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Two lessons from two months of self employment

photo cred The Awkward Yeti

On December 12, 2014, I quit my job to start a year of side projects. The next day, I woke up at 4AM in a cold sweaty panic and started writing. I wanted to publish a book called Working Jobs (inspired by Jonathan Saffron Foer’s Eating Animals) that would explain why America’s tradition of work and the modern workplace were incompatible and that anybody embracing the “work hard, pay your dues, do what you’re told” attitude were going to get replaced by machines and outsourcing.

I was convinced I’d seen the future, so I quit my job and dedicated myself to projects that I thought could help people escape this deathtrap and do more of what they enjoy for a living.

Working Jobs was the capstone of these projects. The podcast, a newsletter, and a steady stream of blogging served to support the mission of getting this life changing insight into the hands of as many people as possible. I worked on it every morning. I went to sleep thinking about it. When I wasn’t trudging through rewrites and edits, I was building things to help premarket the book. I designed an entire Kickstarter campaign once I realized it wasn’t getting enough traction on its own.

After a month and a half, I cancelled the launch.

The decision wasn’t easy, but what started off as a steep learning experience with enormous opportunities to impact people and build my platform as an entrepreneur had devolved into a chore that wasn’t taking shape and wouldn’t get into enough hands.

Harsh reality: I quit my job and fewer than two months later, I quit my book.

I spent a day mourning, but I knew I made the right decision. Any additional investment in the book would have kept me from investing in other, potentially more greedy, projects.

I wasn’t prepared for any of this when I quit my job. Managing my own time 100% is the most profound learning experience I’ve encountered. I recommend it to anybody. I’m eager to continue learning. In that spirit, here are two of my biggest takeaways from two months of self employment.

#1 Never stop celebrating yourself

The choice to employ yourself is a self celebrating decision: you hired yourself. The only reason to hire yourself is because you believe it will bring more joy to your life and better connect you to your mission. I don’t think everybody is ready to leave the comfortable structures of employment, but I do think everybody’s potential for self actualization is higher outside of it.

Business goals are great (and sometimes critical for survival), but don’t let them bully your self-esteem and health. Doing something new is hard. Whether you’re building a startup, writing a book, training for sports, or performing music, the experience of developing skills that match your high expectations is emotional.

Many companies don’t get any value from their employees until several months of training. This is particularly true for the highest paying jobs out of college (e.g. banking, consulting, engineering). They know and expect you to suck at what they need you to do until you don’t suck at it, at which point you’ll start paying for yourself.

It’s harder to accept this when you hire yourself, because, as a boss, you’re a hard ass. You see very clearly your potential and wonder why you’re not achieving it yet. Even if you’re reaching the theoretical limit of your efforts at any given time, the boss side of your self employment wonders whether you’re lazy, stupid, or hopeless.

Don’t lose the plot. You’re employing yourself for more joy and better actualization of your mission. Only enable self-critical experiences if they are helpful. Once they start to produce more suffering than joy and distract you from improving and contributing to the mission, you enter an existential rut wondering why the hell you quit your job.

Along these lines, try and be healthier than you ever were before. Eat healthier, sleep well, build routines that help you do more of what you enjoy and less of what you don’t, surround yourself with people you love, and embrace every day. You’ll find that you’re less willing to give yourself vacations and sick days than even the worst boss you’ve worked for. Avoid burnout by taking care of yourself every day.

#2 Make space for experimentation

Even if I never finish Working Jobs, I won’t feel like I wasted time on it. It helped me build healthy work habits, trained me as a writer and editor, introduced me to the crippling anxieties of creativity, refined my understanding of my mission, and, most importantly, produced several promising byproducts that I continue to nurture.

You see this frequently with companies. They research a certain product and through that process, discover a completely different and more promising product. The majority of inventions that come through a company’s R&D lab never make it to production, but it’s only by producing several unpromising ideas that they come up with a promising one. In tech, companies can’t survive unless they innovate. Facebook’s revenues stagnated until they launched mobile ads, at which point their revenues doubled. Apple’s revenue stagnated until they released the iPhone, at which point their revenues skyrocketed.

It’s harder as a single person to balance going broad and going deep. Most people will tell you to go deep in one thing and avoid spreading yourself too thin. This is true if you want to turn into a very effective cog (employee) that might some day be placed in a very effective machine (company). If you want to make it on your own, it’s much smarter to give yourself space to deliberately dabble.

Dabbling around Working Jobs produced three tangible byproducts:

  1. Why We Work - a podcast about people on a mission and how they accomplish that mission. Originally, this was Working Jobs Radio where I interviewed people in service of learning about their experiences so I could beef up the book. Instead, I realized that the podcast better contributed to my mission of helping people do more of what they enjoy by inspiring listeners with stories of purpose.
  2. Blog and newsletter - trying to write a book means spending a lot of time in front of a word processor. Even though Working Jobs isn’t taking shape, I have an unshakeable habit of writing in the mornings, now, which I cherish. The writing comes more naturally and my capabilities as a writer slowly improve. If you haven’t subscribed to the weekly newsletter yet, you should consider it.
  3. A different book - I unbundled my thinking about entrepreneurship and side projects from Working Jobs and am nearly done with a draft of a different book. If all goes to plan, I’ll hit my bucket list goal of publishing a book by 25 (I turn 26 on March 15th).

I observed myself spending more time and energy on these byproducts than Working Jobs. I found them more interesting and they were getting more traction. This evidence made the decision to quit much easier.

Working Jobs dies and out of its ashes a podcast, blog, and new book that produce more joy and better serve my mission. And while three things are more than one, I somehow have more time each day to chip away at my technical projects and advise startups.

Since I quit, I’ve made an average of $20 per month from creative projects (unsolicited donations... thanks!), but the experience of self employment has been worth the lost income. Thanks for supporting me with your time and energy--exciting things to come.

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