Simplify, simplify: strategic planning for 2023

I'm finally baking Thoreau's advice into my planning. Plus: values, time, and ways of life

As a certain octogenarian president has often been heard to say: “Don’t tell me what you value. Show me your budget, and I’ll tell you what you value.”

This is a post about how I use values to think through my annual process of Strategic Planning for Life, which I do every year on my birthday between Christmas and the New Year. I’m cognizant of the president’s words—though I think the right analog on a personal level isn’t about your budget, but your time, especially your discretionary time, i.e., time not spent earning enough money to live or ensuring that little humans don’t die.

What you do with your days, weeks, and months reveals your true priorities, no matter what you say your values are. Show me how you spend your time, and I’ll tell you what you value.

Of course, one of the great tragedies is that time only moves forward, inevitably and impersonally. It isn’t like money, a resource we can usually hoard until we know what to do with it; our time on this Earth ticks away whether we spend it awake or asleep, whether we spend it deliberately or carelessly. So we’d better figure out how we want to spend it.

I turned 40 a year ago, and in the past 12 months, I believe I’ve managed to make some peace with time and its inevitable forward march. After all, my 40s came despite my resistance. There was nothing I could do about it so, so I might as well just continue on. Another decade ahead, after all.

Then, this year as I sat down to do my planning for the year ahead, I realized something had changed. For the past five years, my annual planning process has been focused on four values (Note: I call them “values,” but really they’re the answer to how I want to spend my time on this Earth):

1. Time outdoors

2. Time with friends and family

3. Continuous learning

4. Creative endeavor

This year, I realized I needed a fifth.

But, let’s back up.

Strategic planning for life

Each year for the past 10 years (with one pandemic-related exception) I have used my birthday to take time alone to reflect and write and think about the year ahead.

The process is simple: after taking some time outdoors to walk and ruminate, I go to a coffee shop or somewhere I can work, and there I write down goals for the next year. Each goal must be stated so that, at the end of the year, I can take either a red or a green, a pass or a fail. You either accomplish something, or you don’t. So for example, “Climb a 5.13 on red point” rather than “Get better at climbing.” Some of the goals get sub-tasks with quarterly deadlines that I can check in on throughout the year. And finally, each goal must be tied to one of the aforementioned values.

I’ve been goal-setting for a decade, but I only added the values thing at the end of 2017, in part based on my realization that it was how I wanted to spend my time that was important—the goals were actually secondary. The point of goals is not accomplishment for its own sake, but to serve the greater purpose of spending one’s limited time on Earth as deliberately as possible.

Those values that I chose in 2017 have stood for five years. But values can change or evolve, and it’s important to give yourself the space and permission to recognize when it happens.

The happiness curve

In 2018, author Jonathan Rauch released The Happiness Curve. He drew on extensive research across multiple cultures to show that life satisfaction starts high, dips in our 30s and 40s, then starts to go up again in our 50s and beyond.

The cause, Rauch says, is a shift in values as we age.

In our 30s and 40s, we constantly compare ourselves to others as we build careers, looking to factors like wealth and status as markers of success. But this constant comparing makes us less satisfied, less happy. As we get older, we shift toward more social values, such as the strength of our surrounding community and our relationships with friends and family. We stop looking for new relationships and start to prioritize strengthening the ones we already have. We shift away from being externally motivated by material goods and money.

It’s all quite obvious, and in fact, writing that summation, it strikes me how long I’ve been aware of the research on this. I’ve always been interested in what it meant to live a good life (I studied philosophy after all)—yet incorporating what I know into my day-to-day existence has been another matter altogether. In my 20s, everyone seemed to be pursuing exactly the materialistic mimetic desires that have been embedded in our culture for decades, and it is always easier to imitate what most others around you are doing than to break from it. Besides, I needed to make a living.

Meanwhile, path dependency is a powerful force. For many years in my 30s, I would feel constrained by various forks in the road from earlier in life. I was a father, for one, with a split custody agreement that tied me to the Washington, DC area—a place fairly preoccupied with money, status, and prestige. It was tough to build community there, and even tougher to get out into nature (the nearest real mountain or halfway decent climbing is a 2-hour drive; the nearest actually good climbing is 5 and a half hours).

The values I chose in 2017 for my strategic planning process were themselves products of path dependency: constrained thus in suburban Maryland, I felt I wasn’t spending enough time outdoors, or enough time with friends and family. So those were two of the areas I focused on in my goal setting.

I put down two goals to try to get more time outdoors: spend at least two weeks climbing and at least two weeks at the beach kitesurfing. By the end of the year, I’d failed at both:

I really was chaffing back then, unhappy in many ways. It felt so hard to get out for climbing or kitesurfing trips. So hard to build community. Like a lot of people, I felt stuck, my choices constrained.

Then, a very unexpected event suddenly unstuck everything.

I was laid off.

Breaking free of path dependency

In the Summer of 2019, I got on a Zoom call for a weekly check-in with my boss at the company where I worked as director of content marketing. It was a great job. I liked the people, I liked the work, and I was well-paid. A few months earlier, I’d received a sterling performance review, getting the maximum raise and the maximum bonus. For all I knew, I’d have this job until I was ready to retire.

But as soon I got on the call I knew something was off. My boss’s face was a kind of ashen white, and there was a woman I knew from HR on the call. My boss told me this was really hard, etc., he had to let me go, etc., and then the HR woman took over—severance package, etc., etc., last day with the company, instructions for returning your key fob, etc., etc.

My mind kind of went blank on the whole thing, I was so shocked.

In retrospect, I should’ve known—the company had taken on private equity investment to grow, and now they weren’t meeting goals for profitability. Capitalism can be brutal, but there it was.

The job loss shook my thinking and broke me free of the constraints that I’d thought were holding me in Maryland. (By the way, if you are employed and feeling stuck, it’s worth running the thought experiment: what would you do if you were fired tomorrow?) Within a month, I and my partner at the time decided we would take a year to do more of the things we had wanted to do but never did, namely travel, learn Spanish, and spend time outdoors. Then covid hit, and the next year was spent at my house in New Hampshire, where my mom was living. We brought the kids up from Maryland for weeks at a time—they were out of school, after all. During the days, I climbed and renovated the garage, and at nights we cooked as a family or spent the evening around campfires outside with our friends.

It took a job loss and a pandemic, but I was finally spending my time how I wanted.

Finding a way of life

Last year, able to travel again, I took a kitesurfing trip to La Ventana in Baja, Mexico (I’m on my way back this week). It was a good time to reset my thoughts, and there I reread the Ninth Path letter Hunter S. Thompson wrote to a friend, one of the best distillations of career and life advice I’ve ever read.

“But beware of looking for goals,” Thompson advised his friend. “Look for a way of life. Decide how you want to live and then see what you can do to make a living WITHIN that way of life.”

But how do you decide how you want to live? We’re usually all so preoccupied with work and family and what’s right in front of our faces that it’s really hard to figure that out. My suggestion is that you have to mentally wipe the slate clean, think in terms of first principles, and break out of path dependency:

Be alone with your thoughts and do it in focused contemplation on this question: removing all the current circumstances of your life, how would you then build a new one from scratch? What would this life look like, from the moment you wake until you go to sleep? What would it look like for a day? A month? A year? Where would you be, what would you do, and who would you do it with?

Looking back over the last few years, it’s clear I’ve been living very close to how I’ve set out to live. In the aftermath of the job loss, I started marketing and strategy consulting. My income became fully location independent, and my hours and workload are now my own. In contrast to the years anchored in suburban Maryland, I now spend huge amounts of time outdoors: climbing, hiking, kitesurfing, and working on house projects outside. I’ve also prioritized time with friends and family. This Summer, I traveled to New Zealand to spend time with my sister and her husband, and three kids. In October, I spent a long month in the glorious New Hampshire fall surrounded by friends and community. In November, I took my son to Spain with a great group of friends and had one of the best climbing trips ever.

I am spending my days, weeks, and months doing the things I love with the people I love, and I consider myself to be extremely wealthy in all the ways that truly matter.

December 2022, at the top of Atalaya in Santa Fe with my dad — time spent outdoors, time spent with family.

Simplify, simplify, simplify

At the coffee shop on my birthday, I stared at the section of my planning sheet for next year labeled Time outdoors. In the past, I would’ve set some goals to make sure I was living that value. Then I thought back to the past year.

Underneath Time spent outdoors, I simply wrote: way of life.

No goal necessary.

Then, I turned to something that’d been nagging me. For much of the last few months, I’ve been thinking about something I wrote last year in Things left unwritten, about whether it was time to start letting go more, to accept that I won’t get to everything I want to do in life—I won’t get to visit all the countries, or launch all the business enterprises, write all the things, or learn all the languages:

Perhaps in your 40s, you begin to triage time.

Or perhaps I will find some kind of grace so that it doesn’t feel like a triage.

A year later, I’m closer to having found that grace, but I’ve discovered it requires more than just meditating or thinking about it. It requires an active process of letting go.

I added a fifth value to my planning document under the previous four: Simplify. I’d already made some choices along those lines in the past few months. Now it was time to bake it into the coming year.

Under Simplify, I wrote down a goal to finally shutter a business enterprise I’d been working on for the last 18 months, and added a few specific subtasks. The business had taught me a lot, and it had even earned some decent money, but I’d known for a while that my heart wasn’t in it. It was time to simplify so that I could focus on other things.

Like the research on values shifting as we age, I’ve been well aware of the wisdom of simplifying my whole life. After all, I first read Thoreau in high school:

Our life is frittered away by detail. Simplify, simplify, simplify! I say, let your affairs be as two or three, and not a hundred or a thousand; instead of a million count half a dozen, and keep your accounts on your thumb-nail.

I’ve come across that famous passage more than a dozen times in life, and I always agreed with the sentiment! But life has a sticky way of becoming ever more complex and complicated. Almost as if subject to its own law of thermodynamics, life trends toward chaos. To craft a meaningful life means to actively prune things from it on a regular basis. Like pruning the apple tree in the front yard of my house, what results is all the more beautiful, and more productive.

Later in the evening, my planning complete, I had my dad, grandmother, and some close friends over for a birthday dinner. They brought guac, beer, and stuff for margaritas. I made tacos. It was exactly how I wanted to spend the evening: with friends and family.