Ask the Headhunter: Should I keep a job I hate for a big payoff down the road?

How much suffering you can tolerate for a job is up to you. But the question you must answer is: Do I need to suffer to be happy and successful?

Nick Corcodilos started headhunting in Silicon Valley in 1979 and has answered over 30,000 questions from the Ask The Headhunter community over the past decade.

In this special Making Sense edition of Ask The Headhunter, Nick shares insider advice and contrarian methods about winning and keeping the right job, on one condition: that you, dear Making Sense reader, send Nick your questions about your personal challenges with job hunting, interviewing, networking, resumes, job boards, or salary negotiations. No guarantees—just a promise to do his best to offer useful advice.


Question: I work for a small software company and my compensation includes stock options. I am about one year into the four-year vesting period. If the company continues to grow, the value of my options could be substantial. Sounds great, right? Well, the problem is, I hate my job. I take the stress home and I have health problems. I'm sticking around solely for the options. How long and how much should I suffer at work for the possibility of a huge payoff?

Nick Corcodilos: Ah, suffering for money! The eternal conflict! How much you can tolerate is up to you. But the question you must answer is: Do I need to suffer to be happy and successful?

I have no argument about holding out for the bucks. But your story begs (sorry) an O. Henry kind of ending: You suffer for years and get the big payoff, but then you drop dead from stress, or your spouse dumps you because you've changed so much. Was it worth it? Four years change a person. Four years of stress change a person dramatically.

Now that we've looked at it dramatically, let's look at it practically. At this company you will have to work hard for four years for a chance at a big payoff, but there's no guarantee. What if you suffer but never get the reward? What then? (See "2 Rules About Working for Start-Ups.")

I'm guessing I'm older than you, because I'd never stick around for any payoff under these circumstances. I believe in investing and sacrificing for work you believe in, and for a reward. But you must also look at the cost of your investment. That is, what else could you accomplish in those same four years? Could you start your own business and come close to the expected payoff figure?

A smart, hard-working person can accomplish a lot in four years. You'd have to work really hard. But you could have more control of the process and perhaps the outcome if the business were your own.

Likewise, another challenge is to find an employer where your life will be better. How do you know you couldn't replace the value of those options with a better job and salary? It's a lot of work to find something better, but so is being miserable.

In the end, you must of course balance the pain and the prize, the risk and the reward. I'm not telling you not to stick it out. I'm telling you to face the issues and make a choice — and then stop worrying about it.

Dear Readers: Would you risk four years for a possible reward? How would you advise this reader? How much is quality of life worth? (That's not a loaded question.)


Nick Corcodilos invites Making Sense readers to subscribe to his free weekly Ask The Headhunter© Newsletter. His in-depth "how to" PDF books are available on his website: "How to Work With Headhunters…and how to make headhunters work for you," "How Can I Change Careers?", "Keep Your Salary Under Wraps" and "Fearless Job Hunting."

Send your questions to Nick, and join him for discussion every week here on Making Sense. Thanks for participating!

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