A couple months ago, I strolled into church a few minutes late and found an open seat next to some friends. As I went to set my belongings down and join worship, I shifted the grip on my coffee. Faster than I could process, let alone react, the lid detached and the cup fell, silent as the grave. Instantly, the liquid disappeared, rushing downhill on the smooth concrete of amphitheater seating. There was nothing to salvage, no saving grace.
I froze. No one around me had noticed—they were singing, and the room was dimly lit. My brain had nothing to pull from, no equivalent scenario to evaluate and adapt to create a disaster response. I take pride in having good hands and proprioception, so I consider dropping something, even alone in an empty room, a significant failure. And here I was, next to my friends, with hundreds of people behind me looking on, and a flow of coffee making its way down the aisles in front of me. I could only imagine it hitting Bibles and purses and phones and changing course as it sought the low ground. Public embarrassment. Nightmare fuel.
I could feel my heart rate increase and face heat up as I comprehended how thorough and total this defeat was. My options were 1) carry on like nothing happened, then once it was discovered, pretend like it had been kicked over at some unidentifiable point by some unidentifiable person, then rally a group clean-up effort or 2) leave and never come back. Don’t think I didn’t consider those choices, seriously. The third option, which involved several trips to the bathroom for paper towels, tapping strangers to let them know their personal belongings had been compromised, and basically crawling on the ground in the dark chasing a coffee trail, was unthinkable. All while a congregation looked on! I was in the fourth row, which limited the damage, but maximized the exposure. I chose option three.
If the following sermon had been the best one ever delivered about pride and humility, it could never have been more effective than living that experience. Even after I got the first round of paper towels and had started the clean-up process, I froze again, because I realized the scope of the project was even bigger than anticipated. By this time, my friends had noticed, and one of them started trying to help when I stopped, which is what jumpstarted me back into motion. No, I had to own this mess.
By the time it was over, I had met a group of people who now exclusively knew me as the clumsy guy who spilled coffee on their stuff then awkwardly cleaned it up. None of the damage was extreme, and I did offer to replace anything affected (no one accepted). I returned to my seat smelling like coffee, and that fragrance lingered the rest of the service.
Before all this unfolded, if you had described the scenario and asked me to name the price I would pay in order to avoid it entirely, I would have come back with a pretty big number. Public humiliation is high on most people’s list of things to avoid, but I would bet I come closer to avoiding it at any cost. I’m nowhere near as shy and introverted as I was as a child, but that’s still who I am at my core.
No one teased me about it, which felt unnatural. Maybe I have better friends than I deserve, or maybe they sensed how unsettled it made me. By the time we got to brunch, though, I was totally over my embarrassment and ready to marvel at the fiasco. I broached the topic and made fun of myself, and I genuinely found the whole thing hilarious.
Now I’m writing about it and drawing more eyes to my failure—why? Well, because there’s a great lesson in that story. Something happened to me that I was terrified of beforehand and mentally tortured during, and, now that it’s over, I’m not afraid anymore. If I had known that was a possible outcome of going to church that morning, I would have been significantly less likely to get out of bed. Looking back, it’s just a funny, harmless story, but that’s not all!
If it happens to me again—can you imagine how careful I have been with my coffee since then?—then I will be prepared to react quickly with only a small fraction of the horror and angst. If I initially estimated it would be worth paying $1,000 to avoid it before it happened, for example, now that I lived through it, I wouldn’t even be willing to pay $100 to avoid it. The fail monster got me, yes, but in doing so it came out of the shadows and wasn’t nearly as scary as my mind had imagined. Now that monster (and my imagination) has less power over me, going forward.
Because of that relatively minor traumatic experience, I am better than I was before. I am more confident I can handle future unexpected situations that come my way. I am more aware of what can go wrong and take steps to avoid it. And yeah, I’ll say it—I am more humble.
There are infinite extrapolations to this. Last spring, I gave a talk to our departing seniors about traveling abroad, and I had a whole section where I talked about failure. Missed flights, stolen baggage, near muggings, getting lost.. one time I actually slept not just in the wrong room, but in the wrong hostel entirely! I see all of those things as positives now, although I never would have chosen for them to happen to me. I am good at traveling, in large part, because of the mistakes I have made. If I had been afraid of what could go wrong and never started, I would have fewer failures, maybe, but my life would be dull, un-full.
The same thing is true of my experience with real estate. I bought my first property five years ago, in 2016, after roughly six months of podcast-fueled research. I have continued my education since then, steadily consuming books and blogs and videos alongside the podcasts, but I have learned the most from doing. Running the numbers, making offers, negotiating, estimating and completing repairs, and, ultimately, buying and selling real property. I’ve worked with realtors and electricians and landscapers and contractors and inspectors and appraisers and tenants and property managers. I’ve made plenty of mistakes, some of them more costly than others, but if anything my conclusion is I should have started sooner! If you want an example of an “L”, here’s one that still stings: a title company sent me a pre-paid overnight shipping label to mail the “option” and “earnest” funds before the deadline, and I mailed them a check just in time, made out to the right company, with the right amount, and unsigned. Useless. My real estate agent’s partner had to drive ~3 hours with a new check and drop it off before the place closed for the day.. see? Failure. Embarrassment. Yet, even though it means mistakes, the hands-on experience has been a fantastic investment in my future, and there is no way to fast-forward the learning process, regardless of my book knowledge.
Third example: I’m a grad school drop-out. That counts as failure, right? Looking back, would I prefer to have never started that MA Econ program at UT-Austin? It drained my savings from my first four years of teaching, and I have nothing to show for it. Well, the way I look at it, that experience taught me a lesson that brought the rest of my life and career into sharp focus, whereas it had been wide open and blurry beforehand. Since I decided to go all-in on coaching and teaching within the classical liberal arts charter school movement, I’ve felt a sense of purpose and fulfillment and I’ve never looked back. I know I’m doing what I was meant to do, and I know I’m good at it. Paying off those student loans was an investment in my future, just not the investment I originally intended. Would I have gotten to this point without a major failure teaching me a lesson? I don’t know, but I do know I’m at peace with it.
The real lesson here isn’t about failure, it’s even simpler than that. It’s about doing. Acting. Going out in the world and having real, live experiences is the only way to grow and learn and move forward. Failure just happens to be an unavoidable byproduct of action. Failure also happens to be the best teacher we have, you just have to give her a chance and be willing to learn!
Both action and inaction are self-reinforcing. All you have to do to start the virtuous cycle of doing things, occasionally failing, overcoming fear, learning from it, and finding yourself better afterward is literally anything. It doesn’t have to start with something uncomfortable, or something you’re afraid of. Start anywhere and grow from there! Whatever direction you go, you start leveling up, which then allows you to take steeper paths, climb higher mountains. On the flip side, the only thing you have to do to initiate the nefarious cycle of inaction—imagining the possible negative outcomes of leaving the bed/couch/house, mindlessly mumbling buzzwords like “awkward” and “cringe”, building these things up in your head, comparing these now “scary” situations to alternatives which typically involve “safety”, solitude and screens, then deciding to remain inert—is literally nothing. Nothing begets nothing; inaction is quicksand.
It’s not difficult to see the forces at work here, and they are all working against us. Want to avoid mistakes? Easy solution! Do nothing. Afraid of the unknown? Easy solution! Do nothing. We have infinite guaranteed dopamine hits at our fingertips, what is there possibly to gain by venturing into the realm of uncertainty, with physical (even public!) consequences? I’ll tell you: confidence, courage, action, achievement, success, stories, and yes, sometimes failure.
Do something, do anything, and start now. It’s okay to be afraid, and yes, you will fail, inevitably. You shouldn’t enjoy failure, but you should recognize its value and, in the long run, reap the benefits!
