Photo by: triviaqueen

Photo by: triviaqueen

Last week I again had the chance to contribute to the “Nine to Five” column in the Globe and Mail. This one was challenging to answer because I found myself just dying to ask more questions about this person and his/her experiences in order to facilitate the self-reflection necessary to make decisions in tough situations like this. Writing into a newspaper to make a serious decision is pretty much the opposite of looking inside oneself for the answer….but I tried to point him/her back to where he will find the most reliable guidance.



I joined a technology start-up technology company 6 years ago in a management position.  At the time, the expectation of the founder and senior execs was that we would build up the company and sell to a strategic buyer within 5 years.  Personally, I would enjoy nice a 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). Well, for various reasons, both internal and external, things have not moved as quickly and I think an exit is still all of 2 years away.  And, there’s still a risk that it won’t happen. I’m wondering whether the opportunity cost of working the last 6 years at 2/3rds of market value is going to be worth it in the end. 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 and have enough money put away to retire without relying on the financial windfall?


Will the past 6 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 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 explain, “What can I say? I went with my gut.” I’ve never heard any of them say, “I shouldn’t have trusted my instincts.”