Can an Entrepreneur Have a Creative Life?

A few months ago, I was walking into my office and felt overwhelmed with a sense of anxiety and dread. A realization hit me. The building that was supposed to be my ‘place’ for creative work had become anything but. 7 years in, I’d lost the creative spark of my work entirely. And I wanted it back.

(Note: I originally wrote this post in Feb 2019. Realized it got lost in the shuffle when we were approached to sell the business so sharing it now.)

So many of the reasons I started a company in the first place have since fallen by they wayside. Some for the better (getting rich and famous) and some for the worse (working with my friends.) But recently, I realized I’d lost something whose importance I’d failed to understand until it was gone. My desire and ability to create.

In hindsight, I can see I start businesses in large part for the creative endeavor. I love seeing something created from nothing. I love imagining with other bright people ways the world could be different. I even love the often painful process of iterating through an early idea as pieces of the model fail and must be re-imagined.
As we’ve worked to scale Twenty20 these past few years, I realized recently I’ve failed to protect that creative space for myself. Or, perhaps more accurately, I’ve forgone it entirely. Shoved it aside for the more important work of a CEO.

There’s no part of my day or week set aside for creative endeavor.

I’ve failed to maintain any accountabilities for myself inside the organization that scratch this creative itch. I oversee finance, planning, staffing, capital, corp dev. But the fun stuff, the customer conversations, debates on product vision, the exploration of how to build a legacy brand, and many other of the creative elements of business building…I’ve delegated these things to others. Much of that delegation is necessary, no doubt, and most of that work is now in the hands of more talented people. But, as a founder, to let go entirely of the creative work of building one’s product and company. I realize now, that’s been a mistake.

The office has become a place of tasks to be done and fires to be put out. I feel I’m living my weeks a slave to my to-do list app. There’s no time or space for creativity. And part of me is shriveled up, threatening to die.

So I’ve begun experimenting with finding my way back to letting the office be a place of creativity for me. I started by doing something that was quite difficult to me. I turned one of our conference rooms into a private office for myself. I did this because I realized as a founding CEO I have a tremendously hard time separating my own mental space from whatever is going on in the team. Sitting on the floor all day every day, while nice from a meritocracy perspective, was destructive to my own creative space. And I decided I needed to be ‘selfish’ and create some space for myself. A room where I could close a door, turn on some music, and do creative work.

I’m also back to writing. Writing is one of the magical intersections for me where something that fuels me creatively, and psychologically, is of great benefit to the business. Writing helps me to clarify my thoughts as a leader. It helps me process the emotions of startup life by acting as some kind of cleansing, refining process. Writing gives my team visibility into my thoughts as a CEO and as a human. My writing had a very positive impact on our relationships with other companies. We have more inbound partnership inquiries, and they are much warmer, because people feel they know us a bit before reaching out.

All those things being so, it’s so damn hard to prioritize time to write. It never feels like the most important thing on my to-do list. So it get’s pushed to the bottom. And months go by where I don’t write. Thus, starting this week, I’m trying something new. I’m blocking time each day to write. I’m drawing a line in the sand and prioritizing a habit and craft that I know is good for me, good for my team, and good for our business.

Curious if I can make writing an active, daily part of my life as a CEO. Excited to be doing so today, in my cozy little second floor office.

Thanks for reading that writing!

Matt