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.


  1. I’m rooted squarely in the same camp as you, wanting mainly to work for myself as an independent agent. However, I’ve also thought of the possibility of working for someone else. My main reason for wanting to do this is the companionship aspect; being a free agent can get a little lonely sometimes, even though I have a lot of relationships and people I hang out with all the time. Being the only person working on my projects kind of makes me feel like an island, and I sometimes yearn to be part of a team working on something bigger.Your list of criteria is great. I particularly agree with the location-independent aspect; I’d love to be able to work from wherever I want, but still be part of a team. 

    •  @Thomas Frank Agreed. It can definitely get a little lonely sometimes! :-)

  2. Yip…those are all goodly criteria for considering working for someone else, and if such a job were to present itself to me I’d definitely ponder on the notion a while rather than just discounting it out of hand. That said, I’ve only just made the leap from full-time to self-employed and I’m really enjoying the growth I’m experiencing as a result of being my own boss. So it would definitely be a long and hard ponder. :-)

  3. Game Changer: How about working “with” someone who operates on the same principles – not “for” someone. They’re out there – confirmed reality.

    • Ah, but I work with people all the time, and the criteria is slightly different then, because I know I’ll be making a lot of the rules. This list is for the (what I consider to be) unenviable position of walking into someone else’s house and living there (metaphorically), as opposed to having a roommate that you shop around for flats with from the get-go.

  4. I totally get this. I started going into business for myself (full time) last year and it’s been rough. So I’ve given thought to working for someone else again. I agree with you that it’s different for someone who’s experienced 1) being free, 2) being in a leadership role. I definitely couldn’t go back to be a grunt. I want work on things that mean something, that — like you said — solve a problem. 

  5. I agree with most of this.
    I feel this way about my current state. I’m tempted to “go back to work” because I truly enjoy the comraderie and teamwork…being around other people all working towards one goal, but man, it’ll have to be an awesome project / place to be.

  6. Assuming one agrees with all these points, (and I do), this also serves as an excellent checklist for one’s current 9-5 “situation”.

  7. Assuming one agrees with all these points, (and I do), this also serves as an excellent checklist for one’s current 9-5 scenario.

  8. As someone who’s never worked for a company for more than three years, I don’t have much clout for a diatribe on commitment. Even so, I like the challenge of work “in” but not “of” a system. My ultimate allies and allegiances are my own and this frees me from the tyranny of false security; it also frees me from the fears which drive people into the details of dead tasks. “Game-changers” can do independently or interdependly; they can never do it with a dependent and subordinate ethos.

  9. I find that working for yourself can be very lonely. Sure it depends on the nature of your business but you are largely working by yourself and on the move… and your day to day contact with people can be very limited. A benefit of working for someone else is that usually other people work for them too and you can get to know some great people who you’d probably never collide with had you not worked for them.Great post, Colin!

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    • Haha, very seldom! On that particular occasion, it was literally the only thing available to drink (including potable water), so I made the most of it and drank dramatically. It’s become a bit of an inside joke between me and the friend I was with, now, so we drink Smirnoff’s dramatically from time to time.

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  12. This is a lot like my perfect job because I like challenges and want to do something good for who I’m working for, but I like temporary the flexible. I could get more done at the times I like working than normal business hours and the moment I feel like the job will take over and I’ll have to stay there with no end I end up not liking what I’m doing very much and feel caged. I’m really liking your blog and hoping that when I’m done with college I could find a system that allows me to travel and works for me.

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