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The Question

I joined a technology startup six years ago in a management position. At the time, the expectation of the founder and senior executives was that we would build up the company and sell it to a strategic buyer within five years. Personally, I would enjoy a nice financial gain from my shares and options that would about double my own retirement savings, enabling me to retire at age 55 (which I turned last year).

For various reasons, both internal and external, things have not moved as quickly as expected and I think an exit is still at least two years away. And there's still a risk that it won't happen. I enjoy my job but I'm wondering if I should go somewhere else where they can pay me full market value and work until I'm 60, so I have enough money put away to retire without relying on the financial windfall?

The First Answer

Colleen Clarke

Corporate trainer and career specialist, Toronto

The best laid plans of mice and men. Whether the cost of working the last six years at two-thirds of your market value has been worth it or not is a moot point; the last six years are over. The question is how to make the most of your remaining work years.

You have a couple of options, and since money seems to be the motivator to go or stay, you need more variables. You could start looking around for another job, check out the marketplace, see how saleable you are. If a dream position presents itself at the rate of pay you require, then you have more factors to consider as you make your decision.

Nothing is for sure, and a new position doesn't guarantee you a job for five years any more than your present company may find a buyer in two years. It is really a matter of the devil you know and the devil you don't know.

Make a list of pros and cons for both options – staying and going. Which side gets more points? Put a value on each point. Add up the points on each side and examine how you feel and think about the answer.

If I were to tell you "Get a new job," how does that make you feel? If I tell you "Stay where you are," how does that make you feel? You need more variables to make this decision.

The Second Answer

Rachel Weinstein

Executive coach, Toronto

Will the past six years be worth it in the end? Look at it this way: You've spent them at a job you enjoy (you must know this is not a small thing – just survey your friends) with your eye on a best-case scenario that made your work exciting. Sounds like that in itself had worth, and I hope you can take credit for granting yourself the experience. I know you want the story to end with fireworks and celebration. But as you've witnessed, it's impossible to accurately predict the future; there's always an element of gambling.

Quick: If you promise yourself to abide by my "stay" or "go" recommendation, what do you secretly hope my answer will be?

Go with that one. Because my gut instinct is that you have a gut instinct. Not about the business outcome, but about the right move for you. The decision that will allow you to sleep at night is the one that best aligns with your personal values. If you're the type to say, "What's life without taking chances?" you are clearly an adventure-seeker who will have a hard time forgiving yourself if you leave and the company is sold.

On the other hand, if you're known to say, "Whatever happens, I'd rather be sure," then predictability is important to you and it's likely time to find a full-paying job and plan the details of your retirement at age 60.

After navigating through ambiguous circumstances like yours, I have heard both disappointed and delighted people tell me, "What can I say? I went with my gut." I've never heard any of them say, "I shouldn't have trusted my instincts."

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