I’m the CEO of Digital Press, a thought leadership agency for other founders and C-suite executives.
To be perfectly honest with you, I’ve been working 7-days per week for as long as I can remember.
Even back in high school, when my peers would count down the minutes until the weekend so they could hang out at the mall or a movie, I would make lists in my notebooks of all the things I wanted to achieve in the World of Warcraft. I didn’t care about going to parties. I didn’t see Saturday and Sunday as “days to do nothing.” I saw them as opportunities to get ahead on all the things I cared about — and ultimately wanted to achieve.
After college, when I was working at a digital marketing agency, I treated my weekends exactly the same. While all of my peers posted pictures of themselves at Sunday brunch, ‘cheers’ing mimosas on Instagram, I was posted up at a coffee shop somewhere, headphones in, working on my first book. I didn’t see weekends as time to relax from the long work week. I saw weekends as my only time to make any real progress on the life I actually wanted for myself — which was to become a professional writer.
Of course, a lot of people disagreed with the way I spent my time.
In fact, I questioned even within myself.
There was a huge part of me in my early twenties, and even more so as a teenager, where I really struggled to be OK with ignoring the short-term rewards for the longer term payoff.
As much as I reference my experiences as a hardcore teenager gamer, and see how influential they were on my development as a human, the truth is, it took a toll on me. I spent many, many nights both obsessed with my goals and borderline depressed from spending so much time alone. And when I was fresh out of college, I remember so many nights declining invitations to do something social, forcing myself to sit at my desk and write instead. It was hard to see other people my age living a life that looked like so much fun — meanwhile continuing to invest in the idea of a future that had yet to materialize.
But eventually, it did.
Everything I said I wanted to happen, happened.
After 4 years of investing almost every single weekend into my aspirations to become a writer, I published my first book, Confessions of a Teenage Gamer.
The same day, I left my 9–5 job and went all-in on becoming a full-time writer. My first month, I doubled my previous salary. My second month, I doubled it again — ghostwriting for a handful of CEOs who wanted to position themselves as thought leaders in their industry. My third month, I doubled it again. And by the end of 2017, I decided the next logical step was to build a company.
Exactly 1 year later, Digital Press has 15+ employees and 30+ clients around the world — and we still have a long way to go.
When I look back on all of the experiences that got me to where I am today, my gut reaction is to drive home the point that you have to forgo short-term rewards in order to see the long term payoff.
And my rationale for that perspective is because that’s what I had to do in order to make it happen. I was living in a tiny studio apartment in Chicago, where my rent was 50% of my monthly paycheck. I didn’t have air conditioning. My heater was from the 1950s (and had an open flame). My kitchen was the size of a small closet, and the cabinet under the sink was broken — one of the doors wasn’t even on the hinge, it just sat on the floor and rested up against the other cabinet. For 3 of the 4 years, I slept on an air mattress because I couldn’t afford to buy a real bed. I couldn’t shop at Whole Foods because it was too expensive, so I had to shop at the shady grocery store down the street instead. And I wasn’t making enough to be able to take cabs around the city or eat out anywhere nice, so every Friday night I would ride the train home from work and treat myself to a bowl from Chipotle, before diving into my list of goals for the weekend.
Grinding every single weekend is what it took for me to become successful. And I was OK with that.
But now that I am the CEO of my own company, and I spend 95% of my time talking to CEOs of other companies, I don’t fully agree with my previous logic.
I think as a kid and a young adult, I was so starved for success, so hungry to make something of myself, that I felt guilty about ever spending time doing anything else. I saw my goals as deeply personal promises to myself that I couldn’t break, and even on the rare occasions when I would allow myself to go out for a night, I struggled to enjoy it. I felt bad for wasting that night out at a bar with friends, when I could have taken one more step toward the future I actually wanted for myself.
Today, it’s easier for me to see that I could have been a tad easier on myself.
I have more responsibility in my life right now than I’ve ever had in my entire life (arguably combined).
I have more projects on my plate than I’ve ever had before. I have more people to cater to, more people to hold accountable (and to be accountable to), more of every single variable — and I am giving myself more “down” time than ever in the past. Because I’ve learned that there is a tipping point. You have to be productive and driven up to a certain level, a certain daily or weekly or monthly benchmark. And then once you hit that, anything beyond starts to work against you. Instead of getting “more” done, you end up getting harder on yourself. Instead of being “more” productive, you become less productive — and more critical of whatever it is you’re doing. Instead of getting better, faster, stronger, you start to slow down, get sloppy, until finally burning out.
Being the CEO of a company, especially, isn’t about grinding until you fall asleep face-first on your keyboard. That’s what being a hardcore gamer is about — and you can do that because the stakes are a lot lower. You aren’t responsible for people’s livelihoods, their salaries. You aren’t responsible to clients who are paying you real money to do great work. You have the luxury of burning out.
As the CEO, your job is to stay sharp, well rested, emotionally stable, and self aware. The moment you stop being any of those things, you suffer, your team suffers, your work suffers, and your company suffers. Which means, the name of the game isn’t to do “more.” The game is to do more than enough, so that you are competitive and making terrific progress, but not so much that you’re running a sprint pace during a marathon.
How you spend your weekends are a great indicator.
I still work 7 days per week. I rarely go a day without spending at least a 2–3 hours doing something related to my company or my own writing. But I’m learning that, some days, some weeks, 2–3 hours is more than enough. And what’s more important is knowing where you’re at, emotionally, and giving yourself time to rest, reflect, and recharge.
I used to think being the CEO meant you worked harder than everyone else.
And in many circumstances, that’s true.
But being the CEO means working smart — and sometimes the smartest thing you can do is to not work at all.