Metaphors: the 'Life Path' and Denali

For nearly two years, I worked every day, seven days a week, with no vacation.

On Tuesdays, Wednesdays, and Fridays through the weekend, I worked my full time job as a reporter at the Albuquerque Journal, showing up to work around 10 or 11am and often working through until the newspaper’s 10:30pm deadline.

On Mondays and Thursdays, I went to classes for my graduate degree at St. John’s College. Those mornings, I usually had around a hundred and fifty pages to read before classes started at 5pm. When they ended at 10pm, classmates and I would often go down the hill to Del Toro for a beer and to decompress.

When I graduated in 2006, my dad offered me a graduation present, and asked what I wanted. I told him: I need a break.

So, he bought me an airplane ticket to Alaska.

The problem with the “Life Path” metaphor

There are a thousand guides to help you figure out your purpose in life. And they all use some version of the same metaphor, from “What Color is Your Parachute” (the cheesy career guide it seemed everyone my age was handed upon College graduation) to the long blog posts from life coaches about how to find your life path, always with a stock image of a wood plank path stretching in to a lush green forest.

If you are religious, perhaps you were taught to find your calling. In one of my favorite movies of all time, Tom Skerrit asks his son, newly returned from attending Dartmouth, what he plans to do with his life. It’s a charming scene of what happens a father’s expectations run up against a son’s uncertainty (just watch until his priceless “deer in the headlights” face at 3:48):

Ah yes, your “calling,” or your purpose, or perhaps your “Ikigai,” roughly translated as your “reason for being.”

All of these are all some version of the “life path” metaphor. Some times we come to forks in the path. And some times we read with pleasure classic poems about forks in the path, and how we are to choose between them, and roads not taken.

But with all due respect to the great master Robert Frost, I think the metaphor itself has led us astray. The problem with a “life path” is the suggestion in the first place that life has paths.

Most of us are trained from a young age to look for our purpose, to search it out, to find our path, as if we are wandering in the wilderness and need only to wander until we find the road, and when we find it, the way forward will be clear. But what if there are no paths and no roads? What if life isn’t some forest with futures laid out that we only need to search for and find in order to move forward? What if there is only… life?

I say we need a different metaphor.

Hiking through Denali

After graduating from grad school, I flew to Anchorage with my hiking backpack, my tent, ten days of food, and a lot of bug spray. Anchorage feels like a frontier town, founded only in 1914 and still a gateway to vast wilderness.

My first night, I walked from the hostel to the downtown and had the best lobster chowder of my entire life, served in a perfectly baked bread bowl, along with a crisp, perfect Alaskan beer. I stayed up until 2am watching the northern sky, and then, it finally got dark.

The next day I boarded the Alaskan Railroad en route for Denali National Park. The park encompasses 6 million acres of wilderness - an area the size of New Hampshire - and nearly all of it accessed by a single, lone road.

After taking my required bear awareness course, the park official gave me a hiking permit and a topographical map of the park, and assigned me to a zone where I wouldn’t run into other hikers (they do this to lessen any collective impact on the land).

Next, I boarded a bus loaded with senior citizens in retirement. The bus took the one road into the park, where it deposited me and my backpack in the wilderness. I remember the senior citizens were looking at me like I was crazy. After all, they had just seen a distant bear from the bus window. What was I doing, hiking off into the wilderness, no trail, no camp in site?

In Denali, there are no paths

That’s the thing about Denali National Park. There are no hiking trails, and no campsites. There are mountains, wildlife, glaciers, rivers to cross, dense brush to bushwhack through, valleys, and scree fields. But one thing there is not are paths.

As I started walking away from the road, the faces of the senior citizens in the window still staring at me as I trundled out into the vast emptiness, there was no particular direction to head, except away. There was no campsite I had to reach that night. There was no trail to follow. Just the wilderness in front of me.

If I wanted, I could hike up one valley toward a glacier, and spend the next ten days camped there doing nothing at all. I could spend my time searching for wildlife - I did come across several caribou as well as the remains of some beautiful Dall sheep, their large, curled horns and skulls scattered about a hillside. Or, I could spend my time following a river, or hiking through the lowland brush. Or, I could explore several valleys, turning back on myself whenever I pleased. I could do four miles a day or twenty. When it came time to pitch my tent, I could do it anywhere, whether on a hill with views in every direction, or tucked into a mountainside.

The world was open.

And now you see what I’m getting at.

A new metaphor

Life is like hiking through Denali. Whether you stay in bed all morning doing nothing, or get up to water the plants, commute to work, see your kids, play video games, or whatever else it is that you choose to do that’s in front of you is completely up to you.

If you are wondering what your path in life is, or what your purpose should be, perhaps you should rethink the metaphor itself: life doesn’t have paths. We are not on a road to Damascus; we are wandering through the wilderness, and there is no promised land on the other side. We are not choosing the road less taken; we are simply choosing how to spend our time, and there are infinite possibilities.

This way of thinking about the time ahead of me is lonesome and at times scary, like sailing through an unknown tempest in the middle of a vast ocean with no thought that land even exists. If there is no path, then I will never know whether I’m on it, or on the right one, or whether there is a right or a wrong one. There will only be the direction I choose to go.

As much as I love Robert Frost, it’s always been this way for me. I’m not religious, but my religious friends have sometimes asked me how I could go through life without that feeling there is a path God has chosen for me, or without the comfort of a higher power, or without the guideposts for action that are laid out by moral dictates like the commandments, or Jesus’ teachings, or any number of great books through the times.

And I say in response that I don’t know: it’s frightening and uncomfortable to believe that there is no path - and no amount of searching will get you to one. But of course it’s also liberating.

Sometimes I wish life did have paths, and that I could find the right one, and know that I was on it. I hiked up to a new climbing crag a few weeks ago and along the way I found those comforting rock cairns that signal: this is the way, you are headed in the right direction.

It’s always nice to come across those cairns. But the truth is, ultimately I prefer a hike through the wilderness. Maybe that’s a false sense of power, a mistaken belief that I am in control of more than I am. Maybe there really is a God and a path and a purpose and a plan for my life.

But I doubt it. Regardless, whether there is or isn’t, I’m sticking with my Denali metaphor. There are no paths - at least, no predetermined ones. There is only how you choose to spend your time.

Podcast - Episode 4: Nate Murphy


On this episode I talk with the great Nate Murphy. Nate is a rock climber, adventurer, entrepreneur, and van life aficionado with nearly 160,000 subscribers to his YouTube channel.

From the moment I started this podcast, I knew I wanted to get Nate on as a guest because he is particularly thoughtful about one of the questions I’m most interested in: how to spend your time according to what you want, and not what society expects. I was super excited to get ahold of him in his van in Catalonia to talk about that and more - enjoy!

Show links include:

How I do strategic planning for life

In my 20s it didn’t appear that my life needed much planning. Like many young, educated professionals, it appeared that my career had a momentum of its own: opportunities presented themselves and I either took advantage of them, or declined. The goal was simply up: more money, higher job titles.

I had a loose idea of what direction I wanted to head, and when certain forks in the road of life arrived I made my choice and continued on. It all seemed to be going well. At 29, I was director of communications for an internationally recognized climate think tank based in Washington, D.C. My office in Dupont Circle overlooked the entire Northwest part of the city, and in the distance, I could gaze on the National Cathedral, a gorgeously imposing work of Neo-Gothic architecture that declared to me: I had arrived.

And then, everything crashed.

First, it was my relationship. I was a new father to a perfect one-year-old boy, but the relationship with his mother had never really worked. It unravelled over the course of a year, punctuated by brutally painful, soul-destroying fights.

In the middle of all that, the climate think tank laid me off. Its finances had been declining for a decade due to some unspecified combination of benign neglect and poor financial planning. In any case, the communications and marketing people are always the first to go under such circumstances.

The prerequisites for strategic life planning (Or, what to do when you’re a single parent and jobless)

This might go without saying, but it’s near impossible to be deliberate about planning your life when you are a single parent without a job and no savings.

Strategic planning for life isn’t something I would ever have the audacity to recommend for someone in this situation. My only recommendation would be the obvious one: go get a job. Any job. Get stable, financially.

Which is what I did. I called an old colleague who had started a boutique marketing agency, and I asked if he had any work. As it turned out, he was launching a rebrand for one of his clients and needed someone to handle the social media channels. He sub-contracted the work to me, and I had my first client.

In time, I got more clients, and in some more time I was able to breathe long enough to think about the other things in my life other than money. It took a few years, but the lesson I learned from that time was this: when you have kids and are stressed about money, nothing else matters that much.

Thinking back on it, I simply embodied one of the great facts of being a new parent: my dreams of a different path were on hold until a later date. A few years later, that date finally came.

My first strategic plan

My largest client in 2013 was an emergency physicians group. I was increasingly integrated into their business, and I was invited to the company’s annual strategic planning retreat.

Emergency physicians are trained to think on their feet, lead a team, and handle anything that comes through the doors of the ER, whether it’s multiple gunshot wounds or a baby with a fever. One thing they are not trained in is long-term strategic planning.

That said, the doctors who led this particular group had gone to extraordinary and fairly effective lengths to train themselves as managers and business leaders. They had a pretty good process for strategic business planning, and it went like this:

  1. Each year, the group’s senior partners created four broad goals for the next year. They never went beyond one year because their industry was changing too fast to make any meaningful goal beyond that year.

  2. At the retreat, a wider group of senior leaders divided themselves into four groups according to their interest in each of the goals. These sub-groups came up with a plan for achieving the goals, as well as quarterly milestones for each of the initiatives.

  3. At the end of the year, each group reported back with a simple “red/green” - green if they achieved the goal; red if they didn’t. Reporting back in this way forced the company to articulate goals in such a way so that there was no room for ambiguity. Goals had to be expressed in such a way so that it was clear: either they had achieved it, or they hadn’t.

A few months later, I decided to adopt parts of this framework for my own life. First of all, I liked the short time frame. One year seemed long enough to achieve something substantial, but not so long that changes in my life could derail the original intention.

Second, I appreciated the simplicity of declaring a goal either red or green and of having to phrase my goals in straightforward, unambiguous language.

On my birthday that year (which incidentally comes a few days before the New Year), I parked myself in a coffee shop and outlined my goals for the next year. I created a Google Doc, and declared at the top of it that at the end of the year I would take a red or a green for each of the goals. I divided the goals into three categories - creative, financial, personal/social - and added quarterly deadlines and milestones.

Here’s what the top level “Creative” section looked like at the end of the year:

In the span of the next 12 months, I succeeded in:

  • Training myself how to use Premiere Pro

  • Writing a 10,000 word short story and submitting it to 20 journals for publication

  • Writing a 120-page feature length screenplay about Ferdinand Magellan

  • Directing my first short film (18 minute run time) and submitting it to festivals

It was, without a doubt, the most productive year for my creative goals that I had ever had in my life.

I also completed most of my financial goals that year, although I took a red on fully paying off my student loans (that would come the following year).

In the “social/personal” category, meanwhile, I failed to meet any of my goals. One of the major ones in that category had been to find a personal or professional group to join in order to expand my circle of friends. It never happened (thus presaging a years-long struggle to develop close friendships in the D.C. area).

Still, I considered my first year in “Strategic Planning for Life” to be a wild success.

Learning how to drop goals

One of the major lessons I learned in the first few years of going through this process was how to drop goals. Each year on my birthday, I would again sequester myself in a coffee shop to plan for the coming year. But I would also look back on the achievements - and failures - of the year behind.

I realized that in addition to creating a system for achieving life goals, I had also stumbled upon a system for dropping them. After all, the “reds” that I took weren’t just failures; they were indications that I was not fully committed to that project.

As I looked through what “reds” I had taken at the end of each year, I decided to carry a few of them over to the coming year, and altered my approach and milestones appropriately. But the large majority of them I simply dropped from my list, having learned a little more about myself and what I truly valued.

Not only had the process led me to achievements beyond anything I had expected, it had also become a testing ground, a way for my ambitions to sort the wheat the from chaff, so that I could learn what to leave behind and what to continue on with.

Time well spent

For four years, my annual strategic planning session had become somewhat of a ritual. Before that I had always approached my birthdays with some degree of dread: another year passed, another year older, and still without having achieved any of the things I wanted to in life.

But the strategic planning had made my birthdays into something a bit different: a way to mark what I had achieved that year - and the achievements were many. In 2017, I wrote and directed a feature film, a gigantic undertaking and the realization of a life-long childhood dream. I was proud and still am.

Still, I realized I needed to make a change to the way I thought about my life. This was in part motivated by the Time Well Spent movement (founded by Tristan Harris, who has since created the Center for Humane Technology). What Harris crystalized, for me, was something that had already been germinating inside me for a while: the most important decision in life that we make each day is how we spend our time.

Time is everything. It is our most precious resource as humans. It gets spent whether we spend it deliberately or not, and once gone we never get it back.

Most of us spend our time without ever thinking about the choices we make along the way. The most important decision we make about time is almost always related to our work and our career, since work and career is where we spend most of our waking hours.

But I didn’t want to spend this precious resource of my time doing work that I didn’t like or didn’t care about. I wanted to spend as much time as possible doing the things that I did care about, which meant: I had to figure out what I cared about.

A major evolution to my strategic planning: incorporating values

At the end of 2017, I made a major change to my process. As usual, I loaded up last year’s Google Doc and took my reds and my greens. But when I began the document for next year, I added a new section to the top of it: values.

Here’s that list:

  • Time outdoors

  • Time with friends & family

  • Continuous learning

  • Creative endeavor

This is how I wanted to spend my time: outdoors, with friends and family, and pursuing continuous learning and creative endeavors.

In the next section, I revised my goal categories. Instead of three categories labeled “creative, financial, and personal/social,” I created goals tied to four categories, one for each of the values.

Under time outdoors, I committed to specific amounts of time spent rock climbing and kitesurfing. Under time with friends and family, I committed to specific amounts of time spent sharing a roof with them (that Summer, I rented a house in Galicia and invited my family to join; it was a glorious month on the Spanish coast).

And so on.

Adding those values forced me to clarify the why. Perhaps I needed those few years of simply focusing on the achievements themselves, of racking up wins after having put off for so long simply making the attempt. But at 36, I was truly beginning to feel the march of time with a vividness I hadn’t experienced before.

I needed to make sure that as this precious resource ticked ever away, that I at least observed it do so with intention.

The 5/25 rule

Later that year, I came across a story about Warren Buffet. The story goes that one day Buffett had a conversation with his pilot, who had been working for him for ten years.

Buffet joked that the fact that the pilot had been working for him for so long was a sign that Buffet wasn’t doing his job. The pilot needed to direct his own path and move on. To help, Buffet asked the pilot to list his top 25 life goals, which the pilot assiduously proceeded to do.

Then, when the pilot had the list, Buffet told him to circle his top five. Then, Buffet asked what the pilot planned to do with the other 20, and the pilot responded that they were all still very important, but secondary. He would focus on the top five, but he would also keep the other twenty in mind as he thought about where to focus his time.

But Buffet explained to him that he had it wrong: the other 20 were the “Avoid at All Costs” list. No matter what, the pilot was to ignore them and focus only on the top five. Only then would he have the clarity needed to achieve what he wanted to in life.

How I integrated values and goals, both short- and long-term

For a few weeks, I was obsessed with Buffet’s 5/25 rule. I made the list of 25 myself, and then struggled and struggled to select a top five. Each time I thought I’d had it narrowed down, I would wake up the next day and revise the selections.

I spoke about my list with my family, and I asked them for input and advice. After a few weeks, I thought I had settled on a top five, but I still proceeded with a certain unease.

For years, I had been focusing only on the year ahead, and with great success. This was the first time I had actually written down goals beyond that time horizon, and they were life goals at that. I felt in over my head, overwhelmed, even a bit paralyzed.

I was prepared to think more long term about what I wanted to achieve in life, but at the same time the enormity of the project conflicted with the limited scope of the strategic planning process I had already been using with such success.

Today, the 25 priorities are in a spreadsheet in my Google Drive, with the five I’ve selected as my top priority shaded in yellow, for in progress. Over the past year, I’ve accomplished two of them - those are now shaded in green, signaling complete.

Meanwhile, when it came to my annual ritual at the end of last year, I used the five in yellow as a rough guide to articulating my narrower annual goals, which are still grouped according to values. In this way I’ve melded the two methods together: a list of annual goals according to values, but with specific achievements chosen according to priorities chosen from the list of 25.


The only problem with this approach is this: every once in a while (but certainly more often than we’re ever truly prepared for), life throws you curveballs.

For me, it was losing my job earlier this year. All of a sudden, I had far less money than I could count on in the future. On the other hand, I had far more time.

This led to a re-evaluation of both my short- and long-term goals. Fortunately, I had done the work. I knew what my values were, how I wanted to spend my time, and what I wanted to achieve. And as the shock of the job loss began to wear off, I realized I could actually achieve far more of what I wanted to over the coming year than I could have with the job.

Suddenly, my desire for travel and learning, and other goals which I thought were years away were suddenly all within reach. I had the money in savings - I had been wise, that way. What I hadn’t had was the time and the freedom. Now, I did.

Even the search for a new job (or, more accurately: any method of earning the money I needed which would best support my life goals) had guideposts to it in terms of what I valued and what was important to me, and those guideposts were far away indeed from the mile markers of my 20s, which had read simply “more money” and “higher job titles.”

That is what I wish for everyone, really: a life that transcends the base societal expectations of ever-greater wealth and ever-greater status; a means of work or money that supports their life, and not the other way around; and time on this earth that is well spent according to how they wish to spend it.

On writing honestly

When I started this newsletter roughly two months ago, I typed down an idea for a post that sat dormant until now. I included no links, no references, no excerpt from a news article or addition thoughts. All I wrote was this: “A chance to write honestly.”

I’d had a nagging feeling for a long time — for as long as I’d held my previous job — that I had not been writing honestly. Jobs can do that to you. When your income (and therefore your family’s wellbeing) becomes dependent on someone else’s good graces, you begin to make compromises. We all do.

My compromise was this: I withheld, obfuscated, and omitted. I was not writing honestly.

So what?, you might ask. That’s civilization. As soon as we are around other people we bend ourselves to be agreeable. We preserve our relationships above all else because we are social animals. If that relationship is with our boss, we bend all the more. And, perhaps, protecting relationships at the expense of full truth is good and right. What is it that we live for if not strong relationships?

But there is a perversion that goes on when money is involved, and it will always be there so long as we remain financially dependent on others. That’s what I’m concerned with here. When you become financially independent, you can, quite literally, do whatever the hell you want. Say what you want, write what you want, and be as disagreeable as you’ve always dreamed. It’s not called “fuck you” money for nothing.

How exactly I was being dishonest

The writing I did on behalf of my company and the clients I had is one thing: marketing people are used to, shall we say, writing around the ugly parts of the story. Marketers must be anchored to the truth in the content they put out, but they don’t exactly write the content with that intention. They write to support business goals.

That’s not what I’m talking about here. I’m talking about the ways in which I was distorting even my non-business writing. I would publish occasional stories on my personal blog, but I was always careful to avoid certain topics.

I didn’t, for example, write about how often I traveled. Though I worked remotely as a supposed full time employee, I often switched states, traveled on work days, even left the country a few times without telling anyone at work. My travel never impacted the quality of my work, or my output - but still, I felt that I was hiding a certain part of myself, simply by not being able to talk openly about the travel experiences which I valued so much.

I also avoided talking too deeply about healthcare — the business I was in. As a marketing person, I had to be a cheerleader for my industry. In marketing, you can be honest in your personal life, but not too honest. Everyone working in every industry maintains willful blindspots about the nature of the business they’re in. In my case, it was the business of emergency medicine. The people I worked with took care of patients when they needed taking care of the most — and that was good. But I never thought too hard or too deeply about the ugly implications of what it really means to make emergency care into a for-profit business. (I have started to do that in another healthcare-oriented newsletter.)

Mostly, though, I avoided writing about my profound discomfort with the nature of work itself. For example, many people I worked with liked to refer to us all as a family. At least, a “work family.” That phrase always offended me, but I could never say that, at least not in public. I already have a family, thank you very much. My work is my work. I do it to support my family, not because they are like a family.

“Work as family” is just one of the ways in which companies - not just the one I worked for, but many others around me - create a sort of myth to convince its employees of half-truths in order to get them to devote more of themselves than they otherwise would in service of profit. But your labor is one of the most sacred things you can give. It should not be given lightly.

I also have a profound discomfort with the nature of the U.S.’s brutalistic form of capitalist striving, and with the idea that my company should own my time. Once I was at a meeting of company leadership — about three hundred people were there — where I was asked to donate money out of my paycheck into the company’s Political Action Committee. You see, legislation was currently being debated in Congress which threatened the business, and my money was needed to make sure the company’s view of the situation prevailed.

Now that I’m out and have had a chance to dive deep on the issue in question [click this link if you are a healthcare wonk], I am glad I decided not to give.

Does it even matter to be able to speak honestly in public?

So I wasn’t writing honestly on my personal blog. So I wasn’t saying all the things I really wanted to say about the world. Did it even matter? It’s not like I was suffering under some semi-despotic regime that was monitoring my every communications, looking for apostasy.

Honestly, I could have said everything I wanted to in public, on my blog, on social media, wherever. But I did risk damaging my work security by doing so. Anyway, I could always talk with my family and my friends. My free speech was not being impinged. I didn’t live in a totalitarian regime. So who cares if I was self-censoring?

Well. I suppose I cared.

To write honestly is to strive toward truth

I care about being a writer, and writers have to be read, and if I’m going to care about that, I better damn well care about writing honestly and publicly.

It’s not clear to me that every writer feels this way. Many, including myself, write for money, and perhaps it’s better for all of our income earning potential to write dishonestly. I can think of more than a few political opinion writers who would rather be sensational than honest because it will get them more attention, and more attention will get them more advertising dollars. Give the people what they want, I suppose.

There are plenty of incentives floating around the world which would lead writers to write dishonestly. I’m just not interested in making myself beholden to them, and maybe that means my writing won’t get as much attention, and maybe that means I won’t make enough money to keep devoting all this time to it, and maybe that means there will be less honest writing out there in the world.

That would be fairly tragic. In my humble opinion.

Maybe I’m being too hard on myself. It wouldn’t be the first time, and it won’t be the last. Or, perhaps it’s time to turn to fiction. There, one can be as honest as one likes, because hey: the character said it, not me.

Yes indeed.

Like this writing? Please consider subscribing for $5/month. Yes — I am aware of how odd it is to solicit money for my writing directly after the above article. But hey: it’s a nuanced, complex world out there.

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