Today marks my 20 years working in the software industry. I was going to write a post about what I’ve done over that time and my takeaways from all the weird and beautiful things I’ve done. I might still do, but below is something that’s taken me nearly 20 years to realise. I don’t know why it’s taking me so long. Perhaps it’s age, getting things wrong (a lot), reflecting more on what I’m doing or all of the above. Whatever it is, I wish I understood this when I was younger. Who knows what I might have accomplished otherwise?

Either way, I know it now, so let’s see what the next 20 years hold now that I’m pushing myself and worrying a lot less about what happens.

Push your own flywheel.

There are many opportunities out there, but the vast majority won’t look like opportunities. It will only do so after the fact. The best thing you can do is push yourself forward and try different things. There’s no guarantee that the things you try will work or even be successful long-term. But the more you do, the more opportunities you’ll find yourself in. It starts becoming a flywheel, but to get it moving, you’ve got to push it first. One of the most complex parts of this approach is how long and hard you’ll have to push. Most people (me included!) give up too soon, usually at the first attempt, as it didn’t work out as you expected. 

The more comfortable you get with pushing yourself, the easier it becomes to move your flywheel. But suppose you’re constantly looking for external sources to push you or waiting for the right opportunity. In that case, you’ll either be waiting for a long time or worse, when the opportunity comes, you’re nowhere near ready to take full advantage of it. 

But when you are proactive, people begin to spot that you’re the person who can do things. They will start pushing opportunities forward to you – the flywheel starts moving from external sources. People often need to see you are ready (or close enough to be ready) before they likely push you forward for that opportunity. You can try faking it until you make it, but people often spot that you’re faking. Why? Because they’ve never seen you do anything else. So why would you suddenly be able to do it now?

Pushing my own flywheel 

About ten years ago, I started talking at conferences as it terrified me, so what better way to try and get over it than by doing it more? Luckily, it worked. However, I often questioned why I put so much effort into overcoming this fear. It was costing me more (lots of personal time and anxiety) than I was getting out of it (any recognition that anyone got anything from it). But I found things I enjoyed and kept at, slowly becoming more comfortable and better. 

Over the last two years, I’ve also been doing a lot of work around psychological safety for reasons I’ll not go into here. Still, I’m happy to talk more (message me). I have put together a talk on fostering more psychological safety in our teams. However, I was still determining what to do with it. 

Then, in late September 2022, I heard the organisation I work for would have a whole-day in-person internal-only engineering conference. So I approached the organisers to see if I could get a slot. I did, but it was only 10 minutes, so I had to cut back and focus on the message. 

At this conference, I might have given my best talk to date. It’s also one of my shortest but has taken the most effort to put together. It took almost 18 months to develop my understanding of the subject matter to know what I wanted to talk about. Then, getting feedback (massive thank you to all that did) and iterating on it months before to come in under ten minutes. Plus, the ten years honing my presentation skills. 

It was not until weeks after the talk that I realised this was one of my most significant opportunities to push forward the work I’m trying to do. There was no way I could have done that talk the way I wanted in the space of 2 weeks between asking to be able to speak and getting on that stage and delivering it. 

This one 10-minute talk led to two other more significant opportunities. My past speaking gigs got me on the radar of a track host at QCon. So when they asked if I had anything suitable, my psych safety work was perfect. But I only had 4 weeks to turn it around while still doing my day job. Luckily, I’d already done much of the hard work and just needed to pull it all together. Speaking on the Staff+ track at QCon in March 2023 was an opportunity that very rarely comes around. Especially for an engineering conference that doesn’t usually have testers (for a 3-day 6-track conference, I may have been the only one); in addition to that, most speakers are invited rather than the usual calls for speakers, making it much harder to secure a slot. 

The second opportunity didn’t come around until another 5 months later and, at first, didn’t look like much. An internal team had seen my 10-minute psych safety talk and asked if I could do one for their upcoming away day. I now had my much longer QCon talk, so I offered them that, which they agreed to. It was a remote talk, so I didn’t get to meet the team on the day, but I got some nice comments after and didn’t think much more about it. 

It turned out that the room was full of HR representatives from all over the other parts of my organisation. Who all went back to their teams and told them this was the talk to see. Let’s just say I’ve run more workshops and talks in the last few months than I’ve done in the last few years! Massively accelerating my work with psychological safety throughout my department and across the organisation. And all because I could react so quickly to the opportunities, it allowed me to take maximum advantage of them. But to be able to do so was taking the gamble months, sometimes years before, without knowing how they would help in the future.

Connecting the dots

This reminds me of a quote from Steve Jobs during his 2015 Stanford Commence speech:

You can’t connect the dots looking forward; you can only connect them looking backward. So, you have to trust that the dots will somehow connect in your future. You have to trust in something–your gut, destiny, life, karma, whatever.

Steve Jobs 2015 Stanford Commence speech

It’s only with hindsight that I can now look back and see how things have connected to where I am today. I had to push myself in the present moment because whenever you look into the future, it’s almost always full of uncertainty and failure. And that’s the thing: there are always more ways for things to go wrong than right, but if you wait for certainty on the outcome, there is a good chance you will be too late and unable to exploit whatever opportunities come your way. 

This is why there are many opportunities out there, but often, they only look like it after the fact. Sometimes, you have to take a risk and see where it gets you. 

This is not to say you shouldn’t bother planning as you can’t control the outcomes, but recognise that your plans may not always go the way you intended. So, being adaptable and having a willingness to change can be advantageous. And more so if you’re willing to push through unknowns and failures. So far, the best way I’ve found to do this is to have a direction you want to head in and follow where the road in front leads you. As long as you look up occasionally to check your heading in the right direction, you will eventually get there. 

The other point to mention is that a lot of things that happen to you are chance. We live in a complex world, often doing quite complicated things. The best way to ensure nothing bad happens to you is to do nothing, but that also means nothing good will happen, either. Sometimes, you’ll get lucky and be in the right place at the right time. But you can improve your odds by doing more, which allows you to see more and be in the right place at the right time more often than not.

So find a way to push your own flywheel, and don’t worry too much about how things will connect. As long as you look up occasionally to ensure you’re still heading in the right direction, you’ll be alright. And you never know; those opportunities you’re chasing might start chasing you instead.