The startup world does a terrific job painting the picture of success at the end of the journey.
The big exit. The IPO. The offer to get acquired. Or the slow and steady road that eventually leads to an accumulation of other companies—until eventually either (repeat): exit, IPO, or getting acquired.
It’s a game of decisions. And for those of us playing the game competitively, it’s hard to do much else than be entirely consumed by the journey.
Which is probably why the startup world does very little to talk about the mental health aspect of things.
I was recently having a conversation with one of my closest friends, Matthew Jones, who is a licensed therapist. We were random roommates in college, and even though I’ve never taken a psychology class in my life, I feel like I’ve acquired an informal psych degree through our friendship.
In our conversation, we were talking about the ups and downs that inevitably come with building a startup (and simultaneously dealing with the ups and downs of life), and I said something I don’t think I’ve ever vocalized in the professional world, but as soon as I said it, I believed it wholeheartedly.
I said, “If you are a startup founder and you don’t have a business coach, and a life coach (except not a life coach, I really mean a therapist), you’re screwed.”
And I believe that to be 100% true.
On the business side of things, we have a number of advisors for my company, Digital Press. Some have built massive companies employing hundreds, even thousands of people. Some have built small, nimble startups that were successfully acquired. But all of them bring a unique perspective to the table. And whenever we find ourselves with an obstacle we’re not sure how to overcome, we talk to one (or all) of them, and are instantly given a level of perspective that would have taken us years to acquire on our own.
That’s the business side.
On the mental health side, I’ve actually been in therapy on a weekly basis since I was 22 years old (and had been in it for a few years as a teenager). In my younger years, it was a forced activity, as it is for most young adults. But as soon as I graduated college, I realized the immense value those conversations could have on my continued development—specifically related to things like meditation, mindfulness, and emotional growth. So I reached out to my spirituality teacher in college (I went to a liberal arts college, if you couldn’t tell), who offered individual work outside for students who had graduated, and told him I wanted to keep working on myself.
We’ve been working together ever since. It’s been nearly 8 years.
As a startup founder a year and a half in, I can remember moments when I fell out of practice—like when I moved from Chicago to Los Angeles. And while it didn’t seem like an issue in the moment, my falling out of practice with myself ultimately caused huge problems. I became more stressed. I became less self-aware. My relationship suffered. I rarely talked to my family. All the things you hear about founders experiencing from a distance, I experienced. And it wasn’t until I started getting back to my daily habits that I realized just how far “off the track” I’d gotten.
If you’re a founder—or honestly, if you’re anyone looking to achieve greatness in your career—here are the mindfulness habits I use as a startup founder to stay grounded, and focused, on a daily basis.
1. Every single morning, I go for a walk.
This is my newest daily check-in exercise, and it has become a foundational part of my daily routine.
Every single morning, as soon as I wake up, I turn my phone on silent and put it on my desk. I don’t touch it. I don’t check my email “real quick” (it’s never quick). I don’t open Instagram or Facebook. I don’t read the news. I put my phone down, I grab my jacket, tie my shoes, and walk outside.
As soon as the air hits my face, I immediately know what type of day it’s going to be—or I should say, I know where it is I’m starting from, emotionally, that day. Some days, I wake up energized and ready to go. Others, I need to ease into things. Some days, I know I’ll crush any sales-related task. Other days, I need to capitalize on my creative juices. But if you don’t know where you’re starting from for the day, then you will start to react to the day.
And the moment you start “reacting” is the moment you are no longer proactively defining and living your life.
2. In the middle of the day, when I make lunch, I turn everything off for at least 15 minutes.
As a founder, your day will never be done.
Your To-Do list will never be complete. Your inbox will never reach zero. Your company Slack will never sit idle. Your cell phone will never stop buzzing. Your entire world, as a founder, is constantly vibrating—which means, in order to find quiet time, you can’t wait for it to find you.
You have to be the one to draw a line in the sand and make it happen.
This is actually something I encourage all of our employees at Digital Press to do, whenever they need it. I will tell people constantly, “Go take a walk. Go grab a coffee. Go read a book for half an hour. Go reset, if that’s what you need.” I fundamentally don’t believe in measuring success in 8-hour increments. It’s the reason why we don’t track a single person’s time at the company. I don’t want the work we do reduced down to hours, in the same way I don’t measure my value as a writer based on word count.
Productivity requires breaks. So, take a break.
Just don’t sit on your phone during your break. That defeats the purpose.
3. Every Tuesday, I show up for therapy.
I’ll tell you, the biggest thing I didn’t anticipate in starting a company was how much of the job was emotional.
This is something I rarely hear startup founders talk about, and yet I think it’s the most taxing, and simultaneously most important part of the role. In order to be an effective leader, you have to “hold the space” for everyone else. All day long, people are coming to you with questions. People are coming to you with concerns. People are coming to you with wants, and needs, and completely fair requests. People are coming to you with unreasonable requests. People are coming to you with their own ideas, their own feelings, their own desire to feel heard, and seen, appreciated and validated.
And that can be extraordinarily exhausting.
Not because anyone is doing anything wrong. It is what it is. When you’re the founder (or one of the co-founders), you’re the one steering the ship. You’re the one with the answers. You’re the one people need to interact with, in order for them to be successful in their roles. And the bigger your company gets, the more time is being asked of you, to the point where hours and hours will go by, and you’ll realize you have made emotional space for everyone except yourself.
Again, all part of the job.
But holy hell, if you don’t give yourself somewhere to be heard and seen and validated too, then you are headed down a dark and twisted path as a founder. You aren’t superman. And as much as startup founders love to say, “I can handle it. I’m fine,” the truth is, you’re not fine. And if you don’t know it yet, you will soon.
This is something I really appreciate about the relationship I have with my co-founder, Drew Reggie. We’ve been friends for over a decade, and know each other so well that we are able to spot when the other person needs to talk something through, or take the afternoon to just relax. Without this sort of co-founder relationship, I couldn’t imagine building a company.
But, in addition, I also have a therapy appointment every Tuesday after work hours. And every Tuesday, right before I show up, I think to myself, “You know what? I’m fine. Life’s actually pretty good. Maybe I don’t need this after all.” And then 30 minutes in, I realize I’m not fine. I’m drained. I’m mentally exhausted. I’m <insert 17 more things>. And all I needed was to vocalize it, have someone give me the emotional space to feel heard, and then I’m able to reset.
Founders, listen: the game we’re playing is a sport. In the same way, when I played hockey, I needed to stretch and take care of my body, we as entrepreneurs need to take care of our mental states as much as possible. And that doesn’t mean reading a business book, or watching a documentary on Netflix. Those things are great ways to relax, but they’re not fixing the issues at the root. They’re not going to keep your head in the game over the long term.
4. After 8 p.m., I’m no longer available for business.
This was a horrible, horrible habit of mine in the early days of launching our company.
I would work from 7 a.m., through lunch, through dinner, and late into the night. Non-stop. I might, might, walk outside to get take-out food from a restaurant down the street. I didn’t go to the gym more than once or twice a week (if that). And that nightly personal writing habit I used to swear by, no longer existed. All I did was work.
And I paid for it. Dearly.
I had to learn the hard way that there are two very clear sides to me. On the one hand, yes, I am an entrepreneur. And when you’re an entrepreneur, there are a wide range of skill sets you need to constantly be refining in order to be successful in all necessary areas.
On the other hand, I’m a writer. The only thing I love more than entrepreneurship is writing. It’s the foundation of our entire business. It’s how I’ve been able to build a career for myself. It’s how I’ve been able to work with such impressive people. So, for me to stop writing and just work, was the equivalent of me only staying true to 50% of me.
And that’s tolerable in short-term sprints, if needed.
But it’s a very, very poor long-term strategy.
Now, I really force myself to stop working by 8 p.m. After that, my email closes and I’m no longer reachable. I try, best I can, to take my mind “off the work,” and instead do something creative. I write (like this here). I make music. I paint. I draw and journal. I write down titles of books I hope to write at some point. I do things that force me to use the other part of my brain—and bring me back in touch with my emotions.
The reason why this is so crucial (at least, for me) is because I find the days I give myself this creative break, I come back the next day even more driven, even more focused on the company we’re building. And the days I deprive myself of this creative freedom, I find myself a little more burned out the next day—and a little more burned out the day after that, and so on.
Entrepreneurs love to preach the mantra: grind, grind, grind. And maybe that works for some (“works” being a subjective word), but for me, it doesn’t. When I work, I work hard. But in order for me to be the most effective version of myself, especially over a long period of time, I need both. I need to separate. I need to see the forest, not the trees. I need to give myself permission to express what I’m feeling along the way. And in giving myself these freedoms, I am able to show up the next morning ready to tackle the obstacles of the day, head on.