I was talking to someone who was encouraged to post on the company’s blog, but refused, because he was worried he’ll make a mistake. In fact, he told me he wakes up in the middle of the night to fix a typo in a document.
This made me realise that people have a lot of misconceptions about making mistakes, even if not as blatant as the one above. So I wanted to share some mistakes that have held me back for years:
Myth: We should minimise mistakes.
Reality: We should maximise the value we add.
Explanation: Say you do 10 things, and 2 of them go wrong. Suppose you’re not happy about this — you want to make fewer mistakes. So you’re more careful, and spend more time on each task. So you end up doing only 7 in the same time. But one goes wrong. In the first case, you delivered 8 successful tasks, and in the second, only 6.
There are a few things to notice here: first, if you want to make fewer mistakes, you have to spend some time to that end, time you could instead have used to do more work. Second, you’re still going to make mistakes. Third, being more careful than necessary is not good because you’re imposing an overhead on every task to catch mistakes in only some tasks. This is no different from an airport security queue where everyone is slowed down to catch an occasional miscreant.
So, don’t focus on reducing your mistakes; focus on doing more work and adding more value.
Myth: When I make a mistake, I’ll look bad to colleagues.
Reality: You won’t.
Explanation: When I was concerned about that, I got less done, and so ended up looking bad to colleagues. Conversely, when I took initiative, I got more done, and was perceived more positively by colleagues.
In general, you shouldn’t do things out of fear, any more than a tennis player going out into the court embarrassed that he might hit the net will succeed.
Besides, if Tesla isn’t embarrassed about losing many rockets, we don’t need to be embarrassed about our mistakes which are nowhere as dramatic:
Myth: When I make a mistake, it paints my company in a negative light.
Reality: It’s usually not taken seriously.
Explanation: Some of us think that we’re on a stage, and the entire world is looking at us make our next move, but we’re not. And even if your product is imperfect, users don’t look at our products as closely as we team members do.
Myth: Mistakes should be prevented.
Reality: Mistakes should be corrected.
Explanation: This misconception probably comes from our education system, where we’re penalised for mistakes, whether by being marked down in a test or by being criticised in front of the class. After years and years of such experiences, it’s drilled down into us that mistakes should be prevented. But this is one of the many bad habits the education system leaves us with.
A better mental model comes from Jeff Bezos, who classifies decisions as reversible and irreversible. The majority are easily reversible. They’re like walking through a door — if you don’t like what’s on the other side, you can walk back. By contrast, irreversible decisions are like selling your users’ data. You should be careful before making an irreversible decision: think through all scenarios, get data, get multiple perspectives, get sign-off from the CEO, etc. But you should make reversible decisions as rapidly as you can . Most decisions are reversible, so aim to correct, rather than prevent, mistakes.
Myth: Work should be done by qualified people, like design by designers.
Reality: You become qualified after you do it, not before.
Explanation: Many people have the mental model of a doctor or a pilot, who’s qualified before he does the job. But most jobs aren’t like that. In this example, your company or team may not have a designer, or he may be busy with other things, and if you don’t do it, someone no better than you may end up doing it. I was able to learn multiple things, whether being a tech lead, people management, project management, product management, design or business development, by doing them when I wasn’t qualified to. Nobody will invite you to do these things. But doing them gives you a much better grasp of the job than any kind of theoretical knowledge like reading a book or taking a course. You do it, and you then become qualified to do it, not the other way around.
Myth: We should take pride in our work, and so do high-quality work.
Reality: You are not your work, so don’t tie your ego to it.
Explanation: Perfectionists are the way they are because they’re scared that they’ll be judged negatively if they put anything out there that’s less than perfect. You should be open to making some mistakes, just as your favorite bands have some bad albums. By doing work, you learn, and you learn what actually matters, rather than going by your preconceived notions of what matters. Reality is the best teacher. If you’re avoiding it, you won’t be at your best, and won’t have a path to get there.
Myth: Do it once and launch it.
Reality: Work in iterations.
Explanation: Many people haven’t internalised the idea of iterations. They still have the mental model of making a physical object like a chair, which you can’t modify once it’s in customers’ hands. This mental model also comes from school and college, where you complete an assignment and hand it in, or complete a course and take an exam. But that’s not how the real world works. Work in iterations. It’s okay to make a mistake and correct it in the next iteration. In fact, when you know that another iteration is going to arrive soon, the stakes are lower.
Myth: Iterate and launch.
Reality: Launch and iterate.
Explanation: When you want to launch, people often say “Before that, let’s do A, B and C”. These people want to iterate and then launch, even if they don’t recognise it as such. It comes out of a desire to reduce mistakes. But when you accept the previous points about working in iterations, and that the entire world is not looking at your next move, the conclusion is to launch and iterate. When you launch, you have a much better understanding of what to do next, so launch and iterate is not about doing the same thing in a different order, but about building a better product faster.
Myth: If I spend more time, I’ll do things better.
Reality: There’s a sweet spot where you get the most bang for the buck, but beyond that spot, you have to spend a lot of time for a slight increase in value, which doesn’t make sense.
Explanation: The other problem with overdoing things is that your initial idea may be wrong, in which case you end up building a very polished implementation of a bad idea. It’s better to do things only at the required level of quality. And, when you don’t know what that is, err on the side of less rather than more. If the quality isn’t enough, and Finally, overdoing a task doesn’t leave time or focus for other tasks that may be more important than the last few percentage points of improvement in the original task.
Myth: I should ask for approval from my manager (or other authority).
Reality: Ask for forgiveness, not permission.
Explanation: When you ask someone for permission, they have to figure out an answer, which takes focus away from their own work. Making decisions is draining. And since they’re signing off, they’ll take the blame if it backfires, so they’ll be more conservative. You’ll grow much faster in your career if you do things independently, so ask for forgiveness when you make the occasional mistake, rather than asking for permission every time.
Myth: We’re paid to think.
Reality: We’re paid to work. We’re closer to gardeners than to philosophers.
Explanation: Some of us, especially recent graduates from elite colleges, prefer to mull over things rather than get our hands dirty. Thinking is necessary, but not the thing that we’re ultimately valued for.
Myth: We should have a plan before we do things.
Reality: Some things require planning, but others require trial and error to figure out.
Explanation: I’ve been told that you should have a plan before you do anything. But that’s the wrong mental model. Often, you need to experiment. Especially if you do new things. Or things new to you. (Which you want to do to grow. ) I used to feel uncomfortable when doing tasks that didn’t have an obvious plan, so I used to either refuse them or fall back to planning because I had a wrong mental model that everything requires planning. But that got me stuck in analysis paralysis. If you don’t know what to do, do something, anything, to get unstuck, get moving and get the experience based on which you can come up with a good course of action the second time. Trying and making a mistake is better than sitting on your ass. Even the word “mistake” has the wrong connotation. They’re often waypoints on the path to your destination. So, have a bias for action.
Myth: If you have two options and you’re not sure which one to take, wait till you’re clear.
Reality: It’s often better to pick one.
Explanation: It’s better to be wrong than indecisive. Because if you’ve picked the wrong option, you’ve made progress, by eliminating one option, and learnt something about the work that puts you in a better position to decide. Whereas if you keep waiting for clarity, you’ll never get it. It’s better to be wrong than indecisive.
Myth: If there’s a problem, take it to your manager, who’ll solve it.
Reality: Take the problem to your manager, ideally along with a proposed solution, however bad.
Explanation: Your manager is overburdened with a lot of things, so you’re helping him by going with a proposal. Don’t worry that it’s wrong. Even if it is, he may not have any better an idea (managers aren’t all-knowing). Or he’ll be happy that you’re taking initiative and making an effort to solve the problem. And forcing yourself to come up with a solution often helps you understand the problem better, even if the solution itself isn’t useful. And when you do this ten times, from the eleventh time onward, you’ll be able to come up with useful solutions that others aren’t able to.
We have a lot of misconceptions about mistakes that hold us back. Change your mental model about making mistakes, and you’ll grow much faster in your career.
 This BTW is why big companies suck: they try to prevent mistakes that should instead be corrected. Working at a big company is the equivalent of wearing a bulletproof vest when you go for a walk.