This story originally appeared on the Gents Cafe Newsletter. You can subscribe here.
As I approach my mid-40s, I’m feeling like there are still many things I want to experience. I’ve realized that decision-making now carries a different weight than it did a decade ago. I’m thinking soon I’ll have more years behind me than ahead of me; the stakes feel higher, the time horizon shorter, and my decisions come with consequences. Every choice seems to echo not just through my own life, but through the lives of those who depend on me.
As with most men, we want the freedom to try things – even if we fail. We want to be able to try without life-changing repercussions. Let us be honest, people like to say you’re never too old to (Insert goal here); the truth is, the luxury of endless experimentation is passing. Where once I might have changed careers on a whim or tried a new business venture, I now find myself calculating the impact. I’m not being pessimistic, but acknowledging the realism shaped by responsibility and experience.
What’s changed most is my relationship with time. In my twenties, I’ll admit I felt like I had time. Poor decisions could be undone, paths retraced, and mistakes transformed into learning experiences with some, but minimal, consequence. Now, with roughly twenty years left in my career, each professional decision carries more weight. Should I take the risk with opportunities or stick with my current path? The answer depends not just on personal ambition, but on mortgage payments, retirement savings, and college funds.
Yet this constraint has brought unexpected clarity. With fewer years to waste on the wrong choices, I’ve become better at discerning what truly matters. I’ve learned to distinguish between opportunities that align with my values and those that merely flatter my ego. The fear of missing out and not letting people down has been replaced by the wisdom of knowing what to say no to.
Marriage has taught me that major decisions are rarely solo endeavours anymore, and ignoring what is discussed can cause major issues in the future. The city you want to live in, the house we buy, the jobs we take, even the weekend plans, everything becomes a negotiation between two people with their dreams and constraints. This shared decision-making has made me more thoughtful, more patient, and better at seeing the gaps in my own reasoning.
The financial reality of middle age adds another layer of complexity. You hope that by this time in your life, you are well on your way to financial maturity, but that is not always the case; it can take just one decision or even a health scare to change everything. Decisions that once affected only my bank account now impact retirement projections and the care needs of my aging parents. I’ve learned to think in decades rather than years, considering not just immediate consequences but also long-term sustainability.
Perhaps most importantly, I’ve discovered that perfect decisions don’t exist. The goal isn’t to make flawless choices but to make thoughtful ones, decisions that honour both who I am today and who I want to become tomorrow. In your forties, wisdom isn’t about having all the answers; it’s about asking better questions and making peace with uncertainty while moving forward with intention.
