How to Live the Perfect Year

This is a research proposal.

Planning for a Perfect Year

Annie Dillard has this famous advice in The Writing Life:

“How we spend our days is, of course, how we spend our lives. What we do with this hour, and that one, is what we are doing.”

That’s great, and true, but practically speaking sometimes you need a broader focus than just today. You’ve heard about the ant and the grasshopper and all that. You can’t just eat, drink and be merry. We are going to die, but it probably won’t be tomorrow. 

I like the way my friend Barbara framed it up: “Balancing the philosophy of Memento Mori with hopes, plans, dreams and a savings account ...it's tricky.”

How do you live, remembering that you’re going to die, while also covering the bills and planning for the future? 

That’s the question.

What would a Perfect Year include? 

A few years ago, Angel and I started this conversation. We’re getting old now. In a perfect world, what would the rest of your life look like? 

It’s a hard question. Where do you even start? 

It’s basically the same question. How do you live, remembering you’re going to die, while also covering the bills and planning for the future?

That was too overwhelming so we pulled it back to something more specific. Forget your whole life–what would a perfect year look like? 

That feels more approachable. 

If you can put together a perfect year, maybe you can stretch that out into a perfect life.

How we spend our years is, of course, how we spend our lives.

We talked about this question with my mom on the Camino in 2023. We thought about trying it, as an experiment–puttting together the perfect year? Maybe we’d try to pull it off in 2025, our 45th year on the planet? It seemed poetic. 

It didn’t pan out for a variety of reasons, but a few things happened towards the end of this year that made me realize that a perfect year might be coming together for us unintentionally in 2026. 

Did we manifest it? I don’t know, but here we are.

What is this opportunity, and how did it arise? 

When Angel and I talked about our perfect year back in 2023, we had slightly different views on what it should look like. However, we did agree on a few core things:

1. It should involve travel for about half of the year, and being at home the other half.

2. It should involve a roughly equal mix of work and freedom. 

3. It should include walking a Camino and spending a lot of time outside. 

4. It should involve going to a new place or two, and returning to some place we love.

5. It should give her the space to work on her business, and me the space to write.

6. It shouldn’t break that bank. 

7. It should give us significant time with friends and family. 

8. It should be spent entirely in summery climates.

About a month ago, it hit me that 2026 is shaping up for us in a way that looks very much like that. 

From January through March, we’re taking a trip to Bali, Egypt and Spain. We’ll spend a few months hanging out in the sun with old friends, seeing new places, and walking another Camino.

That’s been on the books for a while. But then, a few weeks ago, Angel’s brother told us that he is getting married in Ohio in July. We found a remarkable deal on a flight from Auckland to New York, so we booked it one way. We’ll make our way to Ohio from there to spend time with Angel’s family, before catching up with my brother in NYC. 

It’s a long story, but earlier in the year we also managed to double book ourselves tickets from Madrid to Auckland. So, It makes a whole lot of sense to just change the dates on one set of tickets. We can hop over to Europe from New York, spend some more time there, maybe walk another Camino, and fly home to New Zealand once winter has passed. 

Family and friends are covered. Half-year of travel is covered. Summery climate is covered. Caminos are covered.

All of this travel is possible because of a confluence of other events. Angel’s work has shifted entirely to her online business. We can work on it from anywhere, and we’re optimistic about our ability to use it to cover expenses while we’re on the road. 

Finances and productivity, covered. 

Earlier in the year, we moved into a small studio apartment, and our landlords are very flexible about us coming and going. I’m casual at my job, which means that I can come and go as I please. So, even though we didn’t plan it intentionally, we have an opportunity to live out the elements of our perfect year, risk-free.

When you have an opportunity like that, you have to take your shot. 

What is perfect?

One challenge is, when you make plans for something like “a perfect year,” you run into all sorts of subjectivities, such as:

“What does perfect even mean?”

“Whose version of perfect will you pursue?”

“How will you know whether you’ve achieved perfection?” 

You can do all of the things that–in your fantasy world–you’ve always wanted to do. 

It could be an exercise in hedonism. 

Or you could go the opposite route and do the most good you can, for the most people. 

It could be an exercise in philanthropy.

You could be a pragmatist or an idealist. You could be rigidly scheduled, or you could go with the flow. 

You can get into your head about it in a thousand ways. What you eventually come to is that, in the end, “perfection” is a meaningless concept. 

So what is this really? 

The thing I can say is that it’s an attempt to live the sort of year that you’d want to repeat. 

It’s one where you’re both getting as much from life as you can, and giving back as much as you can.  

It’s not a year of independence, because independence isn’t real. But it’s a year driven largely by personal preference rather than external determinants. 

I don’t know if it’s sustainable or universally applicable, but what it is, is a practice exercise. Something that will help shape the rest of your life in a way that you want.  

What is the model for the Perfect Year?

Another challenge is, what are you actually supposed do?

I’ve been reading a lot of Henry David Thoreau, and at some point it struck me that he already took a shot at this “perfect year” project. 

I’m not sure whether you’ve read Walden, but that’s what it was about. Thoreau went to live in a cabin in the woods on a little pond in Massachusetts because he wanted to live the best life possible. His project has been interpreted in thousands of ways, but from his perspective, this is what he was attempting to do: 

“I went to the woods because I wished to live deliberately, to front only the essential facts of life, and see if I could not learn what it had to teach, and not, when I came to die, discover that I had not lived. I did not wish to live what was not life, living is so dear; nor did I wish to practice resignation, unless it was quite necessary. I wanted to live deep and suck out all the marrow of life, to live so sturdily and Spartan-like as to put to rout all that was not life, to cut a broad swath and shave close, to drive life into a corner, and reduce it to its lowest terms, and, if it proved to be mean, why then to get the whole and genuine meanness of it, and publish its meanness to the world; or if it were sublime, to know it by experience, and be able to give a true account of it in my next excursion.”

His experiment lasted two years, but still, same difference. 

I can get behind “living deliberately, to front only the essential facts of life.” Also, I need a model to follow.

So, I made a list of the things Thoreau did while he was at Walden and used it to make a “to do list” to shape my routines. Alongside all of the travel that will provide the framework, I’ll experiment with this:  

• Live life with one foot in nature, one in civilization. 

• Focus energy on paying attention and recording what I see, especially outside.

• Read meaningful books across a broad spectrum of traditions seeking “the iron thread” of wisdom in human culture.

• Use journaling as a tool for reflection.

• Give verbal and written accounts of what I experience along the way. 

• Live as simply as possible to minimize the time, energy, and money I waste. Thoreau had a famous quote: “I make myself rich by making my wants few.” That’s the goal.

• Walk around a lot. Thoreau has this other famous quote: "I think that I cannot preserve my health and spirits, unless I spend four hours a day at least—and it is commonly more than that—sauntering through the woods and over the hills and fields, absolutely free from all worldly engagements." 

• Go on pilgrimage. Thoreau didn’t talk about it in Walden, but during the time he lived at the pond, he left for a period in order to seek true wilderness in the Maine woods, on an extended trip to Katahdin. 

• Engage in principled action and practice making myself useful. 

• Write a lot. Thoreau published his first book while he was at Walden, wrote extensive journals and observations, and recorded the notes that eventually became his book about the experience.

I’m no Thoreau. I’m not going to build a cabin in the woods. But I am going to make myself a part of a long tradition of people who’ve followed in his footsteps intentionally, in some way or another (John Muir, Jack Kerouac, Ed Abbey, Annie Dillard, Thomas Merton, Yvon Chouinard… they all did it). I’m going to use Walden as a model–or at least an inspiration–for this perfect year. I’m going to do the stuff on the list above. I’m going to be intentional, pay attention, and try to drive life into a corner. And also, I’ll talk about the experience with you all. 

What’s in this research project for you?

Another problem to solve with a project like this is, who cares? 

The thing about life is this: it doesn’t feel good if it doesn’t help. 

So who cares? 

I’m sure some people will think this project is annoying, for the same reasons that people think Walden is annoying.

But here’s the thing that’s troubled me since my dad died 10 years ago, and even more since 2016 happened: 

How do you live a good life in tumultuous times? The sort of times where the news makes you anxious and mainstream cultural norms are a set of train tracks leading to the edge of a cliff? What are you even supposed to do? 

This is another reason Thoreau and Walden have been interesting lately. He was asking the same question. It was pre-Civil War America. Things were worse than they are now. His neighbors were engaged in slavery and genocide. (He saw the impacts first-hand because his family home was a stop on the Underground Railroad.) The wilderness around his town was being deforested. His family was wrapped up in the industrial revolution, and he was worried about what it was doing to them and to society. Then, his brother died in his arms from lockjaw—a sort of painful, ugly death that TDAP vaccines prevent today (at least until RFK gets his way).

Thoreau left a normal life behind and went to the woods to find a better way through. 

That seems like something that’s needed, again and again. 

This is a reason that the perfect year is valuable enough to experiment with and chronicle.

Like Thoreau at Walden Pond, it is an intentional experiment. It’s performance art. It’s an experiment in monasticism. What does it look like to step out intentionally and find your way through these days? What will you find along the way? 

That’s what I’m going to keep asking myself.

Maybe it’ll come to nothing. Maybe I’ll find is that it’s hard to live intentionally and usefully in an imperfect world. 

I’m not sure. In any case, it’s not an attempt to provide absolute prescriptions. If this were research, it wouldn’t be a meta-analysis. It’d be a case study. 

“What happens if you arrange life exactly as you want it to look, and intentionally follow time-tested routines to build meaning?

Hopefully that’s useful. 

I’ll write about practicalities and philosophicalities. I’ll share travel stories and photos and other stuff. I’ll pay attention to the things that seem like they’ll be valuable for you, and share them.

How will you know how this Perfect Year is going?

The internet, mostly.

It’ll work it’s way into future book projects, probably.

But the thing with books is that they can feel so disconnected. Books are separated from experiences by years or even decades. 

That is great because it gives you time to let your ideas mature. However, that also takes a while, and loses something. 

Social media and the internet are fast, which is useful, because of the immediacy. It’s like you’re reading someone’s journal–experiencing what they’re thinking and feeling while they’re in the midst of an experience.

I’m working on journaling every day in some form or another. I’m less committed to posting daily on the internet, but my thoughts will often find their way to social media or blog posts. Instagram, Facebook, my mailing list (don't forget to sign up!) 

It’ll be relatively freeform, but it’ll all be coming out of this experience. 

What’s it like to try to put together a perfect year? What does it teach you about a perfect life? 

It makes me a little nervous to tell you this, but...

We’re going to find out this year.

2026, here we go.