It Might Not Be That Important

When I graduated from college in 2005, I spent three months searching for a job. It felt like the longest, heaviest three months of my life. Every application, every interview, every email and call had so much weight behind it — as if I were trying to pay a mortgage on a five-bedroom house. I wasn't. I was still on my parents' payroll, with a car that was paid for and an apartment furnished with groceries. I treated those three months as if they were my make-or-break moment. They weren't even close.

When I got laid off the following year, I ended up with five job offers. I agonized over the decision-making process, weighing every pro and con. I overanalyzed what offer to take and why. Looking back, it wouldn't have mattered which one I picked. I was 24 years old. Things would have worked out in some form either way.

When I was weighing the decision to leave media after ten years and switch to real estate tech, I consulted everyone I knew. I went back and forth, often losing sleep. Turns out it was the right move — but in hindsight, it probably wouldn't have mattered if it wasn't.

I know I sound flippant here, but the truth is I think we put too much energy and emphasis on these decisions.

Yes, the decisions you make matter. The paths you choose matter. The people you align yourself with matter. The risks you do or don't take matter. This is all true.

But I just think we spend too much time overanalyzing things that generally work themselves out.

Last week I got a call from someone weighing whether to leave a role for a $20K raise. This person was losing sleep over it. My response: "It doesn't really matter." I said, you can stay and earn it there, or leave and get it now — either way, you're probably thinking about a new move in 12-18 months regardless of what you choose.

We assume the decisions we're making right now are the single most important ones ever, and they're not. When you look back years later, you realize it wasn't really that big of a deal.

I had five job offers out of college: NBC TV, Concur, a branded merchandise company, a digital marketing company, and a billboard advertising firm. I chose NBC. It kicked off a ten-year media career — but I could have chosen any of the five and still ended up here in some shape or form.

Your career is long. Longer than you give it credit for. Think about the journey overall, not the stress of every micro-decision that probably doesn't matter nearly as much as you think it does.