Learning How to Rise to the Challenge

Failure doesn’t exist; only success and experience to increase your chances of success later.

Despite my love of video games, I’ve never been obsessed with winning. Don’t get me wrong, winning is the ideal outcome. But I’m not bothered when I lose. The most negative reaction you’ll get out of me is, “Well, that sucked,” and I’ll either move on to something else or start up a new game.

The same goes for life. As someone who’s freelanced the majority of my career, I’ve gotten used to making mistakes, projects not panning out, toxic clients and partners, and a whole smattering of other issues. Despite the rejection, the stress, the lean months, the ups and downs, the depression and anxiety — among many other things — I still enjoy what I do enough to keep doing it.

For me, the fun comes from adapting. Being self-employed is living life in hardcore mode; all of your eggs are in your own basket so you are the sole responsible party for your success and failure. That might be terrifying for some but for me, trusting an uncaring corporation that sees me as an asset to exploit is the scarier option.

While I’m still working on my goals, I take pride in how much I’ve learned over the years, becoming more competent, well-rounded, patient, and resourceful. Where most people see chaos — from the pandemic to the shaky economic thereafter — I see opportunity.

When I first started freelancing 12ish years ago, it took me about 14 months to go full-time. This most recent time when I started Mad Mage Consulting, it took me 4 months to get over the break-even point, scaling an idea into a profitable business in a third of the time. I credit that improvement with hard-won experience earned not from the success I’ve enjoyed, but the setbacks I faced.

In this article, I want to teach you the joy of losing and reshape your thoughts on failure. Because fear is one of the greatest obstacles to succeeding on your terms, practice looking at life and its trials as one big game. Therefore, if you want to succeed, it’s about learning how to play.

What Would You Do If You Couldn’t Fail?

Let’s make a bold statement: failure doesn’t exist. Mistakes, setbacks, losses, sure. But unrecoverable failure? In most cases, you wouldn’t be aware of it because, to me, true failure is synonymous with death. As long as your heart is beating, you’re cognizant, and have the power to reason, you’re still moving forward.

A lot of this mindset is shaped from my interest in game theory — that everything boils down to different factors that govern probability for various outcomes. We’re taught at an early age that if you’re not winning, you’re losing, but that’s simply not true. If you’re still in the game of life, you’re either winning now or bound to win later.

Sure, luck is a factor, but it’s out of your control. So, focus on what is: your reaction to whatever circumstances you find yourself in.

• Don’t know a skill you need to succeed? Learn it.

• Don’t have the money for a class? Find free resources online or check your local library.

• Not sure what resources are good quality? Ask the librarian or someone you trust to help you.

• Don’t know those kinds of people? Go find and meet them.

If you’re someone who really wants to win at [pick a goal], this list makes sense. But if you’ve rolled your eyes reading any of those steps, I want you to explore why you might dismiss this.

Is it doubt? A lack of belief in yourself? Or does it seem like too much work (and the thing you claim to want just isn’t worth the effort so… do you even want it)?

People will resist putting in the effort because they’re at risk of resigning from the game of life. If it’s not easy, it’s not worth it; if you fail, it’s a reminder that you’re incapable.

Neither of those statements are true. 

Allowing them to take root is its own kind of death. Instead of living and honing yourself into the person you want to be, achieving the goals you want, you don’t even allow yourself to start or are unwilling to stomach the discomfort that comes with growth.

Don’t worry. There’s a cure for that.

Stumble Early and Often

As someone who loves reading self-help books or blogs on whatever skill I want to learn, I know it’s easy to fall down a rabbit hole of knowledge. However, if you’re not careful, you’ll soon develop a habit of living vicariously through the journeys of others as you struggle to begin your own.

No matter the reason holding you back, find a way to start practicing, doing, or moving towards the goal you’ve named as your primary focus.

You might find you have a natural affinity to what you’re doing but in most cases, it’ll be messy, awkward, and riddled with mistakes you’ll feel silly about. But this is the process. It’s meant to feel weird, uncoordinated, and scary. That’s why measuring your progress and immersing yourself in what you’re doing is so important to ensuring you get to where you want to be.

For instance, if you want to become a master potter, your first time at the pottery wheel is going to feel strange as you find the right speed, pressure, and the amount of clay you need to make what you want. But after practicing for a week, two weeks, a month, a year, it gets easier — or, at least, you understand how the process works and adapt.

From bodybuilding to writing to climbing the career ladder to starting a business, every skill, project, and goal follows this progression. But it progress only happens when you take action.

You can read about proper lifting techniques all day, but until you start picking up the heavy circles consistently, you’re not going to build muscle. You can watch how-to videos about starting your own ecommerce store, but none of that matters until you build the platform and get your first sale.

It might happen quickly, it might take a while. Allow yourself to stumble. Just make sure to identify why you did and how you fixed the problem to avoid stumbling like that again if you can.

The Sting is Temporary

When I was about five years old, my parents enrolled me in martial arts, starting with karate and finally getting a black belt in Tae Kwon Do. It took me 10 years, having started over when I moved from one style to the other — which is fair but was still frustrating for a kid who really wanted a black belt.

I trained at least three times a week for two-hour sessions. Over that time, I was in dozens, if not hundreds of sparring matches where the sting of defeat was quite literal. But I learned to enjoy the pain, not for its own sake but as a reminder I was on the right path. The feeling of my muscles being sore after a good work out, the knitting of bruises after a particularly rough bout that reminded me to maintain eye contact and proper defense. It was all a part of the journey I signed up for.

By the time I tested for my black belt, I had the highest score in my cohort at the time of testing across a region of 10 states. It took longer than I wanted but I was grateful I finally made it. Despite all the times I wanted to give up, especially having to restart after switching schools, being given my first long-term prize was worth it.

While this example talks about literal pain, I want to make one thing clear: there is a difference in being tolerant of necessary stress and growing pain and dealing with unnecessary abuse. I’m not advocating you endure hazing or people bullying you as a means to “break you down to build you up.”

But growth usually has pain in some form, whether that’s the stress of learning new project management software your boss wants you to use or coping with the soreness of your first leg day in months. Pain can also take the form of anxiety as you stress the uncertainty of a new mode of doing things or self-doubt trying to erode at you before you even begin.

But all of that is temporary. The pain might linger but you get stronger and more capable dealing with it. Soon, any problems and setbacks that might’ve been earth-shattering for you as a novice are a no-brainer for you as a master. But you don’t just become a master overnight and nothing worth having comes easy; even if you were lucky and achieved your goal quickly, do you have the wisdom to appreciate it?

Going back to game theory and probability, the nice thing about any goal is that you only need to win once. Loss, therefore, is simply learning a way to not win (or, at least, that door to victory is shut for now until you complete other steps first). I only needed to pass my black belt test once to get that sought-after piece of fabric.

So don’t fret the temporary sting of defeat. If you’re motivated by fear, train yourself to be afraid of the permanence of calling it quits on everything before you’re dead and buried. Because if your heart’s still beating, you’re still in the game.

Don’t let setbacks keep you from the life you want.