I’ve been “retired” for two years now, and I’m still not sure I’ve figured out the best way to “be retired” yet.
That might surprise you if you’ve read anything else I’ve written about intentional living or early retirement or know me personally. I left a demanding executive career in tech, traveled, am writing a book, coach individuals about their careers and start-ups on how to run great product teams. I also run the CS Capstone program at UW-Madison and just launched a new initiative called CS Marketplace at the University. Not to mention that we’re planning to move to Portugal once our kids graduate and the prep for that has already started. From the outside, it probably looks like I have a full, purposeful, well-designed life. And I do. But I still feel like I’m focusing too much on the wrong things sometimes.
The truth is, I’m still calibrating. Still figuring out which challenges belong in my days and which problems I really want to solve. I’m still learning what it means to do hard things by choice rather than by obligation and how to find the right balance between the ebb of rest and the flow of something hard that I think matters.
Here’s what I’ve figured out so far.
The Three-Year Rule and Why Challenge Is Non-Negotiable
A mentor told me something years ago that has stayed with me ever since: three years is a good span for any one job. One year to ramp up and learn the landscape. One year to really perform and do your best work. And a third year to figure out what comes next and begin handing things off.
Why?
After three years in any one position, you’ve figured things out and your work isn’t as challenging anymore. You’re not learning as much. I’ve tested this theory across most of my career, and it holds up remarkably well. The challenge and energy of the first two years in a role are real and sustaining. By year three, you start to find the edges of that growth. The problems that were interesting when you arrived have become familiar or solved. The growth is slower. The interesting challenges, which got you out of bed every day, have started to recede.
I’ve left jobs more than once specifically because of this. The challenge dried up and I knew I would start to become less happy in the role. Not every departure was comfortable. But every single one was right.
Here’s the thing I didn’t fully understand when I retired: the need for challenge doesn’t retire with you.
If anything, it gets louder.
What Happens When You Stop Challenging Yourself
When most people leave long careers, they’ve spent years (sometimes decades) running at a pace that wasn’t sustainable. The burnout is real. The exhaustion is real. And so the instinct when you finally step off the treadmill is to do the opposite: to rest, recover, decompress, and drink margaritas. (Which, if you’re over 40, you quickly realize leads to terrible sleep and you stop doing that.)
That makes complete sense for a while. Rest is not optional. It is not laziness. It is, as Alex Soojung-Kim Pang argues in his book Rest (which I reviewed here), the necessary counterpart to good work. Pang’s central finding is simple and radical: most of us are capable of about three to four hours of genuinely deep, productive cognitive work per day, and then we need rest. That rest isn’t wasted time. It’s the thing that makes the next day’s deep work possible.
Rest is the necessary counterpart to good work.
– Alex Soojung-Kim Pang (Rest)
Work and rest aren’t opposites. They’re partners.
But here’s the flip side that doesn’t get talked about enough: rest without challenge, sustained over months or years, stops being restorative and starts becoming…boring. A life with no hard things in it doesn’t feel like freedom. It starts to feel, after a while, like drift.
The tendency in retirement is to correct for years of overwork by going to the opposite extreme: to avoid challenge altogether, to stop starting things, to mistake a quiet schedule for a full life. In my observation, and in my own experience, that is a mistake.
What Cal Newport Gets Right About the Ebb and Flow
I’m currently reading Slow Productivity by Cal Newport who is also the author of Deep Work, a great book, which I’ve written about before, and it’s giving me a useful framework for something I’ve been trying to articulate about the rhythm of a good life.
Newport’s thesis is built around three principles: do fewer things, work at a natural pace, and obsess over quality. I’m in the “work at a natural pace” chapter and he’s talking about seasonality, or, the idea that the most creative and impactful people throughout history didn’t grind continuously. They moved between periods of intense focus and rest. Those transitions weren’t signs of laziness, they were what made their great works possible.
His main example is about how Lin-Manuel Miranda took eight years between the first draft and the Broadway debut of In the Heights to get to a quality, finished product. He did not grind away at it every day, but returned to the work when he could, gathered talent to help him, stepped away, and returned again.
The mistake we make in today’s modern society, in both work and in retirement, is forgetting that we need both rest and challenge. For people coming out of demanding careers, I think the lesson is this: you need the rest first. Take it. Give yourself permission to do less than you think you should. But understand that the rest is in service of something and that the fallow period exists so the next season of growth can happen. Rest is not the destination. It’s part of the cycle.
Some Things I’ve Started (And Why Each One Mattered)
In my own retirement, the projects I’ve started haven’t come from a strategic plan. They’ve come from the same thing that drove my best career moves: curiosity and the pull of a real challenge.
Duolingo and language learning. I’m at 838 days on my streak, having completed the entire Italian program and I’m now working through Brazilian Portuguese as we prepare to move to Portugal. This is a skill I’ll hopefully use when we move abroad and I’ve always loved languages (my second major was Spanish Linguistics) so it’s fulfilling, useful, and fun at the same time.
My second book. Writing gets me into flow and even when I’m not writing a book, I’m writing this weekly blog post. Sharing what I’ve learned and what I’d like to see more of in the world, is also one of the most satisfying things I do regularly. I connect with people through writing. I get feedback. When I get blocked in the editing process, it’s challenging and I learn something new every day. I don’t think the link between satisfaction and challenge is a coincidence. The difficulty and the satisfaction are connected.
The CS Marketplace at UW-Madison. When the opportunity came to build something new at the Computer Sciences Department, a program that connects student developers with jobs at campus organizations, I said yes partly because I believed in the mission, and partly because building something from scratch is one of the things that has always made me feel most alive. It was hard in the ways new things are always hard: ambiguous, requiring decisions without enough information, requiring persuasion, coordination, and iteration. It felt exactly like starting a new job. And it gave me exactly the energy that starting a new job used to give me.
I’m Still Working On Getting This Right
Here’s what I want to say directly, because I think the honest version of this story is more useful than the polished one: I haven’t figured out the balance yet.
The phenomenon I described at the beginning of this article, leaving jobs because the challenge dried up, is exactly the challenge I face in retirement. But it’s harder now, because I don’t have the structure of employment to shape my days, and because the stakes feel different when the choices are entirely mine.
My biggest ongoing struggle in retirement is not finding things to do. It’s finding the right things, the ones that are hard enough to engage me, meaningful enough to justify the effort, and sustainable enough to become part of a real rhythm rather than just a burst of energy followed by burnout.
Some days I get this right. Many days I’m still calibrating.
What I know for certain is that the answer isn’t to stop trying. The balance is not something to be optimized in a single season, but it is something to be iterated on steadily, across time, with rest built in and ambition waiting on the other side of it.
The three-year rule applies to this too, maybe.
I’ll let you know.
If you’re thinking about the balance of rest and hard work in your own life, I’d recommend starting with Alex Soojung-Kim Pang’s Rest and Cal Newport’s Slow Productivity. They make the best possible argument for taking both sides of the equation seriously. And if you want to talk through what the right challenges might look like for your particular season of life, coaching might be a useful next step, so feel free to reach out.
