Wow. That was quite a journey. I’m honestly still processing the fact that I managed to complete everything. Looking back, I’ve spent over two decades setting goals, and the highest I ever reached before was maybe 60% completion—and that was with a modest list of just ten goals. When I first considered taking on this challenge, I almost talked myself out of it, remembering past failures. But turning 50 flipped a switch in me. I figured I might not succeed, but I knew I’d regret it if I didn’t even attempt it. Maybe not the most optimistic mindset to start with, but if this experience has taught me anything, it’s that with discipline and structure, you can fundamentally shift how you approach things.
Coming up with 50 goals was an adventure in itself. The first few were easy—I pulled from old, unfinished goals and added new ones that felt both exciting and challenging. But once I hit the 30-goal mark, I struggled. That’s when I had to shift my perspective. I started thinking about what turning 50 really signified. I reflected on what I had accomplished, what I had always wanted to do but never got around to. And then it hit me: I had spent years assuming there would always be time. But what if there wasn’t? Shouldn’t I seize the moment now, while I still had the energy to truly enjoy it? That realization changed everything. Suddenly, the list filled itself. Visiting my father’s hometown in Italy. Buying my dream guitar. Sipping on really old Scotch. Once I reframed the process, it became much easier to round out the list. I even left a few open slots, which I later filled with “Explore AI” and “Complete a Bob Ross painting tutorial.”

As I got deeper into rounding out the 50, I found myself turning to the internet for inspiration. Seeing what others had on their goal lists helped me refine mine. Some ideas resonated, some didn’t, but the process helped me think outside the box. And ironically, one of my late additions—learning about AI—ended up being a game-changer. AI became an essential tool throughout the year. With a goal of blogging about my experience, I faced an immense workload, closing in on nearly 300 posts. Without AI’s help in researching topics, I would have been buried under the effort. I even used AI to critique my writing, offering an unfiltered, sometimes ego-bruising editorial lens that ultimately improved my work.
To keep myself accountable, I knew I needed rules. Once the 50 goals were set, I committed to not altering them to make things easier. But I’m also pragmatic—life happens. In the early months, I tore something in my shoulder, which derailed my fitness-related goals. So, I built in a contingency: I allowed myself to swap out five goals if necessary. This gave me a degree of flexibility while ensuring I didn’t just swap out challenges for convenience. I ended up using four swaps (documented on my website), and two of them were due to physical limitations rather than avoidance.

So how did I pull this off while managing a full-time job, two small kids, and a marriage? With structure. I built a framework that allowed me to make progress without compromising what truly mattered.
The first rule: priorities first. My family always comes first—no exceptions. I didn’t pursue these goals at the expense of time with my kids or my wife. I still coached my kids’ teams, played with them on weekends, and handled all the usual parenting duties. I made sure my wife and I kept our Friday lunch dates, giving us uninterrupted time together. And work? That stayed a priority too. I enjoy my job and wasn’t about to let this project interfere with my professional commitments. With those priorities locked in, anything else became negotiable.

The second rule: do something every day. Even on chaotic days—work was crazy, the kids had back-to-back activities, and my wife was out of town—I could still do something. Read a few pages of a book. Practice Italian on Babbel for five minutes. Write a quick gratitude journal entry. Even brushing my teeth at night, I could squeeze in a small action. The consistency was the key. After a few months, it became so ingrained that skipping a day felt like a glitch in my system. These small, daily efforts accumulated, creating momentum that accelerated progress over time.

The third rule: find hidden time. It’s there if you look for it. That hour-long commute? Perfect for listening to educational podcasts or checking off an album from my music list. Instead of doom-scrolling my phone during lunch, I’d read, write, or learn something new. Even waiting for my kids to finish practice became an opportunity—reading on my Kindle, researching goals, or sketching ideas. Once I stopped treating time as something to kill and started seeing it as something to use, my productivity skyrocketed.

The final rule: track everything. This was huge. I needed to see my progress at a glance, so I built a spreadsheet with progress bars and a dashboard to keep me motivated. If one goal was lagging, I’d shift focus to bring it up to speed. As the months passed and those bars turned blue, I felt the inertia pulling me forward. That visual reinforcement made a huge difference. I also used OneNote to collect ideas, notes, and drafts, which kept me organized and efficient. These tools gave me a comprehensive view of where I stood at any given moment.

As the year progressed, I started identifying areas of wasted time and replacing them with intentional actions. Little by little, I started to see myself as someone who followed through, rather than someone who set goals only to abandon them. That shift in self-perception was a turning point. Once I hit 75% completion, I could see the finish line. In the last 60 days, I went into overdrive, laser-focused on getting everything to 100%. I don’t think I could have sustained that level of intensity for an entire year, but as I neared the end, it felt like shifting from marathon pace to an all-out sprint.

But of course, there were downsides. Sustaining focus for an entire year was mentally exhausting. Between work, family, and this challenge, there were weeks when I was completely burned out. Fortunately, some of my goals—meditation, hiking, drawing—helped counteract the stress. On particularly rough weeks, I leaned into those activities, taking long hikes with my kids to reset. Still, there were stretches, especially in the summer, where I did nothing, and guilt crept in. Eventually, I realized that guilt was unnecessary. I wasn’t trying to become a productivity guru or a social media influencer—I was just a 50-year-old guy trying to accomplish something meaningful. And as I watched my goals falling one by one, I realized that even with breaks, I was still on track.

Another major downside? Free time took a massive hit. Movies, TV, video games—I barely engaged with any of them. I didn’t play a single hour of video games all year, missed most new film releases, and barely kept up with my sports teams. (Not that the Jets gave me much to miss.) These things might not be “productive,” but they’re enjoyable, and I realized I missed them. Sometimes, you just want to unwind and watch your favorite team blow a late lead.

Ultimately, I learned so much from this experience—not just about discipline and productivity, but about balance, adaptability, and what really matters. There were tough moments, but overall, I’m glad I did it. And now, looking ahead, I’m excited to see where these lessons take me next.