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What should you fail at?

I love the work of Tim Ferriss, and on a recent podcast episode he interviewed someone who talked about choosing our failures instead of our successes. (I highly recommend Tim’s book – life changing)

We often ask ourselves, “what do I want to succeed at today?” Maybe it’s going grocery shopping. Or maybe it’s something much more grand – finishing a college degree so that you can get a good job.

What we don’t realize is, every time we pick something to succeed at, it means we are also picking something to fail at. Life has limited time, money, resources. By succeeding at something, you are ignoring something else. Maybe that’s OK; maybe you aren’t ignoring anything important. But just maybe, you are ignoring something important.

So, instead of asking yourself what you want to succeed at today, ask yourself what you are OK with failing today. This frames the question in a way that you can identify things you are ignoring in your life, which you wish you weren’t ignoring.

An example for me, is that the men in my family have always been relatively guilt-stricken over doing a “perfect” job at work. We stress about making sure we are always making the best choices and treating those who work for us perfectly. OK, this is a worthy goal. But the obsession over perfection here, may mean that I’m failing in other areas – like raising my family. Framing it this way, it helps me to see things in a new light, and to realize that actually, I’d rather succeed in raising my family and fail sometimes at work. I’m not talking about making any really bad decisions at work or being lazy, I’m just talking about dumping the perfectionism. What are you willing to fail at today?

As you can see (below), this week I succeeded in buying my kids two awesome new mountain bikes. This means I failed at putting that $1000 into a retirement account. But when I frame it this way, it’s easy for me to see which I’d rather fail at. I’d definitely rather fail at investing than fail to pass on to my kids the joy of mountain biking, my favorite sport.

Bonus topic: The question of what to fail at becomes harder and harder to answer the older and more successful you become. When you are young, it’s easy to put off big purchases because you don’t have kids yet, and you don’t have any money, and the goal of getting financial stability is all-encompassing. You save, invest, buy a house, eat beans. Great. But as you get older, the numbers become more abstract. Will it really make that much of a difference to put 5% more in my retirement account this year? Will that be better than buying mountain bikes? Not such an easy question. Because saving for retirement is a very volatile proposition, and depends on a lot of things like – how the stock market will do, how long I will live, etc.

Therefore, since I can’t predict the future, I simply have to choose what I want to fail at today. I can’t succeed at everything. Today, I succeeded in getting my kids on some dirt trails. Honestly, I don’t really care what I sacrificed to achieve that goal, because it was worth it!

(and yes, maybe disc brakes for a 5 year old is a little overkill, but the bike is geared fantastically for Tahoe hills and it has 2.8 tires! Duh!)

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