I grew up a perfectionist. Great to school, but not ideal for practicality (and awful for baseball). I had an awful habit of thinking things, but not necessary executing on them. I’ve done a fair share of physical challenges. Simple 0/1 type things are relatively easy for me – you do them or don’t. But when it comes to larger decisions, I tend to vastly overthink things – always overanalyzing and thinking of every single possible outcome – the good, the bad, and the ugly.
While great for financial analysis, pretty bad for taking personal action in the real world. My head continues to function like an excel spreadsheet if I don’t actively tell it otherwise – I’ve always been programmed like this. I would go through all the potential outcomes, assigning probability weights to each, and figure through the ramifications of the probable result. Throughout my life, this has posed a few significant obstacles – inordinate wastes of time, overweighting suboptimal outcomes, and, contrary to my intent, a decreased aptitude to take on risk.
It finally dawned on me early in 2023 that I needed to make a wholesale change. The sheer number of sage conversations I’d had over the years with folks who had said “If only I had XYZ,” got to a point I couldn’t handle anymore. Everyone has a different risk appetite, but nearly everywhere you turn, you can find someone who wishes they had taken a chance, made the jump, at an earlier point in their life.
While in high school, a dear friend of mine used an analogy that has resonated with me ever since, but hadn’t ever truly clicked until this past spring, “Live your life like you’re writing a a great story.” Stories with no twists, no turns, no risks, no stupid decisions, tend to be quite bland. So why not take the path less trodden? Take the risk, make the jump, embrace a little bit of uncertainty.
So how did I get to the point of getting out of my head and taking the risk? Small steps… Starting in January when I asked, “what if I take a break from writing my daily notes and gratitudes?” What would realistically change? I began to think in the present – maybe I would lose track of being productive, maybe I would not be so focused on meaningless goals to get me through the day, maybe I would look at things just a little differently. Lo and behold, the change took effect.
As I started challenging myself to take more risks, little by little, I reoriented my focus to “what is the worst possible outcome?” And if I could deal with the worst possible outcome, then I could take the risk.
So, one thing led to another, and I ended up quitting the corporate job to pursue something where I felt I could truly generate value for a greater mission. Now if I had followed that advice without any conviction, it may have been a little ill-informed. So how did I garner the conviction to make a larger decision, one where the worst-case result might have broader repercussions?
Historically, in making such a decision, I would incorporate all the different likelihoods, thinking through every possible outcome and ultimately putting myself in a position of stagnation – unable to decide because of the sheer number of potential outcomes. I’m not saying I don’t still weight every option, but I try to focus on three – Worst case, best case, and most likely. To build conviction, you have to focus on the best and most likely case. If you focus on the best case, you’ll be blinded by the opportunity. If you focus on the most likely, it can be hard to instill conviction in others. Blend the two, for your own good.
If you see an opportunity, and the best case is life-changing and the most likely outcome is a life improvement, there’s reason to have conviction. If the best case is life-changing, but the most probable is no improvement or a downgrade, conviction becomes a little more difficult.
All this is to say, take a chance when you see opportunity. If there’s enough reason to think the result will be even a minor improvement, why not jump in.
Go take a sabbatical. Go start a business. Go ask the girl (or guy) out on a date. Don’t let your head get in the way – live more, think less.
No matter what you do, fall in love with the process, embrace whatever decision you make, and be grateful for whichever outcome may result.
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