I get a lot of email. Most is encouraging, but now and then I get an email from a reader irate that one of my articles didn’t speak to them personally, so they write me a scathing critique.

A common template goes something like, “You think it’s easy to do _____. Just wait until you have kids, tons of debt and a mortgage bub.” The idea being that I’m somehow at fault for not giving them personalized advice because they had made poor life decisions.

But it does bring up a good point: if you’re young, it is easier to do harder and riskier things. If you’re smart, you take advantage of that.

Being Young and Taking Risks

When I say risks, I’m talking about the long-shot, high-reward, low-cost kind: starting a business, living in a different country or building something interesting.

Of course, you don’t need to be young to do any of these things. On the contrary, risky, difficult things would seem more feasible as you gain more experience and resources.

But the more you have, the harder it is to justify giving it up. There’s a lower opportunity cost to invest hundreds of hours in a speculative project when you’re earning $10 per hour than $100. Spending a year living abroad is harder if you need to convince a spouse or kids to come along for the ride.

You don’t need to be young to take on difficult, risky things. I know people twice my age who are more adventurous than I am. But the life trajectory people take usually makes it harder to do.

Fail When It’s Easy To Fail

I started thinking through this idea when I was contemplating starting my MIT Challenge. On the one hand, my business was becoming more consistent. One year’s worth of work improving my courses and distribution would have been tens of thousands of dollars in extra income.

Instead I chose to spend a year doing something I thought was interesting and had a possibility of sharing the passion I have for learning and self-education with a larger audience.

The benefits aren’t purely emotional. If the challenge were to be successful, it could help build better credibility for my methods and attract new customers. Even if I were being strictly motivated by money, it wouldn’t necessarily be a bad idea, just a riskier one.

I could take on this project because I could afford to fail at it. My lifestyle is still inexpensive, so even if I didn’t have my business, a year’s worth of bills would have been less than a year in a university. I had no outstanding commitments and no dependents.

Taking on risks isn’t just about being bold, it’s about being able to handle the possibility of failure. If you can’t afford to fail, you can’t afford to try, so fail while failing is still cheap.