Give Me Back My Five Bucks

If you’re not failing, are you really trying?

Rock climbers will often tell you that if you don’t fall, it means you’re not pushing yourself hard enough. As a (former) climber, I often pushed myself to jump for nearly impossible holds. Most of the time I ended up falling, but sometimes I’d end up getting it. And that feeling of accomplishment was worth all of the failed attempts.

However, unlike rock climbing, I have shaped my entire adult life around the idea of protecting myself from failing at something. I always put up safety nets, choose what makes the most sense, and almost never take risks that have a good chance at resulting in failure. Because I expect so much out of myself, I’m scared of failing. I’m afraid the disappointment will somehow destroy what little confidence I have. Which means, the softer the landing I can provide, the better, and more in control I feel.

But everything changes when we learn to take chances. Life happens. You learn quickly from your mistakes, and a good argument can be made that you learn more from failure than from success. Especially when you’re in your 20’s. Risk is made for young people.

So if we never find ourselves failing at anything, are we really pushing ourselves? And how do we break past the fear of failure?

We set boundaries for ourselves every day. We are taught that success is good, and failure is bad. So we limit what we think is possible, and we go with what is comfortable because it’s easy. You can spend a lifetime telling yourself that you can’t do something. But how do you really know it’s not possible unless you take the time to try? Even the most outrageous goal can be achieved if we are willing to take that risk of potentially failing.

Nearly six years ago, I told myself that I was going to get out of over $20,000 worth of debt in less than 12 months. There was a very good chance I would fail, because I was a complete financial disaster. I didn’t have a plan, but I was going to try as hard as I could anyway. And the thing about not having a real plan is that you stop thinking. You stop trying to convince yourself that you might fail. You stop second-guessing your choices. You stop all of that over-analyzing bullshit, and you just DO. It’s amazing what we can accomplish if we just work hard and let our instincts take over.

Quitting my full-time job to take on a freelancing career is probably the scariest, riskiest thing I’ve ever done in my life. Sure, I could end up killing it and becoming a freelancing rockstar. But, I could just as easily fail. The point is, I don’t care. I’m willing to do whatever it takes to succeed. So that in the end, if I do end up failing, I’m still really winning.

Author: Krystal Yee

I’m a personal finance blogger and marketing professional based in Vancouver. I’m a former Toronto Star (Moneyville) columnist, author of The Beginner’s Guide to Saving and Investing, and co-founder of the Canadian Personal Finance Conference. When I’m not working, you can usually find me running, climbing, playing field hockey, or plotting my next adventure.


  1. I love the philosophy. You never want to look back with regrets! I think what you’re doing is both brave and super cool.

  2. Nice stuff Krystal.

    I agree. You need to crash and burn a few times before you can really succeed.

    Failure is bad only if you don’t learn from it :)

    Have a very Merry Christmas and Happy Holiday on the West Coast!

    Oh, don’t forget to check out my Christmas poem, you’re it it amongst other bloggers I follow.


  3. There are smart ways to fail and dumb ways to fail, or to take into account your mountain climbing analogy, smart ways to fall and dumb ways to fall. A skilled climber who attempts a difficult climb, but has a good climbing buddy and safety harness so that if he falls, he can get up and climb another day with maybe just a few bruises and a good story to tell? Pushing boundaries in a smart and constructive way. A beginner who tries a climb without any assistance and breaks his hip (or worse), not so smart. I wouldn’t even call that pushing boundaries.

    I think the same goes in life and personal finance. Pushing boundaries is good, as long as you go about it the right way, and you make sure that you don’t gamble what you can’t lose.

  4. And just to add, your freelancing attempt is a very smart way of pushing your boundaries. You have a great safety net (money in the bank and a frugal lifestyle), and you have already laid the groundwork (freelance contracts, contacts with editors and bloggers, magazine exposure, etc.)

    If someone have NEVER freelanced a day in his/her life, and suddenly decided to quit his job and say he’s going to replace his $70K income, that’s a different story.

  5. JA says:

    I will take a slightly different view on this. I don’t think we need to fail to learn. Its better to learn from others’ mistakes than to make the same mistakes ourself.

    There is also the other aspect of … why does everyone need to take risks? In certain cases the payoff from a risk is greater than the loss incase it doesn’t pan out. Thats the right kind of risk to take. However more often than not we tend to take the wrong kind of risk and end up on the wrong side of the equation.

    Perhaps its not necessary to reach for the extreme all the time. Go for what is realistic and practical. That does not mean that it cannot be outside your comfort zone.

  6. PKamp3 says:

    For some reason “If at first you don’t succeed sky-diving is not the sport for you” sticks in my head…

    Do small goals count? In the gym I go for small gains so almost every time I’m overcoming some fear of failure. Of course, lots of times you actually do fail, so that’s why it’s great to have a spotter, haha.

  7. Col says:

    Thank you! I feel like you wrote this just for me! Thank you for the inspiration!

  8. I think the point about setting big goals and trying your hardest to make them even if they are near impossible is a great one. I think your title says it all, too: If you aren’t failing, you’re simply not aiming high enough.

  9. Cloback says:

    Excellent advice. I think you’re right that a lack of failure is often very telling. I need to start aiming for things where my odds aren’t good because, if nothing else, it will push me further than if I hadn’t tried at all.

    The only criticism I would make is that a lot of aspirational motivational talk and self-help is very individualistic, sometimes encouraging us to put our goals above all else. I’ve met some self-help junkies and recognisably ambitious high achievers who seem to reduce their peers to tools who they can justifiably pump for information and use for an end before stepping over them in order to reach the golden prize (whatever that is).

    We all have the right to a little self-absorption so we can honour our true selves and be all we can be but we need to recognise that there are other people all trying to find their truths and “win” too. Instincts are all very well but ethics are important too.

  10. I love this. And I’m going to write a blog post about it, because it so aptly describes my life right now. Thanks for the inspiration.

  11. Chris says:

    Thanks for this post, very inspiring!

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