Russell Max Simon Wants You to Maybe Settle Down a Bit

Meet the climbing- and writing-loving, frequently transitioning, equanimous, and post-nomadic Russell Max Simon.


This interview with Russell Max Simon is part of The Unfollowables Series. The series’ goal is to help you find actionable ideas and inspiration from others’ most extraordinary experiences.

Three of my favorite takeaways from Russell are:

  1. Sometimes the best decisions in life are counter-intuitive.
  2. There’s plenty of time to dramatically change your life story—multiple times.
  3. Mellow out. It seems to happen to all of us as we get older, so why not start now?

If you’d like to be featured in The Unfollowables, or have a suggestion on someone else to interview, please contact me.

1. 👣 Life Story

Q: Briefly, what’s your life story so far?

Sometimes it feels like multiple life stories.

I was born in Santa Fe, New Mexico, but raised on the East Coast—we moved around a lot as a kid, leaving me feeling like a pretty rootless adult. Never had a real childhood home, which might be why I’m so obsessed with the idea now.

I started out as a newspaper reporter. Tried to save the world as a climate activist. Helped run a U.S. Senate campaign, volunteered for two presidential campaigns, then even ran for office myself. 

Had another career in marketing and communications (having failed to save the world). Shortly before the pandemic hit, I was laid off, so went into business for myself doing marketing and strategy consulting.

Also started writing my Substack around then, and transitioned my life from being oriented around work to essentially being oriented around rock climbing, a passion I’ve had for 20 years. I’ve visited 40+ countries and lived all around the U.S., including 10 years in Washington D.C., but this Summer I’m finally moving abroad—to Barcelona, Spain with my son.

Russell Max Simon writing

2. ❄️ Quirks

Q: What fun facts and/or quirky things make you you?

I really care about good writing. Maybe to my detriment. Like, maybe I shouldn’t put so much emphasis on it, and instead just be happy in the outdoors and rock climb. But I come from a family of writers, and I’ve always really admired great writing and what it can do.

I definitely need to be engaged in some kind of creative pursuit—I was an indie filmmaker on the side for five years. I eventually burned out on the difficulties of film production, but in the meantime, I was part of a good community and made some films I’m proud of (here’s the trailer for the feature I made!)

I once ran for city council in Santa Fe, New Mexico. But I was a bad candidate and lost the race (the hubris of youth!). I worked in politics and advocacy for a long time in various roles, but I was always better at the communications and writing parts of it than the people aspect.

3. ✊ Mission

Q: How are you trying to make the world a slightly better place?

I’m trying to do this mostly through my writing, especially with my Substack.

I’m ostensibly writing for location-independent folks and digital nomads about travel, climbing, and the like—but the real goal is to help people find meaning and purpose

I’m also a big proponent of what Voltaire wrote about in Candide, that in some respects, all each of us can do is “tend our garden.” That is: take care of the people and things around us: our homes, our family, our community.

4. 🦸‍♂️ Role Model

Q: Whose life do you look up to?

A lot of writers come to mind, but recently I’ve really been admiring what Sebastian Junger has done with his career. 

Several of his books made a big impression on me, starting with A Perfect Storm, which was one of the few books I read around college that made me really admire great creative nonfiction writing.

If I could recommend one Junger book though it would definitely be Tribe, where he goes deep on not just the importance of social connection in small groups, but on the importance of connection combined with shared purpose.

Junger has also merged a reporting and writing career with some truly extraordinary life experiences. Embedded for years in Afghanistan. Illegally hiking cross-country along rail lines in the U.S. 

He’s thinking big, and translating those experiences into important writing and projects. 

And the guy is just a badass: he’s put his life on the line, and his themes are central to the human experience: freedom, family, death, life, war. There’s a lot to admire there.

5. ⚡️ Huge Zag

Q: Can you tell the story of a decision you’ve made that has had an enormously positive effect on your life’s trajectory?

I made a big, counter-intuitive decision about where to go to grad school that has been absolutely formative.

I’d been accepted to American University’s joint International Relations-MBA program, which seemed like a great option for me. All the traditional sources of wisdom (parents, society, etc.) would have smiled on that decision, and I was internationally and entrepreneurially inclined. It would also have been a natural extension of work I’d already done on political campaigns.

But I remember thinking at the time: going to do that would be like getting on a fast-moving careerism train, and it would be hard to get off. 

Instead, I zagged: decided to study philosophy via the Great Books curriculum at St. John’s College. My very sensibly-minded dad was worried about the decision, but oh my God was it the right one.

For starters, I got my first reporting job through the program (the editor at the newspaper was tired of hiring journalism school students). And, the tight-knit alumni network led directly to a lot of other career advancements.

But more importantly, that program, which is totally unique in the U.S., was the foundation for so much learning that came after. It prepared me on a very fundamental level to exist and thrive in a complicated world where it’s hard to discern what truly constitutes a life well lived.

I remain extremely grateful for that decision and that education.

6. 🙃 Unusual Practice

Q: Do you have any unusual practices that you think more people would benefit from trying?

I do an annual “strategic planning for life” every year on my birthday. I’ve written about the process a few times, and it’s evolved over the years (most recent iteration here).

As I’ve gotten older, I’ve perhaps become less goal-oriented than when I started, but the process has nevertheless been a huge way to signpost my time and ensure I’m being deliberate about what I’m doing with my life at least once a year.

7. 👀 Change of Mind

Q: What have you recently changed your mind about? What caused this change of mind? How has your behavior changed as a result?

Something kind of big happened when I turned 40, which is that it finally sank in that I was not going to accomplish everything I wanted in this life. That was the big mind change.

Until then, I’d more or less been in constant existential crisis about needing to accomplish everything. Visit every place. Write every article. Launch every business. And my 40th birthday loomed like a deadline, like if I didn’t get certain things done by then I’d be a failure.

I think letting go of some of this ambitious need to achieve, leave your mark, make a dent in the universe, or however you think about it, is an important part of aging with grace.

So, since then, I’ve started being kinder to myself about not getting it all done, and I think that’s been good for my mental health.

8. 🥊 Disagreement

Q: What might you and the person reading this disagree about?

I’m not sure who’s reading this, but I recently wrote about how there’s nothing inherently good or noble about having traveled to lots of different countries. Being well-traveled won’t automatically make you a better person, wiser, more tolerant, or even more worldly.

In fact, a lot of people travel to a lot of places and come back essentially unchanged from who they were before. 

Digital nomads in particular seem to exist in this space where perpetual travel is seen as inherently valuable, without ever explaining what it is they’re doing or defending the wisdom of moving from place to place. Meanwhile, I think one gives up a lot by not investing in a particular community, with in-person, friendships and relationships. So, if you’re going to make travel a way of life, I think you need to be much more deliberate about the why, and what it is you’re seeking, and giving up.

9. 💡 Life-Changing Learning

Q: Can you share a source of information (book, podcast, video, etc.) that pushed you to take action that improved your life?

There’s a great YouTube video that has informed a lot of how I approach creative work called How An Artist Turns Pro, on the Storytellers YouTube Channel.

The message, in short: greatness in creative pursuits only comes from putting in the work. You can’t wait for the muse to strike you. You’ve got to sit down, open your keyboard, and start. Only then will the muse bless you with inspiration.

It’s essentially a distillation of the ideas in a book by Steven Pressfield, The War of Art. But the video adds to it with a lot of great portrayals of writers in film—there’s also a great clip in there of Stephen King on stage with George R.R. Martin talking about craft.

Well worth a watch.

Russell Max Simon climbing

10. 🔬 Curiosity

Q: What are you currently excited to learn more about?

Maybe niche but the next big thing I want to learn is new route development in rock climbing.

I’ve spent almost 20 years climbing on routes put up and established by other climbers, often at great time and expense. Now I really want to be able to give back to the sport and the community and learn how to establish new routes.

I’ll admit there’s also something egocentric about it—developing a cliff is a way to leave a legacy, which is also appealing.

11. 😰 Struggle

Q: What are you currently struggling with? How might the person reading this help you?

I’ve been struggling with being a better “solopreneur,” i.e., whether or how to scale my marketing and strategy consulting business (I mainly do B2B content marketing for healthcare clients), which provides most of my income.

I like working with clients, but at the end of the day (and every month, year, etc.), it’s delivering services, and that’s always time-intensive. What’s the next step there, and what should I be building to help me transition?

12. 👍 Wonderful Thing

Q: What’s something you own that, if you lost it, you would rebuy the exact same model without looking at alternatives?

Maybe a boring answer but my Macbook Air with the new chip is pretty great. Perfect machine. Just don’t mess it up Apple!

I also have an Osprey Porter 65 travel backpack, which I’ve owned for 20 years and which has gone everywhere with me, to every country, on every climbing trip. But I think Osprey doesn’t make it quite the same way anymore. But that old version of the bag is perfect.

13. 👊 Challenge to Readers

Q: What one thing do you challenge the person reading this to try this week?

I periodically try to do something very close to what Seneca advises: “Set aside a certain number of days, during which you shall be content with the scantiest and cheapest fare, with coarse and rough dress, saying to yourself the while: “Is this the condition that I feared?”

For me, that translates into a kind of minimalist fasting, which a lot of people recommend for health purposes. But instead, I recommend going into it for the same reason as Seneca: it’s a kind of practice and path toward equanimity.

14. 🎤 Question for Readers

Q: What would you most like to get an honest, unbiased answer to from the person reading this?

I really, really value constructive feedback on my writing. It’s so hard to get, and each little tidbit is so valuable. If you feel so inspired, head over to Post Nomad and feel free to email me your thoughts.

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About the author

I'm Chris. Canadian, husband, dad, writer, investor, athlete, and obsessed explorer of the secrets to living a never-boring, always improving, unfollowable life story.

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