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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:

1. 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.

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