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Freedom in Failure

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| October 13, 2022

Freedom in Failure

For most, failure is something to be feared. The potential for things to go wrong or for reality to not play out in the way we imagine can produce a great degree of uncertainty and accompanying fear. This is often powerful enough to prevent many from even trying something in the first place. As anyone who’s ever started out as a beginner and managed to reach some level of proficiency can attest to, failure is just part of the process—not something to be scared of.

Uncertainty can also be thought of as potential. Not knowing what is going to happen or how things will end up can be exciting. Sure, things might end up disastrously, but on the flip side, things might turn out better than expected. I often preach failure as the best means we have of improving upon our craft and growing as both people and creatives. However, beyond just its ability to reveal our weaknesses, guide our growth, and teach us valuable lessons about ourselves, failure can also provide peace of mind.

There’s a certain freedom that can only be found in failure—in being able to say you tried, and despite things not working out the way you would have liked, that you made it out to the other side in one piece. And that’s just it—this is the true benefit of failure, freedom from uncertainty. Having taken those bold first steps and gaining first-hand experience, you now have an understanding of what it feels like when things go wrong, and if that’s the worst that can happen, and you’re still ok, what’s left to be afraid of? The worst is already behind you.

Freedom in Failure in Creative Work

The degree to which you can gain an intimate, firsthand understanding of failure is the same degree to which you gain freedom from uncertainty—the uncertainty that prevents you from leaving your comfort zone to try new things with the potential of damaging your ego. Far worse than wondering what might happen is wondering what might have—what might have happened if you had mustered the courage to take the leap and see what’s waiting for you on the other side. Because once you take that leap, you’ve done it. By actually taking action, whether you succeed or fail, you gain new information and remove some uncertainty, and for that, you should be proud.

Say, for example, you had a stroke of luck last year and your work caught the attention of the right person at a major tech company, leading to loads of additional work and substantially boosting your visibility. As a result, you’re now being sought after for speaking engagements at design conferences and being asked to lead workshops. As someone who’s just spent the last couple of years working from their bedroom, the prospect of suddenly being thrust into the spotlight in front of a live audience is quite intimidating.

However, you know that these sorts of opportunities are rare and have the potential to significantly impact the trajectory of your career, so you accept. You then spend the next couple of months rehearsing and sweating the details of what will amount to just 20 minutes on stage.

Finally, on the day of the event, one of two things will happen: success or failure. Starting with the latter, let’s say you make your way up to the stage and suddenly, despite the countless hours of rehearsal, the second you see those bright lights and hundreds of people staring back at you, all of your carefully crafted lines and witty remarks vanish. For a moment, you freeze. You start to feel your throat closing up and can barely manage to choke out a hello. Fortunately, there’s a teleprompter in front of the stage and the remainder of your presentation is read from your deck verbatim as it’s all you can do to keep from running off stage.

So that’s the worst-case scenario. Let’s take a look at the aftermath. While the presentation was less than ideal, once you get off stage, the event managers are understanding and comforting, and try to cheer you up by sharing anecdotes of past horror stories far worse than your own. The clients you worked with before probably didn’t even see the event and those who did don’t like you any less. In fact, because you followed through and made the appearance, you’ve earned a new set of fans among audience members who found your struggles relatable and endearing. You’ve still been seen, and this exposure has led to some contacts from new clients waiting in your inbox when you get home.

Sure, that was embarrassing, and it felt like the end of the world at the time, but at the end of the day, it was only 20 minutes, and all things considered, you still came out on top. Not to mention, you have new information that will make you better prepared for the next time should the opportunity present itself. By acknowledging your fear and stepping forward anyway, you’ve become more resilient and you’ll never have to wonder what if.

Freedom in Failure in Creative Work 2

What if things had gone in your favor, though? What if you got on stage, only to find that you feel completely at home in front of an audience? Your jokes were landing, your questions were thought-provoking, and you had the audience on the edge of their seats, fully engaged in the presentation and hanging on your every word. You wouldn’t have to imagine how that would feel, because you would know. Now, not only have you discovered something new that you love to do, but because you did it so well, you’ve got clients from all over the world reaching out to have you speak at their event. With each speaking engagement, not only are you gaining visibility and landing larger clients, but now you’ve got a new source of income that continues to grow with each appearance.

So what would have happened had you allowed the fear of failure to prevent you from accepting the opportunity to speak in the first place? Well, you’ll never know. Sure, you’ve saved yourself the humiliation of the worst-case scenario, but you’ve also robbed yourself of the highs of the best-case scenario. You’re left where you started, but now, with the weight of a huge question mark that will always have you wondering what if. Compared to the way both the best and worst-case scenarios played out, I think choosing to take the engagement was clearly the better option no matter how you look at it.

Freedom in Failure in Creative Work 3

Failure is not permanent. When things don’t go as planned, simply take some time to regroup and reflect, learn from what went wrong, and squeeze out every possible ounce of insight you can to take with you as you move on to your next attempt. Failure is the key to accessing our untapped potential. Ultimately, failure is nothing to be afraid of, but you’ll only learn this if you have the courage to try in the first place.


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