: I’ve said my whole life that I’m not a business guy. Now, after running a coaching business for about a year, I’m training and coaching others on how to run their businesses. Practice, bitches.

There have been plenty of times where I wanted to stop playing chess because I felt like I had plateaued. But I just kept playing and practicing.

I’ll leave you with one of my favorite comics…

A comic about practice

Swimming is hard

A happy man riding a bike during a triathlon
(Not me.)

I completed a sprint triathlon yesterday morning with my best friend.

A quarter-mile swim. A 12-mile bike. Then a 5k run.

I didn’t prepare for it nearly as much as I should have. Prior to the event, I only swam three times and ran two. Not ideal.

The swim was the toughest part by far. My arms were exhausted during the last few laps. Once I got out of the pool, it felt like I won the entire event…despite being like 200 people behind.

We went into the pool one by one, swimming through each lane down and back, then under the rope and into the next lane. We went in based on our swim times. Naturally, I went in with the last group because I assumed I would need to take a few breaks. I made friends in line and we bonded over our lack of ability.

My buddy went in way ahead of me….He had prepared properly. I got into the pool 15 minutes after he got out. Our plan to complete the triathlon together went out the window.

I was feeling insecure coming in because of my lack of training. I feared being surrounded by a bunch of super-athletes judging me for not taking this as seriously as I should’ve. But I learned something powerful yesterday.

There were folks of all kinds of shapes, sizes, ages, and capabilities competing. Here’s the lesson I gathered from seeing all these wonderful people do their thang:

There will always be a shit ton of people who are way better than we are at something. There will always be a shit ton of people who are way worse than we are at that same thing. It doesn’t make sense for us to compare ourselves to either group.

We should learn from and be inspired by those ahead of us and help and teach those behind us. We need only compare ourselves to who we were in the past. Am I better than I was last month? Last week? Yesterday?

When I was in line for the swim, I met an 82-year old who has done a ton of these events. I’ll leave you the advice he left me.

If you’re not having fun, you might as well stay home.

82-year old badass

First day back

The past month has been the best month I’ve ever had financially. It’s also been the worst month I’ve had mentally in 2021.

I’ve felt unorganized, my habits have slipped, and I’ve just been uncharacteristically not taking care of myself as well as I tend to.

But this week, I feel like myself again. I’ve had several ‘first day back’s. What the hell does that mean? (And is that grammatically correct? Probably not.)

Well, when we step away from something—a habit or routine—coming back to it, getting back on the horse, is always uncomfortable and full of Resistance.

When I skip the gym for a week, my first day back is always a sluggish, difficult workout. The same is true for my morning routine, reading, running, jiujitsu, chess, and any other activity that’s important to me.

The problem many of us face on our first day back? We forget that there’s something beautiful on the other side of Resistance. Better skills. More confidence. Improved health.

The crazy thing is that we once knew what these things felt like, but now they feel like distant memories.

When I was in high school, I could dribble and juggle a soccer ball with ease. I could shoot on goal for hours and place the ball where I wanted at times. Now, when I shoot a soccer ball almost a decade later, I have no idea where the ball will go. I’ve lost my touch.

There was a thing I once knew but have lost because I’m out of practice. Now, I’m not saying I’m going to start training to be a soccer player again…but if I truly wanted to, I could get it all back.

I’d just have to show up on my first day back, deal with the fact that I have to earn back my skills and flow, and keep practicing.

Nothing’s wrong

One plus one equals three
A real photo of my senior thesis.

I got coached by a friend yesterday. I came into the session with the past two weeks containing more stress and anxiety than I’ve felt in years. Here’s what happened.

It went well. She’s a great coach. But often times we go into a coaching session thinking we’ll leave with total relief and clarity. We believe if we come in with negative emotions, we’ll talk out our feelings and reach the insight that we don’t need to feel them at all.

But that’s not always true.

When she asked what was going on, I told her that in the past two weeks:

• my biggest possible client pulled out
• I have a big presentation coming up, and
• I’ve been falling off with my habits

Talking this shit out is always powerful. Talking it out with a coach who knows what she’s doing is always 50 times more powerful. These were my three biggest takeaways:

1) Nothing’s wrong.

Feeling discomfort—stress, anxiety, uncertainty, doubt, fear—is a natural part of the human condition. Why then do alarms go off when we feel these ever-occurring emotions? Our fight or flight response is activated and our bodies tell us in one way or another that something’s wrong.

I had to remind myself that I’m constantly stepping out of my comfort zone, I’m running my own business, I’m new at it. Rather than thinking I don’t need to feel stressed, I came to the realization: Of course I feel stress! And that’s okay. Who wouldn’t?

In other words, nothing’s wrong.

2) Three magic questions.

Be it with my coaching, my hobbies, or anything else I want to pursue in life…I basically boiled down my life purpose into three questions:

• Am I having fun?
• Are other people having fun?
• Is this helpful?

The answers to those three questions tell me whether or not I’m in the right space.

3) I always figure it out.

I have flunked out of college, tried to kill myself, and been in $80,000 worth of debt with no job. And I’m still here…typing out this blog.

We often feel like if we don’t “figure it out” (whatever the hell ‘it’ is), we’ll fall into a black hole. But no, we just wake up the next morning. We adapt. We figure it out.

The important thing is to continue to be vigilant about figuring it out. Ask questions. Get a coach. Share thoughts and feelings.

When we do all of these things consistently, we come to understand that no matter how we’re feeling…nothing’s wrong.