Who Could Hire Me

Opting to work for myself — forever and ever — was one of the best decisions I ever made.

I started my first company at 19, and back then I had ideas, but little practical knowledge of how to run a business. I had a few successes and a lot of flops, and it was exciting, but it wasn’t sustainable. I ended up taking a job when I graduated from college, and after a year of that, decided to give working for myself another go.

Thankfully, by that time I had acquired a fairly large body of knowledge involving the nuts and bolts of business, not just big, bold, brash ideas of how I was going to do everything differently and better than it’s ever been done before. Melding my vision with reality has been a harsh pill to swallow sometimes, but I’ve found that certain supposedly-unbreakable rules can be bent, and in many cases, bending can be most satisfying.

It’s with this in mind that I present you with a list of reasons I would work for someone else.

I should note ahead of time that I’m not planning to work for anyone else, nor do I particularly relish the thought, but I’ve been asked the question, “Would you ever go back to working for someone else again?” in the past, and have always answered (incorrectly) that there is no way in hell I would ever do so…I love the freedom of what I do now far too much.

Giving it more thought (as I’ve been able to do with a LOT of things during this road trip I’m currently on), however, I’ve come up with some properties of a job that would convince me to work for someone else (at least for a while), rather than being an independent agent, answering to no one but myself, as I am now.

1. Temporary

I’ve found that the best things in life tend to be temporary. Relationships can be better, for example, when they have a time limit, because then both people stay excited, don’t get hung up on tiny issues, and are able to make the most of the time they have.

I see the same theory working well with employment. I feel that I would be far more effective and excited about the work I was doing if I knew when my stint doing that kind of work for whomever I was working for would end.

Ideally, this would be somewhere between 6 months and 2 years, though it would really depend on the work, and who it was with. I wouldn’t want to get started and leave before I could achieve anything noteworthy and cool, but I also want to know when I’ll be done, so that the little things that would normally bug me otherwise about such work situations can be back-seated, and the opportunity can stay firmly in the honeymoon stage for the duration.

2. Flexible

Remote working would be ideal, but I could even fathom doing something where I was stuck in one spot, so long as I had super-flexible hours.

Ideally, it would be something with loose hours but firm goals; I like reaching goals, but I also like to know that if I reach them in a clever, time-saving way, I won’t be punished for doing so with more work to ‘fill the hours.’

It would also be nice to have the opportunity to explore different facets of whatever industry I’m involved in, which is not always a possibility, especially in cog-meet-machine style work environments.

3. Game-Changing

There are a lot of ways to get into work you’re doing, but I make it a focus to spend my time on things that I consider to be epic in some way.

This can mean being involved with the construction or promotion of some industry-upsetting technology, working with people who are aiming to do something that’s never been done before, or even just getting to participate in a field that’s unusual or nifty.

Fields I think are amazing: private space travel, electronic currency, augmented reality, decentralized internet-style networks, higher-education alternatives, new publishing; there are others. You bet your ass.

4. Challenging

I can always make money, but challenges worth applying myself to are fewer and far between.

To work for someone else, I would have to know that what I was doing would challenge me to learn new things, push my limits, and, hopefully, solve some problems along the way. When I go to sleep at the end of the day, I like to know I made a difference in some way. The same would have to be true for any job I might consider taking.


Of course, this is all just speculation, and I doubt something will come along that fulfills all these requirements, and I’m totally okay with that. I like where I’m at and where I’m going.

But this is a list I think every entrepreneur should make for themselves and have handy, just in case an opportunity comes along to work for someone else that might otherwise be missed because of misguided dogmatism.

After all, rules can be bent, and sometimes it’s most satisfying when they are.