The Art of Failure

I learn more from my failures than I do from successes, and so as a result, I have done a lot of learning in my career. My list of failures is long and growing. Among my more notable ones include not being able to get a software job out of college, not creating a successful Dotcom business when it seemed everybody and their brother was doing it, not being able to start a cloud monitoring business out of Dell, and not being able to successfully convince Boston venture capitalists - most of whom knew me - of the viability of public cloud management in 2012.

Each of my failures came with the expected emotions: a feeling of inadequacy, a loss of self esteem, and sometimes even a little jealousy at the success of others. I will confess: I still don’t understand why everyone but me was able to start a successful Dotcom startup? 😀 Failure is hard, unpleasant and something most of us seek to avoid. But failure is also human, and most of us will have as many professional failures in our career as we do successes.

As a near certified expert in failure, I thought I would share a few bits of wisdom, gained the old fashioned way: through repeated failure.

#1: Nothing Ventured, Nothing Gained

You cannot gain what you are not willing to risk. If you want to achieve a goal, you must take the risks necessary to make it happen. If you are by nature conservative like me, you may do everything in your power to limit the downside risks of failure. But in the end, sometimes you need to get out on the skinny branch to get that apple (thank you Ed). Yes I could have stayed as VP of engineering of a startup with a steady paycheck and a lot more free time - but I wouldn’t have fulfilled my goal of starting a company at the intersection of my two professional passions: cloud computing and IT management.

#2: Own It

I remember interviewing a candidate for a software job who told me that all his previous employers “had sucked”, and he was hoping his next one “didn’t suck too.” He took the easy approach to failure: denying it. Failure is something we all seek to avoid, but when it happens, you need to own it. You get more respect by admitting your failures and your resulting lessons than through denial. Also, no one likes a sore loser - especially when he or she is your President.

#3: Persevere

I jokingly tell people I have been turned down by every venture investor in Boston. The inside joke is this: it’s not a joke. I pitched almost every venture firm in Boston on CloudHealth at least once. Along the way I heard every possible objection: enterprises won’t adopt the public cloud, the market is too crowded, the money is in the private cloud, the problem is too easy, IT management is a bad investment. When you fail, you have only one path forward: pick yourself up, dust yourself off, and get back in the game. It’s not the failure that defines you but what you do next.

#4: You Are Never Alone

Everyone fails. If it doesn’t look that way, it’s because some of us are better at hiding it than others. In moments of failure, I like to think of other well known people who rebounded from failure - e.g. Howard Shultz’s 217 rejections from investors on his way to building Starbucks into a $100B+ company; Evan Williams pivoting his failed podcasting startup into Twitter; etc... You are not the first to have failed at what you are trying and you certainly won't be the last.

#5: Know When To Give Up

Did I say you should never give up? Well, that’s true except... when it’s time to give up. Sometimes failure is telling you something - e.g. you need to change your time horizon, your plan, your goal. It’s not always easy to know when to pivot and when to persevere. I actually wanted to start CloudHealth in 2010 when I was looking to leave Dell. After hearing nothing but negative feedback and not seeing a path forward, I gave up and took a job at a cloud computing startup, where I grew my expertise in this industry. If I had not given up, I almost certainly would have started CloudHealth too early for the market and with a lot less relevant experience.

#6: Make Failure a Part of Your Personal Narrative

This is a story I have told often that represents me making failure a part of my personal narrative:

When I tried to start CloudHealth in 2010, I was told by venture investors I had a “really really bad idea.” After realizing there was no interest in funding a cloud management startup, I decided to fall back to a plan B of taking a VP of engineering role at a cloud computing startup called Sonian. After working a year at Sonian - where I experienced all the problems of scaling and managing efficiency in the public cloud - it was clear to me that I was right with my original idea. And so in 2012, I quit my job, went back out to venture investors, and was promptly told that I had a “bad idea.” So in two years I went from a “really really bad idea” to just a “bad idea”, which in the world of entrepreneurship we call: progress.

In my personal narrative, I directly address the failure, add a little good humor, and then tie it into my future success. Failure in a personal narrative tells everyone where you came from, how you have dealt with adversity in the past, and what you are capable of in the future.

Last Thoughts

It’s hard to discuss failure without someone reciting the great Thomas Edison quote: “I have not failed. I’ve just found 10,000 ways that won’t work.” While it’s a powerful quote, have you ever thought about what it must have been like as one of Edison’s scientists? After pouring your hard work into an approach you are certain will produce a working light bulb, you see it result in abject failure. To make it even worse, your tyrant boss tells you to pick yourself up and start all over again. I don’t know about you, but somewhere around failure 5,672, I might have thought about just sticking with candles.