Three Tips to Stop Second Guessing Your Career Decisions

Have you ever turned down a job only to question your decision months or years later?

Or maybe there was a hot lead for a new opportunity that you simply didn’t explore because you were comfortably happy in your job, only to find out six months later now with a new boss and more responsibilities that you’re miserable.

Well, according to a piece on Harvard Business Review (via, it’s time to stop fretting. Could have, would have, should have should really be tossed out the door. 

1. Get input. For starters, if regrets are weighing heavily on your mind (and maybe you have too much free time — but that’s a whole other blog post altogether), the piece recommends asking others to think differently about your regrets. Maybe they’ll be able to spin it into a positive. For instance, perhaps there was a job you didn’t pursue; well, maybe headlines are now announcing layoffs within that company.

2. Ask “what if” questions. Based on this input, start creating questions to see things from a new point of view. Maybe you regret going into digital media ad sales. One question to ask yourself could be, “What if I did this for a skill I wanted to develop?”

3. Explore ideas to act on. What fun is sulking and beating yourself up about hindsight 20/20 vision if you can’t actually create something productive to act upon? The piece suggests exploring ideas to act upon. If the what ifs and should haves really stir your soul, it could be just the spark you need to pursue that concept and/or opportunity further.