How to make a job decision you will never regret

mm Russ Finkelstein

I suffer from an acute case of what I call “perfectitis.”

It hampered me when it came to choosing which college to attend: William & Mary, Vassar, or Connecticut College (go, Camels!). So, as a high school student, I developed a spreadsheet with fifty variables including “books per student” – the volume of books in the library divided by the total number of students. While I was happily immersed in books at Connecticut College, my happiness was not directly related to this.

What I’m saying is: not all data is ultimately useful for making big decisions, and it’s possible to overthink things, and worry too much about them.

I sometimes have a similar issue when it comes to booking hotel rooms. In this case, I consider price, proximity to meetings, and what the best location in the city might be. I sometimes draw up spreadsheets. Don’t get me started on making appliance purchases.

When it comes to people considering jobs, graduate education, or a career transition, it isn’t about amassing as much information as possible. Rather, it’s about knowing what matters and amassing those key pieces of data.

You can usually know more by being clearer with yourself about what you want, and what actually is being offered. While most of us can do the work to make more informed decisions (although we often don’t), we won’t and can’t have perfect information. So how can we get the best possible information?

Even if there was a button to press that guaranteed full information, things change. The sickness of someone in your immediate family impacting your priorities, your boss accepting another job handing you over to a less liked or unknown manager, or falling in love with someone who lives across the country. Suddenly, what you wanted or what was available is very different. Things change. All you can do is know what is being offered, and what you want at that moment.

For example, I was contacted by a recruiter recently about a moderately interesting job. When they reached out I shared that I had several reasons why I didn’t feel like it was the work I wanted to pursue, but I would happily recommend other people who might be a good fit. I love recommending people to recruiters.

When we spoke, the salary number was revealed, and it almost winded me. I started to do paycheck and retirement math in my head. I reaffirmed my lack on interest, but it was not easy, although knowing my priorities made it easier. According to my calculations I passed up on a package equivalent to being the 456th-best paid player in the NBA. I know this because I made a spreadsheet.

I revisit my decisions. I think about that position, and a long-ago opportunity to run a small, well-funded international educational organization, or even the decision to leave Idealist now and again. I left behind economic certainty because other things mattered more when I took a step back and considered deeply what I wanted for my life.

How might my life be now if I followed those other paths? I’ll never know. I do know, though, that I did the best I could with the information I could locate and by being very aware of my priorities.

These are “what-if” moments, and you shouldn’t let them haunt you.

I can never know for certain what would have happened had I made other decisions. Neither can you. What I do know is that given all the information I had about the opportunities and what I cared about, I made the right decisions because I was intentional about the choices I was making.

You owe it to yourself to put the work into making your best choice. I’m not suggesting you draw up a spreadsheet in each case, necessarily. But being intentional about your choices is the closest you can get to making decisions you won’t regret. Otherwise you are setting yourself up for endless days of ice-cream pints and Netflix, and those should really be saved for special occasions.

Russ Finkelstein is Managing Director of ClearlyNext, a guided online career program that helps people of all backgrounds and incomes figure out what to do next. Read more >