Learning to Fail

I want to reach out a little and talk about something I have seen a lot of conversation around lately. Failure is a word that brings all of us a sense of fear and dread. It has been built up into our collective psyche as the end, that unrecoverable act from which you cannot ever redeem yourself. Failure takes many forms and inhabits many spaces in our society, and rarely is it something that you cannot come back from, but it definitely makes us feel “less than”. It is that “less than” feeling that goes with failure that makes us fear it so much and it is that very feeling that I want to talk about.

I know that I am a privileged, and incredibly fortunate and lucky, white male. I have built a good career and have a good income and good life and while I worked my a$$ off to have those things regardless of my privilege, I am not so blind as to say that I have not benefited from who and what I am. I know others have much harder struggles. That does not mean that I have not failed, many many times over in often spectacular fashion. I have been married multiple times, had many relationships end, I have had my kids tell me they hate me, I have lost friends for countless stupid reasons, lost jobs for even stupider reasons, and overall have had plenty of setbacks and losses that were both brutal in their pain and humbling in their lessons.

This is sort of how my boss did it…

Most recently I was let go by a company that I had literally bent over backward to build something for. The thing I built was most definitely not a failure, it is still going on and still running under my name, and I am proud of that accomplishment. No my failure was more subtle and more defeating; I failed myself by not recognizing that the job was killing me sooner and leaving when I realized this (over very good advice and urging by others who know and care about me). I thought I could stick it out and turn things around even when it was increasingly evident I could not. That was the first lesson: quit when you know it’s time.  Our gut feelings are rarely wrong and mine was screaming at me to get out while I could on my own terms. Instead I stayed and fought harder and worked myself into burnout and mental lapses that only got worse. Ultimately one small mental lapse in a string of high-pressure situations resulted in my unpleasant and abrupt departure, and illustrated the second lesson: don’t keep fighting when you know you’ve lost.

Failure is only failure if you make the same mistakes. I know many who have worked for and with me over the years have heard me mention that. In this case it was doubly true. I was humbled and stung by the whole situation and resolved never to find myself in that place again. I began my job search and resolved not to believe the hype and trust the salesman trying to get me to come on board. I went in with my eyes wide open and found myself asking better questions and more of them. What’s the vision for the role? What defines success? Is it funded? Do you want a full acknowledged “$hit disturber” who will challenge you or does that just sound like a good idea? What kind of pace do you want to move at? It was exhausting to search for a job. In fact, it sucks. If you do not like failure, and you are not prepared for it, rejection hurts worse. Let me give you an idea of failure in action:

This happens a lot – it’s not the end of the world…

I applied for well over 100 positions over the course of a couple of months (I had a very narrow set of roles I was interested in – developer evangelism/advocacy is a small world). I got an actionable reply (good or bad) from less than 20 (many of them several weeks or even months later – Salesforce, I am looking at you). Of those, I got positive replies (let’s talk) from 5. I made it through multiple interview rounds with 4 of the 5 (wasn’t a technical fit at 1, too expensive for one, too senior for a couple), and of those I got 2 offers and accepted 1. These are not staggering numbers, and I am not trying to show off or make my situation dire, it is just a set of illustrative numbers. The point is to show you that even with a strong resume, a long and well established career, great skills, plenty of experience, and overall desirability for the roles I applied to, I had a 4% hit rate of “success”. FOUR. PERCENT.

You know what? I thought that was pretty damn good too. Part of accepting rejection is also understanding reality, and the reality is that even though I am a great candidate, I am not a great candidate for every organization, role, and skillset. I was told I was not technical enough, too experienced, too expensive, not strong enough as a leader, too strong as a leader, and every possible form of “thanks, but no”. This happens all the time in our daily life and takes the form of getting turned down for a speaking gig, an application for something or other, your recent code changes that don’t compile, and otherwise general “sorry, but no” sorts of rejections. Fear of that moment leads a lot of us to never try in the first place, and this is completely to your detriment and to ours! How will we know what we are missing if you do not put your “hat in the ring” as it were? Rejection also makes us stronger, when we figure out the source of the rejection. Always, and I cannot overstate this point, ALWAYS ask for why. You won’t always get it of course, but it is invaluable to understanding what you can do better next time around. It isn’t always about you in the end, a lot of times I have found I was simply not in the right place at the right time and it happens. It’s a lot easier to move on from rejection and failure when you understand the why behind it.

No matter what you do, and how you do it, keep trying. Failure is a painful lesson, but it is only truly failure if you let it keep you from trying again!