It’s easy to say if I could do it over again, I’d do…whatever. But the thing is, it’s the “I wish I could do this over again” moments that shape us sometimes the most. Would I be who I am today if I hadn’t majored in the wrong thing, trusted the wrong people, spent years of my life focused on the wrong efforts, communicated the wrong way, worked for a failed startup, and more? Probably not. For one, I wouldn’t have the insight now to want to go back and do it over again. I’d simply be less knowledgeable about the things you can only learn in the school of life, which is itself a far more practical teacher than any college or university (most of the time).
And if I could do any of it over again, would I be better for it? Would the world? Would my friends? Who’s to say?
I don’t have very many regrets, but the ones I do have are all about how I’ve communicated things I ultimately don’t regret communicating. I’m sometimes blunt and abrasive and lack tact, and I don’t always like that part of me. But I’m most frustrated with the me who didn’t speak up when she needed to. Hands down, it’s this version of me I’m upset with. And if I could do anything over again, it would be to speak up when I was quiet about things that mattered.
Our culture is increasingly a communication cluster. And I think that’s why sometimes I find myself paralyzed about the best way to say something in a way that is both true and helpful. It’s very difficult to have conversations about ideas anymore without someone interpreting something as a personal attack. More and more it feels like the safest conversations are the shallow ones. But I don’t want to live in a world where our only conversational refuge is chit-chat about the weather.
So, instead of talking about what I would do over, I want to talk about what I’m going to do differently the next time I’m in situations I’ve handled poorly in the past. How will I communicate better the next time? And is there a way to be honest and say true things without making a mess of it?
I want to believe there is. I really do. And I plan on working on that from here on out so I’m ready. Because truth matters, and learning how to communicate truth without offending, blowing people out of the water, triggering, and whatever else is likely to be a coveted skill in the future.
If I could do it all over again, I wouldn’t. But I’ll make sure I do it better next time.