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.

So just start

Last night was my friend’s first day of jiujitsu.

She learned a submission and we rolled for a few minutes. For someone who had never done it before, she did fantastic.

When we slapped hands and began, she said the exact same thing I said when I rolled with my coach for the first time:
“I don’t even know how to start.”

To which he said to me:
“So just start.”

It didn’t matter that she didn’t know. She came. She completed day 1. Next up: day 2, then day 3, and so on.

On my first day, I flopped around like a flounder. Now, I can hold my own against other beginners. The same will be true of her if she continues to show up and practice.

Progression only serves those who continue to show up.

When we don’t know how to start, the only option is…to start.

Cliches are true?

People often say: “It’s cliche but it’s true.”

That’s always confused me. Of course it’s true! That’s why it’s a cliche.

Here are a few that I live my life by:

1) If you want something different, you have to do something different.

In other words, if we’re doing the same thing over and over again, we can’t complain that we’re not getting the results we were hoping for.

For many months, I wanted a thriving coaching business but was unwilling to put myself out there and make it happen. Needless to say, I wasn’t reaching enough potential clients. Only once I gritted through the fear did I really start to make the business sustainable.

2) You get back what you put out into the world.

The happiest and most fulfilling moments of my life are always when I’m the most positive, grateful, and compassionate person I can possibly be.

Shockingly enough, people enjoy being around folks who make them laugh, make them feel listened to and supported, and make them feel inspired to take action.

It’s similar to another cliche:

If you’re not getting what you want in life, help more people.

This has been true for me in business and in my relationships.

3) Do what you love.

I know, barf.

But let me explain.

I hated my full-time job and had to quit and start my own thing to keep my sanity. I’m well-aware that most people have no interest in doing that.

Doing what we love doesn’t mean we have to uproot our careers and fight tooth and nail to make money with our passions. I have a ton of friends who work jobs they don’t necessarily love so they can pay their bills and have the time and money to have fun on their days off.

Doing what we love can mean:

  • Trying more new things
  • Developing our passions
  • Spending more intentional time away from anything to do with work
  • Taking more trips
  • Spending more quality time with loved ones

I love writing this blog, so I cut out a chunk of time each morning where I type away. I say no to most things on weeknights so I can do jiujitsu. I play chess every day. I take one vacation each month. And yes, I work my ass off to continue this career I absolutely love.

It’s cliche…but it’s true.

Think again

A gorilla thinking
Me when reading the book.

I just finished Adam Grant’s newest book Think Again: The Power of Knowing What You Don’t.

In it, Adam masterfully proves the beauty of being willing to rethink one’s stance. People who are eager to change their minds are more successful and fulfilled in what they do.

It got me thinking about where I’ve changed my mind lately. Here are just a few examples…

1) Pop music is awesome.

I used to think pop was garbage and not real music. It took me a while to realize that I only thought that because it felt cool to be part of the “counter culture.” If a song makes us feel something and we enjoy it, that’s enough.

Justin Bieber is my savior.

2) Conservatives are actually humans too. Yes, even that one guy.

I was a card-carrying liberal in college. I only talked politics within my bubble of people I agreed with and was shocked when I met my first Trump supporter in 2016. It was like meeting an alien.

They really exist??…I thought. Needless to say, it was an incredibly unproductive way to approach another human being.

I can still give 3-hour rants about the Trump presidency…but once I left school and began listening and exposing myself to more conservative views, I realized that conservatives were not the racist, apathetic, and heartless creatures I once thought they were.

Turns out they’re also made of bones and organs and they have the same rights as I have. What a concept.

3) I don’t have to read anything I don’t want to read.

This might sound simple to most. But I love reading and for years I assumed I had to read all the classics.

After trudging through several “must-reads before you die,” I had to come to grips with the fact that when it comes to reading…I’m a basic bitch.

I need action. I need easy-to-read. I don’t give a shit about challenging myself with dense or complicated texts. Give me teenage wizards please.

It was a relief when I let go of this invisible pressure to read books I didn’t like.

Conclusion

I highly recommend Think Again. It was a lovely and informative read.

The best question to ask ourselves or someone we’re arguing with is: What evidence would change your mind?

If the answer is “nothing,” then the conversation is a dead end.

What have you rethought recently?

Let go of (some of) your dreams

Darts in a dart board

In the self-improvement world, saying something like that is sacrilegious. But let me explain what I mean with a story.

In the past year, I’ve become obsessed with chess. Yes, mostly inspired by watching Queen’s Gambit. But I play every day and will be entering a tournament soon.

I’ve had it in my head that I want to become an International Master. To the layman, this means being in the 98th percentile of chess players. Players at this level and above study for hours in a day. They enter professional tournaments. They read all the best chess books.

This would be me, I confirmed.

But over the last few months, that’s panned out to be much harder than I anticipated.

I would set time aside to study and build my chess skills, but if something else came up, that allotted time would be the first to go. When I would sit down to work through a dense practice book, the Resistance would be so high that I would quit and just play matches online. My chest would fill with anxiety when I would be practicing my endgames instead of working on my business or anything else to make money. One of my favorite hobbies was becoming a guilt-inducing chore.

It took a while to realize what I had to do…I had to give up on my dream of becoming a world-class chess player.

This statement sounds more dramatic than it actually is. Let me explain.

I did not, and will not, quit chess. What I did quit was the mentality of invisible pressure I put on myself to reach some sort of benchmark.

Once I did that, there was a wave of relief. Since dropping the dream, I’ve actually been studying and practicing chess more—not because I have to, but because I want to.

In a session yesterday, a client wisely said, “Going to the gym doesn’t mean you have to be Arnold Schwarzenegger. Playing on a wreck team doesn’t mean you have to make it to the NFL. Doing an open mic night doesn’t mean you have to be Bill Burr.”

We can simply do things because we enjoy them. We don’t always need a profound reason or purpose.

When I couldn’t study chess at the level of Master, I had to ask myself, Do I actually want this?

No. I just liked the idea of reaching that level. But I hated what it took to get there. And guess what…

That’s okay.

Maybe I’ll never get there. Maybe I will. Regardless, there’s zero pressure on my shoulders and that will let me have fun playing and studying the game I love.

What Justin Bieber taught me

A crowded concert

Until a few years ago, I was certain I hated The Biebs.

My reasons:

• He probably doesn’t write his own music

• Pop lyrics are basic and lack depth

• His stupid face

One day, I was listening to the Skrillex and Diplo song Where Are Ü Now, and I asked my buddy, “Do you know who’s singing?”

He looked at my blankly and retorted, “Are you joking? It’s Justin Bieber.”

My universe turned upside down. Everything I thought was true and real turned out to be a mirage. My very being turned to ash and I had no idea who I was…

Joking aside, I was struck. How could this person I despised make me feel such joy and raw emotion with his simple lyrics and angelic voice?

That’s when I realized my hatred for the young pop singer had nothing to do with him. I was just being a jealous twat.

He had more money and women at age 18 than I’ll ever see in my lifetime. All he had to do was sing a simple song and millions (if not billions) of people would listen and love it.

I was humbled when I realized I had been singing along with JB for months without knowing it was him on the track. It sounds ridiculous but that was the moment I thought, Maybe pop music doesn’t have to meet my expectations. Maybe music is just any collection of sounds that people find enjoyable.

Thank you, Justin (we’re on a first name basis), for enlightening me…and serenading me.

Lessons:

• It doesn’t really make sense to hate someone for their success—they’ll still do what they do, and we’ll just be salty about it.

• Just because we dislike a certain kind of music or entertainment doesn’t mean its bullshit (e.g. For the life of me, I don’t understand how most TikToks are good, yet they have millions of likes so fuck me I guess).

• When we have powerful feelings against another person, it’s important to check in with ourselves and ask why.

Car engines and shitty clients

Gears spinning

Yesterday, my coaching friend was venting to me about a shitty prospective client experience. Also…my car died. The engine completely gassed out. What a day.

With my friend and her possible client, they had made an agreement and when she called to set up the first payment, she discovered that this prospective client blocked her on Messenger and was ducking all her calls.

She asked me what I thought.

How I felt about that situation is exactly how I feel about my car dying:

Naturally frustrated…but empowered.

Shitty, wildly inconvenient, and aggravating circumstances are guaranteed in our lives. Meaning, we have absolutely zero control over when they will occur (the definition of inconvenient).

What we do have control over, however, is how we handle and what we learn from these events.

She will have more frustrating ordeals with clients. I will have more car troubles.

But now, we’ll both be better equipped to take action and respond with cooler emotions under the stress.

Now she knows how to reach out with love and respectfully call a person out. Now I know how to simultaneously schedule a car tow and mechanic appointment.

Don’t wish things were easier. Wish you were better.

Jim Rohn

10 Saturday morning tips

A cup of coffee on a heart of coffee beans

1) Whether you’re working on a project or watching Netflix, leave your phone in the other room and on airplane mode. Do what you’re doing and enjoy it.

2) It’s much better to say, “I can’t believe I did…” instead of “I always thought about doing…” Just do whatever that thing is. Worst case: you have a great story or experience to share.

3) It may feel cool to reject exercise and fitness. But what’s really cool is being able to do something athletic and not be out of breath.

4) Train yourself to meet people where they are, not where you want them to be. We have absolutely zero control over whether or not someone changes. We have total control over how kind and compassionate we are to them.

5) Make amends. Even if you were never at fault, apologizing and getting closure is so much better for the soul than living with resentment.

6) Never judge another person’s music taste. We like what we like and if it makes us feel something, that’s enough.

7) A conversation can easily be made more vibrant by asking Why or How questions.

8) Ask someone, “What would you love to be working on right now?” They almost always have an answer and you learn about their aspirations.

9) Write more. Even if it’s once a month. Writing makes you a better speaker and thinker.

10) If you haven’t ‘failed’ several times in the last six months, then you’re not challenging yourself enough. Do more difficult things, fail at them, and learn.

Getting choked out five times in five minutes

In the past month, I’ve experienced an increase in skill in Brazilian Jiujitsu. As a white belt, these confidence boosts are incredibly motivating.

Few feelings are better than the feeling of improvement. I feel more capable of helping and teaching newer students. Certain submissions and defenses are becoming more automatic. I was feeling high.

Then yesterday, I rolled against a purple belt in front of our coach. Naturally, he wanted to show his stuff…so he absolutely destroyed me.

He may as well have been wrestling a toddler.

All of the ego boosts I’ve felt in the past month turned to ash during those five minutes. But as horrible as it was, it was a truly beautiful experience.

Why? Because of the useful reminders which came from it:

1) Be proud of your improvements, but know that the work is never done.

2) There will always, always, always be people who are much better than you.

3) Everyone has something to gain by (respectfully) getting their ass beat.

How to get people to read your stuff

A man playing basketball

Here are all the things I’m proud of at the moment:

• The strength of my relationships
• My fitness
• My coaching business
• The fact that I know at least basic martial arts skills
• My intermediate chess abililites
• This blog
• My ability to listen to, connect with, and coach other human beings

What do they all have in common?

They’ve taken a fuck-ton of time (in metric units).

The cliche goes:

“It’s only taken me ten years to become an over-night success.”

Perhaps there are freaks of nature who are naturally good at the things they do. Good for them. But for the other 99% of us, getting great at the things we care about will take countless repetitions.

I’ve been writing this blog every day since October 2019. Those first pieces make me cringe. I had no idea how to string ideas together and I used big words to sound more academic. And for months, each blog was averaging two readers: myself and my super supportive friend. (Thanks Grace!)

Now, there are hundreds of folks tuning in each week and I couldn’t be more grateful. But that hasn’t happened because I’ve found the perfect way to market my stuff or because I’ve shoved it in the faces of enough people.

It’s like that because I’ve sat down each morning and typed out my thoughts. Eventually, I got a little better at writing. My average of two readers went up to three. Then four. And so on…

I’m always skeptical when I see ads like, “Get 100x MORE followers in ONE month!!”

Fuck off.

Maybe methods like that exist, maybe they don’t. I personally have zero interest.

The only thing I care about is consistently showing up to do the work.

This leads to improvement, which leads to higher quality, which leads to more value, which leads to more people interested, which leads to improvement, and on and on it goes…..

Having difficult conversations

A man and woman talking to each other at a picnic table

A person’s success in life can usually be measured by the number of uncomfortable conversations he or she is willing to have.

Tim Ferriss

I had one yesterday morning.

After months of patiently figuring out what I wanted to say and when I wanted to say it, I called one of my best friends.

The goal was to lovingly and respectfully tell him that I didn’t want to be the only one putting in effort in our friendship anymore. In so many words, I said, “I know you love me and care about this relationship, I just wish you would show it.”

As expected, he took it incredibly well. He apologized immediately and declared he could easily make a change.

I felt so grateful. One, because I have a friend I can have open, honest, and productive conversations with. But two, because one of my strengths is initiating possibly difficult conversations.

Not all of my uncomfortable phone calls have been successful, though.

There’s no guarantee that the other person won’t get insulted or defensive. The only things within our control are our energy, our intentions, and how well we listen.

All easier said than done.

Here’s a simple checklist I use before preparing for a difficult conversation:

1) Do I care about this person?

2) Will having this conversation benefit both of us in the long run?

Example: Ending a relationship you don’t feel invested in—hurting someone in the short term, but saving them even worse heartache in the long term.

3) If they were to handle this horribly (this meaning my open and honest thoughts and feelings), is this someone I want in my life anyway?


I’ve had a number of difficult conversations over the past few years—most received well, some received poorly.

Here’s what I’ve learned…

Firstly, people are surprisingly willing to have deep and uncomfortable conversations…but most people are hesitant to initiate them. In other words, they want to resolve the tension, they’re just waiting on us to make the first move.

My advice: Get good at making the first move.

It takes practice, but it’s a crazy rewarding and useful skill to improve.

And finally, as we improve this skill of starting necessary conversations, we improve as people.

We begin to get clearer on what we value and what we don’t. We also get better at fighting for those values.

What do you value? When’s the last time you had a difficult conversation about it?

Untraining

A mother and her daughter doing yoga

Two of the hardest things I’ve ever done have been:

• getting myself to stop saying “like” as a filler word, and

• getting out of the habit of talking shit about people.

The first step for both was to practice mindfulness and simply acknowledge when I was doing them.

I would start and stop thousands of sentences because I noticed I would automatically use “like” four times in four seconds.

I would also have to pause in conversation because I realized my friends and I were naturally complaining about another person behind their back or insulting them for laughs.

We can train ourselves out of habits that aren’t serving us. What’s more, we can replace them with ones that do.

One of my strengths is my ability to speak and articulate my thoughts. Not saying “like” every other word has helped with that tremendously.

As far as talking shit about people when they’re not around, it’s poisonous. It creates this tendency to look for the bad in people. Plus, it chips away at the trust in relationships.

If you have a friend who talks shit about everybody when they’re not around, what makes you think they don’t do the same thing to you?

When I was trying to untrain myself out of this habit a few years ago, I would force myself to add to the conversation something I respected about the person in question. This can feel unnatural at first, but what I found was that no matter how I felt about someone, there was always at least one thing about them I could praise.

Slowly but surely, I felt myself seeing people in a much more positive and appreciative light.

There’s a lovely piece of advice from Kevin Kelly:

“Compliment people behind their back. It’ll come back to you.”

What would you love to untrain out of your life? What would that take?

What I want to be when I grow up

A mother holding her daughter in a corn field

Here are all the things I’ve ever wanted to be:

• astronaut
• teacher
• rescue swimmer (shoutout Aston Kutcher)
• boxer
• running back at the Naval Academy (lol)
• kicker for a D1 school
• guitarist of a punk rock band (“Where are you?”)
• pro soccer player
• psychologist
• business owner (#entrepreneur)
• music producer
• German translator
• drummer
• sailor
• actor
• father (ladies)
• famous podcaster
• famous YouTuber
• blogger
• web designer
• life coach
• International Master in chess
• purple belt in jiujitsu

I look back at many of these and smile.

The reality is that most of the things we’ve ever dreamed about being or doing in life won’t come to fruition. NOT because we don’t have what it takes, but because we only have so much time and energy to expend in one lifetime.

For many of these, I liked the idea more than doing the actual work it took to make it a reality.

I enjoyed learning how to keep a beat on the drums, but in order to become great, I would’ve needed to practice all the time. Since I had no drum set, no money to pay for lessons, and had a full course load in college…becoming a drummer at that time didn’t feel like the right move.

And there’s the main point:

If the Resistance of the thing outweighs the value we get from it, it’s okay to strategically quit.

We’re not failures for cutting off the energy we’re putting into something. By saying no to one thing, we’re saying yes to something else.

Last year, I tried to do a daily vlog—posting a video of my life and thoughts every single day for four months…

I made it two months before I completely burned out. It became a chore I dreaded; not a fun and challenging creative pursuit.

So I quit.

I said no to a thing I set out to do. But in turn, I said yes to giving more time and mental energy to building my business, making it one of the best decisions I’ve ever made.

There’s a stigma against jumping around from hobby to hobby. People say, “I don’t really know what I’m passionate about. I can never really stick to one thing.”

Who said we have to?

Why can’t we just do what feels exciting and challenging at the moment?

If we do that, two things will happen:

1) We get to experience a bunch of cool shit by trying new things, and

2) We up our chances of finding something we’re willing to keep putting time and effort into.

Learning to swim

A pig swimming
I’m the pig.

This June, my best buddy and I are doing a triathlon.

I’m super confident when it comes to the biking and running portions…but I have no idea how to swim even one lap without having to stop to rest.

So I did what any sensible person would do: I recruited a friend for help—she was a D1 swimmer and has 14 years of experience competing and teaching.

I felt bad for adding another commitment on her plate, but she got even more excited than me. (As I said in my article about exchanging value with friends, people usually love sharing their skills with others.)

Yesterday was Day 1. She arrived with training equipment and a set of drills to improve my technique and stamina.

I thought swimming correctly would be incredibly difficult…

And it was.

It was one of the hardest fucking things I’ve ever tried to do.

She showed me how to properly align my shoulders, chest, and hips in the water. I would watch her and swimmers in nearby lanes swim down and back with ease. It all made sense to me.

Then I would push off and try it all myself and after swallowing a liter of water I’d have to stop about halfway to catch my breath. I’d come up laughing and shaking my head. It looks so easy, I thought.

I kept reminding the both of us that this would take practice. While slightly discouraging, I knew I wouldn’t become amazing at it immediately.

“This is why we’re here,” I repeated to myself.

She was patient and supportive and slowly but surely, I could feel slight improvements. I was able to swim further and further without stopping. By the end of our hour and a half time slot, I could swim from one end to the other without taking a break.

In the grand scheme of things, that’s not a big deal. But compared to my first attempted lap, I felt like a totally new person.

Day 1 was a success. It was fun. And it was my first step to being prepared for this triathlon.

The major lessons:

• You don’t need natural ability to improve in something.

• Just focus on getting 1% better right now.

• Ask people for help; they’d probably love to take part.

I’m not a natural

At a recent dinner, I heard one of my least favorite compliments.

When discussing my coaching business and my podcast, someone claimed, “He’s a natural.”

They were trying to show support and truly meant well, but I’d like to dissect that claim a bit.

Though it’s not the intention, using the word “natural” tends to ignore the countless hours of practice, anxiety, and discomfort a person must go through.

You would never call Tom Brady a natural. He’s been playing football almost every day since he was a child. Along the way, he’s been intercepted, sacked, and doubted tremendously by others and by himself.

When people tell me…

• I’m a natural at podcasting, they haven’t heard my first podcasts where I couldn’t string a single idea together.

• I’m a natural at coaching, they haven’t seen all the hours I put in each week to be a better coach and business owner.

• I’m a natural at living a disciplined life, they haven’t seen my first 23 years of being a true mess—failing out of college, accruing massive debt, and trying to end my life.

99.9% of people aren’t natural at anything. This shit takes work.

You never know what’s going on behind the scenes. The next time you see a master, don’t think, They’re really good at this; instead think, They must’ve been practicing this for a long time.

2 stripes

Last night, I got my first two stripes on my Brazilian jiu jitsu belt.

This is my first ever milestone in the sport. It tells others, “I’m still a newbie, but it’s not my first day.”

I remember in the first three months of starting, I literally thought to myself, I’ll never get better at this.

It’ll be so fun to think back to that thought when I earn my blue belt, purple belt, and so on…

The lesson:

If you feel like you can’t get better at something, practice it every single week for a year and see what happens.

Lessons from Denver

The Rocky Mountains

As always happens, the incredible vacation I’ve been enjoying this week is suddenly coming to a close.

Tomorrow in the early morning, I hop on a plane back to Maryland.

Here’s a short list of my favorite things I’ve done this week in Denver as well as the lessons from them:

1) Spending every day with some of my closest friends.

Friends are meant to spend quality time with. We’re social creatures and the relationships in our lives shape who we are and what we’re capable of.

Yesterday was my best buddy’s birthday. We all spent the day at the biggest park I’ve ever seen, drank spiked Kombucha, and played spike ball. (Wow, so much spike.)

Visit your friends. Invest time and money into the people you love. It pays dividends as the years go by. I’ll remember that day at the park forever.

2) Playing chess every day and going rock climbing.

There will always be a part of me that loves to party: staying up late, drinking, experimenting with drugs…

But at the ripe age of 27, I find I don’t have time anymore for relationships where that’s all we do.

It’s important to find friends you can do challenging things with, have beautiful conversations with, and inspire each other to learn and take action.

I brought my buddy into the world of chess. It excites me to see him beat his other friend with the lessons and practice we’ve shared. It also excites me to show him how much I improve at rock climbing since he and his partner brought me into that world.

3) Waking up to the view of Denver and the Rocky Mountains.

From my friends’ high rise apartment, I can look out right now and see the entire Denver skyline, Red Rocks amphitheater, and three enormous snowcapped mountains.

I’ve never seen so many dogs, Teslas, and open spaces for humans and dogs to roam around…in one place.

It’s important to go exploring. It’s always a lovely learning experience when you get out of your little bubble and meet other humans in their bubbles.

Getting out of my bubble for a week has been well worth any amount of time or money I put into this excursion.

In short: Visit your friends, find friends you can do challenging things with, and get a dog…or a Tesla.

Learning to climb

Someone rock climbing up a mountain

Yesterday, my friends took me to their local rock climbing gym here in Denver.

I’m deathly afraid of heights. As in: when I look down and see nothing between the ground and my feet, I lose physical control of my body.

It was nerve-wracking and exhilarating watching my friends climb up the 50-foot wall, seemingly with ease.

Naturally, I started small. Just some low-level bouldering.

It was challenging, exhausting, and exciting. I would slip and fall off close to the top of my little 12-foot wall and my competitive nature wanted to jump right back on it and try again.

It was a humbling reminder:

With anything you want to do in life, you have to start on day 1.

Most people are afraid of the discomfort of the early days of improvement.

You could embarrass yourself. Everyone else is an expert and you have no clue. You don’t belong here.

But that’s all nonsense.

Anyone who’s better than you at anything…they started on day 1. The only difference is that now they’re on like day 1149 and you haven’t started yet.

So if you want to improve, start. Then do it more. Do it a lot. Get really fucking good at it.

Eventually, someone will look at you and think, I could never do that.

Then you’ll gently remind them that you were there too once.

One day, I’ll climb that 50-foot wall and talk about how I used to be terrified of heights.

Uncomfortable leadership

Soldiers saluting the American flag

The skill I’m currently working on improving is the skill of leadership.

It could go by other names, but in general what I mean is:

Setting standards and limitations and sticking to them—at the risk of making myself or others uncomfortable.

This includes:

• Calling someone out for being late to a call.
• Telling someone I’m disappointed in them for not following through with a commitment.
• Being offered money and saying ‘no’ to a prospective client I don’t see as the right fit.
• Voicing frustrations to close friends, colleagues, or even acquaintances.
• Telling a friend I can’t or don’t want to hang out, without giving a long-winded explanation.

Putting some of these into practice has made my heart pound and my face hot with nerves.

It’s scary to risk tension with another human being. But so long as it comes from a place of love and respect, and not superiority, it’s absolutely necessary.

But again, this is a skill.

It’s an art and a science.

I’ve heard people try to be a leader when they were really just being condescending and belittling. That’s not effective.

What is effective is telling someone with your words or your actions:

I love and support you completely. Here’s what you can expect from me. And here’s what I am expecting of you.

Last month, I gave a client a challenge to create a step-by-step system for the business he wanted to start. Two sessions in a row, he didn’t do it.

As promised, I told him I was disappointed. Not because I am the big bad boss who gave him homework…but because he was neglecting actions to better his life and do what he really wanted. I said, “This is for you man, not for me. When this happens, it makes me feel like you’re not taking what we’re doing here seriously.”

That was that and we moved on. A week later, when we next saw each other, he looked over at me at some point and said, “Thank you for laying in to me and calling me out. It’s exactly what I needed to hear.”

I can’t promise every situation will be received so well. Again, this is an art and it will take practice setting your own standards and maintaining them.

People will get defensive. Some will fight back.

But so long as you are coming from a place that’s looking out for everyone’s best interests, trust that you’re not being an asshole.

You’re being a leader.

A person’s success in life can be measured by the number of uncomfortable conversations he or she is willing to have.

Tim Ferriss

How to win no matter what

I like to set up systems where no matter what, I win.

In my coaching system, for example, my goal is to have as many fun and fruitful conversations as possible. It has nothing to do with closing a certain amount of clients or making a specific amount of money. Ironically, that stuff often happens naturally when I just focus on bringing a ton of value to the conversations I’m having.

I reach out to a ton of people, and most don’t reply, which is totally normal and okay. But when someone does reply, even if they’re not interested in any sort of coaching experience, I get to catch up with someone from my past or meet someone new.

Even if they don’t turn into a paying client, I still win. I win when I have a conversation and enjoy it.

How can you turn a loss into a win? By changing the definition of winning.

I love chess and Brazilian Jiujitsu. In both, the only way to improve is to play (and lose) a lot. Having a competitive nature is healthy, but if you get pissed every time you get checkmated or tapped out, you’ll never become a grandmaster or a black belt.

The subtext here is that every time you make a mistake or suffer a loss, it opens the door for you to find lessons and make improvements.

I watched a YouTube video about how to defend an ankle lock in jiujitsu. Then, last year, a guy got me in an ankle lock, didn’t really know what he was doing, and yanked on my foot. I popped several tendons and was out for a month.

While that video was great, the experience will stay with me forever. I haven’t been caught in an ankle lock since. I’ve prioritized the defense so I never have to go through that again.

You can read the best book or watch the best video on what you want to improve…and you should!

But learning on the job is the only real way for you to track where you are on your journey.

Dive in. Make mistakes. Learn. Repeat.

One skill to rule them all

A keystone skill is a skill which can be used to enhance multiple areas of your life.

One of the most important keystone skills is that of conversation.

If you are really good at listening to another person, displaying curiosity and helpfulness, and communicating effectively…you will be a force to be reckoned with.

Since these are all skills, that means they can be practiced and improved. Doing so is well worth your time.

Why diets don’t work

Because they typically require that you overload yourself with a bunch of new rules and habits.

Now, if you’ve read any of my stuff in the past, you know I love rules and habits. They are the path toward a healthy, fulfilling, and ultimately free life.

But they need to be learned and adapted slowly, progressively.

If the 95% of failed New Years resolutions teaches us anything, it’s that going balls to the wall with good decisions isn’t enough. Those decisions have to be engrained in your day to day…set in stone.

When something is a habit, it’s easier to simply do that thing than it is to think about doing it. It feels like it does itself.

Making extreme and immediate changes to your routines may bring you success in the short term, but there’s a reason every single winner of The Biggest Loser has gained all (usually more) of that weight back within two years.

Overloading strong habits will inevitably lead to burnout and a sense of failure. Surprisingly, this doesn’t lead to lasting change.

I’ve had many clients feel pumped up after a coaching session and do this. At the end, when we come up with their Next Actions, they get antsy.

• “I’m gonna go to bed before 11am each night.”
• “I’m gonna exercise every morning.”
• “I’m gonna read at least 20 pages every day.”
• “I’m gonna meditate every morning for 30 minutes.”

Every single one of these actions is beautiful and would certainly be powerful if applied to one’s life. But going from zero to all of these is impossible to maintain.

Naturally, they come back and tell me in the following session that they fell off with their Next Actions, usually with a tone of failure.

But that’s not a failure in execution; it’s a failure in planning.

It sounds boring as hell, but the only true way to build strong habits is to ever so slowly integrate them into your life.

I have strong exercise habits; it took me three years.

I have strong productivity habits; it took me nine years.

I have strong relationship habits; it took me 27 years.

The things that will sustainably change your life will take time. That sucks to hear, but it’s the only way.

From strangers to family

Carlos Catania Brazilian Jiu Jitsu

Last night was my first day back to the jiujitsu gym in four months.

I took time off because I had a bunch of family events for the holidays and trips and flights I didn’t want to miss out on. I didn’t want to increase my chances of getting COVID.

Spoiler alert: I got it anyway.

There are a number of life lessons I could write about (and have written about) from my short time doing jiujitsu. But today, I want to talk about something you can apply to any type of practice or community.

Being a n00b

Last winter, I remember hopping into class for the first time. It was fucking terrifying.

The thing was, I wasn’t really scared to get my ass beat—though that would happen each and every night. I was aware that that was simply part of the process going in.

No, what intimidated me was jumping into something with a group of people who already knew each other for years.

My thoughts: They are a family. I am an outsider.

I felt the same way when I started acting in the theatre program in college. They are a family. I am an outsider.

It’s tough when everyone:

• tells stories you were never a part of
• knows everyone’s names and facts about them
• is constantly talking and laughing with everyone else besides you

How to change things

To be clear, by no means was I ever excluded or belittled at my gym. There’s just a noticeable difference between feeling truly close with the people you practice with and not.

The lesson here: That closeness doesn’t happen overnight.

It’s analogous to building trust with someone. It’s an organic and slow process.

Slowly but surely, I would talk more, tell more jokes, and get enough time in with my gym peoples to tell stories of my own.

One day, I was talking to a classmate before class, and I said something like, “People should feel lucky to come in and join your guys’ gym.”

She raised an eyebrow and unironically retorted, “You mean, join our gym.”

Holy fuck. I’m in.

Conclusion

I got lucky to become closer with an amazing group of people. Not every group of coworkers, athletes, or neighbors will come together in such a way and that’s okay.

The point here is: When you enter a new community, the feeling of being the outsider can be daunting and often discouraging.

You may think, They already have their group. They don’t need me.

But if you keep showing up, keep listening, keep caring, and the group is a good bunch…then after a bit of patience and consistency, you’ll find you have another family.

My old thoughts: They are a family. I am an outsider.

My thoughts now: We are a family. Outsiders welcome.

Use people’s names

A smiling bartender

Yesterday, I went on an errand run in the morning.

I got my teeth cleaned at the dentist and my car tuned up at the shop.

Dale Carnegie’s self-help classic, How to Wins Friends and Influence People, is quite archaic in its language (consistently referring to women as secretaries, etc.). But it’s a classic because of its timeless tips on how to conduct yourself in social and professional settings to more easily connect with others.

My favorite tip is probably the simplest:

Use people’s names.

You don’t have to be Donald Trump to love the sound of your own name. Everyone does.

Whether its your nurse, your server, or your mechanic…using someone’s name does several things:

1) It gets their attention.

When the two guys were walking around and fixing up my car, I used their names after reading their name tags. Before then, they were asking me routine questions without making much eye-contact. When I used their names, they would basically stop what they were doing and look directly at me.

When I was a server, whenever people would use my name (if they weren’t an asshole), I felt like I wanted to do more for them.

“Hey Dillan?” will always get more attention than “Excuse me sir?”

2) It shows respect.

When you use a stranger’s name, they will very often look pleasantly surprised—as if no one has ever called them by their name before.

This is probably because for most of us, we’ll meet someone, learn their name, and forget it completely after one or two seconds.

That’s because we don’t genuinely care to learn their name in the first place. But if I told you I’d give you $100,000 to go to the grocery store, meet 20 people, and remember all their names…you would do it effortlessly.

Actually using someone’s name—especially right after learning it—is a surefire way to remember it quickly.

Just don’t overdo it. I got pitched by a salesman last week and a typical sentence from him sounded like:

“Dillan, that’s awesome. And you know what’s so awesome about that Dillan…is Dillan, when you told me that…”

Dude, I get it. You know my name.

It’s obvious when people are doing it to appear respectful versus when they genuinely want to treat you like a human being.

Which brings me to the last benefit.

3) It reminds everyone that we’re all just a bunch of humans.

It’s very easy to go about your day and see others as nameless, faceless extras in the movie of your life.

But she’s not Dentist 1 and he’s not Mechanic 3.

Those are humans who have families, hobbies, and anxieties. Treat them as so.

It’s a great habit to get into. And you never know…you could make someone’s day.

The 5-step formula for developing a passion

A buddy and I were discussing our passions yesterday. Music and coding for him. Coaching and chess for me.

To mirror Cal Newport’s thesis in So Good They Can’t Ignore You, we both agreed that we didn’t begin to feel passionate until we got really good at what we were doing.

Many people think they have to have innate talent or aptitude for something for it to be their ‘thing.’ That’s nonsense.

My friend told me it took him two years to develop a love for programming. It was supposed to be a means to an end for him. He got good enough to land a well-paying job to support himself and his interests. Once he got good enough to quickly put pieces together and solve interesting problems, it became more than just a 9 to 5; it became exciting.

On a smaller scale, I’ve been interested in chess for the past year or so. Within the past month, however, I’ve experienced a serious uptick in my skill level. This has correlated to a spike in my interest. What was once a hobby is now a passion.

I’ve known many people who have sadly stated they are unsure of what they’re passionate about. This is tough, but there is a formula to solve this problem:

1) Try a shit ton of things→

2) Ditch the things that feel like pulling teeth→

3) Practice the thing(s) you like most every week→

4) Get really fucking good at it→

5) Boom. You now have a passion.

It’s not easy and it doesn’t happen quickly, but it is simple.

Keep going.

Never too late

Yesterday, I caught up with an old friend for a few hours. It was lovely.

In the past, she was flakey and non-communicative. This was frustrating.

She told me she was working on it. So I curiously asked her what strategies she was using to work on her communication skills. She looked up at me and said, unironically, “Stuff like this.”

I smiled.

I don’t mean for this to sound condescending, but it’s never too late to improve: skills, relationships, habits.

Seemingly out of the blue, a friend has reappeared in my life. All her own doing.

It’s not too late. It’s never too late.

That one song

Workaholism

Some call it that.

Whenever I spend a decent time away from work, I’m always itching to get back into a productive space.

I’m incredibly grateful for this.

I couldn’t imagine having a job where I’m counting the days until the weekend.

Actually I can….I did this for a few months and I quit.

Whenever I talk to my friends who have full-time jobs they don’t necessarily love, it always feels like I’m shitting on their life choices. That’s not my intention at all.

My stance: It doesn’t have to be your work, but every single person should have an activity or a skill that excites them—that makes them ‘itchy’ when they spend too much time away.

Studies show that people enjoy their jobs more when they spend more time outside of them doing things they love: tennis, writing, playing an instrument.

I recommend that your thing not be something passive like watching Netflix. Movies and shows are lovely and they should be consumed, but it would be much more fulfilling if you had an active practice that was totally your own.

What excites you? What challenges you? What skill do you love improving?

Do it. Do it all the time. Get better at it. Repeat.

The 2 types of fun

Here’s a short article everyone should read.

It’s something I’ve been thinking about as I’ve been sick in my apartment with nothing but time on my hands.

Basically, we define fun as something that is purely pleasurable and enjoyable. But there are actually two types of fun:

Type 1 Fun: Pure fun, untarnished by setbacks

The traditional idea of fun.

These are the things that provide us with dopamine. With smiles and laughs.

For example, when I play a riveting game of chess where I defend well, set up brutal attacks, and win in style…it feels amazing.

Dillan Taylor having fun winning in chess
A well deserved win after a long, tactical game.

When you think about improving in a skill, Type 1 Fun is what gets the spotlight in your mind. It’s the magazine cover. The glamor shot.

It’s fun to imagine yourself as a chess champion, or in great physical shape, or as a phenomenal writer.

But what actually gets you there?

Type 2 Fun: Suffering now; fun after the fact, in retrospect

This is all the ‘behind the scenes’ stuff.

Type 2 Fun is an investment. You sacrifice your comfort now so you can reap the rewards and experience more Type 1 Fun later.

Running sprints does not sound like fun. But it’ll feel great when you finish. You’ll get a runner’s high, be in better shape moving forward, and you’ll feel a sense of accomplishment.

My version of this has been working through chess exercises.

A not so fun chess exercise
The goal is to find the winning combination in your head.

What sucks about these exercises is they can be incredibly boring.

But the worst part about them is that they’re incredibly necessary.

Firstly, they can occasionally be fun. Staring at a puzzle for ten minutes and finally figuring it out is a lovely feeling.

But the point of this Type 2 Fun practice is to set you up for future Type 1 Fun.

You may not notice it in the moment, but it’s almost always boring practice that gives you the skills to play better and improve at what you do.

Playing hours of scales is boring, but those scales are setting you up for more improvisation and soloing, which is fun.

Therefore:

Playing hours of scales = fun

It’s the same with exercise, writing, coding, editing, or any other skill.

Conclusion

Spend more time doing Type 2 Fun. Deliberate practice. Repetitions.

This will bring you much more fun and fulfillment in the long run.

We are all familiar with the life-changing Harry Potter books.

But none of us saw JK Rowling locked in a hotel room banging her head against her keyboard for hours on end.

Because that’s not fun…not yet.