A letter to my younger self about taking risks

September 9, 2015 — by Matt


This post is adapted from an email I wrote to my youngest brother as he was debating taking a risk involving travel and creative pursuits. But as I wrote it, I realized it was really an article to my younger self, who often avoided similar risk in order to play it safe. I don't know if I have any real wisdom for the college-age generation, because I'm trying to figure it out too. But if I were able to write to them or to myself at that age, I might write something like this.


Since we last spoke, I’ve been thinking a lot about taking risks or making “less stable” decisions – especially in the context of the “typical” American upbringing.

There will be an abundance of folks around you who will applaud the safe or “standard” route – both on the large scale of life direction and on the small scale of individual decisions. People, in general, gravitate toward what gives them the least fear, and will usually recommend the same for others.

From an evolutionary perspective, fear is a survival mechanism. Fear, doubt, and the pursuit of safety kept us from getting eaten by wild animals or sustaining an injury that, without modern medicine, would lead to death. But we haven’t had enough evolution time for our instincts to catch up to our relatively safe modern-day environment. Our fear response has a tough time differentiating between truly life-threatening scenarios and those that are just less comfortable. The “unknown”, in our primitive brains, is still something to be avoided in order to survive. So most people gravitate toward safety and stability.

But I believe there are very few people that have found true success, or happiness, or really followed their passion, or built their ideal life without taking some substantial risks. With risk, of course, comes failure, but failure is rarely insurmountable. I know for someone as strong as you, it certainly isn’t. Failure won’t break you; if anything, it will give you the ammo to tackle the next risk with more artillery and a higher chance of success. Failure isn’t actually “failure” in the negative way – it’s really just education, experience, and context for the next attempt.

“Failure is simply the opportunity to begin again, this time more intelligently.” —Henry Ford

When I say “risk”, I’m not talking about “recklessness”. There are certainly risks that are not worth it, where the potential reward is greatly outweighed by what failure could bring. I’m talking about calculated risks. But many of us, myself probably included, are so predisposed to avoiding risk that we skew too much toward safety. We might naturally view things as riskier than they really are. So it might be in our best interest to accept a dose of what we see as “recklessness” just to defeat our own thinking and swing us closer to a healthier safety/risk balance.

We grew up on stability and safety; it’s in the DNA of how many of us were raised. We might not have been given the leeway to test our own boundaries, take our own risks, and make and learn from our own mistakes. I think that means 2 things:

  1. see the above paragraph. It might be harder for us to accept and take risks. And
  2. maybe we shouldn’t expect the people around us to necessarily see the point of choosing the potentially “risky” route.

It doesn’t mean the people in our lives who prioritize safety are wrong or at odds with our ambition; it just means they may not be the best advisers for some situations. At a certain point, you need to seek advice from the people whose thinking aligns with your goals. Some people are great resources for guidance in some areas, and not in others. No one is the perfect adviser for every situation. But if you’re looking for advice on how best to accomplish (goal A), you’re better off seeking advice from someone who has followed (path A) than someone who followed (path B).

Anyway… all the above is general life stuff that I’ve been thinking a lot about over the last year or two. If you’re currently deciding what you want to do, or debating whether to go all-in on your dreams or find something safer, see if any of this applies. Test your appetite for failure and iteration. Figure out how much risk you can tolerate. The “what is the worst possible outcome of making this decision” question is a good litmus test to assess the true risk of a decision. And unless you’re going to end up dead, homeless, or being bitten repeatedly by a gang of angry chipmunks, taking the risk is worth considering.

I don’t know. If my 21-year-old-self had your opportunity, he probably wouldn’t take it. Hell, he had a ton of opportunities that he passed on. As my 30-year-old self, I would tell my 21-year-old self that he had to do it. But that’s me. You have to figure out what’s right for you.

I’m not saying any of these things as a person who has taken the big risks or followed his desires to find success and happiness. Rather, I’m saying them as someone who is 9 years older, who has generally favored stability in his decisions rather than risk, and has done a lot of introspective thinking about where he is today and where he could have taken more chances in the past. The popular slogan to boldly proclaim is “I have no regrets, everything has made me the person I am today.” That’s fine, and the second part is, of course, true. I agree with it and have enough self-love to accept myself for who I am now. As a result I have to accept everything that made me the person I am. And I do.

But that doesn’t mean I have “no regrets” – I have them. Not for the things I have done (with a few exceptions) but for the things I haven’t done. And at 30, I’m finally realizing I need to take the big risks if I want to get to my ideal self.

That doesn’t mean I’m good at taking those risks yet – a life of the safe route leaves that muscle fairly undeveloped and paralyzed by underlying fears. And like the first few workouts in the gym, risk-taking is painful at first. But I believe (or hope, since I’m not there yet) that it becomes more natural as you go on – and through failure, learning, and trying again you get better at it. That route, even with its frequent failure, sounds better to me than accepting mediocrity.

You have your entire life to take the safe route. That also means you have all the time in the world to recover if you fail. (And again, experiencing and learning from failure is a GOOD thing). Now is the time to risks in general, and when the risk-to-potential-reward ratio is so favorable, these decisions become that much easier to stomach.


Is there anything you’d tell your younger self? Have you taken any big risks in the past that have paid off: either directly, or through the lessons learned from failure? Leave a comment below!

Post image courtesy of Jannelle Fontes, (c) 2015

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