Grindset: a funny term for one’s ability to work their ass off every day without anyone telling them to do so.
Some people are able to build on their own, get lost in deep work, and grind away using only their passion and discipline. I am not one of these people.
Let me explain.
When I interviewed Courtland Allen, founder of Indie Hackers, he mentioned the accountability problem.
“It’s crazy how most people don’t do the things they know they should,” he said. “Exercise, spend time with friends, eat well, create things…We know this stuff makes our lives way better but we don’t do them. But we’ll easily show up on time to a nine-to-five job we don’t really like every single day. That’s crazy to me.”
Why is that so much easier? Because we have people holding us accountable to do so.
If we show up late to a job, we experience some sort of damage. It’s embarrassing. We could get written up. Our bosses and coworkers are watching.
But when it comes to writing a blog, recording a podcast, or building a solo business…it’s just you. There’s no one over your shoulder telling you what to do and when to do it. If you take a day off to watch TV, no one will reprimand you.
Earlier this week, I wrote about how my creative projects burnt me out. Aside from reorganizing and reigniting myself, I did something else to help with the problem mentioned above.
I got an accountability partner. Actually, I got two.
They’re both fellow life coaches and dear friends. With one, we log our working hours using Toggl and send the other person our weekly summary every Monday. With the other, I got a bit creative.
I made a shared document between the two of us with a weekly list of my creative goals:
2-3 YouTube clips
1 podcast episode every other Thursday
a reflection of how it went
As I work on these goals, he can see which ones I get done. If they’re not all completed by the following Monday, he gets to grill me. A la accountability.
I can already feel the power of having to report to someone. I love the freedom of not having a boss but accountability keeps me at this desk until the job is done.
If you’re having trouble exercising, for example. If you hired a personal trainer and bet $3000 you’d never be late to a session, it would become super easy all of a sudden.
We often don’t do things because we don’t feel incentivized to do things. We say things like, “I can never remember people’s names,” or, “I can’t wake up early.” But if I told you I’d give you $1m to remember the next 20 names you meet and wake up at 5 am every day for the next month…you’d have no problem.
So what do you want to do more of or less of? Who can you ask to help hold you accountable?
Many of you may have noticed I took a hiatus from this blog for several weeks. Between the coaching business, the podcast, and finishing the first draft of my book…I’ve felt creatively burnt out.
For the first time since starting this blog in October 2019, I opened up WordPress, began typing, and stopped after writing a couple sentences. Anything I posted would’ve been forced and inauthentic.
So I took a week off.
One week turned into two. Then two became three. Just like working out, the more we skip something, the easier it is to continue skipping it.
Even after revamping the workflow of my podcast, I still felt overwhelmed and unclear as to how I was going to get everything organized. I took entire days off. I procrastinated and avoided all my creative work.
In other words, anything that required me to sit alone in my office and push through resistance…didn’t get done.
Coaching and getting on calls were non-negotiable. The accountability of another human being waiting for us is a powerful thing.
So what to do?
Well, after getting coached on it, I did two things.
1) Check your health-trio.
Diet, exercise, and sleep.
What are you putting into your body? Is it a lot of processed foods, sugar, and empty carbs? You don’t have to be a nutritionist to know you’re not feeding your body well.
I try to go 80/20—80% of what I eat is well-sourced protein and produce, nutrient-dense, and optimized for health rather than pleasure. The other 20% is for me to enjoy life. Pizza, burgers, cheesecake…
When it comes to working out, you don’t have to be a model or an athlete. But you have to do something that gets you sweating every week. 15-minute workouts, going for walks or runs, playing a sport you love…There are simple and enjoyable ways to move your body. You’ll feel better and will eventually start looking better.
I highly recommend the app FitBod; it’s the reason I’m in shape. Hiring a personal trainer is also great. But if you want to start small you can just find a friend who you can go on walks or runs with.
Finally, how many hours of sleep do you get each night?
Sleep is often the first thing people sacrifice and it’s arguably the most important medicine we can take. The good news is there are minimal side effects and it’s free.
97% of adults need seven to nine hours of sleep each night. Not consistently doing so leads to increases in anxiety, cravings, and avoidance. It also decreases motivation, focus, and happiness levels.
Sleep trackers are incredibly useful. I recommend the app SleepCycle or the Whoop strap.
If you’re putting garbage into your body, sitting still every day, and sleeping poorly…you’re obviously going to be struggling to get organized. That’s like driving a car with all the warning lights on. Take care of the machine that is your body.
2) Break everything down.
Take all your personal and professional projects, and chunk them into their simplest, easiest, clearest steps. This is something we should do every week.
James Clear said, “Most people think they lack discipline when they really lack clarity.”
The most common reason we procrastinate is that our tasks are unclear. When things are ambiguous they seem much more difficult than they actually are. We have to really flex our problem-solving muscles.
Or we could just take the time to make things clearer.
Last week, I wrote out all my “projects.”
start posting podcast clips again
declutter office and room
finish first draft of book
Nice and simple, eh? Nein.
For weeks, I would put things like “take care of car stuff” on my calendar. Then when it came time to do it, my brain would go, “What the hell does that even mean? What’s step one?”
And that’s the key. Can you break down whatever you need to do into the next three actionable steps?
For me, “car stuff” became “call the title office, go get the emissions tested, and go to Home Depot for screws to put on the front license plate.”
Ah, much clearer. That all seems manageable.
When our brains need to take more steps to sift through the fog, they become much more likely to throw in the towel.
So this morning, with my health trio in check, and with my projects broken down, I feel much more prepared to get things done this week.
How do you combat overwhelm? Email me and let me know.
Last winter, I experienced my first serious bout of burnout. For a week and a half, I felt zero positive emotion and ran away to a cabin in the woods.
Luckily, I haven’t felt anything like that since. But I’m hyper-aware of the warning signs of overwhelm. Certain questions pop up:
am I avoiding things?
is there a ton of resistance?
am I excited by my projects or dreading them?
Since launching my new podcast back in August, I’ve been dancing with burnout once again. The show is called The YouTuber’s Guide to the Galaxy. I interview YouTubers with over 10k subscribers to dive into their creativity, share their strategies, and inspire new creators.
I was oozing motivation right out the gate. My expectations for output were high: one episode every other week, three clips per week, and three to five TikToks per week.
I kept that up…for two weeks.
It turns out, treating something like a full-time job is difficult when you already have a full-time job (my coaching business) and two side hustles (writing my book and leading my coaching community). There’s also this blog which is a fun lil proj.
But as I’ve been interviewing successful creators and entrepreneurs, I must admit I’ve been taken in by the glamor of sacrifice and hard work. James and Anthony Deveney sacrificed all their free time for a year to build their show, Raiders of the Lost Podcast. CupppaJoe5 has been working 100-hour weeks in his pursuit of becoming a full-time content creator. Ryan Twomey has uploaded a TikTok every day for almost two years.
Here’s what I learned while grinding away these last two months: I don’t want to do any of that.
It comes down to the essentialist question: What are the most important things in your life right now?
For me, my entire being is dedicated to building the life I want most. I have my dream job and work with incredible people. My physical health and relationships will always be my top priorities. I want quality time with my friends and family. I also need to work out at the gym and go to jiujitsu class. I’ve gone on a few dates with a woman I like and am curious to see where that goes. I play and study chess practically every day.
No matter how awesome it sounds to have a full-time podcast that makes me money and has a ton of listeners, I’ll never sacrifice these things mentioned above. I’m not willing to put in the level of work that my guests have put into their channels. And that’s okay.
So what will I do?
Well, the goal is still the same: 100 episodes. I have three episodes on deck and two interviews scheduled. The show goes on.
But I’m deleting the high-friction activities and doubling down on the low-friction ones. I hate video editing. So I’m changing the YouTube channel so that it’s only short clips of episodes and not full conversations. Then, I’ll be trimming down the podcast audios so they tell a much higher-quality story. Finally, I’ll upload one TikTok per week.
The goal here is to make things much easier for myself and to make it harder to quit. I’ll stop doing what I hate and do more of what I love.
I’ll leave you with these questions:
What are the three most important things that demand your focus right now?
What are you doing too much of that’s getting in the way of these things?
What aren’t you doing enough of?
This show has been my favorite creative project I’ve ever worked on. And it’s not even good yet. Just wait.
Awesome guests to come. If you want to check it out, all the links are here.
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.
writing blogs and books
running a podcast/YouTube channel
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.
The second episode of my podcast is out now. It was the most nervous I’ve ever been for a conversation.
Eric Rosen is one of the biggest names in the chess space. He has…
575k subscribers on YouTube
225k followers on Twitch
an International Master title in competitive chess (there are only 4000 of these in the world)
This conversation was recorded for my book back in May. It took me about 30 minutes of talking to understand that it was real.
That may sound silly to most, but I’ve been enjoying this guy’s content ever since I got into chess back in 2020. I’ve seen well over 500 of his videos and I’ve taken all his online chess courses. Meeting him was wild.
He was so kind and so generous with the details of his journey and business. He took me through all his revenue streams, his processes, and his goals for the future.
I loved the conversation and I think you will too if you enjoy creating.
Since I was a kid, I had always wanted to be an actor.
I remember watching my favorites. Folks like Daniel Day-Lewis, Natalie Portman, and Christian Bale. I’d memorize scenes and perform them when I was alone. It was mesmerizing to me to be taken to a completely different world. What floored me most was knowing it was a set with actors, directors, and producers…yet finding it 100% authentic in the moment.
I wanted to do that for other people.
But when it came to taking opportunities, I wouldn’t. I avoided being a “theatre kid” in high school. I was too busy smoking weed and making fun of the theatre kids. I didn’t audition for anything during my first three years of college. I had a good reason not to.
I was terrified.
The semesters would pass by and I’d see flyers for the new shows being put on. Next semester, I’d tell myself.
Then, at the beginning of my senior year, I was walking through the liberal arts school. I happened to see a girl I knew who was in the theatre program. We chatted for a minute or two.
“What’s the play this semester,” I asked.
“To Kill a Mockingbird,” she replied. “The last day to audition is tonight at 6!”
Shit. I had nothing going on that night. Which meant I had no excuse to bail.
The day went on and I found myself back home watching the first season of True Detective. I wanted Matthew McConaughey’s swagger to inspire me. I sipped some whiskey to calm my nerves.
An hour or two before auditions, I convinced myself not to go. I wouldn’t know anybody. They’ve all been acting for years and I had no experience. The community and culture were probably already set in stone and I wouldn’t belong. I’d make a fool of myself.
Then I had an insight.
I wanted to be an actor. That was true. But how did I want to secure that for myself? I imagined the director knocking on my door.
“Hello,” he’d say. “I know you didn’t audition. But you strike me as someone who’d be really good at acting. Would you like to be in my play?”
I laughed because there was a 0% chance of that ever happening. No one was coming to hand me anything. I had to put myself out there and go for it.
I sighed and started walking to the campus. I tried to step fast enough to get there with plenty of time to settle in, but slow enough to not be covered in sweat.
As I panted through the building’s doors, I could already hear the cacophony of conversation coming from the theater. I followed the noise and to my horror, everyone was talking to everyone. I grabbed a script from the pile by the door and meekly took a seat toward the back of the stands.
I felt like the new kid in school who didn’t belong. I wanted to flee. Ten minutes passed and I thought, it actually makes sense for you to leave.
Then the director walked in. I expected the place to become silent.
It got twice as loud.
Students left their seats and walked up to start talking to him. I was screwed. But it was too late to weasel my way out. He took center stage and everyone sat down with their scripts.
At random, the director would pick scenes from the play and we would go up and cold read as any character. It didn’t matter who it was, guy or gal. The goal was to give him a sense of what we looked and sounded like.
I sat in my seat pretending to look at my script because I was too horrified to go up. Then I noticed too shiny brown dress shoes next to my feet. They were attached to the director. I looked up.
“We haven’t seen you yet,” he smiled. “Why don’t you read for Scout?”
My plan to remain invisible had failed. I crawled up there and did my best Matthew McConaughey I could muster. I was sweating profusely.
But I did it.
After the first round, I stayed up and read for another character. It got easier and easier. No one was laughing at how stupid I was. No one whipped their phone out to start filming me. As it would turn out, everyone else was just as nervous as I was.
I went home and despite doubting I’d get a part, I was proud of myself. After years of thinking about going for it, at least now I could say I actually tried.
My actor friend messaged me a few days later while I was at work. I got a role. My first role in a play.
It was a small part. A side character with ten lines. I was elated. Ten lines? It’ll be impossible to forget them!!
That semester was my first experience being in a theatre company. I became familiar with the rehearsal process, learned my way around the back of house, and made new theatre friends. I also started taking acting classes.
It was a perfect timeline:
Got that first role in the fall of 2015.
Got cast as a protagonist in the following spring production.
Became convinced that I wanted a career in theatre after college.
Got cast in the more intimate play that following fall with a different director. He taught me how to tell a story and helped me drastically sharpen my skills.
But there was a problem.
Here’s the thing…
As my years at university drudged on, I was doing worse and worse in school. I was skipping classes, not handing in essays, and using that time to sit in on acting classes. I was too deep into my major to switch to a theatre degree, so I had to improvise.
Obviously, this was unsustainable.
My girlfriend at the time was an actor too. That winter, we took a bus up to NYC and auditioned for grad schools. We had spent months preparing our monologues and resumes.
It was a thrilling and anxiety-inducing experience.
Hundreds of actors from around the country would wait to be called into a room. It was a small banquet hall where 50 people with clipboards were facing a small stage with a chair on it. We’d walk in, head to that stage, arrange it how we wanted, then introduce ourselves and perform two monologues.
We had two minutes starting when we spoke our first word. At the two-minute mark, the time-keeper in the back would raise his/her hand and say, “thank you!” Then the gods would decide our fate.
She and I both got several callbacks. It was an exhilarating way to spend a day: running around a giant Broadway hotel to different masters program scouts from around the globe.
Here’s the punchline to this drawn-out story: I got accepted into three different schools. One in Long Island, one in San Francisco, and one in Birmingham, England.
I couldn’t go to any of them because I flunked out of college that spring.
Emailing each of them back was one of the most depressing things I’ve ever had to do. But things got worse.
After an unsuccessful “college try,” I moved back in with my mom with my tail between my legs. I’m all for people living with their parents to save money and figure something out, but this wasn’t my choice. I was back to square one. No job. No real skills besides acting. A ton of debt.
A few weeks into that summer, that same girlfriend broke up with me. She had graduated and wanted to explore the world and herself. I was in a hole with no idea how to start digging myself out. It made total sense. But it crushed me.
Unfortunately, none of those events motivated me to begin climbing that mountain. In fact, in June of 2017, after stealing a bunch of prescription pain pills and anti-depressants from various people, I tried to kill myself.
That sounds awful. And it was. But it wasn’t out of intense depression. It was almost out of laziness.
I had so many things to figure out and repair. The second I thought about the first few steps, I’d get overwhelmed and would avoid anything and everything. It seemed truly insurmountable. So I tried to bypass it.
I’ve shared that story before and can go into more detail in a future blog. But all you need to know for this one is that it was my breaking point. My rock bottom.
Waking up from that, everything clicked.
Whatever I had been doing up until that point clearly wasn’t working. Something had to change. Many things had to change. So I started at the beginning.
I began applying for jobs—bigger restaurants in my area. I opened a new checking account since my old one was closed due to prolonged overdrafting. I got a gym membership and started working out 2-3 times per week.
But the question remained: When would I have time to audition and perform in plays? There were numerous theatre companies in my area. How could I make it work?
It was both one of the easiest and most difficult decisions I had ever made. I wasn’t ready.
I wasn’t prepared to pursue arguably the most grinding, unforgiving, and least lucrative careers in the world. I could barely take care of myself. I needed to grow up.
Many of the successful paid actors I know today have one or two (sometimes three) side jobs. They’re scraping by.
I didn’t want that. I don’t ever want to live anything close to paycheck to paycheck ever again. I didn’t know what I would pursue instead, but I knew it would be something much more likely to make a great living. I had an inkling it would be in the world of business.
So I haven’t done any sort of acting since failing school in the spring of 2017.
Will I ever be on stage again? Maybe.
Theatre will always be a love of mine. Going to shows is one of my favorite ways to spend a night out. I’ll always have a deep respect for the craft of acting and storytelling. I still act out my favorite movie/television scenes when no one is around.
But if I never act in another play again, I wouldn’t regret it.
I have so many other things I’m passionate about. My business. Creating content. Writing. Chess. Jiujitsu. Connecting with others.
I’m not the lost 23-year-old I was when I was…23 (that’s math). For now, I’m content with going to see as many performances as I can. I also have a bunch of old theatre friends creating their own shows and doing incredible work. Seeing them do their thing makes me smile every time.
For me, acting was like the perfect guy or gal you meet at the worst possible time in your life. It brought me tremendous joy, fulfillment, and friendships. But wasn’t the right time. I had to learn how to live first.
It wasn’t you; it was me. We had our time. Maybe I’ll see you again. 🎭
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
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.
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.
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.
(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:
I live my life
I reflect on all my insights, mistakes, and fears
I write about them here
You either enjoy them or go, “meh.” 🤷🏼♂️
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 bookDo 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.
I’m aware that these blogs have been a bit scattered for the past two weeks. Here are my excuses.
Most of my writing lately has been for my book, which I’ll discuss more today.
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.
I’m building a group for founders/entrepreneurs. In other words, my creative energy has been kind of diluted.
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.)
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.
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.
A few weeks ago, I interviewed Lynne Tye for my book. She’s a badass entrepreneur who wrote the article which inspired me to launch my business.
The conversation flew by as we laughed and vibed over building stuff. Our discussion was full of gold but I wanted to share a simple framework that I found super useful.
The difference between quitting and giving up.
According to Lynne, giving up is when we still want the result.
“I gave up the other day,” she said. “I was running and stopped halfway through and walked the rest…which is trash. I still wanted the result of getting in a good run, but I stopped putting in the work needed to get that result.”
Quitting, on the other hand, is a strategic choice. It’s when we decide to put our time and energy elsewhere because we no longer crave the result.
In 2020, I was certain I wanted to become a YouTuber. I started posting a vlog a day. After two months, I realized I absolutely hated it and didn’t care about filmmaking. So I stopped.
Did that mean I gave up on my dream? No. It meant I stopped wasting valuable mental and creative energy so I could channel it into something I did care about.
“Quitting is such a valuable thing,” Lynne told me. “Like quitting cigarettes. What we want is constantly changing so we need to keep taking stock of that. More people should quit more often.”
So the next time you want to stop something, ask yourself: Do I still want the result of this?
Then you’ll know if you’re choosing to quit or if you’re simply giving up.
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.
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.
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.
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:
Reaching out to people individually, connecting with them, and building a relationship.
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.
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)
My friend and I are recording a podcast episode today. Our first one didn’t go so well.
It wasn’t absolutely cringe, as the kids say. But it was tough to listen back to.
We gave too much backstory. We didn’t interrupt each other enough. It felt like we were taking turns giving TED Talks.
But we wanted to start a podcast simply because we enjoy our conversations and hope others would too. Something happens when you hit “record,” though. When you see that blinking red light, the butterflies settle in. It’s easy to feel like everything spoken must be funny or groundbreaking.
I’m so glad we had a mediocre first recording. We can’t grow or improve until we run a test and gather data.
We could’ve prepped and planned for months, trying to create the perfect conversation. But what we did was so much more efficient.
We said fuck it, let’s just do it and see what happens.
Done is better than perfect. Because perfect usually means doing nothing.
According to Steven Pressfield, there are amateurs and there are professionals. Here’s what sets the pros apart:
1) We show up every day.
Vacations are nice and rest is necessary. But inside those boundaries, we’re on the clock.
2) We show up no matter what.
Again, time away from working is rejuvenating. But if we only do the work when our bodies feel like it, we’re doing ourselves (and those we serve) a disservice.
3) We stay on the job all day.
Our to-do list should be reasonable and doable. And our day ends when it is complete, not when Resistance begins to settle in.
4) We are committed over the long haul.
Perhaps we’ll be doing something different a year from now. But we’ll still be working consistently with purpose, providing value, and growing our skills.
5) The stakes for us are high and real.
We don’t create because it’s a hobby. We create to pay our rent, buy groceries, and afford trips with our friends.
6) We accept payment for our labor.
We are here to serve people and solve problems, yes. But we must be compensated for doing so. Otherwise, we’re not working; we’re running charities.
7) We do not over-identify with our jobs.
We write. We collaborate. We design. We’re not writers, collaborators, or designers. Our work is not our life; it fuels our life.
8) We master the technique of our jobs.
We improve each week because we know we’ll never know all there is to know. We become black belts in what we do.
9) We have a sense of humor about our jobs.
While the stakes are high, we don’t take ourselves seriously. We shrug off failures as part of the game. If we’re getting pummeled it’s because we’re on the field and not in the stands…and we’re grateful for that.
10) We receive praise or blame in the real world.
Some people love what we’re doing. Some people despise it. Both are okay. We appreciate the kind words and learn from or disregard the nasty ones.
I certainly don’t embody all ten of these each and every day. But all I can do is take care of myself and remind myself of the simple truth…
That the hardest thing to do in the world is to sit down in this chair and do the work.
Taking inspiration from people we admire is great. But seeing someone as God-like or more than human seems creepy to me.
That said, one of the people I look up to most is Derek Sivers.
His book Anything You Wantis the reason I wanted to start my own business. He’s given several TED Talks. And last month, I interviewed him for my book on creating.
I’d like to share an answer of his and how it inspired my newest creative endeavor.
“Why is absolute control over what you create so important to you? Self-publishing (and printing) your books, coding your website in HTML, building things with your hands, etc.”
“I hate bloat. It feels like pollution.
Quick-publish tools are filled with bloat because they have to cover every scenario.
Or just type “<html><h1>Hello!</h1></html>” and save it as index.html, uploaded to a simple Linux server, and voilà. You now have a website with only one file and one line of code. No security holes. No problem to maintain it.
I hate dependencies. I have no subscriptions. Well-meaning companies say, “Oh don’t you worry about that, we’ll take care of it for you for only $10/month!” I think long-term so $10/month is $6000. And now you’re dependent on this company. If they raise their rates or go out of business, you’re screwed because you made yourself dependent on them.
So for each of these situations, I’d rather avoid the bloat, save the $6000, be un-dependent on any company, and just figure out how to do it myself.
That said, for the book publishing, I just wanted the highest possible quality, and I wanted to keep the rights so that I could do whatever I want with the books in the future. I could license them, translate them, rename them, give them away for free, or whatever I want. When you sign your rights away to a publishing company, the copyright is no longer yours to do what you want with.”
My first thought was, Shit, I use WordPress for my blog. Am I a loser?
While I might in fact be, I got an idea. In the next year, I’m going to transfer this blog over to a website that I code entirely by myself.
I’ve tried my hand at learning to code before. I got the fundamentals of HTML and CSS down. But I’ve always stopped short because I never really had anything to work on. There are only so many sample cat websites I can make until I get bored.
This won’t happen this month. It’ll be a slow and steady process. And I’m excited.
As I do with my book, I’ll keep you updated with every step along the way. Stay tuned.
I got to ask one of my favorite questions yesterday.
In a session, a client told me he wanted to take more action toward his career. When I asked him what his next steps were, he said he needed to learn more and be better prepared.
I thought, prepared for what? The apocalypse?
“So you’re telling me that you want to get into action, but before you can do that, you need to learn more?” I thought, How much more have you decided you have to learn? On what date will you know enough to start taking action?
But instead, I asked a more direct question:
“If I told you I’d give you and your father each $10,000,000 if you got one customer to pay you for a service in the next week…how would you spend this week?”
His eyes got big and he smiled. “I’d reach out to as many people as I could and offer my services to them. Every day. I wouldn’t care about how many rejections I got because I’d only need one person to work with me.”
“Fuck yeah,” I replied. “So what’s stopping you from doing that now?”
His mouth opened and closed. “You know what, I don’t have a good answer for that.” We laughed.
The power of this question is that it removes the barrier of “I don’t know how.” When so much is on the table, our brains go right toward a version of: I’d do whatever it took.
The action is there. The creativity is there. It’s often just the drive that’s lacking.
When I asked another client that same question last week, she said, “Jesus. Hypothetical money is a powerful motivator.”
So let me ask you:
What’s something you really want in your life right now?
If I told you I’d give you $10 million if you created it this week, how would you spend your time?
By no means am I an expert in content creation. But I’ve made this blog, YouTube videos, and podcasts and have released them out into the world.
Whenever people tell me they’re thinking about creating something like this, I give them the same advice: do it.
That’s because they have no reason not to. Let me explain.
When I prepped all my audio equipment to record my first podcast in 2018, I was terrified. People are going to make fun of me. They won’t take me seriously. They’ll play my content for their friends and have a cringe-fest.
These emotions were even stronger when I started making videos. I was afraid I’d come off as a poser—someone going for something and it just not working.
However, with both of these ventures, I realized a refreshing truth:
No one gives a shit.
It turns out, people I went to high school with were NOT lining up in my comment sections to bash me. There was no one there.
When we start a creative pursuit, aside from a few supportive friends or family members (shoutout Grace and Aunt Pam!)…no one is interested. There are two main reasons for this:
We aren’t that good yet.
Building trust (i.e. interest) takes time.
Attention is a valuable resource. How easy is it for us to click out of something if it isn’t lighting us up?
I’ll occasionally go back and read my earlier blogs. I’m stunned anyone ever read one in its entirety. The question for any piece of content is: Why am I sticking around? What do I get out of this?
We need to agree that something brings us value if we’re going to continue coming back to it. I won’t subscribe to a YouTube channel unless I’ve watched at least 10 videos and loved them all.
So what can we do with this truth that nobody really cares about what we’re doing in the beginning? Simple…
We experiment. We have fun. We try things because we have nothing to lose.
Two years ago, I would write about habits, politics, and finance. I was throwing things at the wall and seeing what stuck. What did I enjoy writing about? What did people engage with?
I wrote blogs I disagree with now. Some blogs even make me cringe. But here’s the kicker.
I didn’t lose any readers…because I didn’t have any readers.
I remember being hesitant to do a podcast where I shared some political opinions. “I don’t want to be divisive,” I said. Then I remember there was no one to divide. I doubt I would’ve had much impact on the three people who listened to that episode.
When there’s no one there to disappoint, it can be a difficult time…or it can be an empowering one. It’s an opportunity to develop our skills, find our voice, and just have fun trying shit.
To anyone thinking about creating content of any sort, my loving advice is:
Just start. You have nothing to lose. No one cares (yet).
The book I’m currently writing is a decision out of necessity.
Over the last four years, between myself, my friends, and my colleagues, I’ve witnessed a disappointing phenomenon. It has to do with the fact that regardless of our skills or interests, every single one of us wants to create something.
A more fulfilling life, a business, a blog, a podcast, anything…
For 24 years, I repeated the notion—in my head and out loud—that “I’m not a business person.” I don’t get it. I’m not business savvy. I could never run a successful company.
Eventually, between obsessing over self-improvement and getting yelled at by Gary Vee enough times, I decided I wanted to try this here business thing.
But I had no fucking clue how. How does one just create a product or service and find customers to sell to? The answers eluded me. So I read every business book I could find.
They pumped me up. I learned so much about the mindsets and habits of productive CEOs and founders. I did this for two years, crafting the perfect library of knowledge.
But I looked around and noticed I still had no service and thus no customers. That’s when I realized what was holding me back. It wasn’t my lack of information. It was me.
I was waiting for permission to create what I wanted to create.
I knew way more about running a team than the kid on my street corner manning his lemonade stand…but that kid was actually doing the damn thing. I was merely imagining doing it.
He wasn’t comparing himself to his friends’ LinkedIn pages. He gathered a base of understanding, got some help setting everything up, and started selling.
We think we need more information. What we really need is to dive in and learn as we go.
We don’t need anyone’s permission to start something. We can just start.
This weekend, my photographer friend told me he’s making the decision to start posting on Instagram again.
I deleted mine last year because it was sucking too many hours away from my days. But this was a monumental move for him for a different reason.
He obsesses over who likes his pictures and over how many likes they get.
“There’s nothing more pathetic than scrolling through the list of likers several times a day,” he joked. This hit home.
There are two types of people who post on social media: those who check the likes, and liars.
While he didn’t ask for my advice directly, his predicament got me thinking…How do I manage to post consistently and not let the dopamine/validation/comparison train run me over?
Two things came to mind…
1) Be clear on the intention.
Why do we post something?
For my buddy, he said it’s fun to show his work. He has a skill for taking photos and he’d like to share that with friends and colleagues.
For me, I love sharing lessons I’ve learned. I write this blog every day except on Sundays. In the hopes that they resonate with someone who reads them, I post my favorites (including this one) to Facebook.
It doesn’t happen with every blog, but the most rewarding aspect of sharing my insights is when someone reaches out to tell me how a particular idea landed with them. This means they didn’t just read the words, they felt the emotion beyond them.
But above all, I write this blog every morning to dump my thoughts. It’s a way of holding myself accountable for a journaling habit. It helps me articulate and communicate better in other areas of my life.
If we’re going to create something and share it with others, we have to like it first.
Call me douchy, but I like my blogs. I enjoy reading them. I couldn’t do this every day if that weren’t the case. And I would’ve certainly quit during the early months where no one was reading them had I not simply enjoyed writing them.
When we start creating something, it’s probably shitty. Mediocre at best. People aren’t going to be too interested.
Since that’s the case, we better love it. If not, if we instead focus on creating something we hope others will love but we detest…now it’s a lose-lose. They don’t like it and we don’t like it.
The simple process is this:
Start creating something we enjoy.
Do it consistently and get better at it.
People will slowly begin to stick around to hear what we have to say.
If the intention is something we can’t control—money, subscribers, likes—that’s unsustainable. If we just keep at something we love doing, all that shit will come later.
2) Understand we’re human.
The human brain takes millennia to evolve. The meat in our skulls is pretty similar to that of our ancestors from 30,000 years ago.
Yet we live in an impossibly advanced society. Our technology has improved more in the last 20 years than the previous 200 before it.
The world around us is moving at rocket speed and we’re still running with software that has yet to be updated. We crave instant gratification, acceptance, and importance.
What’s more, our billion-dollar social media companies know this. They pay people millions of dollars to exploit these natural human weaknesses which keep us looking at our devices. We feel good when we get a like. Someone has shown us approval and belonging.
This may sound a little depressing, but all I’m saying is…
We’re not morons for checking our phones. This shit is designed to be addicting.
If we’re questioning our social media usage, we can simply ask:
In the past week, two different people have asked me why I don’t use my blog or newsletter to promote my business or try to get leads.
The answer is simple: I don’t want to. But here’s why.
1) It doesn’t work.
Not in my line of business.
Coaching is about building relationships with people through fun and powerful conversations. This is all done by reaching out, getting curious, and diving deep with individuals…not by sending a mass call to action and impersonally asking people to come to you.
Scenario 1: Someone you went to high school with posts the link to their website in a Facebook status telling everyone they’re giving free coaching sessions.
Scenario 2: Someone you went to high school with messages you asking how you’re doing. You hop on an hour-long call with them and share stories of what you both have been up to for the past decade. You discuss how you both have grown and the direction you’d like to head toward. You hear them talk about their coaching business and how passionate they are about helping people. Maybe at some point they invite you to a coaching session as a gift to see if they can help you too.
Which of these is more likely to lead to you sitting down and doing a session?
You might be thinking: neither. That’s normal. Most people don’t know what life coaching is. They’re afraid of being open and exploring vulnerabilities with someone they barely knew in high school.
But some people are totally down. So if they are, we schedule a call and explore what’s possible in their lives. But this only happens after the proper time has been taken to build that connection.
Here’s the catch…there is no catch. I love connecting with, reconnecting with, and learning more about people. So no matter what, I win. If we have a lovely hour-long chat about what they’re up to, I invite them to a coaching session, and they say no thanks, I still got everything I was hoping for.
I’m not here to “close” clients, hit my numbers, or get any sort of result. I’m here to have as many fun and powerful conversations as I possibly can. If a conversation leads to a paying client, cool! If not, cool!
Which brings me to the main reason I don’t promote my business on my blog or newsletter…