CTO Compass

Win or Learn

Have you made a mistake? If there was ever such a rhetorical question, that would be it. The reality is that we make many mistakes every day.

As Abraham Maslow said: “There are no perfect human beings”.

And guess what, you and I will not be the first! That ship sailed a long time ago.

Facing the music

When you make a mistake, big or small, what do you do?

Perhaps it’s our ego, shame, or embarrassment, either to ourselves or, worse, in front of others, that means we often just shrug it off, brush it under the carpet, or rationalise it away. Mistakes can easily make us feel bad, and we’d rather not come face to face with our weaknesses.

Making mistakes and facing up to them is uncomfortable. For example, perhaps it’s something as banal as showing up to a meeting late or unprepared. Once or twice is human; that’s okay. But if you regularly fail to live up to your promises, what does it do for your reputation? Others will begin to see you as untrustworthy and unreliable. And you’ll likely feel harried and more stressed, which means you won’t be at your best in that meeting. It probably means that the meeting will be ineffective, and you’ll have wasted your time, and everyone else’s in that meeting.

Over time, you’ll come to see yourself as that person and be frustrated with yourself, resigned to the fact that you’re never on time and under-prepared.

It’s like the definition of madness. When we don’t proactively learn lessons from making mistakes—especially the small, almost unnoticed ones—we’ll likely keep repeating them over and over. It’s a recipe for frustration and stagnation. And you’re more likely to exhibit the traits of a fixed mindset. You downgrade your own abilities, and you’ll become more depressed and hard on yourself.

Mistakes are opportunities for growth

But what if we changed our perspective? What if we saw mistakes not as failures but as opportunities to learn and improve? By embracing our mistakes, we open ourselves up to personal growth and development. We gain valuable insights into our strengths and weaknesses and can use that knowledge to become better versions of ourselves.

One of the essential traits of a growth mindset is taking on challenges, making mistakes and learning from them to fuel your growth.

By reflecting on our missteps, we can identify patterns and consciously change our behaviour. This process of self-awareness and self-improvement is essential for personal and professional development. Ultimately, the choice is ours: we can either run and hide from our mistakes or face them head-on and grow.

Win or Learn – how to systematically learn from our mistakes

Intuitively, we know we should learn from them. But thinking it and then doing something about it are two entirely different things. And then, when we do try to take ownership, are we actually doing it effectively?

The most successful people have systems to learn from their mistakes. These systems are a combination of simple tools, techniques and learned habits in taking action.

Heroic has a simple but effective tool called “Win or Learn”. Practice it daily as a quick after-action review process.

It consists of 3 questions you can ask yourself after every performance. I formally make it part of my daily work shutdown process to review my workday, but I try to use it as often as possible in the moment, too, taking a few brief moments when I notice I’ve made a mistake to learn from it immediately.

Here’s a recent example from one of my daily shutdowns.

Let’s walk through it.

1. What Went Well?

It’s important to start the process by reflecting on what you did well in the circumstances. We don’t want to only focus on the negative. Let’s celebrate our wins.

In my case, I recognised two important things I’m trying to cultivate.

  1. I do things, even (especially) when I don’t feel like it. I do what I say I will do.
  2. Some things happened that in the past would have had me totally spiralling out of control. Instead, I kept a positive mental outlook and reframed the challenges as opportunities for me to grow.

2. What needs work?

First, note the specific words here. It’s not “What didn’t you do well?”. We’re not looking to shame ourselves. We’re more interested in x-raying our actions and behaviours as more impartial observers, acting like scientists and gathering data. We’re asking ourselves, what needs work here?

What happened, and can you learn from it? How did you act in a sub-optimal way?

I acknowledged here that while I might have stayed more positive, I was thrown off track by the events that occurred and specifically and crucially, I didn’t follow through fully with my 3+1 task targets for the day.

3. How will I get better?

The third step is to step forward into growth and decide what you will do differently next time.

In my case, there were several things I resolved to improve on. I realised that I didn’t focus enough on my fundamentals when things went a little wobbly. Specifically, I chose to grease the groove more in my work sessions, ensuring I keep moving every 1000 seconds to keep my metabolism up. Then, I also want to take more opportunities to use my breath training and meditation practices to help recentre, especially if I’m distracted by external circumstances, and maintain focus on my work.

A couple of other quick notes that may not be immediately obvious to you.

First, the things I’m going to do differently. I’m not waiting for some nebulous future date when a big event hits me. Hopefully, they’re few and far between. What I want to do is practice the fundamentals such that they are so ingrained. I’ll do them as a habit, and when a big challenge comes along, I can take it in my stride. As James Clear said in Atomic Habits, “You do not rise to the level of your goals. You fall to the level of your systems.”

Second, this process doesn’t need to take long and isn’t onerous. I like to write mine down to review further down the line to look for longer-term patterns, but they’re just bullets. There’s no need to write prose. You can choose just one thing for each question.

Win or Win

“Win or Learn” is a simple mantra to help you remember to follow this process often. Start by reviewing your day, and then try to get more granular throughout your days. Turn it into a great habit for the smaller, daily decisions and inevitable mistakes you make. Use it any time after a performance, no matter what that might be.

When you use it all day, every day, you’ll either win or learn. And if you learn something, then you win. In which case, we win, or we win! Keep spiralling up.

⚡️ Thinking Time ⚡️

In your Thinking Time this week, practice Win or Learn. Think about a recent disappointing or sub-optimal performance, and run it through the Win or Learn process.

1. What went well?

Always start by celebrating what you did well or what generally went well.

2. What needs work?

What could have gone better? What did you learn from it?

3. How will I get better?

Take the lessons you learned and state what you will do differently next time.