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Writing about my journey getting sober, building tech companies, and pivoting into a simpler life owning and operating dog daycares

We live in a world of infinite choice. If you’re a millennial, growing up you were likely told you can be anything you want to be. I was long paralyzed by that endless choice. What if I should have been a doctor? Should I go back to law school before it’s too late? How old is too old to go and get an MBA?

Sometimes I wondered, wouldn’t life be simpler if I came from a long line of tradesmen and my destiny was just to be another generation of brick layers.

Instead, I was left with near-constant decision-making remorse. If I would have just studied something else, dated someone else, lived somewhere else, my life might then be perfect. It’s a great recipe for unhappiness despite all the beauty and joy that comes from the decisions I have made.

So I’ve learned to let go of decision-making remorse. It’s a lot like buyer's remorse. I obsess over backpacks, watching endless Chase Reeves reviews (if you’re looking for a new bag, he’s your guy). When I order a new one, if it’s not perfect, if it’s not everything I ever thought a backpack could be, I instantly regret it and send it back. I return to youtube and start looking again for perfection.

But there is no perfect bag and no perfect life. There are just lots of bags, in all different shapes and colors, for all sorts of activities. Some are great for travel, others for walking around town. I’m also allowed to own more than one bag - they’re not cheap, but they’re not Ferraris either.

Instead of returning things now, I make a decision and let it rip. I do the same thing in life. I watch the reviews, I do the research around big life decisions just like I do when trying to buy a new bag. Then, I come to a conclusion, make the decision, live in that, and don’t look back.

I can always make another decision when the circumstances change. That's the beauty of bags and decisions - you can have more than one. I don’t need to regret the choices I’ve made that got me here. Who knows, maybe if I had been a lawyer, I’d be dead!