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.
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.
Last night I was in the Las Vegas airport, waiting for boarding to start on my flight. I went there an hour early because I didn't have time to play poker, so I figured I could get on wifi and get some work done. I knocked out a couple small SETT bugs, and then remembered about getgoing.com, the YC-backed discount flight site. The way it works is you pick two deeply discounted flights that you'd be willing to take, put in your credit card, and getgoing picks one for you. You don't know where you're going until after you've paid. When I first got invited to the site I mucked around with it and found some really great fares to both Beijing and Shanghai.
Maybe I should go to China, I thought. Twenty minutes later my flight to Shanghai was booked.
I like making impulsive decisions like this. My past is filled with them, and none that I can think of have ended in regret. Actually, if I were asked what I thought my biggest strength is, I would probably say that it is making good decisions very quickly.
I wasn't always good at making quick decisions. Twelve years ago I had the opportunity to fly on the Concorde for $1000. It was usually over $10,000 round trip. I really wanted to do it, so I called a few friends to see if anyone else was interested. There was some hemming and hawing, but no one was ready to commit. Well, I thought, I'll wait until tomorrow and buy a ticket then if I still want to go. The next day came and the deal was gone. Now the Concorde is decommissioned and I'll never have the chance to ride it. Strange is it sounds, this is probably one of the bigger regrets in my life. I really wish I got to ride the Concorde before it folded.
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Second, we have this wonderful tour-de-force interview: it starts by covering how Tynan made the shift from unfocused to focused, how to derive internal enjoyment from things, useful actionable exercises you can do right now, Tynan's method and mindset for producing creative work consistently, how to set up great habits and an excellent mental and physical work environment, and how to make blogging work and similar endeavors work for you.
Total Focus; Total Enjoyment by Tynan, as told to Sebastian Marshall
When I turned 30 and I had a minor freak out… I thought, "I'll be 40 in not long, and then 50… there's things I want to do in my life, and they're not happening at this pace."
Before that, I had a general idea of things I wanted to do and have in my life, but I went about in an unstructured way. It was good in a lot of ways. It made be a broad process, but not much depth.