Favourite Failure.

Next month on the 27^th of June, we are having another Silver Fox evening at Karen Country Club, and I am privileged to be moderating the conversation. It’s a men-only event for guys in midlife, hence the silver grey mandevu. Although some of us are just foxes without the silver, hehe. The discussion will be about what happens when a man fails, particularly in midlife.

Failure in our 40s, 50s, and even 60s often feels final—and sometimes even fatal—compared to when we messed up in our younger days. Back then, time was on our side and we still had sufficient energy and runway to pull up. Failing or feeling like a failure (there is a difference) later in life is much gloomier. It’s easy to give up and resign ourselves to the fate at hand. Yet there is still room for both improvement and recovery in midlife. In fact, the second half of life is guaranteed to be better than the first, but there’s a catch. We have to do the internal heavy lifting and take stock of the wisdom and skills we have accumulated thus far. Only then can we determine how to use them to live significantly in the second half of life.

I meet many agemates at midlife crossroads who are restless. Some are like a deer in the headlights. They know something is off—that a significant shift has happened or is happening—but they are not yet ready to stop and inquire about what’s going on. Emotions are information. Instead of ignoring them, we should pay attention to what they are telling us. Unfortunately, many of us remain stuck in halftime, and even start a downward spiral because we are scared or simply unwilling to look within and begin the work of crafting our next life. Transitions tend to be messy, but in that mess lie key clues and signs indicating what we should do and where we should start heading. Accepting to live with uncertainties is highly recommneded in this season.

That’s the conversation we will unpack for the gentlemen who will be in the room next month. How can we use our failures as bridges to success? We will explore what it means to acknowledge our regrets, how to recover from them, and how to reinvent ourselves to live a life of significance. Life, just like golf, is determined more by how we finish than how we start. The past is past, so no point dwelling there. Instead, we can pick gems from failure and use them to finish strong. By pausing to dig into that heap of failures, we may discover some stones that now appear as diamonds because we are looking at them through the lens of being older, and hopefully wiser.

I came across a powerful question in the book, Tribe of Mentors by Timothy Ferriss: “How has failure or apparent failure set you up for success?” Folks, do you have a favourite failure? I know many of us have probably never considered that question. Our default setting is to treat failure like a plague and run as fast as possible in the opposite direction. Yet some failures have been incredible turning points for some people.

My favourite failure occurred in my 40s when I was running my events business. Things were going well, and there was no reason to fix anything because nothing was broken, or so I thought. I missed the signs to start pivoting, or even plan an exit while I was still at the top of my game. When I had to close the business because we were no longer compatible, I was both humbled and stressed.

A business is like a marriage. Biashara people can relate to what I’m saying. And for Happening Ventures (my business) and me, we hit rough waters and I had to exit due to irreconcilable differences. The result was a crash-landing that forced me to work ten times harder to start a new curve in my second half. I kicked myself for missing—or, more accurately, ignoring—the signs to pivot when I was doing well. It would have been much easier.

But through the lens of celebrating failure, I view this outcome differently now. That failure earned me the stripes to coach folks on what to look out for and how to prepare for transitions in midlife. Had I exited my business at the opportune time, selling it for a handsome price, I might never have found my current purpose: helping people find and live meaningful lives. I have since discovered that broken crayons colour diffrently (almost better).

I carried that shame of a poor finish for some time, trying hard to hide that scar from others. Now, that scar has become my star. I view that ‘business failure’ as a launch pad for my current assignment as a transitions coach. I’m now determined to recklessly pursue my passion and leave my dent on the universe, even though I still get distracted and stuck a few times along the journey—and that’s maisha. The detours are also part of the journey.

Folks, allow me to encourage you to befriend your failures and learn from them. Overcome the temptation to avoid thinking about them and instead, sit with them for a while. Think deeply about what led to your failure and what it now represents to you. What you discover might surprise you.

Are there answers or outcomes you have been looking for that are proving hard to come by? Perhaps they are buried beneath your failures, and you need to go back there. After all, they say that experience is the best teacher, ama? You might just find a failure to thank, hehe. Plus, a side benefit of learning from failure is that it loses its power over you. I no longer feel the shame of ending my business in a less-than-desirable way. I even realised I could blame COVID and get away with it, hehe.