Mistakes Matter, So Make More of Them

I’ve been doing a series of coaching calls with a wide range of successful people, to learn what’s holding them back in life. One of the most common fears: the fear of making mistakes. And it’s no wonder…

It’s election time. And political discussions tell us that anyone who makes a mistake should be shunned for life, barred from public office, and labeled a “flip-flopper” (especially if they change their mind as a result of learning from their mistake). Success literature, however, tells us that we should learn to be comfortable with failure and make mistakes! One of my most accomplished business school professors once said: if you’re not making enough mistakes, you’re not taking enough risks. How about you? Do you know how to make the most of your mistakes?

If you’re not making enough mistakes, you’re not taking enough risks.

Bad Outcomes Don’t Necessarily Mean Mistakes

Our school system trains us for decades that not getting the right answer means we were wrongand somehow didn’t work hard enough. Once we get into the real world, we bring that mindset along with us. If we don’t get the results we want, we assume we made a mistake.

This isn’t necessarily so. Here’s a thought experiment to understand why. Imagine you have two quarters. One is perfectly fair. It has 50%/50% odds of flipping heads or tails. The other is weighted. It has a 60% chance of flipping heads.

We have two Coin Operators, whose job is to flip heads. They’re allowed to choose either coin to flip.

Peyton, Coin Operator #1, chooses to flip the 50/50 coin and gets HEADS.
Harley, Coin Operator #2 chooses to flip the 60/40 coin and gets TAILS.

Who made the mistake? If we look at the outcomes, it appears that Harley made the mistake. But before we know the outcome, we would favor Haley’s decision to choose the coin that is weighted towards heads. Haley pursued the outcome using the right process, even though it was the wrong outcome.

“Stuff” Happens

I hear you cry, “But Harley made the right choice! The outcome should have been heads!” I agree! We really want to believe that our actions will give us the results we want. The real world, however, is sadistic: sometimes things work, and sometimes they don’t. We have a name for this. We call this luck.[1]

We can do the right thing, have bad luck, and get the wrong outcome. We can do the wrong thing, have good luck, and get the outcome we want.

This gives us a critical insight into the nature of mistakes: it isn’t the outcome that lets us know we’ve made a mistake; it’s what we did to get the outcome, our process, that lets us know if we made a mistake.

We’re not taught to think this way. We’re not given societal support to think this way. We don’t evaluate our political candidates this way. We don’t evaluate our employees this way.

But if you want to train yourself to get what you want in life, don’t measure mistakes by outcomes. Burn these definitions into your brain:

  • Success is using a high-quality process, regardless of outcome.
  • Mistakes are using a low-quality process, regardless of outcome.

Other People May Not Suck as Much as We Think

Deep down inside, we all love judging other people, especially politicians. But this new definition of mistakes means we need to be careful. If we judge them based on outcomes, we might end up deciding that the Peytons of the world are amazing and awesome and worthy of backrubs, while the Harleys of the world should eat rocks.

Unfortunately, however, unless we’re paying attention during the entire effort, we rarely know what process someone used to reach their outcome. That makes it harder to judge them accurately.

I took a mediation class, where I had the joy of mediating a 10-party negotiation between the heads of several organizations. Each organization cared about different things, with different priorities. The real estate developers wanted more land. The conservationists wanted land made off-limits to developers. The Mayor cared about economic development and tourist trade. The historical society cared about limiting changes to any part of the city.

The final agreement satisfied no one, but at least everyone was equally dissatisfied. To each organization, the outcome surely looked like a failure. But the representatives reached the best agreement they could, given the conflicting interests, the time available, and the fledgling abilities of the mediator.

It’s easy to say “my [politician, boss, representative] failed by not getting outcome I wanted.” If we really want competent leaders, however, we do better to judge the process they use. Do they take steps to understand the issues? Do they understand whose support is needed and build the necessary coalitions? Do they compromise where needed, and hold firm where needed?

When evaluating others, don’t judge their success and failure from their outcomes. Look as closely as possible at their process.

Getting the Most Out of Your Mistakes

Although mistakes are a sign that you’re really moving, stretching, and growing yourself, that doesn’t mean you want to make the same ones over and over. You want to learn as much as you possibly can each time things don’t work out.

When a mistake happens, hold an After Action Review. Take time to reflect explicitly on what worked, what didn’t, and why. Consider what happened on the ground—what worked out the way you expected, and what didn’t. What happened that you didn’t plan for, and what didn’t happen that you did plan for? Also consider what happened in your head. How did your a priori beliefs factor into what happened? Were your interpretations of what was going on correct? Where did you waste time paying too much attention to trivialities, and where did you miss opportunity by not paying enough attention?

Making mistakes, combined with a good after action review, helps you refine several important aspects of your future thinking.

Mistakes Refine Cause/Effect Thinking

We all have theories about what causes what. Some of our theories are pretty good. We believe that watering a plant will help it grow. We water the plant. It grows. Our cause/effect works, we’re happy, and the plant is happy (maybe even ecstatic, depending on how long it’s been since you last watered it).

Some of our theories really don’t work at all. “Step on a crack, break your mother’s back” isn’t orthopedically sound advice. If you want to protect mom’s back, teaching her proper posture and good form when lifting heavy boxes is a far better plan.

And some of our theories about cause and effect are sort of true. “Work hard and you’ll get ahead” certainly works great while we’re in school. But once we’re in the work world, the link between hard work and advancement is much more tenuous. In many cases, it doesn’t hold at all.

Avoidable mistakes often help us refine our notions of cause and effect. Many people believed that putting money into the stock market would result in a consistent, positive return on their money. In 2008, an entire generation discovered that cause/effect in stock investing is more subtle, and less dependable, than they thought. Next time a financial advisor happily informs them “invest in fund X and you’ll make 11% interest for 43 years,” they’ll (hopefully) know to refine their notion that giving money to a financial advisor automatically leads to a comfortable retirement.

Mistakes Refine Discrimination Abilities

We don’t just learn rules about cause and effect. We also learn how to discriminate between different situations. For example, with the label side down, a tube of toothpaste and a tube of athlete’s foot creme might look identical. One might simply look in the drawer, see a tube, squeeze it onto a toothbrush, and pop that brush right into their mouth and start brushing.

One might then discover one’s mistake. This will lead quickly to the learning that although tubes look the same face down, there are subtle clues as to which tube belongs in the mouth, and which tube belongs in the foot. For example, fine print on the back of the tube that says “for treatment of athlete’s foot and other topical fungal infections. Don’t eat it, you moron.”

That particular mistake is the one that got me to start paying close attention to the difference between tubes of cream.

Then there are my singing lessons, where my voice teacher forced me to listen to recordings of our lesson. When I was able to stop gritting my teeth, I began to develop the ability to distinguish between a tritone and a major fifth. It turns out that when you’re singing harmony, that distinction matters.

Mistakes help us refine the distinctions we make in the world.

Mistakes Refine Luck

And finally, mistakes help us understand the role of luck in what we’re trying to do. To return to our coin toss example, if we know Harley chose the 60/40 coin to flip, and it still came up tails, that tells us that luck played a factor in the outcome. While we would have prefered that Harley flip heads, we can be confident that the outcome of tails reflects luck, and not Harley’s abilities.

We might think mistakes are bad, but nothing could be further from the truth. Mistakes help us learn if we respond correctly. We should understand the roles luck and skill played in our outcome. Analyzing our process will tell us if we our good process gave a poor outcome, or whether we had a genuinely poor process. And we should refine our understanding of cause/effect, our discrimination abilities, and the role of luck. Our greatest advancement happens when we learn when things go wrong. To do anything else would be a mistake.

  1. If you’re a physicist, you call it a wave function. Or quantum mechanics. Or alternate universes, or something. But you’re not a physicist, so let’s stick with luck.  ↩

The Right Conversation will Get You What You Want

If you want to change your life, how do you do it? I used to think it was hard. Then I realized that most of the opportunities in life have come through one simple activity: talking to people…about stuff. Who you talk to, and what you talk about, ends up building your reputation, and gets people thinking of you in ways that lead to new opportunities.

You don’t always have the power to talk to the right people, but you always have the power to talk about the stuff you think is important. Once you start talking about what you care about, you quickly find the other people who care, too.

People Will Self-Select

Start by changing the conversation with your current group of friends and colleagues. They’ll make it clear really quickly if they’re the wrong audience.

A mid-50s postal clerk called for career coaching. She’s close to retirement. In her spare time, she’s designed a low-cost, easy-to-assemble housing unit she believes could revolutionize third world housing. Her co-workers all pooh-pooh her idea: “You should realize you’re just a postal clerk with delusions of grandeur. At your age, you should just be thinking about retirement.”

Those weren’t the people to talk to. Talking to me was a good next step. I don’t have third-world housing connections, but I know people who do and can refer her. She changed her conversation and is already getting closer to people who can help realize her dream.

Jump on Opportunities

Be on the looking during the conversation, and pounce on opportunities as they arise. Last year, I was going through career angst. The only things that seemed exciting: theater and saving the world. Sadly, theater is tough to make pay, and there weren’t any save-the-world job openings on Craigslist.

I was talking with my friend Jason about my desire to save the world. Lo and behold, he had just been tasked with the job of … creating a conference to save the world! Hosted by MIT, the SOLVE conference would convene movers and shakers, technologists and policy makers, and be about initiating real action to solve world problems.

I immediately asked to get involved. I presented my ideas to the SOLVE team, and was given an invitation as an attendee to SOLVE 1.0. Will SOLVE be the right vehicle for me? Who knows. But one way or another, it introduces me to a new community to talk to, who share my concerns and aspirations. And therein lies opportunity.

Change Your Life

Now it’s your turn to change your life by talking to people … about stuff:

  1. What change do you want to make in your life?
  2. When you’ve made the change, who will you be talking to? About what?
  3. If you can reach those people directly, pick up the phone.
  4. Otherwise, start having the right conversations, and let people guide you to the right audience.
  5. If you run out of people and still haven’t found your tribe, try Facebook, LinkedIn, Google, etc.

What makes a good driving question for life?

If you were only allowed to ask one question of yourself to move you into action each morning, what one question would have the greatest chance of creating the best life for you?

In a recent Get-it-Done Guy episode, I explored the nature of using driving questions to shape your life. My episodes are often created from events in my own life. As many of you know, several years ago I did a three year experiment in Living an Extraordinary Life which later turned into a TEDx talk, a webinar, and a series of talks. You can even download an MP3 of the Living an Extraordinary Life webinar.

The driving questions episode came from my decision (largely made unconsciously and revealed to me by my unconscious mind in the late afternoon of June 17, 2014) to re-start the Experiment discussed in the presentation. In short, what driving questions drive an extraordinary life?

Here are some candidate questions so far:

  • What am I grateful for?
  • Who do I want to hang out with?
  • Who do I want to serve?
  • What do I want to do?
  • Who do I want to be?
  • What do I want to build?
  • What would I do if I were on vacation?
  • Who are the people I want to become?

These are all good questions to ask as part of a periodic life review. That’s very different from the way I’m proposing to use them, however. The proposal on the table is that one of these questions–or some other question entirely–can act as a daily launching pad for life. Which question is the one that will serve best as a daily launching pad? They propel you in a very different direction, depending on which is answered.

Want to change yourself? Change the system.

While reading “The Lucifer Effect,” it’s becoming increasingly clear how much of behavior is a product of situations and systems. I think that coaches and psychological change agents are missing this piece, big-time.

I have many people tell me that “if a person just gets clear on their big passion, they’ll make the change they need to make.” Or if they “just have an inspiring vision,” that’s enough. And yet that simply hasn’t been my experience. People go to a change agent, come back all pumped up, and six weeks later are back where they started.

(Besides, do you want a surgeon who has passion, or a surgeon who has training? There really is more to life than just having passion. Indeed, there’s research that says passion often comes from doing something you don’t like and growing to like it.)

Yes, not having an internal change will often keep you stuck. If you sabotage yourself at every turn, you’ll be stuck wherever you are. But my new opinion is internal change only works if it gets you into action. But not just any action; action needs to help create a new situation or new system that will support the new identity or new vision, or the change will eventually die out.

You don’t hear that side of the story, though. When a change agent fails with a client, they don’t trumpet the failure from the mountaintops and examine what happened in detail, to find out if their (the change agents’) models of change are insufficient. And the clients who don’t change don’t trumpet the story for obvious reasons.

My new formula:
change = change in mindset (identity, role) + change in actions + change in systems

In my NLP training and my coach training, identity has been considered a powerful shaper of behavior change. And it is, it just turns out that Situation and System can be even more powerful than identity. It also turns out that identity is shaped by behavior, even if the behavior is undertaken for neutral reasons1.

The Power to Change



  • Changing a system or a situation is the most powerful creator of change, because it forces behavior to change.
  • Changing behavior is the next most powerful, when done in a way that reshapes identity.
  • Changing identity is the least most powerful of the three, but still very powerful, because it can provide intrinsic motivation which can lead someone to change their action and their systems.

  1. see the Social Psychology literature on “commitment and consistency,” in which small behavioral changes produce identity changes. 

Is the very concept of work doomed?

I just read an excellent article on XConomy by Wade Roush in which he asks the question: is technology destroying the very basis of our economy to offer employment? And assuming it is (as a thought experiment), what might we do to stop it?

First, read the article. Otherwise, my commentary won’t make much sense.

First of all, I found it fascinating that Finland and Sweden have lower taxes than the US, despite having much better social benefits. “What!?!?!?” you cry, “lower taxes? But they’re inefficient, evil socialists! It destroys the prevailing Capitalism is Best Ever narrative to say such a thing!!!”

Well, let’s take a look. My state tax is 6.25%, my Federal taxes are 33%, and my FICA taxes are 14%. Add those together and we discover that I’m paying 53% in taxes, which is about 18% MORE1 than the 45% tax rate Wade quotes for Finland and Sweden.” The big difference is that my tax dollars go mainly to private defense contractors, private insurance companies, and other private providers of services hired by the government.

What about motivation?

Wade correctly points out that such welfare states have a problem motivating people to work. But is this a problem? If the promise of industrialization is coming true—to wit, that technology will free us to pursue things that are personally meaningful rather than productive—then decreased motivation to work doesn’t seem like a huge problem.

Perhaps what we need to do is make work either voluntary, or a phase of life (say, ages 25-40), after which you can continue to work if you enjoy it and are challenged by it, otherwise you must go out and create artwork.

Warren Buffett hasn’t needed to work in any economic sense during my entire lifetime (and then some!). But he has done so, and even took on the stressful job of running Solomon Brothers. Why? Not because the money was the big incentive, but because challenge and meaning, and rescuing an institution was important to him.

This implied theory that people’s only motivation is money continues to mystify me in an age where the #1 complaint people have about their jobs is that their jobs are meaningless, paper-pushing wastes of time that are nothing more than an excuse for a paycheck.

Do any of Wade’s solutions work?

I think Wade’s option #8 is really the only viable one. Solutions like “grow our way out of it” don’t solve the underlying systemic problem. First of all, you can’t grow everything fast enough forever, so you end up in the same situation somewhere down the line. Secondly, those solutions still cling to the notion that the only legitimate way to get paid is by doing valuable work. But if the fundamental premise we’re up against is that machines are devaluing the work rapidly, then any solution that starts with the assumption that there’s enough valuable work for everyone is doomed to fail.

As for retraining, I just have to laugh. People already accumulate a lifetime’s worth of debt for their first education that will let them spend a decade to advance to a solid, mid-level, middle-class job. While I hear this meme tossed around a lot, I challenge anyone who claims it’s possible to quit their job and retrain in another unrelated job that gives them the equivalent income. (Must be unrelated because again, the premise is that the first job has been rendered economically less vaulable by technology. Thus, the replacement job must be substantially different.)

What do you think? If technology really has made a great many humans redundant for the first time in history, we’re in uncharted waters. Where do we go from here? Anywhere we want to. Where do we want to go from here?

  1. The math is a bit weird here. What I mean is that if I make $100 in the US, I pay 53% tax, leaving $47. Someone from Finland pays 45% tax, leaving $55. That’s 17.78% more than the Fins. Actually, to do this correctly would require looking at the different tax brackets and drawing a big graph of income ranges, etc. At the end of the day, however, it’s hard to argue that most middle class people pay much lower taxes in the U.S. If you factor in their need to pay for the services that Finland and Sweden provide nationally (e.g. health insurance, mortgage insurance, maternity leave, etc.), Americans definitely have lower take home pay to spend on non-essentials. 

Efficiency Might Be Bad

I’m a huge fan of system dynamics and the understanding of complex systems that has come from the field that Jay Forrester invented.

This is a superb article by the late Donella Meadows about the leverage points in complex systems, in ascending order of effectiveness.

Alas, most of the things we do to try to change our social and economic systems use only the least effective levers.

Tonight I’m especially struck by #9, delays in systems. Delays of information and material movement can throw a system into or out of sync in ways that utterly change the system’s characteristics.

For many years, we’ve been operating as a society under the implicit assumption that speed = efficiency. The faster things are, the fewer delays, the better off we are.

But this isn’t necessarily true. Increasing the efficiency of communication decreases the time between communication we have to understand and respond. We end up in reactive mode, rather than thoughtful mode. That’s one of the pernicious effects of email. Many people take action on email as it comes in, rather than taking action only on what’s important. That can make the difference between overload and achievement.

Removing communication delays also seems to reduce our tendency to prepare. When you can make changes to your presentation all the way until the night before it’s due, then you will. In prior years, when you had no choice but to finish early enough to send your slides to be duplicated, you actually had time you could then use to rehearse and concentrate on delivery, rather than on making last-minute changes.

Read the article. Let me know your thoughts, if you still have enough attention span to make it through, after all the years we’ve spent training ourselves to operate in a purely reactive—but oh, so efficient–mode.