The Regret Test: A Different Way to Think About Career Decisions

4. Confronting Your Boss About Something Important

If we’re honest with ourselves, we have far too many issues at work that go unsaid because we’re afraid to bring them up with our bosses. Sure, we complain to our co-workers—about insane workloads, unrealistic deadlines, and the way our managers treat us—but that doesn’t do anything to fix the problem. So we just endure it, steaming inwardly until we can’t take it anymore and decide to look for something new.

But later, it hits you: What would have happened if you simply tried to amend the issue with your boss?

I worked at a previous job for about a year, and I had a multitude of issues with my boss, from the way we communicated to the responsibilities she assigned to me to the way I was compensated. I let the frustration build until I finally left for another company. While I’m happy in the new role, I still wonder what would have happened if I had at least tried to confront my boss about the issues, rather than let them drive me away.

You have to ask yourself: Years from now, will you regret staying mum and letting the issue continue?

In any of these situations—and more—your decision could easily go either way. But looking at the situation from behind a filter of the future of your career can help you make a decision that you know you won’t regret.