I am now thinking leaving a stable role, taking a pay cut and joining a start up as first counsel. I don’t know if this is the right move or not but I just feel like I need to do it. Many of us have made career decisions that seemed risky or unconventional at the time. Looking back, what was the best career move you made? And how did it work out in the end?

I guess sometimes the most valuable career lessons come from decisions that weren’t obvious.

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Don't do it man

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Definitely not taking a pay cut to join a start up.

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I have seen it work and when it didn’t many have returned to the stable corporate roles where available.

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The only way to make real money in house is to seek out leverage. That leverage can be working for companies with risk, big bonus and high at risk compensation. I never regretted seeking out leverage. Sometimes it worked, sometimes it didn’t.

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I’m retired so not researching anything. My point is that most people will gladly trade money (or the possibility of money) for security. In order to maximize your in house return, you should trade security for leverage. It worked for me.

First in house job was at a smaller integrated energy company. Made a bunch of money before it ran into problems. Took a lucrative buyout after a merger. Went to a manufacturing company that was in chapter 11. Helped get it out of bankruptcy but knew it was going back in. Jumped to a sponsored manufacturing company. Did really well until the Great Recession. Kept that company out of bankruptcy and watched it soar until it merged with a large German company. I had all my options priced below $25 that went to over $100 in the merger. Stock in my 401k bought at under $2 went to over $100. Road out the German company for 5 years until I retired. Each choice I made was to chase leverage. Worked a couple of times; failed once or twice.

I would write down on a piece of paper two columns- one column of the pros and one the cons - after thoughtfully writing on each side, see which side makes more sense to you. But even though I am only a legal administration assistant/ paralegal- from experience in leaving one firm and going into another. I regret it because even though the second firm was enticing, I missed the professional relationships I formed with my management counsel team. Sometimes what seems better in the newer isn’t what it seems. I miss landlord tenant law and greatly regret the day I didn’t take my bosses pleas to not leave. I’m sure you are in a different circumstance, but I would really try that column exercise before making a final decision. And also if you are partnered/ married with a family- really speak with your family about their feelings regarding this as well, because I’m sure as a start up, you will most be likely working 24/7. I was involved with an entrepreneur in the legal field once and he was so busy I literally almost had to buy a retainer to have some of his time. If you have a family, I honestly would recommend thinking of the impact of quality time. Wishing you the best in your decision!

I left law firm for in-house role in a start up company. The stress level is unexpectedly a lot higher because no system yet, very messy, tasks are piling up, and most importantly no one give you guidance. And they expect you to know everything just because you are a "lawyer".

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