“Today is the day I let you go… You need to do your own thing, and I’m helping you do that.”

When you have a platform like this site, the temptation is to only show the good things: the bits of knowledge, the tropical Instagrams, the career victories. But, life isn’t all wins, and I shouldn’t try to convince anyone that it is.

I’m no longer working with SumoMe (now Sumo.com). I’d been there for 8 months, and while the first 6 months were great, the last two were… less than ideal.

That’s no fault of the company, the people there, or anything external to me. I stand by the fact that it’s an amazing place to work, and if you’re thinking of applying, you shouldn’t take my departure as implying anything bad about them (I hear they’re looking for a marketer).

I’ve learned, now, that I’m largely unable to work for other people.

I shouldn’t be surprised: since elementary school, I’ve done the bare minimum when someone tells me to do something, preferring instead to focus on whatever project I’m obsessively infatuated with at the time.

If I’d never made money on my own, these maverick propensities could be managed. I would accept that doing things you don’t want to do and having a 9-5 is part of life. But the intense high of entrepreneurship and experiencing complete self-ownership has corroded my ability to work on something that isn’t mine.

After a two-month decline, followed by a week offline in Medellin and publishing an article broadcasting my desire to start a life of independent work and travel, I realized it was time to move on, and they realized that they should let me go before investing more time and energy.

The Ideal Job

“If you were in my place, what would you do? Would you take the job from your ideal mentor? Or travel the world and do your own thing?”

Two and a half years ago, I started a company called Tailored Fit providing algorithmic clothes shopping recommendations (think Pandora + Shop Style). We raised $125,000 (though only collected $75,000), and burned it all because we had no idea what we were doing.

Then, a year ago, my friend Justin and I started Programming for Marketers. This went better. Instead of burning $75,000 of other people’s money over a year, we made $50,000 in 5 months. That happened right as I was wrapping up college, leaving me in prime position to run the business while traveling the world a la 4-Hour Workweek.

As that was happening, Noah (SumoMe CEO) and I started talking about me joining SumoMe. I was stuck between two incredibly attractive offers:

1. Learn from someone I deeply respect as an Internet marketer and join a fast growing startup
2. Run my own business from the beaches of Argentina, sipping Malbec and eating steak

Originally, I had told myself that I wouldn’t work for anyone after graduation. Having tasted self-ownership from Tailored Fit, I knew it would be hard to work for someone else, and seeing Programming for Marketers take off only reinforced that belief.

That said, I knew if there was one job that could change my mind, it would be doing marketing for SumoMe. It had everything I needed:

1. Flexible schedule
2. Significant control over my work
3. Fun team
4. Amazing mentor
5. Huge learning possibilities

I decided to take it.

Shower Thoughts

“I’d say it’s hard to do a really good job on anything you don’t think about in the shower.” – Paul Graham

Six months in, I realized something had shifted. Nateliason.com was gaining traction after a few very popular sex articles and I found myself spending more of my time focused on its growth.

That’s a problem in a startup. Early employees have to put the collective identity above their own. It’s the only way the organization functions.

If the employees are more focused on their own brand than the collective brand, the company won’t get their best work and there won’t have been any point in hiring them in the first place.

A simple test for where you have your “work identity” is what you think about in the shower. In the beginning, my shower thoughts revolved around growing the SumoMe user base. Then around February, they shifted more and more to how to grow Nateliason.com.

When I brought up this problem two months ago, I knew there was, at least, a 10% chance I’d be fired on the spot. Conventional wisdom would say not to tell your employer that you’re dissatisfied and thinking of leaving, but I knew we either had to fix it or I had to go.

We tried a lot: adjusting my schedule, offloading the tasks I didn’t enjoy, hiring other people, but that “Nat’s unhappy” idea had been planted and it only got worse.

Be the Hydra

“Hydra, in Greek mythology, is a serpent-like creature that… has numerous heads. Each time one is cut off, two grow back. So harm is what it likes.” – Nassim Taleb, Antifragile

When I told my parents that I was planning on leaving a high paying job with no intention of taking another one, and then told them a few days later that I’d been fired anyway, they were… less than excited.

The traditional view of jobs is that you should have one, that losing one is bad, that getting fired is especially bad, and that if you find yourself in a situation without one then you better hustle to get a new one.

But that’s the traditional view.

If the proverbial ax falls and you lose your head, you can behave in two ways: like the chicken, running around clutching at your stump. Or, like the Hydra, growing back two in its place.

When I shut down Tailored Fit, I gained the time and energy to start this site and learn marketing. When I quit doing freelance projects, I grew Programming for Marketers faster and with more energy. When I slowed work on Programming for Marketers, I could better grow SumoMe.

In each case, the prior project taught me something about myself and provided me new skills. Those allowed me to double down on the new project, and learn more and grow faster than I ever could have in the old one.

So with this head cut, what grows in its place?

What’s Next

“The old rules are crumbling and nobody knows what the new rules are. So make up your own rules.” – Neil Gaiman, “Make Good Art” Keynote Address 2012

If I can have the ideal job, get dissatisfied, and blow it up in 8 months, then it’s unlikely I’ll be able to be satisfied working for anyone.

So I’m not going to. I’ve created the self-imposed restraint that I won’t look for work, or even take on freelance projects unless I reach a point where I have less than 2 months of savings left.

Looking at the Runway Calculator I’m fine at my current burn rate in Austin until my lease runs out, and then I can travel to any major inexpensive nomad city (Medellin, Chiang Mai, Las Palmas, etc.) and work from there almost indefinitely.

I don’t regret the decision I made a year ago. I learned a ton from the role and am significantly more prepared now to break out on my own creative projects than I was then.

Like Tailored Fit, and so many projects before it, SumoMe didn’t work out in the end, but I wouldn’t trade anything for the learning experience. “Failure” gets a bad rap, but in many cases, it’s the best teacher.

As for what I’m working on now, it’s a combination of things:

1. A book. More on this soon.
2. This site. My favorite project, and which the book is an extension of.
3. Programming for Marketers. It’s fun and it keeps the lights on.

If you want to be part of that journey, be sure to join my list. Aside from new articles, I’ll be putting together some communities around the books and projects I’m working on, and it’d be fun to have you in them.

Nat