I asked my top readers these 4 questions

Earlier this year, I reached out to my top 10 readers (based on email open rate, clicks, and engagement). I asked these questions:

  1. Why haven’t you unsubscribed from this blog yet?
  2. What have been your favorite pieces and why?
  3. What should I improve?
  4. What would you love to see more of and less of?

I love feedback. Craving it and asking for it is one of the most powerful shortcuts to mindful growth.

My friends and I do annual feedback sessions where we check in with each other. How have we made the other uncomfortable? What impresses us most about the other? Etc.

I’m working on a free ebook to promote to my podcast audience. A buddy and I had a call a few days ago where he shared his screen and tore my first draft apart. I implemented each of his notes last night and it looks 20 times better than the original.

There’s no such thing as perfect. But humbling ourselves and seeking new perspectives is one of the healthiest and most rewarding things we can do for ourselves.

The best writers have editors. The best athletes have coaches. There’s always something to improve. Something we’re not seeing.

That’s why I sent these questions to my most active readers. It’s also why I encourage anyone to email me suggestions. I don’t have to agree with all of them, but I do have to be open to receiving criticism.

Here were the most common threads from the responses I got:

1) Why haven’t you unsubscribed from this blog yet?

  • Many of my friends are long-time subscribers who want to support me and stay up to date with what’s happening in my life.
  • Subscribers enjoy the variety of content: me learning chess, my travels to different countries, and huge life decisions I’ve made.
  • Most of all, readers enjoy hearing stories and experiences they can relate to: insecurities, death, navigating through difficult emotions, etc.

2) What have been your favorite pieces and why?

3) What should I improve?

  • I tend to be vague when referring to evidence while making a point (e.g. “Studies show…”). Moving forward, I’ll be more specific and avoid making sweeping generalizations without providing data to back them up.
  • My content creation career will be a never-ending journey in improving my storytelling skills.

4) What would you love to see more of and less of?

  • More stories, fewer lectures. (Check out my conversation with professional storyteller Diane Callahan—She explains the difference between showing and telling in a story).
  • A few people miss my old newsletter where I would give subscribers four cool pieces of content every Friday: something to watch, read, use, and listen to. So moving forward, I’ll give more links and references to podcasts, books, and videos that get me thinking.

As always, if you have any feedback for me, write it down on a sheet of paper, go outside, and throw it in the sewer because nobody cares.

Kidding. Just send me an email. I read every message.

Hope you like the improvements. New website coming soon.

This book is taking longer than I thought

Woman typing away on a typewriter

I set out to write a book in July 2021. The plan was to interview creators: people who built something cool, shared it with others, and made money doing so.

Since then, I’ve sat down and had conversations with people I’ve looked up to for years. I interviewed the woman who wrote the article that inspired me to run my own online business. I spoke with my favorite YouTuber who’s the reason I love chess. I’ll also be including my chats with my favorite author and my biggest inspiration in the entrepreneurship space.

My harshest lesson: it’s so incredibly easy to not write a book.

If you’re ever looking to procrastinate more, just tell people you’re writing a book. It sounds amazing. Hearing the praise from friends and family about your new venture. Setting up Zoom calls with people you never thought you’d meet. It’s been exciting and wildly rewarding.

But hidden underneath all these rosy scenes is the most boring and painful activity: sitting down and actually writing the damn thing.

Here’s a list of tasks I’ve done instead of fighting the resistance to writing:

  • color code each sublabel in my Gmail accounts
  • buy Christmas gifts in March
  • outline ideas for my next book

One of the most common questions asked when creating something is, “Why is it so hard to do my work?”

While there are hundreds of factors at play, I think the answer is simple: Because when we actually try to do something, it’s possible to fail. Planning is simple. Executing is messy and uncomfortable.

NBA players never miss shots in practice. It’s stunning how accurate they are. Then in games, their percentages go way down. Things are tougher on the main stage when the stakes are higher and everyone’s watching.

For me, sitting here and writing these blogs each week is basically effortless. I get up between 5am-7am, make a cup of coffee, then black out for 45 minutes until I’ve crafted a masterpiece for you all. That’s my basketball practice.

Chipping away at this book feels like game day.

It takes longer to write the same amount of words because I feel like there’s so much more on the line. A mediocre blog will be forgotten in a day. But the difference between an excellent and crappy book could change the trajectory of my career.

Not entirely logical but that’s certainly how it feels.

That’s why people get so caught up in prepping: business plans, roadmaps, and outlines. That stuff is useful to a point, but most people just use them as ways to avoid doing the real work: reaching out to people, building something people can use, getting feedback and iterating on it…

There were periods when I didn’t write anything for months. So I had to create a weekly system that ensured I put at least something down every other day.

Blog writing two mornings a week. Book writing three mornings a week. Even if it’s just 30 minutes of deep work. That absolutely crushes the alternative of zero minutes of deep work, which was my default state for a while.

Anyway, here are my biggest updates to prove writing this book hasn’t just been one big scam…

  1. I’ve finished all my interviews.
  2. I’ve transcribed each interview and completed round 1.
  3. I have a list of every individual chapter I want to write (one to three pages each).
  4. The first draft should be completed in the next two months.
  5. I’ve decided to self-publish and market it with the help of all of you and by partnering with the folks I interviewed.

To those of you who ordered pre-sale copies for half off, sorry for the wait. I promise it’ll be worth it.

This project has been more fun and fulfilling than I ever imagined when I started this journey. I get to WhatsApp with some of my favorite creators and entrepreneurs. I bond with other friends who are in the midst of writing their first books.

It’s funny. The book is called Do The Thing! That’s the simplest advice. It’s also the hardest thing to do.

If you want to order your own copy before it comes out, here’s the link. I’ll sign it and write a personal note to you.

Now please stop distracting me so I can write.

2023 feedback review: my results (part 2)

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

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

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

Biggest positives:

1) I practice a growth mindset.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

  1. life coaching
  2. writing
  3. podcasting

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

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

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

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

3) I’m an active listener.

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

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

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

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

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

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

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

Let me know your thoughts.

The curse of caveats

A woman arguing with her iPhone

I’ve been writing this blog and uploading podcasts since 2019. Since then, I’ve said a lot of things that pissed people off.

Perhaps not as many things as Kanye. But I’ve learned a lot about expressing oneself on the internet.

Back in the day, you had to be an author, politician, or activist to be able to spread your ideas to the masses. Now, you just need wifi. There are obvious pros and cons to this.

On the upside, more people have more freedom to exercise their basic human right to free speech. Individuals can go on social media or build a simple website, type out their thoughts, and criticize their own government if they want. That’s a beautiful thing. There are dozens of countries where this is unthinkable.

On the flip side, any shmuck can log on and build a community around the idea that the earth is flat. Anyone’s aunt can go on Facebook and start a comment war with her political opinions. With more access to ideas comes more energy needed to sift through the shitty and divisive ones.

Every single one of us has easy access to something that only a few people had 20 years ago: an audience.

Social media, algorithms, blogs…The internet is designed to spread ideas that get clicks and keep people on the platforms. What awesome power.

When I started writing this blog, it took months to get any sort of traction. I wanted badly to have a voice and share my philosophies and strategies for living a good life.

But once people started actually tuning in, I watered down my writing.

Since I’m a fairly agreeable person at heart, I tend to avoid rubbing people the wrong way (agreeable: wanting others to be safe and comfortable). That meant I was super hesitant to share any sociopolitical opinions, especially ones I knew my friends would disagree with. I also muzzled my more tough love and hardline approaches to self-improvement.

Even when I did write about these things, I would caveat and qualify every single point I tried to make. I read one of my old blogs a few days ago and counted five justifications.

At the time, I thought this made me a strong thinker and arguer. I believed it would broaden my scope and allow me to reach more people.

But it just made my writing stale and lifeless.

There’s a great quote I try to remind myself when I type these blogs and produce my podcasts: “When you create for everyone, you create for no one.”

Thus is the curse of caveats. If you walk on eggshells to avoid anyone’s disapproval or disagreement, your perspective has no meat to its bones.

Let’s look at two examples.

1) “Cats are terrible pets.”

2) “A lot of people think cats are terrible pets. Obviously, not everybody thinks this. And it must be said that even those who prefer dogs can enjoy petting a cat from time to time. I’m not trying to insult any cat owners. I just want to get to the truth.”

(Genuine caveat: I love cats. It was just an example lol.)

#2 will reach no one. It reads like a boring academic essay and makes no one feel anything. It proves I don’t have any conviction in what I’m saying.

#1 on the other hand is bound to be polarizing. It’s guaranteed to invoke emotion.

Readers who have a cat will likely get pissed and baffled by my making an objective statement from a subjective feeling. Readers who hate cats might bask in the mutual humor of benign hatred.

In summary, I’m looking for one of two possible results. The first is someone reading my stuff and it really resonating. They see their own thoughts and experiences in my words. The second is someone challenging what I say and offering their own perspective.

I’ve had countless emails where people send me one of these two reactions. And I love it every time. It leads to deeper connections and fruitful conversations. I always come away with a clearer picture once I’m forced to think even more about whatever it is I wrote.

That said, I encourage any of you to reply to any of these emails. I respond to all of them.

Almost every topic is nuanced and complex. But that doesn’t mean we have to caveat and qualify every minute point. When someone calls that stuff out, we can just continue to explain our meaning or begin to have our minds changed.

That’s called conversation.

4 questions to avoid repeating mistakes

A table full of writing utensils

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

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

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

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

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

Too much.

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

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

1. What did I intend to accomplish?

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

It’s threefold:

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

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

2. What happened?

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

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

3. Why did it happen that way?

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

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

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

In summary: unrealistic expectations and a lack of organization.

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

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

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

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

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

I think these questions will help.

The simple rule that helps me get work done

A typewriter on a desk

I tend to work on a ton of things at one time.

Studying chess. Building a coaching business. Writing a book. Running this blog. Launching a new YouTube channel and podcast soon (more on that later this week).

Getting distracted can be quite the wrench in my day. So aside from a few of the popular tricks and tips—a Pomodoro timer, starting small, leaving my phone off and in the other room…there’s one rule I follow that makes everything else 10 times easier.

I stole it from Niel Gaiman, the prominent fiction writer.

When he’s writing a new book, he sits down and gives himself two options:

  1. write
  2. do nothing

That’s it. He can’t do anything else.

The freedom to not write removes any guilt associated with not getting work done. And it doesn’t take long until writing becomes less boring than just sitting there doing nothing.

I do the same.

When I’m not doing whatever deep work is needed from me, I’m sitting here daydreaming and talking to myself. Sometimes it lasts 60 seconds. Other times it lasts 20 minutes. But eventually, I always come back to the task at hand.

The impulse to check something is omnipresent. Email. Facebook. YouTube. Facebook again.

But those aren’t one of the options.

The rule must never be broken. Otherwise, it’ll be broken every day. So instead, I sit here and work…or do nothing.

I’ve quit nearly everything I’ve started—Here’s why

I’ve tried my hand at many creative endeavors. I gave up on all of them except for this blog.

Here’s the timeline.

2010, high school: a punk rock band with my friends.
2015, summer: standup comedy.
2016, in college: theatre.
2018, winter: a podcast about people’s passions.
2019, fall: this blog and a YouTube channel about self-improvement.
2020, fall: a daily vlog.
2021, winter: sketch comedy videos

Clybourne Park, 2016.

Aside from acting, which I was deeply passionate about, each of these pursuits ended the same way.
(I’ll tell the story of why I quit theatre in another blog.) The process went like this.

First, I would get inspired by other people whose skills I enjoyed. In high school, it was Blink 182. For standup, it was Louis CK. I started vlogging because of Casey Neistat.

I wanted to be as talented as these guys. I envisioned myself on stage captivating crowds or being recognized on the street by one of my million subscribers.

So I’d start the thing.

I learned every 2000s pop-punk song on guitar I could. I forced myself to sign up for an open mic. I bought a camera and microphone and started recording.

It was always exhilarating. For a week or two.

But each time, reality would quickly settle in. That reality was: If I want to get good at this thing and have other people enjoy it, it’s going to take a ton of time, consistency, and persistence through being mediocre.

Basically, I would suck at something and wouldn’t get the results I wanted fast enough. Then it would rapidly feel more like a chore than a passion project. Once the Resistance grew tall enough, I couldn’t justify continuing to work on it. I’d stop enjoying it or begin dreading it entirely.

The worst part about this cycle was it would make it difficult to trust myself. When I’d feel interested in a new venture, I’d think in the back of my mind, “But how long do you think this will actually last?” Then I’d hesitate to start.

Our Blink 182 cover band setting up, 2011.

So why does this happen?

I mentioned it above briefly, but the answer is quite simple: it’s due to unmet expectations.

We see the thing we want: fame, glory, high-quality entertainment. Then we go for that thing.

But as we start to put our heads down and do the work, we see that the things we wanted are hidden behind countless hours of grinding practice, boring or stressful tasks, and little to no recognition. It’s all the unsexy stuff we never see from those we admire.

When I wanted to be a standup comedian, I wasn’t fantasizing about all the empty clubs I’d bomb in at 2am. I just wanted a Netflix special.

When I started vlogging, I didn’t think about how many hours a day it would take to think of something interesting, film it, and edit it in a fun and captivating way. All I wanted was a following and ad revenue.

If our goals are the end results, we’ll never make it. It’s unsustainable to be driven by money, subscriber count, or viewership. Because when we start, we’re pretty bad at whatever it is we’re doing. So those incentives will naturally take a very long time to experience.

Let’s look at the only thing I’ve stuck with from that list above: this blog.

From day 1, I never cared about how many people were reading it. For the first several months, it was just me and one supportive friend. I still loved it.

Because I cherished the process. There was never a result in mind.

Now, this blog has way more subscribers. So I obviously feel more inclined to make it good and worth reading. But at the end of the day, I just get joy from typing my thoughts out a few times each week.

The first podcast I ever recorded, 2018.

So when we’re thinking about pursuing something new and creative, I’ve learned it’s crucial to ask this simple question: Do I actually want to do this work, or am I just craving the end result?

In other words: Am I okay if no one cares about this for the first year of doing it?

If the answer is no, it might be worth reconsidering.

I sold out and got a Patreon

Voted World’s Okayest Blogger 2022.

(Here’s a short and fun video on the term “sellout.”)

What I’ve done

I don’t actually think I’ve sold out. But I’ve just done something I thought I’d never do: I created a Patreon.

For those who don’t know, Patreon is a service where people can support creators they enjoy—YouTubers, artists, bloggers, etc. Oftentimes, those creators offer bonuses and exclusive content for those who help at different degrees.

This seemed silly to me for the longest time. But then I started interviewing creators for my book.

James and Anthony Deveney took me through their journey of quitting their full-time jobs to run their podcast, Raiders of the Lost Podcast. (If you like movies and television, I highly recommend their show.) They were able to do so because of the level of support their patrons provided.

Eric Rosen, my favorite YouTuber, broke down all of his revenue streams when we spoke. Merch, ad revenue, Twitch subscribers. But in the early days, he said it was mostly from people donating on his streams.

It’s never been easier for one person to reach (dare I say…influence?) a large number of people. Steph Smith made a great point. She said, “Britney Spears was a content creator. She wrote songs and shared them with millions of people. Today, some bro can film himself in his apartment and have a million followers on TikTok.”

I’m not some bro and I don’t have a TikTok. But it’s been wild to type my thoughts out and have a bunch of friends, family, and strangers read them.

And with the popularity of things like podcasts and YouTube, free content has never been more prevalent. It’s expected, actually. Anyone else get triggered when they click on a NY Times article and get asked to pay for a subscription?

I do every time. But then I think, There’s a team behind this…It’s someone’s job to produce this.

Why I did it

To be clear, this blog will always be free.

The site has a simple system:

  1. I live my life
  2. I reflect on all my insights, mistakes, and fears
  3. I write about them here
  4. You either enjoy them or go, “meh.” 🤷🏼‍♂️
  5. Repeat

I don’t see that ever having a price tag. Making a subscription service like Substack doesn’t interest me.

But there is a dream life I’m working toward. It’s pretty simple.

I want to be a full-time writer and coach. I’ve got the coaching thing down. But in the future, I’d like to be publishing a new book every 2-5 years, write 2 or 3 blogs on here each week, and have 5-10 coaching clients. In between would be plenty of time to travel, work on other projects or programs, and do all the non-work things I love (chess, friends/family time, jiujitsu).

With all that said…if any of you get value out of these posts and want to support the blog, you now have an avenue to do so. Only if you really want to. If not, you’re dead to me.

Whoops. I mean, *if not, that’s totally fine! Nothing will change on here.

But for those who do, you’ll get some bonus stuff. Extra blogs, video updates from me, access to a Q&A, monthly Zoom calls, the running draft of my book Do The Thing, and polls for what you’d like me to write about next. I’m even working on setting up an advice column.

Whether they’ve chipped in financially or not, I’m forever indebted to anyone who has taken two minutes to read anything I’ve written. I wasn’t even planning on having ten readers. Now this blog has hundreds. Onward!

If you’d like to become a patron, you can do so here.

Thanks, thanks, and ever thanks. 😎

Unsubscribe from this blog

How this thing began

In November 2019, I lost half of my subscribers in a single day.

That was because I only had two readers and one unsubscribed.

Still, it was devastating. How could one of my friends unfollow my poorly written and unoriginal thoughts on self-improvement?

794 blog posts later, I’ve become at least slightly better at writing—trying to share my stories and insights in a concise manner. People seem to dig it, as we’re now at 417 subscribers (thank you).

But after making the recent decision to email these directly to you, four people, two of which I know personally, have unsubscribed. And I couldn’t be more thrilled about that. Let me explain.

We’re starving for validation in the early days of creating something and sharing it with others. Do I suck? Is this good? Like and subscribe!

The problem is, we do suck. We haven’t found our voice, created any value, or developed enough skill yet. So why would people stick around?

Well, in my experience, it started with an early adopter: my friend Grace. She was so pumped that I was blogging and publishing something. She read every post.

For months, it was just the two of us reading my mediocre blogs on habits and mindset. I was basically just writing things I thought she would enjoy. But every now and then, I’d write about a personal story or an educational topic and other eyeballs would appear.

Slowly but surely, more and more people would visit the site. As I entered new communities, people from different realms would tune in: a new gym, an online coaching community, and past jobs.

For two years, I wrote a new blog every Monday through Saturday. Most of them were terrible. I cringe when I go back and read my old stuff. I was overly confident without any real-world experience to back my ideas up.

But I was getting in the reps. I showed up to practice almost every day. And as a result, I was accidentally becoming a clearer and more effective writer. It was quantity over quality.

I discovered that most people enjoyed it when I shared personal stories from my own life. I used to think that would make me sound self-important and boring. But it turned out that real-world experiences made people feel most connected. So I started telling more stories and giving fewer lectures.

At first I was afraid

Building an audience with the people already in my life: Facebook friends, coaching colleagues, high school acquaintances…It’s been a wildly rewarding thing to pursue.

I love when people comment or email me about their own thoughts or experiences based on something I’ve written about. It feels like a purer form of social media.

But the downside has been a deeper craving for approval. Since I have a personal connection with many of my readers, I have felt a heightened pressure to not upset them.

In the early stages of the blog—before I felt secure in my voice—whenever someone unsubscribed or criticized my ideas in a Facebook comment, it would eat away at me.

Any ounce of disapproval meant I wasn’t cut out for creating content or sharing my opinions. Then I would get twice as gloomy because I would recognize how strongly I needed people to like my work.

Pushing through

After these uncomfortable moments, I’d have to remind myself that I only had 20 subscribers and that it wasn’t even close to the end of the world. As it turns out, I’m still alive. Someone I went to high school with left a frowny face on my Facebook post and it didn’t end my life.

I kept posting and sharing. I continued to sharpen up my writing skills. And more people enjoyed it each month.

I don’t know when “getting over the hump” happens. But there came a time when I had gotten enough validation in the form of subscribers, praise, and my own security. This validation allowed me to simply let go of the fear of pissing people off. It made it easier for me to speak my mind.

It’s like having an incredible group of close friends nearby. With that community secured, it makes it easier to be yourself. But if you were to move to a new city where you knew no one, you might feel less loose with your words and actions. The need for approval would be more present.

That’s how I feel now.

So, when people unsubscribe or message me when they disagree or dislike what I say, I welcome it. I try to use these as opportunities to improve and gather perspectives outside of my own.

If someone finds these posts boring, how can I make my stories more captivating and my insights more relatable or usable? If the emails get annoying, how can I shorten these blogs?

Rejection is always a good thing. It weeds out the people who aren’t the right fit. Dates, clients, subscribers, etc.

Just like I would hate going on a date with a woman who didn’t actually like me, I’d feel awful if someone was subscribed to this blog just to be polite…these emails going unread in their inbox only to be deleted.

I want you to enjoy reading these and get value out of doing so. So if you don’t, I implore you to send me feedback or to unsubscribe!

I’ll be sending out a super short survey soon to learn more about what you guys want to read more of and less of moving forward.

Thanks so much for making it this far. You’ve allowed me to turn this side-project into a pillar of my life. I’m wildly grateful.




One of my besties showed me stickk.com. He used it to learn to draw in 30 days.

Here’s how it works.

You make a commitment. It’s usually an attempt to break a bad habit or build a good one. Examples could be: quitting smoking in 30 days, going to the gym three times a week, or reading every morning.

Then, you link your credit card. And with that, you can pick a charity you love (or hate). If you break your commitment, your card gets charged and that money gets sent to whatever charity you chose.

I started this week.

My commitment: Write any amount of words for my book, every weekday for two months.

If I miss even one day, that week is considered a loss and I’ll send $100 to Trump’s campaign. The same is true for all eight weeks. (Not a political statement. That’s just the organization I chose since I’m not a Trump supporter.) So in the end, I could possibly lose $800.

You can also recruit supporters. Friends and family can track your progress and you can even give them the power to say you didn’t stick to your commitment. (If you want to support me, here‘s the link!)

This is incentive, commitment, and accountability at the highest level.

Try telling me you don’t feel like working out when there’s $1000 at stake. We often feel like we can’t when really we just choose not to.

So many people say they struggle to remember names. It’s just because they don’t truly care to. If I told you I’d give you a million dollars to go remember 20 people’s names at the grocery store, it’d be easy for you. You’d have the incentive.

The problem is, when we choose not to exercise, say, there’s no immediate penalty. It’s just our future selves who suffer. But that’s impossible to grasp in the moment.

If you’re trying to stick to something, try stickk.com. It’s made writing consistently an easy task for me because it truly feels like I don’t have a choice.

What do you want to stick to?

Following my dreams

Dillan and Emma Taylor at an amusement park
Here’s a pic of my little sis and me at an amusement park. It has absolutely nothing to do with this blog.

Where are you?

I’m aware that these blogs have been a bit scattered for the past two weeks. Here are my excuses.

  1. Most of my writing lately has been for my book, which I’ll discuss more today.
  2. While slowly recapping my road trip, it’s becoming harder to remember the sequential details of each day. But fear not, I will finish the story.
  3. I’m building a group for founders/entrepreneurs. In other words, my creative energy has been kind of diluted.
  4. I’ve been actively trying to get off nicotine gum for the last seven days. What started as a stimulant for writing became a physical necessity. I’ve never even smoked a cigarette; who would’ve thought? (I’m also almost entirely off coffee.)

So I’ve fallen off the wagon. This is me getting back on it.

I want to share a few changes I’m making to this blog and give an update on the book.


Many of you subscribe to my once-weekly, then biweekly, now monthly newsletter.

That is no more.

It started as a fun little email I would make for my friends. But in recent months, as I spend more time on money-making projects and things that are reaching way more people, the newsletter has steadily become a chore rather than something I look forward to.

Lynne Tye, a badass entrepreneur I interviewed for my book, told me about the difference between giving up and quitting.

Here’s my rule for quitting: If the Resistance of the thing is greater than the value I get from it, I move on.

That’s what happened with my first podcast Fancy, my YouTube channel, and my daily vlog. I was wildly committed to each of them…until I wasn’t. And creating something out of obligation simply isn’t sustainable. Lack of passion is tough to hide.

So what now?

Starting June 1st, you’ll be able to subscribe to this blog.

There are about 45 of you who regularly check this site to see the latest post. Then when I post some on Facebook, depending on the topic, that brings anywhere from 20 to 700 extra eyes to the page. That system is a bit up in the air and it asks you guys to do most of the work.

So at the start of next month, readers can subscribe and get each blog sent directly to their email. Eventually, you’ll be able to choose the specific categories you want. (e.g. blogs about business, personal stories, writing, dating, habits, etc.)

Stay tuned.

Latest book update

I cried last Friday. Let me explain.

Eric Rosen is my favorite YouTuber. Here’s his channel.

He’s one of the biggest chess content creators in the game. His Twitch channel has 219k+ followers. He has close to 600k YouTuber subscribers. His videos have played an enormous role in my improvement and love for the game of chess.

Dillan Taylor interviewing Eric Rosen

I interviewed him for my book on Friday.

It was the most nervous I’ve ever been to meet someone. I logged into Zoom 20 minutes early. When the clock reached 3pm on the dot and I read the banner, “Eric Rosen is in your Waiting Room,” it genuinely didn’t feel real.

We spoke for an hour and a half and it’s one of my favorite conversations I’ve had to date. He was such an authentically kind and giving person. He took me through his entire journey in making it as a professional content creator—from 0 followers to hundreds of thousands, from tutoring chess to beating top 10 players, from learning how to set up a camera to getting tens of millions of views a month.

When we concluded and I closed the Zoom, I sat in this chair and watched the recorded file download to my computer. I couldn’t help but have a big dumb smile on my face and get teary-eyed. So many emotions.

Extremely grateful to spend time with people who are creating cool things. Proud of myself for putting myself out there. Inspired to do great work.

Anyway, hope that clears a few things up. I’m feeling jazzed about the future.

I’ll continue to share updates from behind the curtain of my book. I’ll finish recapping the road trip this week. And finally, in six days, I’ll be living in NYC for two weeks as a trial run before moving there.

Much to come in the near future.

See you tomorrow.

Grow a mustache—Why you should be more polarizing

A man with a mustache and sunglasses looking into the distance

(Yes, ladies. Even you.)

The idea

I want to alienate more people. Let me explain.

The goal is not to go out of my way to piss people off. I don’t want to do or say anything controversial just for the sake of being controversial.

But I noticed recently that most (if not all) of my writing has been curated for anyone and everyone. I’ve been painting with a broad brush in the hopes that any kind of person could sit down and enjoy my stories and lessons.

The consequence of that has been me avoiding certain topics I thought would be lost on most of my readers: the ins and outs of my business, hot takes, possibly-arrogant stories…

Then everything changed when the fire nation attacked.

Whoops. I mean, everything changed when I grew a mustache. Here’s what I mean.

The stache

Dillan Taylor and Hank the dog sitting in his bed
There are more pics of Hank in this blog than there are of me.

I shaved my beard and left my mustache about a month ago. Since then, I’ve gone to a wedding, a bachelor party, and have gone out drinking.

The thing I noticed immediately? Mustaches are polarizing.

Some people (women) wanted nothing to do with it. Others went out of their way to say how attractive they thought it was.

Prior to that, no woman had ever mentioned to me in casual conversation how sexy she thought my face was. I realized that was because I was trying to have a face anyone could get down with.

I went from attempting to reach everyone to only spending time and energy with mustachers. They were bought in. They were my people.

Then I thought about other areas I could apply this.

The meaning

When we polarize people, some folks naturally get alienated. Some hate mustaches. Some don’t care about business tactics.

But for the ones who stick around…the connection with them is 10 times stronger. It’s not about trying to get people to buy in; it’s about investing in the ones who are already bought in.

Lower quantity. Higher quality.

So what does this mean for us?

I’m guessing half of my readership cannot actually grow a mustache (ladies…and some dudes [sorry, gents]). But we can think about this as we create things and as we connect with others.

Do you hold any opinions you’d be uncomfortable sharing with the people around you? If not, that’s a problem. It could be a sign that you just go along with what everyone else thinks and that you have few values of your own.

When creating something, are you trying to make it so everyone can enjoy it (like I did)? When we build something for everyone, we build something for no one. Find your people.

In my coaching business, I have high standards for the people I work with. I want committed action-takers who show up on time and do what they say they want to do. That’s not most people.

And that’s the point. Most people shouldn’t work with me.

It’s not about the ones left behind. It’s about finding our people and giving them the world.

Grow a mustache.

Writing is still hard

A person sitting at their desk and writing with pen and paper

I’m day 69,420 into writing my book. It feels that way at least.

When I decided to embark on this journey last August, I thought I could finish it by December…Silly, silly man.

I’ve pushed back the publish date several times now. Partly out of procrastination, but mostly out of necessity. Here’s what I mean.

When I started, I did what I tell others to do when they’re creating something. I reached out to my network. I asked everybody if they knew someone I should talk to. It was easy to find people to interview.

So I did. It was fun and super low pressure.

Then, I interviewed the hosts of my favorite movie podcast. Then, I email-interviewed my favorite author and speaker. And then, I interviewed an entrepreneur I look up to who wrote the article that inspired me to launch my business. And then, my favorite chess streamer and YouTuber responded to my email and asked to set up a call in May.

This thing is getting bigger. What a lovely problem to have.

I call it a “problem” for two reasons:

  1. I’m still setting up calls with people which means more time is needed to write this thing.
  2. To keep the book short and minimal, I’m choosing to cut out certain people I’ve interviewed. That makes me feel bad.

But on the upside, my confidence has soared as I’m getting people who are huge in my eyes to hop on a call and talk to me about what they’ve created. That lights me up.

Also, here’s the good thing about not being all big a famous with an enormous audience: there’s not a ton of people I can disappoint. Many people bought pre-sale copies of the book. But I doubt they’re checking their calendar and stressing over when they’ll get their $10 back (soon, my friends).

Anyway, here have been my biggest lessons so far:

  • Reach out to people. You can’t get what you want if you don’t ask for it. If they don’t respond, you’ve lost nothing because you already weren’t talking to them.
  • People LOVE being asked thought-provoking questions they’ve never been asked before.
  • Writing is easy. Sitting down to start writing feels impossible.

Stay tuned. ✌️


I’ll be making an RSS feed for this blog soon.

That way, readers won’t have to check it every day. The posts will get sent directly to anyone who subscribes.

Stay tuned.

Next level

A man playing a virtual realty video game

I’m shifting my business. It’s scary.

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

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

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

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

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

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

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

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

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

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

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

So what will get me to the next level?

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

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

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

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

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

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

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

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

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

New rule; fewer blogs

Last month was an eye-opening experience for my mental health. After hitting a wall, I made some changes.

No more working on Sundays. No calls past 3pm. Friend and family time are to be prioritized.

I just made a new rule:

No blog-writing when I’m on vacation.

Simple, I know. But I’d often take my laptop with me when going out of town. That, or I’d write a bunch before leaving and schedule them out.

Either way, it would lead to low quality and throw-away writing.

This is already an “almost-daily” blog. Now even more so.

The freed-up headspace when I was on vacation was refreshing. Normally I feel panic and guilt as I question when I can find time to write a few sentences. It really takes me away from the moment.

Not no mo.

How to know you don’t suck at something

A dart on a dartboard that missed the target

I’ve tried my hand at podcasting, YouTube, and writing online.

The only thing I would consider successful has been this blog. It has anywhere from 40-700 unique readers per blog post.

Nothing crazy. But way more than when I started in 2019. Back then it was just me and my friend Grace reading my overly-confident preachings as I told people what to do and what not to do in their lives.

She still reads the blog today, which is a good sign.

But I want to briefly mention a helpful measure for success. It’s not some arbitrary number of readers, followers, or subscribers. It’s much more human.

People being nice when they don’t have to be.

This can be as simple as a friend sending a message saying they really liked today’s blog. It could also be a stranger reaching out and sharing their thoughts on the work we’ve done.

My blog about moving to NYC got 712 unique readers. That was cool. People shared it on Facebook and LinkedIn. I think it was so popular because it was a “huge” life decision for my personal and professional life.

It felt amazing. For a day.

But a few weeks later, I got an email from a guy in India. I had no idea who he was. I thought it was spam at first. He told me about his favorite pieces I wrote, dating back months and months. He said this:

“I relate on so many levels with your approach to life (Like Core Principles). And I’ve started working on certain things after reading your blogs (Like preparing for high-altitude treks like your triathlon). Your blogs have inspired me to write more too!
Anyway, just wanted you to know, you’ve got a fan from India. Thanks for being you.”

I saved this email. It made my eyes water.

Numbers are great. They mean we’re reaching more people. But messages like this are truly priceless. They keep creators moving. He didn’t have to send me this.

I don’t share this to boost my ego. My point is: If we stick with something consistently, make tiny improvements, and try to bring value to others…eventually, people will dig it.

I can’t give a masterclass on blog writing. I just sit down each morning and write short paragraphs about what I’m thinking and learning.

No hurry; no pause. I don’t have to sprint, but I can’t stop.

To anyone who wants to create anything, my advice would be just that.

(PS—I’m writing a book on creating. It’ll come out this summer. Pre-order it here. Or, send hate mail here.) 😎

My precious

Michael Schur's TV characters, including Michael Scott and Leslie Knope

Michael Schur is an American comedy writer. After writing for SNL, he co-wrote The Office, Parks and Recreation, and other big-time favorites.

His #1 piece of advice for creators:

Don’t be precious with your material.

At Saturday Night Live, they would write sketches that would most likely not be performed. And for the best ones that did see the stage, they’d be over in five minutes. And unless they were the .1% of skits that made it onto YouTube, they would never be seen again.

Years of this taught Michael to not hold so much emotion in the things he created.

“I didn’t try to do shitty work,” he said. “But no matter how funny I thought the thing was, I had to be willing, at any point, to embrace the fact that my work was, in fact, shitty.”

I’ve never written one of the best television sitcoms in history (let alone two of them). But I do write this mediocre blog.

There have been times I chose not to write about something because I didn’t have the mental energy to really flush it out and talk about it in any sort of interesting way. I don’t want to waste material, I’d think. Lol.

The beauty of writing a blog almost every day, and of it being entirely my own…is I can do whatever I want.

I could literally write a blog titled “My ass” with just a photo of my naked butt. There’s nothing stopping me from doing that.

Anyway. Since I can do as I please, I’ll often churn or repeat ideas I wrote about months ago. I can’t keep track of all 1500 blogs I’ve written, so I’m sure I have pieces with the same message, the same jokes, the same sentences word for word.

I also have blogs I can’t stand to read now. I’ve said things I disagree with today. I’ve written things I’m not proud of.

This is all to say: If I held my work as precious, I’d probably be depressed. Good enough has to be good enough.

The second I have too many criteria for something being “good enough” is the second I stop typing.


I got to interview Derek Sivers for my book this week.

He’s one of my favorite authors and TED-Talkers. He showed me that creating a business isn’t this some scary thing.

As expected, his long email of answers was crisp and delightful to read. At first, I was bummed to not get on a video call with him. But I quickly realized that copying and pasting his typed words would save about five hours.

I reached out to a lot of people I look up to with the same invitation. Most don’t respond. Some say No thank you. And that’s totally okay.

Tim Ferriss said, “It’s not about the people who don’t. It’s about those that do, and what you can do for them.”

I’m honored and humbled to have a chapter in DO THE THING! that starts with “Derek Sivers” in bold.

A lesson I’m learning is that we don’t get what we want if we don’t ask for it.

How to become better than me at writing

Dillan Taylor sitting at his desk and getting ready to write
The face I make before I start typing.

I’m not a phenomenal writer.

But I’m 20 times better than when I first started this blog. That was almost three years ago.

I’ve read a few books on copywriting—how to keep my words concise and easy to digest. I can give people simple suggestions to improve their writing…

  • Write short sentences.
  • Don’t use $100 words when $1 words can get the point across.
  • Read this piece and watch this video. They both take 60 seconds.

But I’m not even close to an expert. And that’s the point.

We don’t need to have more information (or even more skill) than others. Most of the time, the people who are “successful” are just the ones willing to put themselves out there.

Did I just call myself successful? Well, I certainly feel like I’ve had success. But I felt that way when just three people were reading my stuff.

I’ve had blogs with over a thousand unique readers. Some of those posts include my thoughts on death, my trip to Canada, and my move to NYC. I’ve had people I don’t know email me talking about their favorite pieces.

I don’t say this to brag. I say this because I never set out to be a “great writer.” I just wrote one of these almost every day for three years. It took a year and a half for people to really start giving a shit.

We can get really good at things if we have two things…

Consistency and the willingness to be messy.

I can’t even read my earlier writing. Most of it makes me cringe. But if I worried too much about that early on, I wouldn’t have written anything and I wouldn’t have improved.

It’s not sexy advice. But to get good at anything, we just have to do it a lot and be okay with doing it poorly.

We don’t need to read “one more” book. We don’t need another course. We just need more practice.

Keep that up…and maybe you’ll build yourself a mediocre blog like me.

Writing is hard

A teal typewriter on a desk with empty sheets of paper next to it

I’ve been working on my book for five months now. Most of that time has consisted of two things.

Interviews and procrastination.

Early on, I was worried I wouldn’t have enough content to write more than a pamphlet. Once I began actually writing and transcribing my recorded conversations, I realized I actually had to cut some folks out. That was a relief.

There were some interviews that, while I’m incredibly grateful for them, just didn’t hit as hard as others. “Trimming the fat” sounds cold. But writing this book felt like less of a chore once I decided to only include chapters that lit me up. I narrowed it down to seven people—including duos.

My last interview was a dream come true. I had a long conversation with James and Anthony Deveney—the hosts of one of my favorite shows, Raiders of the Lost Podcast.

They started their movie podcast in June of 2020, in the middle of quarantine. Since then, they’ve gained half a million followers and have grown arguably the best film podcast to date.

Their story was captivating and inspiring. They were also two of the nicest dudes I’ve ever met.

They took me through their journey of pursuing their dream: being full-time content creators. It’s one thing to see people doing something cool. It’s another thing entirely to hear about what they had to do to get there.

James just quit his full-time job a few months ago once the podcast was able to totally support both of their lives. I’m thrilled to tell their tale.

As for my process of writing, so far it’s looked like this:

  1. Record interview.
  2. Come prepared with strong questions to ask.
  3. Play the interview back with a Google Doc up.
  4. Transcribe the major bits of conversation while playing and pausing the interview.
  5. Use willpower to not immediately edit my writing (i.e. write shitty).
  6. When a story or concept of my own comes to mind, make a note of it in the doc so I can come back and write about it later.
  7. Use the Pomodoro technique for productive time management: 25 minutes on, 5-minute break.
  8. Finish this first run-through before hiring my editor.

Right away, I’ve recognized the necessity of an organized system. If I were winging it every time I sat down at my keyboard, it would be chaos. With this structure, it’s actually pretty easy to write this damn thing.

The only thing getting in my way is initially sitting down to start. It’s the Resistance which gives me all these reasonable-sounding excuses for why I don’t have to start typing just yet.

Luckily, I eventually brush that voice aside and begrudgingly begin writing. Without fail, I enter a flow state in five to ten minutes.

What’s my biggest challenge now?

First, it’s making the time to actually write. I need three to four hours of deep work in order to make meaningful dents in this. Unfortunately (or fortunately), I run a full-time business that’s doing well. That means I have a lot of client calls. Sessions require a ton of mental energy, so I refuse to write for four hours in the morning and then do calls in the afternoon. My brain would be fried.

Second, the debate is creeping in on whether I get a publisher or I just publish it myself. But I’m trying not to focus too much on things that are farther away.

Regarding the first challenge, it’s highly likely that I push back the release date. The plan was my birthday, March 2. The new plan is probably my mom’s birthday, May 5.

Since I don’t have half a million followers like James and Anthony, I doubt anyone will make a fuss about this.

Am I working as hard as I possibly can on this?


Am I having a ton of fun?

Yes. 😇

The R word

Every now and then I talk about Resistance.

The concept comes from The War of Art by Steven Pressfield—a book I read once a year.

Resistance is the invisible force that keeps us from doing the things we want to do and living the lives we want to live.

It takes many shapes: fear, procrastination, justification, anger, shame…

It says: “You don’t have to do this right now. Do it later. It’ll be easier and more enjoyable if you do this in the future.”

Most of the time, Resistance sounds reasonable. We can’t start until we do this thing, until we have more knowledge, until we have more confidence.

I’m writing a book. Each and every time I sit down to start typing, without fail, I find reasons to wait. I set out to begin writing at 9am, but won’t start until about 9:45.

Readers of this blog know I’m not a big grind-hustle-discipline guy. I don’t think we have to torture ourselves to live a life worth living.

But the simple truth is we don’t get something from nothing.

There are plenty of things worth doing that we won’t feel like doing. Whether it’s something small like reading or working out, or something with higher stakes like starting a company.

We can just start. It’s time.

I wrote letters to all the people I love—Then I read them to them

A pencil, a piece of paper, and an envelope lying on a marble table

Back in October, I visited a few coaching friends in Vancouver Island, meeting them in person for the first time.

While at one friend’s house, we were discussing the things we felt incredibly grateful for. The same thought popped into my head that always does when I ponder what I appreciate most: my tribe of friends, family, and colleagues.

But this time, I had an insight.

Rather than vaguely trying to express this more to the people in my world, I decided I would be as intentional as possible.

I would craft hand-written letters to those who matter most. I would thank them and explain as best I could why they mean so much to me. Then, I would read the letter to them.

I’m not even close to totally completing this task (which I think is a good sign). But I have done several and would like to share what I’ve learned.

1) Expressing gratitude is euphoric.

Let’s get the selfish stuff out first.

Anyone who’s ever done a metta (loving-kindness) meditation knows the immediate rush of joy that comes from truly wishing someone well. We imagine someone we love and we picture them being free from harm and fear. We envision them being totally fulfilled. We see them laughing with the people they love.

This felt more impactful because I was sitting five feet from each person I read a letter to.

I could see their smiles and tears. I got to hug them afterward. I got to hear them stumble to find words that match the moment.

The idea of the exercise is to leave nothing up to the imagination. “Here are the specific reasons why I love you.”

Once that message gets across, the powerful connections I had with each person felt twice as strong.

2) This exercise is the easiest thing to do that brings life-changing results. Low input; very high output.

That sounds kind of businessy. Let me explain.

Each letter takes about 20 minutes to write. I type it out in a Google Doc first. This only takes about five to ten minutes because it’s effortless to write words that are sincere.

Then it takes another ten minutes for me to put pen to paper and transcribe the Doc.

The next time I would see the person, I would: tell them what I did, grab the paper as they panicked, and start reading it aloud.

In less than 40 seconds, our relationship would become wildly stronger.

I even gave this as a Christmas gift to my aunt and uncle. I have no idea if that’s just a cop-out from getting a “real” gift. But they both absolutely loved it so I think I’m off the hook.

3) There are a lot of things we keep to ourselves.

Here’s what I mean.

I’m lucky to have candid and loving relationships with my friends, family, and colleagues. But no matter how open and communicative we are with one another, there will always be thoughts and emotions we feel that the other person isn’t 100% aware of.

That’s also why I suggest doing a feedback exercise with those close to us. It paints a clearer picture of the lens our friends use to look at us.

We can let our actions tell the story. That’s a lovely thing.

But we can also remove the middle-man and get right at the heart of things. I’ll end with an example.

I wrote one of these letters to my dad.

In it, I told him what he did that meant the world to me. Last year, when I decided to not go back to school, quit my full-time job, and start my own business, I thought he’d be furious.

I was out front of my mom’s house, pacing on the sidewalk, when he told me on the phone I had his full-fledged support.

When I relayed this to him in my letter, he had no idea about the impact of that moment.

All this to say: We can always express our love and admiration for people more than we normally do. There’s always more to know.

I highly encourage anyone reading this to write just one letter to someone they appreciate. Tell them why they’re loved. Tell them what they mean. Tell them how much they’re needed.

Then see how they light up.

Writing bug

As I’ve been spending more time writing my book, I’ve felt inspired to write more.

I’m planning on publishing more articles on Medium. (Go ahead and follow me there!)

And I’m already brainstorming future books. One step at a time though.

Tomorrow, I’ll update you all on how the current book is coming along.


Work music

I love working to lo-fi, classical music, and videogame scores.

If you enjoy the same while doing deep work—writing, designing, editing—here’s a playlist I made for such occasions.


…these blogs just aren’t that good.



Please don’t give me money…unless you want to

A person putting coins into a piggy bank

Aside from Sundays and the occasional vacation, I’ve written in this blog every morning for two years.

I plan on continuing for several decades, maybe even forever.

The thought of having a 50-year archive of my thoughts, challenges, and stories is captivating to me. Writing these posts has been wildly therapeutic and sharpening. And the fact that people seem to enjoy some of them…it’s an honor.

I’ll never charge a dime for this blog. I write blogs because I thoroughly love to.

But now there’s an option to support my work.

If you’ve ever gotten any value out of something I’ve done, feel free to donate what you think seems fitting. It’ll go toward my work and a portion goes to an organization battling climate change.

There’s also zero pressure to do any of that. Regardless, I’m going to keep typing away.

Whether you choose to donate or not, I couldn’t be more grateful for you taking time out of your day to read my stuff.

Thanks, thanks, and ever thanks!

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.


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.

I really don’t feel like writing this blog today

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

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

Most days, I don’t feel like:

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

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

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