Why I’m working for the man and not doing a startup

After finding out I was going to work for Microsoft,  friend of mine asked “Why are you working for the man? Aren’t you into startups?”  My response was mostly “I like getting a paycheck every two weeks” but there’s more to it than that.

Sure, stability is a huge benefit of a regular full time job. I get health insurance, time off, and the pay is pretty good too. That’s not the biggest reason I don’t want to do a startup (right now). The biggest reason is that there isn’t an idea I’m passionate enough about that I’m willing to devote my life to.

I know that if I just join up with someone else’s idea, I’m not going to be passionate enough to deal with all the stupid stuff that startup founders have to deal with. If I founded a company, I could be left dealing with things like payroll, bills, and legal issues. I don’t want to deal with that right now. I want to focus on making cool shit.

But what about all the stupid stuff you have to deal with when you work for the man? That stuff just isn’t that important. If I forget to log my task estimation hours my manager might send me an email. If I forgot to pay my companies electric bill the consequences are a little more severe.

I don’t have to found a company though. I could join up as a developer and have a HUGE impact on the company. That definitely has some appeal and maybe someday that’s what I’ll do. Right now, I’m enjoying working for “the man” and am happy that the software I work on will be used by millions of people.

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17 Responses to Why I’m working for the man and not doing a startup

  1. “But what about all the stupid stuff you have to deal with when you work for the man? That stuff just isn’t that important. If I forget to log my task estimation hours my manager might send me an email. If I forgot to pay my companies electric bill the consequences are a little more severe.”


    Maybe this is just a difference in outlook, but if I were forced to log my hours it would probably either send me into a fury or the depths of despair. Actually, more likely, I’d quit. Or be fired. It’s happened before.

    Yet I have basically no problem having no safety net, and taking responsibility for my employees, millions of dollars, and the fate of the planet.


    The only discriminating factor I can see is that being forced to log hours makes me feel like a kid unworthy of trust. Any others?

    I feel like I’ve learned something about myself.

  2. Florian says:

    For me it’s not about “not working for the man” (although there’s that). For me it’s about that doing startup stuff and freelancing. It’s really about quality of life, and how much you get out of it. Being employed I couldn’t change that equation. Have to be there 8/5, 4 weeks of paid vacation, get paid X amount $ no matter how much wealth I help create etc.

    Now I get more than 6 months of free time per year, work less for more money and I’m no less insured than before. Now that’s a win situation.

  3. You say that you know if you worked on someone else’s idea you wouldn’t be able to find the passion to sustain you. I would challenge you on that – how can you be so sure? I joined Twilio very early and it wasn’t my idea. However, I took my passion for making software developers happy (and my even more fundamental professional passion for helping people be productive) and connected it with their specific idea. I never would have thought of Twilio, but I’m so happy to be part of making it exist.

    My suggestion: Don’t ever stop prospecting for other people and ideas that you could get behind, because when you find them it is magical.

  4. Jon says:

    You’ll be getting a paycheck and experience, neither of which is a bad thing to have if you do decide to start your own company in the future.

    Some people are more of a slave in their own startup, putting in countless hours for a hope in the future that might not bear fruit. “The man” for them are their clients. It’s a risk either way. I personally like the idea of working for an established company, meanwhile working at home on my own ideas. Part-time entrepreneur.

    I think it’s smart of you to not try starting something if you haven’t found a passion yet, otherwise you may end up creating yet another time tracking app, or contact manager, or to-do list. Ha!

    One other advantage is that when you get home, you can truly relax. Work is work, home is home. The lines get blurred when you own a startup. Maybe it’s just me, but in the back of my mind I’m always thinking about my side businesses. Whenever I play a video game or do anything, I know I could be working and making more money instead. It’s a challenge sometimes to turn off the workaholic tendancies when you run a startup. :)

  5. Don says:

    Your honesty is refreshing. In my experience, people are either hardwired to be startup entrepreneurs or they’re not – but I will add that I felt the same way as you when I graduated law school. I worked for a Wall Street firm for two years and ultimately decided there had to be more to life. I was representing people who had created outrageously successful businesses, and the truth is I wanted to BE on of them rather than WORK for one of them. I’ve been fortunate to have founded a series of multimillion-dollar startups over the last 15 years. Was it risky/scary? Absolutely – especially when leaving the security of a six-figure income meant that I would not likely ever be able to return. Would I do it again? In a heartbeat! Do what makes sense for you now….and just know that your position may change when you realize that you’re just as smart — if not SMARTER — than the people you’re WORKING for!!

  6. Dylan Lacey says:

    I’m with you 100% on the Passion-by-Proxy issue. While working on cool stuff is, well, cool, if it’s someone else’s idea I feel almost jealous that I didn’t have it first. It’s almost a regret that the idea was had by someone else, or perhaps that you haven’t had an idea of the same caliber. It’s bullshit but no amount of telling yourself that helps.

  7. PJ Brunet says:

    “dealing with things like payroll, bills, and legal issues.”

    That’s the problem with the US. The government is too big and has strangled the innovation out of us.

    @Jon “The lines get blurred when you own a startup.” No kidding!

  8. Edwin says:

    @Danielle, in my experience nobody has to “log hours” at Microsoft, as in “why were you only here 37.2 hours last week?” Closest I’ve seen is that some teams keep track of the original estimate and actual time spent for each feature, in order to use the info to do better estimation in future – similar to what Watts Humphrey recommends in the Personal Software Process, or evidence-based scheduling.

  9. TerraFrost says:

    Presumably by the time you’re big enough to have a building where you’d need to pay the electric bill you could hand that responsibility off to someone else because presumably you’d have multiple employees by then.

    If you’re the only person in your startup you can just work from home. No need to lease or buy office space and presumably you’re already paying your electricity bills on a regular basis without any problems!

    That said, I do agree with the whole “you ought not do something unless you’re passionate about it” theme of your post. If you’re not passionate about it then it’s pretty much a second job for which you’re probably not being paid.

  10. fetzig! says:

    there is a world between chaotic startups and billion dollar companies like microsoft…

  11. Lukas says:

    Stability is an illusion when “working for the man” – you could be fired the next day.

  12. Randall says:

    I know. Before Microsoft I worked at a ~200 person company for 3 years.

  13. Pingback: Why I'm working for the man and not doing a startup | farp.blog - hirendhara.in

  14. Michael Dorf says:

    I agree. There’s nothing wrong with a steady paycheck and job stability. If you ARE missing some adventure in your life, start your own gig on the side. You’ll feel like you’re working for a startup (your own!) and still have a job security while you’re “exploring”.

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