Leaving a job after an equity event/payout?

December 5, 2011 5:18 PM

I need help/thoughts on deciding whether to stay or walk after a small equity payout.

I work for an Internet company (in business capacity, not technical) that is in the process of changing hands. I have a small equity stake and will net out with just a hair over six figures, which should land in my bank account in about two weeks. I have another ~$30k liquid in the bank.

In addition to being burnt out at this company, and to a lesser degree the industry, I am in a really bad situation with a new boss who doesn't seem to like me AND seems clueless for working with remote employees (which, technically we both are, but we're in different cites). I think if he had the power at this point he might have already let me go, but considering that he's new to the parent company I think he's kind of in the "probationary period" with that sort of thing. I'm not a big fan of his either, but I've been trying to make the best of a bad situation and not making a lot of headway.

I would really like to take this money and leave the job, taking just a couple of months off to decompress but also take the time to start working on something of my own OR to make a career change. But I'm scared of failure, of course. There is a greater than zero chance that I'll be let go in the spring any way due to restructuring. If that happens it's very possible I could walk away with a nice severance package. If it doesn't happen I'll have missed some significant opportunities in the industry (which given the burn out might not be the worst thing).

If I walk soon after getting this payout I could start looking for a position elsewhere and have a decent shot of landing something interesting/challenging which may or may not make me relocate. My preference is to work where I am as I own a lovely home that I'm loathe to leave. I've put feelers out and a few people seem interested, but my job and the tight knit industry make it challenging for me to full-out look/apply for jobs while I'm employed by my current company due to NDA/contracts.

I could really use some words of wisdom, thoughts on various scenarios or warnings if you have them. Is walking without having something set up the worst idea EVER? Is starting a business of my own in this economy a nutso proposition?

Further data points: I'm female, early 40s, make about $145k but need considerably less to meet my expenses/lifestyle minimums (I'm prone to be a bit lavish at present, but know how to tighten a belt), I live in the middle of the country, will pay off car loan which will leave me with zero debt beyond the home loan. If I was responsible (but not crazy frugal) with the funds from this event they would last me over two years without a problem if I couldn't find work or start up my own something.

posted by anonymous to work & money (8 answers total)

"Start up my own something" is too vague to actionable. If you're interested in entrepreneurial ventures then start defining what you want to do. It's impossible to say if starting a business is a good idea or bad idea until you define the product/market/etc.

Personally, I'd hang out until Spring and hope to get laid off and take the severance package. Since you don't really have a plan, hanging around a bit isn't a big deal. You can always bail in the Spring if you don't get severed.
posted by 26.2 at 6:04 PM on December 5, 2011 [1 favorite]

Bearing in mind I'm an unemployed twentysomething in New York, I know MANY people who would give their left arm to be in the circumstances you're in, with minimal debt, limited expenses, and a substantial cushion. If I were in your position, I'd take advantage of your job for all it was worth, stay as long as you can stand, and think really hard before jeopardizing your financial security.
posted by StrikeTheViol at 7:07 PM on December 5, 2011 [1 favorite]

It is easier to get a job if you are currently employed. If you walk, and don't get a job right away, you will shortly discover the unpleasant pressure of a growing hole in your resume.

Do not, under any circumstances, leave your job, unless you have a clear, defined path. Having a regular income, in spite of your savings, will go a long way to allow you to make more rational decisions on your next step.

Good luck.
posted by Land Ho at 7:31 PM on December 5, 2011 [2 favorites]

Look hard for new work, in tangentially related fields, without leaving your job. You have a year or two's worth of cushion. If your boss is clue-impaired, he and not you may wind up leaving and you might end up in his slot (best case). If you get let go and have nothing brewing you get a guilt-less decompression and you can do whatever you want. If you get promptly hired, negotiate a month's gap before your start date and another month's vacation next year.

Worst case, you get laid off and get to collect maybe severance and certainly unemployment, which you won't get if you just quit.
posted by jet_silver at 8:02 PM on December 5, 2011 [1 favorite]

You could have been me four years ago. $30K isn't much of a nut to start your own thing (I'd counsel more like $100K for a year or two of dedicated solo operation), so I'll say take the money and run. You are going to lose against the boss, and a company's payout is one of the perfect times to job hop. "Yeah, well, the company is going through some changes and I thought I'd look around."
posted by rhizome at 8:12 PM on December 5, 2011

Congrats on the Facebook buyout. :) Coast at your current gig until you find something specific you proactively want to do, and then make the leap -- your skillset and track record of a successful exit will serve you well whether it's another job or your own company.
posted by anildash at 9:09 PM on December 5, 2011

Better to quit than get fired, but find another job first.
posted by empath at 1:53 AM on December 6, 2011

I am in total disagreement with most of the people above. Are you good at your job? As in amazing? If so, leave now for your sanity and chase some of those opportunities you mention. You have $130,000+ in savings which you say could last for 2 years - that's an incredible situation to be in.

If you're really great at what you do, no one is going to care that you took a 6 month sabbatical to clear your head.
posted by thatone at 9:20 AM on December 6, 2011