Step up, don't jump up
Progress happens over time
Hey reader,
Coming to you today from OpenHub Coworking in Mexico City. Far from the mountains, but a big-city break seemed a good way to pass a week while the snowpack stabilizes back in Colorado. We’re at 140 percent average snowpack after a very wet March — meaning the bigger objectives will make for excellent riding into June, least (we’re coming for you, Red Mountain Pass).
In today’s essay, I explain how longevity and consistently striving for small gains have played a significant role in my life. The examples are personal, but I encourage you to apply the same lens to yours — in which areas of life have you gained through consistency? By taking small steps toward a far-away goal?
Community Shoutouts
Welcome to the 12 new subscribers since last week! You’re here among like-minded travelers and outdoor adventurers. I hope you dig this installment.
Next Wednesday I’ll be giving a virtual talk about how businesses and destinations can best pitch their sustainability initiatives to the media. Here is the event info.
Now, let’s climb the stairs.
Step up, don’t jump up
There’s much to be said for longevity. First and foremost, you can’t fake experience. I’ve found the “fake it till you make it” mantra to be more harmful than productive, and the people who endorse it to be largely full of shit.
That’s because there is no good way to go from here — where you are right now — to way up there — where you want to be in 10 or 20 years. You must gain the skills required to get there, hone them, and then execute them.
I’ve made many mistakes in my career, including emailing editors with pitches for stories I’m not qualified to write and letting delusions of grandeur infiltrate my daydreams (my self-published book never took off, not least because I didn’t follow through on the marketing plan that I myself generated).
Major points of progress have instead been the result of a lot of honest work and learning from mistakes. One aspect in which I’ve succeeded is consistency. This essay is an extension of a deep dive into the importance of consistency, stretching out over the long term.
When you jump, you often miss the target
My clearest example of attempting to jump up multiple levels happened with my band, in the 20-aughts. I long held the stance that we needed to act as though we were at least somewhat of a big deal — highlighting any argument I could cling to that emphasized our legitimacy. I reasoned that this would help us land bigger gigs and more quickly climb the ladder of the music scene — effectively sidestepping the decade-long grind that the bands we encountered who were seeing success had put in to get where they were. I wanted the prize and was determined to have it, but I wanted to take the elevator and not the stairs.
This was a shallow ego play above all else. I felt that if I could convince others that my band was at least somewhat of a big deal, this quickly would morph into reality. It took years for me to admit to myself that there is no elevator to success.
I now believe that my delusion of grandeur had a significant negative impact on our overall operation because it consistently placed a target in front of us that we were years away from reaching. Therefore, we, or at least I, continually felt as though we weren’t progressing fast enough.
Fortunately, I learned from this experience.
Step up your personal relationships
On Tuesday, my wife and I celebrated 10 years together. This anniversary was the impetus for our trip to Mexico City — we’ve been here twice before on quick two- or three-night stopovers en route to other parts of the country. Intrigued by the cafe culture and the ease of walkability throughout La Condesa, Roma, Polanco, and the city center, we’d wanted to return for a longer stay.
Ten years is a long time to spend with one person, particularly given how quickly things moved at first — Alisha had just returned from the Peace Corps and had been home from Africa for 48 hours when we met for a drink at the Candlelight Tavern. She was living in a temporary arrangement at her sister’s place. She moved into my 400-square-foot basement-level apartment in Denver within the first few months of our relationship.
I didn’t realize then how much diving head-first into this partnership would force me to re-evaluate every aspect of my life. Alisha is a fiercely opinionated woman of distinction with little tolerance for waffling and, I was certain, no interest in dating someone without direction.
The magazine I edited at that time was about to fold. My paychecks had become increasingly erratic and as such, I’d been unable to ditch working bar shifts on Sundays, and was also booking gigs for a local rock club (this was back during my punk band days).
I was at a decision point in my career — I could either hustle the freelance writing field until I landed another staff gig. Or, I could pursue an easier path in the local music scene where I was already established, but that I saw providing little in the way of long-term viability or financial stability.
I desperately wanted to keep my girlfriend around.
I needed to level up my shit, and quick.
In that sense, Alisha played a major role in my pursuing media work. I knew that’s what I wanted, and that pursuing my passion professionally rather than taking the easier road would help me to be a better person and a better partner.
Furthermore, I was burned out on the music scene, tired of late hours for little money. Those who’d been around longer than myself were jaded and negative. Even the more successful musicians I knew had few positive things to say about being on the road all the time and never getting to bed before 3 am. Even many of them — the people with songs on the radio, the people I’d aspired to be as a teenager — struggled to get by financially.
Not that writing is inherently a high-dollar profession. But when the alternative is a cut of the night’s door take or a $200 guarantee split between four band members and a tank of gas, I knew which way I needed to go.
As the entrepreneur and investor Naval Ravikant says, when faced with two choices, choose the one that requires more pain in the short term. This is the essence of leveling up, rather than jumping. I’m forever grateful to Alisha for motivating and supporting me to keep going.
Other manners in which stepping up is key to long-term relationships:
People change over time. Think to close friendships you’ve had that have faded — in many cases, one person moves forward while the other stays in the same place. Likewise, lifelong friendships evolve as each person moves through the different phases of life — the key being that both people are moving through those phases on a similar timeline.
Raising kids. I’m only 18 months into parenthood but my daughter has shown me more times than I can count that we have to move forward slowly, taking the ramp rather than the stairs (metaphorically, of course, now that she can walk toward the staircase). She gains through small, day-to-day repetition and progression.
In work
I quit the editing role in September 2015 and entered the abyss of freelancing. By October, I’d landed my first byline in the digital travel publication, Matador Network. After completing a few assignments for one editor I began receiving emails from others and leaned into my advantage of being the guy they had on the ground in Colorado.
My plan was simple: work with as many editors as I could. Get them to know and trust me. That way, when a staff gig came up and I put my name in, I’d immediately be at the top of the list.
It took two years and dozens of assignments, but it worked. The email about an open staff role hit my inbox in November 2017. During that time I’d freelanced for numerous other publications and had gained a general understanding of how things worked in the modern media landscape, particularly with digital publications. Not everything went smoothly — freelancing is a game of feast or famine, and months with few assignments weren’t uncommon.
Thinking back on this time, I’m able to identify several factors that contributed not only to getting me on staff at Matador but also to finding good connections even beyond it:
I began listening to remote work podcasts, reading books, and following a handful of influential writers and bloggers in the space. Among them are the Tropical MBA, The 4-Hour Workweek, and Zero To Travel. The key takeaways had nothing to do with writing or pitching — these outlets and the advice I put into action taught me how to run my writing career as a business, gain enough confidence to charge what I’m worth and outsource what I can, and most importantly, how to say “no” (a practice I’m still honing).
The gain here also stemmed from their digital-first approach. Everything they discuss is in relation to working online in a remote-first setting. All are very forward-thinking and taught me to embrace technology rather than fear or ignore it. This was a massive level-up for me, a guy who’d never had the newest smartphone or learned how to code.
Another important takeaway was the realization that a contract is not a job. You have infinitely more leverage working on contracts to remain in control of your time, your location, and your income, because what you do outside of your contracted deliverables is of no concern to the person/company on the other side (and if it is, it’s time to move on).
I networked like crazy. Networking and outreach are everything when you’re going at it alone — in 2016 I joined an online digital nomad community called Location Indie, hosted and attended meetups for remote workers in my area and the places I traveled to, and devised an efficient system of outreach that involved hiring a Virtual Assistant to compile spreadsheets of contacts at publications, online businesses, and other outlets that outsource writing work. I then created standardized outreach templates explaining my services and work examples, set up a portfolio website, and had the VA blast out the emails to all of the contacts. The conversion rate generally hovered around three percent, but when you’re sending hundreds of emails, that’s enough work to pay the bills. (Note: If you want to see these outreach templates, respond to this newsletter and I’ll share them with you).
I began working out of coworking spaces as much as possible. I’m in one right now. I cannot overstate the value of a good coworking space when it comes to finding clients and growing your network (here’s my deep dive on the topic).
For the experienced remote worker, much of this is standard play — but it was (and is) a huge level-up for me, a guy who’d convinced himself that his lack of a career at age 25 wasn’t from a lack of effort but simply due to “a college degree not being worth what is used to be worth.”
Before moving on, it’s important to tie this section even closer to the title of this essay. In another life, perhaps I would have been offered an entry-level job doing rewrites at a newspaper after finishing college. There, I’d be trained only in what was necessary for the job’s day-to-day and would have no frame of reference for hand-crafting a career. I’d never learn to self-advocate, hire an assistant, or travel the world while earning a living on a laptop.
Sure, I might get promoted and even become an editor. But my gain would be so limited in scope that parlaying it into anything outside of that organization or role would require a massive jump and the possibility of a very hard landing. There’s also the high likelihood of the floor being yanked out from underneath through layoffs, as many of my industry colleagues working for Dot Dash and other digital media companies have experienced in recent months.
By slowly stepping up one’s business skills alongside their professional trade abilities, it’s far easier to build a solid foundation that cannot be so easily destroyed.
In hobbies
Buying a splitboard (a snowboard that splits in half to become skis) single-handedly re-ignited that passion. Here, I’ll borrow from this earlier essay which was a deep dive on the topic:
“In short, the progression had stopped. I was riding the same lines at the same resorts, over and over. I’d become as good as I was going to get by doing that, and had seen all I was going to see. My experience as a snowboarder had begun to run in circles, and a quick trip to a new resort each winter wasn’t enough to keep the passion alive.
It was a steep learning curve. But getting on a splitboard opened up a whole new world of snowboarding — where I went and the lines I rode were no longer determined by a resort or season pass but by myself, my riding partners, and the omnipresent force of Mother Nature. If the avy risk on a north-east-facing slope was high on a riding day, we’d ascend and ride a south-western slope. Late in the season, my partners and I researched where to head up high and hit the couloirs and steeps that were too dangerous during winter . . .
The adventure was renewed, and for me, the sport of snowboarding had been revolutionized. Splitboarding allowed me to take the sport into my own hands and go anywhere there were good conditions.”
Now, about the “leveling up” aspect. Progression in any sport happens over time. Becoming a competent splitboarder requires ample time spent in the backcountry, coupled with backcountry knowledge including avalanche safety training and an understanding of snow science, such as it is.
This knowledge and experience are not gained all at once but over the course of a lifetime. At its core, backcountry skiing is the perfect example of “leveling up” in action because it is truly impossible to jump up to a higher level in the backcountry. You learn a little, put that knowledge into practice, and repeat. There are no “experts” in avalanche terrain.
The approach to each of these aspects stemmed from learning from past mistakes and being willing to put in the time it takes to progress. Step up, not jump up.
Mountain Remote news and further reading
This post from Tim Urban presents another angle to today’s topic.
WorldHaus is offering fractional home ownership for traveling remote workers.
This new snowboard from Korua Shapes rides like a surfboard — and it nearly lets you hang ten.
That’s all for now. See you next week!