13 May

Startups and the freedom myth

This article was originally published on katekendall.com
Startups and the freedom myth

I’ve just finished reading Ryan Hoover’s post: Startups ≠ Freedom.

He writes:
“People start companies to become “their own boss” for the same reason — they seek freedom. But in most cases, it’s ironically the exact opposite. As a founder, you’re responsible to your investors (assuming you take money), your team, and your users. There’s no “two week notice” like in a regular job. It’s empowering and scary. Many romanticize startups and ignore this reality when pursuing entrepreneurship.”

This came at a poignant time for me.

When I first started doing entrepreneurial things, the driving factor was about creating freedom: freedom to focus on building things without constraints; to solve problems I was passionate about and to work with people I wanted to. Freedom to work to my own productivity rhythm and schedule. Freedom to say no, and yes to new things. Freedom to experiment and explore.

Five years ago, I quit my management job, sold most of my possessions, travelled the globe and lived in Airbnbs. I was consulting and bootstrapping my first company. It was an extremely liberated state of being – highly independent with full freedom of expression.

Being the CEO or founder of a investor-back startup is a very different experience. You taste a different sense of freedom. Like Ryan says, you’re empowered and have a ton of responsibility, but you aren’t free. It’s a huge commitment and you have to really want to do it. The desire to do it is innate.

I’m lucky in that while my day to day has changed since raising funding, our product is all about putting the ‘free’ in freelancing – connecting marketing, content and community professionals with remote work gigs. If I wasn’t working on CloudPeeps, I’d actually be a Peep! I’d work on clients likeBeather, be a nomad like Briana in South East Asia and start fun side projects like Tom. Witnessing people take the next step on their journey and going independent inspires me all over again.

While this post is less to do with recommendations (asides from suggesting you read this relatedPaul Graham essay), one of the things I’ve found helpful in my funded startup journey is allowing myself the time to still ‘live’ and have fun. If you’re going to give everything to your startup for five-plus years, you may as well do it in a format that energizes and fulfills you.

For me, that’s getting out of the city now and then to work remotely. I’ve just spent 10 days in Mexico where RescueTime tells me I’ve been more productive than at home, where I’ve checked outlocal coworking spaces, got on an early-riser schedule, Slacked with my team, shamelessly Instagrammed, and still enjoyed the odd comically-touristy piña colada. 🙂

DOWNTOWN, Playa del Carmen, Quintana Roo, Mexico

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