Posts Tagged → career

This Was It

I recently took a flight and following touchdown, a crew member made a surprise announcement: this landing marked our captain’s final flight after 30 years piloting aircraft. We all applauded. As we disembarked, the captain stood in the aisle, offering each passenger a farewell.

When it was my turn, I congratulated him. I actually thought about what I’d say. “I hope your next adventure is as exciting as this one was.” His eyes met mine, serious and somber, as he quietly replied, “This was it.” I was swept onward by the flow of passengers, but he held my eye for just a moment longer. The sadness on his face has stayed with me.

Life is full of transitions. I’ve faced many — shifting careers, watching my kids grow up, leaving behind the identity I had built as a lawyer. Most big changes in life aren’t surprises. Retirement doesn’t sneak up overnight, and children don’t grow up in secret. Yet, some of us still find ourselves flat-footed when life’s inevitable curves appear. It’s tempting to ignore change, to stick our heads in the sand, pretending it’s far away, until suddenly we’re facing a stark realization: “This was it.”

I’ve written before about the importance of continuously ​Knitting Your Parachute​. Asking yourself often, “What’s next, and how do I make that work?” is a practice I deeply believe in. It’s an approach that keeps hope alive, turns anxiety into anticipation, and keeps you engaged with life.

This week, I encourage you to spend a few quiet moments reflecting: What’s your next move, and how can you embrace it? Whether you’re graduating, shifting careers, or facing retirement, don’t wait until change feels overwhelming. Life’s bends in the road are inevitable, but how we meet them, that’s entirely up to us.

Let’s commit never to find ourselves in a position where we have to quietly say, “This was it.”

It’s stories like this that led me to make the ​Productivity Field Guide.​

Knitting Your Parachute

At a recent MacSparky Labs event, a few folks started asking about career change—how to do it, when to think about it, and what it feels like to make a big shift.

The questions hit home for me because, as many of you know, I spent thirty years as a lawyer before going full time with MacSparky. And when I made that change, I realized something important: if you ever think you might need a parachute, you’d better start knitting it early.

I didn’t set out to build a parachute. I wasn’t trying to escape my law practice. I just started writing about Apple tech and productivity because it was interesting to me. I started guesting on podcasts because I had things to say. It was fun, and it scratched an itch. I had no idea at the time that I was laying the foundation for a completely different career.

But when I hit my mid-fifties, I started feeling the pull for something new. I didn’t need to leave the law—I could’ve stayed in that world until retirement—but I realized I wanted to repot myself, to take on new challenges and chase new goals. And because I had been slowly, almost accidentally, building something on the side, I had options. I had a parachute.

One of the biggest challenges in making that leap was identity. For decades, I had introduced myself as a lawyer. That wasn’t just my job; it was how I saw myself. And when I started telling friends, family, and colleagues that I was stepping away, I got some puzzled looks. “But you are a lawyer,” they’d say. And sure, that was true—but it wasn’t the whole story anymore. It took time to shift my own mindset and let go of the idea that my career defined me.

So, if you’re in your forties—or even earlier—and wondering if you should start preparing for a possible change, the answer is yes. That doesn’t mean you need to quit your job or make a drastic move.

It just means placing small bets on things that interest you. Explore different skills, build relationships in other fields, and don’t be afraid to try something that might not work out. Even if you never need to pull the ripcord, it’s good to have options.

The real point here isn’t that you must change careers, just that you should be intentional about your future. Take some time to reflect on what you want long-term. The earlier you start knitting your parachute, the stronger it will be if you ever need it.