Stop Playing the "What If" Game

When it comes to making decisions about your career, stop playing the "what if" game and start playing the "I'm glad I did" game.

One of the most toxic things you can do is spend years second-guessing decisions you can no longer change. I hear people say things like, "If I had chosen that company, I might be a millionaire today," or, "If I had accepted that project, I would have been the one who got promoted." Maybe. Or maybe your life would have gone in a completely different direction that you would have hated. You will never know, which is exactly why the game is so dangerous.

You said no. You chose the other company. You moved to a different city, accepted another role, or walked away from the opportunity. That path is gone now. Spending your time imagining the life you could have lived only prevents you from fully living the one you actually chose.

A little over a year after graduating from college, I went to work for a terribly run company. The leadership was incompetent, the decision-making was a disaster, and I was laid off after nine months. I then spent six weeks grinding through interviews before receiving five offers: ABC Television, Concur Technologies, NBC Television, a merchandise branding company, and an advertising startup in the out-of-home media industry.

At 23 years old, I chose NBC, and I never looked back. That decision launched a ten-year career in the media business that included two relocations, tremendous growth, leadership opportunities, and a lot of fun. I had no idea at the time how much one decision would alter the direction of my career. I was simply a young guy trying to make the best choice with the information I had.

My second choice was Concur, which was a rapidly growing technology company that would eventually be acquired by SAP. I would have worked in inside sales supporting East Coast customers, which meant starting at five in the morning and dealing with a commute that could become brutal on the way home. It is funny how some of the biggest decisions in our lives can come down to something as ordinary as traffic, but at that moment, it mattered to me.

If you waste your time obsessing over what could have been, you will miss what your decisions actually gave you.

Could I have been successful at Concur? Absolutely. I probably would have moved into management, benefited from the company's growth, and built an entirely different career. Maybe I would have made more money. Maybe I would have met different people and found opportunities I cannot even imagine today. But that is not the life I chose, and I refuse to treat the life I did choose like some disappointing consolation prize.

There are very few decisions in your career that are simply right or wrong. Every yes creates a list of opportunities, and every yes also requires you to say no to something else. You can second-guess the company you joined, the city you moved to, the house you bought, the money you invested, or what you ate for dinner last night. Everything is available for review if you are determined to torture yourself, but what a fucking waste of time.

Since then, I have made decisions about companies, roles, relocations, teams, projects, and opportunities. Some produced exactly what I hoped they would. Others taught me something I could not have learned any other way. I do not need every decision to have been perfect to be glad I made it. If you waste your time obsessing over what could have been, you will miss what your decisions actually gave you. Stop playing the "what if" game. Start playing the "I'm glad I did" game.