When You Can't Do Both
A lot of life is having the strength to choose and move forward, even when it hurts.
One of the most important life skills, in both life and career, is the ability to make hard decisions.
When I say “hard,” I don’t mean intellectually difficult or managing uncertainty, though those matter too. I mean having to choose between two things that are both equally important to you. Where there’s a fork in the road and choosing one path means legitimately saying no to the other. It hurts because you can’t do both. You must choose. That’s the type of hard decision I’m talking about.
This week, I had the pleasure of celebrating one of my wife’s best friends, James, on his marriage to his longtime partner, Nick. It was a beautiful wedding celebrating a couple so important to both my wife and me. The wedding was scheduled on a Saturday in Chicago, the day before my nephew’s bris in New York. For good reasons, my wife and I were unable to split up, nor did we really want to. But we tried to do both.
We flew to Chicago on Friday, attended the rehearsal dinner, then the wedding on Saturday, and took the first flight out on Sunday at 6:22 AM, scheduled to arrive at in New York at 9:30 AM. The bris was set to start at 9:45 AM. We knew we likely wouldn’t make it, but we took the earliest flight to give ourselves a fighting chance. We’d spent several hours on the phone with American Airlines rescheduling to this flight due to app errors. It was a saga.
But it was hard. I deprioritized being present at the actual bris ceremony for our friends’ wedding. The reality is, if you look at this from an outside perspective, not everyone would make the same choice. Internally, you don’t know if you’ve even made the right choice. But for your reasons, you made it. And it has repercussions: time and moments you’ll never get back. That, in my opinion, has some ripple effect on my future, and I know that.
Now that I’m a father, I’m always thinking about the little moments. The times where you show up, and how meaningful time is. Every second counts. It just really does. Our lives are too short. So this stuff is hard.
I was extremely worried that my brother would be upset. And due to a snowstorm in New York, we were two hours late, ending up arriving when the event was shutting down. Most of the family had already left.
When I finally saw my brother, bracing for disappointment or frustration, he told me not to worry about it. He genuinely meant it. He seemed happy we made it at all. He was more focused on his son and the moment than on our late arrival. We still showed up. That counted.
Here’s what I learned: I spent hours torturing myself over a decision that, in the end, the people I was worried about understood. My brother was more forgiving than I expected. James and Nick knew we had to leave early. The judgment I feared was mostly coming from inside my own head.
But here’s the thing: I also learned that I’m capable of making rational decisions even in the face of difficult emotions. I can look at a scenario, feel torn, and still decide what to do. That’s a muscle worth building.
So I wanted to share a few things I’ve learned that might help you as you make hard decisions:
It hurts. You just have to make a call. There’s no way around the discomfort. At some point, you have to choose.
Give yourself some grace. You can’t control the fact that you’re in this situation. Don’t beat yourself up for being caught between two important things.
You aren’t always doing things to benefit yourself. Sometimes there are more important things at play: family, values, commitments that matter more than your comfort.
You care more than other people care. The torment is coming from inside your own head. People are usually more understanding than you think. They see your effort, even when the outcome isn’t perfect.
Do your best. At the end of the day, you can rest on that. You can’t control outcomes, only your effort and intentions.
Build this muscle. You can’t make progress if you can’t make hard decisions. Each one prepares you for the next.
The most successful people know how to face and deal with hard things. This is what separates those who move forward from those who stay stuck.
A lot of life is having the strength to move forward and do the right thing for your life, even when it’s difficult to do. Hard decisions will keep coming. The goal isn’t to make them painless. The goal is to make them anyway.