Making Big Decisions Good Decisions

When standing on the precipice of making a big decision, it’s natural to wonder whether or not you’re making a mistake. It’s easy to imagine that each imaginary path through our future leads to an entirely different place, and that by following one the other disappears completely.

But that’s not really how it works. Big decisions do obviously matter, but the following hundreds of decisions matter a lot more, and will ultimately dictate whether that original decision was the “correct” one or not.

Let’s say you’re moving to a new city. That’s a scary thing that you might really deliberate on. Is it the right move?

Well, if you go to the city and sit around waiting for your good decision to pay off, it may or it may not. But if you go out and take the opportunity to make a great new group of friends and take advantage of the strengths of that city, it will probably be an excellent decision, whether it’s Toledo or Las Vegas.

Another great example is relationships. Sure it’s great to find someone with whom you’re compatible, but it won’t mean much if you don’t put effort into the relationship to make them the right person for you.

And, of course, career. If you switch careers and put everything into it, chances are you’ll look back at that as a great decision. If you don’t do much with it, you might not.

In general I have a policy of making sure that every big decision I make is a great decision. I don’t do that by deliberating forever (in fact, many of my biggest wins have come from simply making quicker decisions than others), but rather by making everything work out by force of will.

In 2013 nine friends and I bought an island. It was just five acres of undeveloped forest out in the outskirts of Halifax. Nothing about that decision guaranteed success. The last owner bought a generator, cleared some land, and then sold it for a loss (I believe). That may still have been a good decision overall for him if he had a good time there, but I suspect it wasn’t.

But we’ve pushed and pushed to make the island an amazing place. We hand carried materials to build a 900 square foot yurt and a 400 square foot cabin over there. To have a nice dock we (my friend Brian, really) have to wade through cold North Atlantic water to move it with the seasons. We slept a lot of nights in tents in hurricanes. But because we’ve put in the effort and made good subsequent decisions, a bunch of us feel that it’s the best money we’ve ever spent. Many people told us it would be the biggest mistake we’d ever make.

I’m getting married in a few months (surprise!). I’m marrying a really fantastic girl, but I know that the decision to get married will only be an excellent one of we both make it an excellent one. Luckily she knows that, too.

A few years ago I bought one of the cheapest homes available in Las Vegas. It wasn’t a nice apartment, so it could have easily become a situation where I lived in a crappy apartment in a somewhat dangerous neighborhood. Instead I remodeled my place (mostly myself) and convinced 6 other friends to buy up the units around me. Now we have our own neighborhood that feels like the best combination of dorm life and normal apartment living. It took a lot of convincing and footwork to get everyone on board, but we all love it.

Give good thought to the big decisions in life, but don’t expect any results from them. Use them as new environments in which you can do you best and make each decision the right decision in retrospect, even if it wasn’t actually the right decision in the moment.

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Photo is sunrise from my cabin! I just left today, after (hopefully) fully waterproofing it. Can’t wait to get back in the spring or summer.


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