The Mistake That Changed My Career—and Why Future PMs Deserve the Same Opportunity

I still remember the biggest mistake I ever made on a project, 25 years later it still guides me every day. That’s the value of a really good mistake - it’s a lesson that stays with you for ever. Are we robbing future Project Managers of the benefit of making good mistakes?

My biggest mistake

I was a junior and was put into a situation way above anything I’d dealt with before. All the signs were obvious that I was failing. I was working until 3am most nights. I was working weekends. As were the team. As the Project Manager, if the team were working late, I was working late. We were struggling to hit our deliverable. What we had promised to the client just wasn’t possible to achieve with the technology we were working with. But we’d sold it, so we had to make it work. We were moving every mountain of every size to try to get this thing to work. But it just wasn’t playing ball.

One Friday evening, nervous about how the client was perceiving our lack of progress, I called a meeting. I asked if the client thought there was anything we were missing, if they could see how hard we were trying. The client was effusive. She’d never seen a group work so hard to get a problem solved. We had her huge thanks for our efforts. I went home feeling a little bit better about the work in front of me that weekend. However, come Monday morning, the client had cancelled our contract and kicked us off site. Ouch!

The lessons I learnt

The number one lesson that I learnt is that effort and intent don’t cut it. The only thing that matters is the outcome. Anyone who knows me, will know that lesson has stood with me and still directs me today. I am all about the outcome. But there were other lessons too. Lessons about how to propose work to clients which is cutting edge and you’re not sure if it can be done; lessons about sticking with the team when the going gets tough; lessons about owning up to your mistake early rather than trying to cover it up and fix it.

The thing I didn’t know at the time, was that my boss was well aware that I had made a mistake and that I was struggling. He could see the effort I was putting in, the approach I was taking, the lengths I was going to. The best thing he did, was that he didn’t step in. He was carefully managing me to make sure I didn’t tip over and burnout, but he was letting me make my mistake.

His support in the weeks that followed, guiding me through what had happened and what could have been done differently, allowed me to internalise and own my mistake. It made me a better person and it made me a better Project Manager.

I fear that people today don’t have the luxury of a big mistake.

Are you allowed to make a big mistake?

When I look at a lot of organisations today, there’s a huge amount of effort and focus that goes into making sure people don’t make mistakes. You probably have a boss who has been running projects for a while and looks over your shoulder as you deliver. You probably have a bunch of people that you’re expected to share documents, progress and forecasts with. You might have a PMO that query, challenge and test you. There’s an industry put above and around you to make sure that you don’t make a mistake. But at what price?

Human progress should not be measured in terms of output, but in terms of learning. If you’re not making mistakes, if you’re being nudged left and right to avoid the mistake, but you never get to see why, you never get to experience why, you are being robbed of the learning that comes from making a big mistake. If progress is all about learning, you’re being robbed of progression.

In a world where we have to be accountable for every $ spent, where a mistake can be career limiting not rewarding, I fear for the future of our profession.

New parents allow their children to learn through mistakes. We learn language through trial and error. We learn how to walk through making the mistake of falling down a ton of times first. The world is a huge feedback machine and one that we need to learn and progress. This shouldn’t stop when we come into the workforce.

Allow your team the freedom to make a mistake, even a big one. Every mistake is recoverable and the learning is invaluable.