What failure teaches us about ourselves and about the dreams we should actually chase

Failure has long been embraced as a source of learning, particularly in the tech world. However, those entrepreneurs frequently tend to focus on the sort of learning that's concerned with solving a specific problem, often technical in nature.

What might be considerably more meaningful is what such failure reveals about ourselves: whether the thing we thought we ought to pursue is actually the right thing. Failing at anything - a single activity, a hobby, or a life-long held dream - presents an opportunity to ask why we failed.

For example, once I tried and failed to build my own tech company. This taught me that while I loved building things, I didn't enjoy sales, social media campaigns, fundraising, networking, and other activities that are absolutely essential to building a company. My entrepreneurial drive didn't translate to a love for entrepreneurship in this particular sense. For the longest time, I had envisioned a future in which I'd call myself a successful tech entrepreneur. Now that I'd tried and failed, I could face the fact that I didn't actually enjoy doing what it would take to get there. I could put that vision to rest. I'd scratched that itch, so to speak.

Avoiding failure keeps us in a state of projecting ourselves into a brighter future. As long as we haven't experimented with - and failed at - quitting a job and opening that beach cafe or travelling around the world in a van, we will be able to tell ourselves that once we do those things, we will be much happier. These significant life changes may or may not improve our lives (most of them probably wouldn't). But until we attempt to make them a reality - at least in some small way - we will continue to be torn between those hypothetical futures and our very real present. And we will be just a little less motivated to seek fulfilment in the latter.

Of course, there are too many possible pipedreams to pursue. But the process of whittling them down to those we actually need to fail at merely requires some reflection.

First, it requires us to look into our past. What have we enjoyed doing before? If one has never as much as taken a barista class, baked a croissant, or managed a lemonade stand, what should give the impression that opening a cafe is the right goal? Even dreams are grounded in reality. Some dreams might be glorious, but they might not be yours.

Second, where are you holding yourself back? Is there something you've already been doing for some time with a degree of success, but you've never taken it as far as you could? It might be that a fear of failure is at work. For as long as you don't really lean into that thing, there's no way to fail at it either. It's nice and cosy and safe - and you might just be missing out on your dream.

Failure - especially when it comes to personal pursuits - can be crushing. It hurts to find out you're not the person you thought you ought to be. But in failing, not only will you have reduced the number of possible futures for yourself by one count. You'll also have gathered new insights about yourself to set your sights on a much more suitable pursuit. With this in mind, it is worth asking yourself: What do you need to fail at next?

I'd love to hear your failure and discovery story. Please send me your yours - I read them all.