How I Know I Made The Right Decision

In the summer of 2007, my job was an early casualty of the bubbling financial crisis. That fall, I sprayed different resumes to the far corners of the professional world hoping my bullet points got me in the door, but also hoping no one poked on them since each new iteration gradually blurred the lines between peacocking and white lies.

Desperate times.

Fortunately, through the song and dance I landed two job offers late that year. The only problem was that they couldn’t be more different. One was in LA, the other in NYC. One was in finance, the other construction management.

With the economy teetering on the edge, I didn’t want to choose incorrectly. My brain was swirling with pre-regret (pregret?) even before I made a choice.

I called my dad to get his advice. He asked me to explain and defend both options. I did. He seemed satisfied with my responses. As I waited for his clear cut answer, pointing the way to the promised land, he instead shrugged and said, “I don’t know. Pick one.”

Come again.

He continued, “Whatever decision you make is the right decision because you made it with the knowledge you had at the time. What you can’t do if your choice crashes and burns is to say, ‘I knew it! I should’ve chosen the other one.’ Nope. You don’t know that. You could’ve been dead if you chose the other one, or it might’ve been a bigger catastrophe. So don’t look backwards. At the next crossroads you’ll make a new decision. And so is life.”

And so is life.

It’s a great lesson in avoiding analysis paralysis or second guessing yourself, especially when studies show we're awful at predicting what will make us happy in the first place.

Put another way, your life is not a predetermined jigsaw puzzle to solve, it’s a complicated mold that gets shaped through varying inputs and raw materials. There are tradeoffs, there is unplanned grit, there are tribal and familial pressures, there are cultural norms, there are economies and recessions, and there are your constantly shifting values vying for the top spot as you age.

Life is a grapple of who you were, who you are, and who want to be all operating in the same space.

For instance, let’s say you value freedom and travel, but you’re at a job that you hate that allows neither. Why are you there? Because you also value stability and money. So can you value saving money to allow for more freedom and travel? It’s hard because you also value your friends and your social life. You don’t want to be a hermit and risk losing those relationships. I haven’t even mentioned what your parents might think about any of this.

It’s not an easy juggle.

Which is why I don’t put too much weight on things like “The Regrets Of The Dying.” You know, these:

• I wish I had the courage to live a life true to myself, not the life others expected of me.
• I wish I had the courage to express my feelings.
• I wish I allowed myself to be happy.
• I wish I hadn’t worked so hard.
• I wish I had stayed in touch with my friends.

I mean, is there anything really groundbreaking here? Anything surprise you? We all wish we could live a fearless life of truth, self-expression, and freedom—if we could guarantee that doing so meant success, security, and adoration, of course.

And that’s the problem with deathbed regrets. They’re always going to paint some alternative option(s) as a surefire win. But the other life being imagined might have actually sucked, or it might’ve started rosy but then led to other compromises down the road that were impossible to predict.

The advice of the dying hides the context and nuance that they are bathed in.

So, we should all know that—lying on our deathbed—we are probably going to say, “I wish I didn’t work so hard all the time,” but we are also going to be happy that we worked enough so we had the money to at least die on a mattress.

You may have had to live the life others expected of you for a while because if you didn’t, maybe you would’ve been broke, or worse. I know I’ve had to many times.

The best way to keep agency in your life and regrets at bay is to ask ourselves these questions once a quarter, if not monthly:

• Do my current actions match my stated values? Why or why not?
• What value do I want to prioritize that seems at odds with my actions? What’s the simplest way to express that value?

There’s no sense on your deathbed regretting working so much if you never had any thoughts of why you might not want to.

Think critically. Know your values. Do your best. Adjust as needed. Be kind to yourself. That’s all any of us can do. You will never know what an alternate path would actually look like. Stop giving it so much weight.

For me, I chose the opportunity in NYC. I lived there for almost 10 years. I made a name for myself, lifelong friends, and memories to die for. I met my wife there. Needless to say, I can’t imagine my life without New York in it. Might LA have been even better? Maybe. But I’ll never know. Thinking about it would be like staring at a mirage in the rear view mirror. No, I made the right choice the moment I made it.

There’s a line in the song "Ooh La La" by the band Faces that says, “I wish that I knew what I know now when I was younger,” presumably because then you’d never have to second guess yourself. But you’d miss out on the richness of choosing without knowing, and who would want to miss out on that?

Hindsight might be 20/20, but hindsight should keep its trap shut, especially when the mere thought of facing Prime Minister I-Told-You-So keeps you unable to move forward today.