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Advice / Succeeding at Work / Getting Ahead

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

Your career is full of decisions. And I’m not just talking about the life-altering ones, like finally quitting a job you hate or accepting a new role across the country—but the smaller, everyday ones, too, like deciding to make the effort to find a mentor or committing to go to that networking event instead of succumbing to the lure of your couch.

No matter how big or small, the final decision doesn’t always come easily. There’s an internal back and forth, weighing the pros and cons of each side. And then, even if you swear you’re 100% sure about what you decide, there’s usually a follow-up self-reflective question (or at least the passing thought) of, “Did I do the right thing?”

I’ve found that sometimes, it helps to think of your career decisions in the bigger scope of things—to look beyond how it’s going to affect you in this moment and the foreseeable future, but to think of your life and your career years down the road. Ask yourself this question: Will I regret this decision?

It may be a simple shift, but it’s a helpful tool for deciding on what will be best for you and your career. Just take these situations for example:

Working Late

You may not always have a choice in this matter—as Melody Wilding suggests, the occasional stressful period in your career (you know, the type that requires a few 12-hour workdays) is inevitable. But are you willing to accept coming into the office early, forgoing lunch, and leaving late as the standard?

The regret checkpoint question is a good way to ensure that down the road, you did what was right for you, personally and professionally. And it can definitely go both ways. Some people can look ahead and say, “Even if I work 80-hour work weeks for two years, it will all be worth it to land a senior position—and I won’t regret it at all.”

Others, however, may say, “If I work 80-hour work weeks for two years and miss out on important events and spending time with family and friends, I’ll always look back on that time with regret.” Either way, it’s important to make that distinction now, before you find yourself two years and hundreds of late nights later.


I absolutely hate networking. It’s awkward, I’m bad at small talk, and meeting strangers makes me anxious.

But looking back at my career so far, I don’t regret going to the networking events I’ve been to. They weren’t exactly fun, nor am I a natural networker, but little by little, they helped me feel more comfortable in that kind of environment.

I do, however, regret the networking events that I backed out of—the ones I declined in favor of sitting at home with a glass of wine instead. Because a year later, when I was on the hunt for a new job, I didn’t have a robust network of contacts I could appeal to—instead, I had to start at the very beginning to form that network.

Will you ever regret networking? Sure, maybe if you end up spilling red wine on your red shirt or saying something totally awkward (yep, I’ve been there). But for the most part, it’s something that’s going to help you and your career in the long run.

Volunteering for an Intimidating Project

Your company is looking for someone to head up a special project for the quarter—one that will require some extra hours, will involve regular presentations to the executive team, and, in general, will cause you a whole lot of stress over the next several weeks.

Looking at the situation in the present moment can take the decision one way: You don’t want to take on the extra stress, you don’t have the additional hours to commit to the project, and you’re not comfortable putting yourself out there in front of the C-suite yet.

But look at the decision in terms of the future: “If I look back on this in a few years, will I regret not taking the challenge?” Because if you do take the project, you’ll likely gain skills, confidence, and visibility to upper management that could benefit you for the rest of your career. And so, that stress and extra work—especially for only a couple months—may very well be worth it.

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.

Photo of person thinking courtesy of Shutterstock.