Hi Friend, 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. |
In a world where technology is increasingly conspiring to steal our focus and attention, my goal is to teach you how to be more productive with Apple technology. I want to help you achieve what is most important to you and enjoy your life at the same time using technology instead of becoming another one of its victims. Pretty much everything I make points at that North Star. I believe in this message so much that I’ve staked my livelihood on it.
The No List App Hi Friend, This week I shipped an app. It's called The No List, and while it might seem like a simple idea, I think it addresses one of the most important productivity challenges we face today. Let me back up a bit. For years, I've been interested in the idea of building my own app. Part of it was the challenge—could someone who spends their days writing about technology actually create some? Part of it was scratching a very specific itch that no existing app seemed to...
My First Draft of this Newsleter. Hi Friends, I very much have an analog side. Sometimes I find slowing down and writing things down helps me process thoughts a little better. That doesn't mean the things I write with paper and pencil necessarily stay that way forever, but quite often, it's an excellent first draft. As an analog explorer, I've gone down the rabbit hole over the years of fancy pens, including fountain pens. But several years ago, I found an old box of pencils and decided on a...
Hi Friend, Recently, we had a family celebration. The reason is irrelevant, but the means of our celebration was our usual. We went to Disneyland. We’re fortunate to live close, and two of the four members of my immediate family work for Mickey. So, we went to “the park,” where we shared a meal at a restaurant, rode the Pirates of the Caribbean, shared a delicious cookie, and stretched our legs by walking through the park before heading home. It was delightful. While eating our meal, there...