Mistakes, experimentation, and failure are the hot topic in education and creativity circles these days. Here at 99U, we’ve covered Tim Harford’s new book on the importance of making mistakes and adapting, rounded up tons of creatives talking about the fringe benefits of failure, and heard bestselling author Joshua Foer talk about how we must step out of our comfort zones. And if you don’t believe us, the NY Times Magazine just did an edition on why failure may be the key to success.
So when I stumbled on this Dilbert cartoon that spoofs the common job interview question, “Describe your biggest mistake and what you learned from it,” I couldn’t just laugh it off. It actually felt like a question worthy of deep consideration. So that’s what I’d like to ask you to contemplate today:
What was your biggest mistake, and what did you learn from it?
Is making mistakes really all that bad? Can we demystify our fear of failure? I’d love to hear your perspective. Please share your stories in the comments below.
To start the thread, I’ll share mine:
One of the biggest mistakes I made was a poor job transition in 2007. I had been working for an exciting startup called Flavorpill for a little over 4 years. When I joined in 2002, the company was expanding, and I had the opportunity to assemble an editorial team, collaborate with the founders on growing the brand, and work closely with our wonderful design partners to build and launch new products. It was a great job and I learned a ton. But eventually, I knew it was time to move on.
A friend connected me with the CEO of a massive music website that wanted to reinvent its coverage for a new, hipper audience. He was looking for an editor with a vision. I didn’t like their current website, but the allure of having carte blanche to reinvent the site was strong. I was also offered more money than I had ever made, and the opportunity to relocate to Los Angeles. I was ready for a major change, and this seemed like the perfect way to shake things up.
As a result, I probably didn’t do as much homework on the position as I should have. After just a few weeks on the job, I realized something was amiss. To name just a few of the problems:
- My immediate superior and the primary person I was excited to be working with quit shortly after my arrival.
- I recognized that this was not a startup environment. Decisions were hampered by bureaucracy and fear of upsetting what was already a good thing.
- The people whose support I needed were not all on board with the CEO’s thirst for reinvention. Not everyone wanted change.
Recognizing all of the above, it quickly became apparent that the possibility of thinking (and acting) creatively within the organization would be slim, and consequently so was the possibility of affecting any kind of major change.
The people I worked with were lovely, despite the dysfunctions of the larger organization, so I tried to make the best of it for awhile. After it became clear that I wasn’t going to get anywhere, and I decided to get out.
Less than 10 months after I had moved to LA to take that new job, I moved back to New York and started working as a freelance consultant. Within a year, I was working with Behance, and we were planting the seeds for the research that would evolve into this website, 99U.com. In other words, everything worked out great in the end.
Four years after my ill-considered move to LA, I hardly even remember the negative aspects of that experience. What sticks with me are the crucial lessons and relationships that came out of that “failure”:
- I learned that I love the freedom, flexibility, and creativity of startup environments.
- I learned that having enough money is important, but more money will never motivate me if I lack passion or belief in a company’s larger vision.
- I learned that removing myself from my normal environment (in this case, New York) was a great way to reflect on next steps for my career. Even if I did it during a time when I had just made a bit of a career misstep!
- I met a bunch of great people (who all moved back to New York, too) that have made a great impact on my life.
When I look at it this way, it doesn’t feel much like a failure. It just feels like a very necessary learning experience.
What’s Your Story?
What was your biggest mistake, and what did you learn?
You can only learn from a mistake after you admit you’ve made it. As soon as you start blaming other people (or the universe itself) you distance yourself from any possible lesson. But if you courageously stand up and honestly say “This is my mistake and I am responsible” the possibilities for learning will move towards you. Admission of a mistake, even if only privately to yourself, makes learning possible by moving the focus away from blame assignment and towards understanding. Wise people admit their mistakes easily. They know progress accelerates when they do.
This advice runs counter to the cultural assumptions we have about mistakes and failure, namely that they are shameful things. We’re taught in school, in our families, or at work to feel guilty about failure and to do whatever we can to avoid mistakes. This sense of shame combined with the inevitability of setbacks when attempting difficult things explains why many people give up on their goals: they’re not prepared for the mistakes and failures they’ll face on their way to what they want. What’s missing in many people’s beliefs about success is the fact that the more challenging the goal, the more frequent and difficult setbacks will be. The larger your ambitions, the more dependent you will be on your ability to overcome and learn from your mistakes.
But for many reasons admitting mistakes is difficult. An implied value in many cultures is that our work represents us: if you fail a test, then you are a failure. If you make a mistake then you are a mistake (You may never have felt this way, but many people do. It explains the behavior of some of your high school or college friends). Like eggs, steak and other tasty things we are given letter grades (A, B, C, D and F) organizing us for someone else’s consumption: universities and employers evaluate young candidates on their grades, numbers based on scores from tests unforgiving to mistakes.
For anyone than never discovers a deeper self-identity, based not on lack of mistakes but on courage, compassionate intelligence, commitment and creativity, life is a scary place made safe only by never getting into trouble, never breaking rules and never taking the risks that their hearts tell them they need to take.
Learning from mistakes requires three things:
- Putting yourself in situations where you can make interesting mistakes
- Having the self-confidence to admit to them
- Being courageous about making changes
This essay will cover all three. First we have to classify the different kinds of mistakes.
The four kinds of mistakes
One way to categorize mistakes is into these categories:
- Stupid: Absurdly dumb things that just happen. Stubbing your toe, dropping your pizza on your neighbor’s fat cat or poking yourself in the eye with a banana.
- Simple: Mistakes that are avoidable but your sequence of decisions made inevitable. Having the power go out in the middle of your party because you forgot to pay the rent, or running out of beer at said party because you didn’t anticipate the number of guests.
- Involved: Mistakes that are understood but require effort to prevent. Regularly arriving late to work/friends, eating fast food for lunch every day, or going bankrupt at your start-up company because of your complete ignorance of basic accounting.
- Complex: Mistakes that have complicated causes and no obvious way to avoid next time. Examples include making tough decisions that have bad results, relationships that fail, or other unpleasant or unsatisfying outcomes to important things.
(I’m sure you can come up with other categories: that’s fantastic, please share them here. But these are the ones you’re stuck with for the rest of this essay).
I’m leaving all philosophical questions about mistakes up to you. One person’s pleasure is another person’s mistake: decide for yourself. Maybe you enjoy stabbing your neighbor’s cat with a banana, who knows. We all do things we know are bad in the long term, but are oh so good in the short term. So regardless of where you stand, I’m working with you. However mistakes are defined in your personal philosophy this essay should help you learn from them.
Learning from mistakes that fall into the first two categories (Stupid & Simple) is easy, but shallow. Once you recognize the problem and know the better way, you should be able to avoid similar mistakes. Or in some cases you’ll realize that no matter what you do once in a while you’ll do stupid things (e.g. even Einstein stubbed his toes).
But these kinds of mistakes are not interesting. The lessons aren’t deep and it’s unlikely they lead you to learn much about yourself or anything else. For example compare these two mistakes
- My use of dual part harmony for the 2nd trumpets in my orchestral composition for the homeless children’s shelter benefit concert overpowered the intended narrative of the violins.
- I got an Oreo stuck in my underwear.
The kind of mistakes you make define you. The more interesting the mistakes, the more interesting the life. If your biggest mistakes are missing reruns of tv-shows or buying the wrong lottery ticket you’re not challenging yourself enough to earn more interesting mistakes.
And since there isn’t much to learn from simple and stupid mistakes, most people try to minimize their frequency and how much time we spend recovering from them. Their time is better spent learning from bigger mistakes. But if we habitually or compulsively make stupid mistakes, then what we really have is an involved mistake.
The third pile of mistakes, Involved mistakes, requires significant changes to avoid. These are mistakes we tend to make through either habit or nature. But since change is so much harder than we admit, we often suffer through the same mistakes again and again instead of making the tough changes needed to avoid them.
Difficultly with change involves an earlier point made in this essay. Some feel that to agree to change means there is something wrong with them. “If I’m perfect, why would I need to change?” Since they need to protect their idea of perfection, they refuse change (Or possibly, even refuse to admit they did anything wrong).
But this is a trap: refusing to acknowledge mistakes, or tendencies to make similar kinds of mistakes, is a refusal to acknowledge reality. If you can’t see the gaps, flaws, or weaknesses in your behavior you’re forever trapped in the same behavior and limitations you’ve always had, possibly since you were a child (When someone tells you you’re being a baby, they might be right).
Another challenge to change is that it may require renewing commitments you’ve broken before, from the trivial “Yes, I’ll try to remember to take the trash out” to the more serious “I’ll try to stop sleeping with all of your friends”. This happens in any environment: the workplace, friendships, romantic relationships or even commitments you’ve made to yourself. Renewing commitments can be tough since it requires not only admitting to the recent mistake, but acknowledging similar mistakes you’ve made before. The feelings of failure and guilt become so large that we don’t have the courage to try again.
This is why success in learning from mistakes often requires involvement from other people, either for advice, training or simply to keep you honest. A supportive friend’s, mentor’s or professional’s perspective on your behavior will be more objective than your own and help you identify when ytou’re hedging, breaking or denying the commitments you’ve made.
In moments of weakness the only way to prevent a mistake is to enlist someone else. “Fred, I want to play my Gamecube today but I promised Sally I wouldn’t. Can we hang out so you can make sure I don’t do it today?” Admitting you need help and asking for it often requires more courage than trying to do it on your own.
The biggest lesson to learn in involved mistakes is that you have to examine your own ability to change. Some kinds of change will be easier for you than others and until you make mistakes and try to correct them you won’t know which they are.
How to handle complex mistakes
The most interesting kinds of mistake are the last group: Complex mistakes. The more complicated the mistake you’ve made, the more patient you need to be. There’s nothing worse than flailing around trying to fix something you don’t understand: you’ll always make things worse.
I remember as a kid when our beloved Atari 2600 game system started showing static on the screen during games. The solution my brother and I came up with? Smack the machine as hard as we could (A clear sign I had the intellect for management). Amazingly this worked for awhile, but after weeks of regular beatings the delicate electronics eventually gave out. We were lazy, ignorant and impatient, and couldn’t see that our solution would work against us.
Professional investigators, like journalists, police detectives and doctors, try to get as many perspectives on situations as possible before taking action (Policemen use eyewitnesses, Doctors use exams and tests, scientific studies use large sample sizes). They know that human perception, including their own, is highly fallible and biased by many factors. The only way to obtain an objective understanding is to compare several different perspectives. When trying to understand your own mistakes in complex situations you should work in the same way.
Start by finding someone else to talk to about what happened. Even if no one was within 50 yards when you crashed your best friend’s BMW into your neighbor’s living room, talking to someone else gives you the benefit of their experience applied to your situation. They may know of someone that’s made a similar mistake or know a way to deal with the problem that you don’t.
But most importantly, by describing what happened you are forced to break down the chronology and clearly define (your recollection of) the sequence of events. They may ask you questions that surface important details you didn’t notice before. There may have been more going on (did the brakes fail? Did you swerve to avoid your neighbor’s daughter? etc.) than you, consumed by your emotions about your failure, realized.
If multiple people were involved (say, your co-workers), you want to hear each person’s account of what happened. Each person will emphasize different aspects of the situation based on their skills, biases, and circumstances, getting you closer to a complete view of what took place.
If the situation was/is contentious you may need people to report their stories independently – police investigators never have eyewitness collaborate. They want each point of view to be delivered unbiased by other eyewitnesses (possibly erroneous) recollections. Later on they’ll bring each account together and see what fits and what doesn’t.
An illustrative example comes from the book Inviting disasters Inviting Disaster: Lessons from the edge of technology. It tells the story of a floating dormitory for oil workers in the North Sea that rolled over during the night killing over 100 people. The engineering experts quickly constructed different theories and complex explanations that focused on operational errors and management decisions.
All of these theories were wrong. It was eventually discovered through careful analysis that weeks earlier a crack in a support structure had been painted over, instead of being reported and repaired. This stupid, simple and small mistake caused the superstructure to fail, sinking the dormitory. Without careful analysis the wrong conclusion would have been reached (e.g. smacking the Atari) and the wrong lesson would have been learned.
Until you work backwards for moments, hours or days before the actual mistake event, you probably won’t see all of the contributing factors and can’t learn all of the possible lessons. The more complex the mistake, the further back you’ll need to go and the more careful and open-minded you need to be in your own investigation. You may even need to bring in an objective outsider to help sort things out. You’d never have a suspect in a crime lead the investigation, right? Then how can you completely trust yourself to investigate your own mistakes?
Here some questions to ask to help your investigation:
- What was the probable sequence of events?
- Were their multiple small mistakes that led to a larger one?
- Were there any erroneous assumptions made?
- Did we have the right goals? Were we trying to solve the right problem?
- Was it possible to have recognized bad assumptions earlier?
- Was there information we know now that would have been useful then?
- What would we do differently if in this exact situation again?
- How can we avoid getting into situations like this? (What was the kind of situation we wanted to be in?)
- Was this simply unavoidable given all of the circumstances? A failure isn’t a mistake if you were attempting the impossible.
- Has enough time passed for us to know if this is a mistake or not?
As you put together the sequence of events, you’ll recognize that mistakes initially categorized as complex eventually break down into smaller mistakes. The painted over crack was avoidable but happened anyway (Stupid). Was there a system in place for avoiding these mistakes? (Simple). Were there unaddressed patterns of behavior that made that system fail? (Involved). Once you’ve broken a complex mistake down you can follow the previous advice on making changes.
Humor and Courage
No amount of analysis can replace your confidence in yourself. When you’ve made a mistake, especially a visible one that impacts other people, it’s natural to question your ability to perform next time. But you must get past your doubts. The best you can do is study the past, practice for the situations you expect, and get back in the game. Your studying of the past should help broaden your perspective. You want to be aware of how many other smart, capable well meaning people have made similar mistakes to the one you made, and went on to even bigger mistakes, I mean successes, in the future.
One way to know you’ve reached a healthy place is your sense of humor. It might take a few days, but eventually you’ll see some comedy in what happened. When friends tell stories of their mistakes it makes you laugh, right? Well when you can laugh at your own mistakes you know you’ve accepted it and no longer judge yourself on the basis of one single event. Reaching this kind of perspective is very important in avoiding future mistakes. Humor loosens up your psychology and prevents you from obsessing about the past. It’s easy to make new mistakes by spending too much energy protecting against the previous ones. Remember the saying “a man fears the tiger that bit him last, instead of the tiger that will bite him next”.
So the most important lesson in all of mistake making is to trust that while mistakes are inevitable, if you can learn from the current one, you’ll also be able to learn from future ones. No matter what happens tomorrow you’ll be able to get value from it, and apply it to the day after that. Progress won’t be a straight line but if you keep learning you will have more successes than failures, and the mistakes you make along the way will help you get to where you want to go.
The learning from mistakes checklist
- Accepting responsibility makes learning possible.
- Don’t equate making mistakes with being a mistake.
- You can’t change mistakes, but you can choose how to respond to them.
- Growth starts when you can see room for improvement.
- Work to understand why it happened and what the factors were.
- What information could have avoided the mistake?
- What small mistakes, in sequence, contributed to the bigger mistake?
- Are there alternatives you should have considered but did not?
- What kinds of changes are required to avoid making this mistake again?What kinds of change are difficult for you?
- How do you think your behavior should/would change in you were in a similar situation again?
- Work to understand the mistake until you can make fun of it (or not want to kill others that make fun).
- Don’t over-compensate: the next situation won’t be the same as the last.
Inviting Disaster: Lessons from the edge of technology by James Chiles. A series of magazine style essays about major technological disasters in the last 100 years. Includes the Challenge shuttle, Apollo 13, & Three mile island.
The Logic of Failure by Dietrich Dorner. An analysis of decision making mistakes in complex environments. More academic than Inviting disaster, but also more prescriptive.
[First posted, July 17 2005]