I have job offers from Microsoft & a startup. MS has a good salary package & my father is insistent. I’m more interested in joining the startup, but the salary is less. MS can improve my finances, but may be fatal for my career. What should I do?

If you want to do a startup, do it now before you get financially dependent on the corporate teat. It’s much harder to go from a corporate income to startup income than the other way around.

(A little extra info for those who don’t believe in TL;DR…

In my career, I’ve worked as a freelance journalist (I guess that in some ways equates to contractor), freelance software engineer, I’ve worked for large corporations (Microsoft), mid-size corps (Surreal/Midway, Sierra/Vivendi Universal), and small startups (Intelligent Ion, X-Ray Kid Studios).

I learned different things at the different places… Microsoft this time around has taught me a lot more about business analysis, “Nikeing” things (Just Do It… already!) and strategic thinking in a big-corp world where you literally can throw money at problems… Surreal/Sierra were just plain awesome places to work. Intelligent Ion? Interesting, and met some cool folks, but ultimately not a great fit – I took too long to realize it. X-Ray Kid? AWESOMESAUCE… but we ran out of cash in the middle of the economic downturn. That one taught me that no, seriously, I can be a biz-dev guy. I can pitch to execs. And I could be a games designer. And a Producer (something I’d always suspected, since that was half my job at Sierra because they did things Old School – Engineering Leads ran the programming schedules, and architected a lot of the products).

Given that you’ll learn a lot no matter which path you take, take the path which maximizes your opportunity for minimum pain. Right now, for you, it’s a startup. You can always go back to a big corp. But right now your risk/reward curve is absolutely stacked in your favor.

If you have the urge to entrepreneush, that won’t go away. Your ability to exercise on it may as your maneuverability declines as you get older.

If, however, you decide to go to Microsoft, that’s not a bad plan either. But if you ever want to be an entrepreneur, you’d better be living a very frugal lifestyle and banking as much cash as possible. Don’t start a family. Don’t buy a house unless you’re sure you’ll come out on top of that deal – which also means a 5 year commitment usually. Save up money like it’s going out of style).

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