Jobs for the Traveling Climber: Tattoo Artist and Outdoor Educator

In this interview series we talk with people who spend their time traveling and climbing, while still holding down a steady income. From nurses to coders, writers to outdoor guides, we want to show that you don’t have to go full dirtbag to live the itinerant life. Because contributing to your 401k while seeing the world doesn’t sound so bad.

Name: Amy Borch

Job: Tattoo Artist and Outdoor Educator


Editor’s note:

Amy and I met at Rumney, NH, while on a trip that was my first ever paid writing assignment. They (being Amy and Jared) were mindfully enjoying the peace and solitude of early evening climbing on a mid-week day. Then I showed up. I began by badgering them, asking if I could take photos as they climbed. But they were friendly and gracious to my intrusion. We got to talking, told bad jokes, solo’d Clip a Dee Doo Dah, then had beers by the Baker River.

Amy has had a varied and exploratory life, full of arting and climbing. Hope you enjoy her perspective!

Amy also doubles (triples, quadruples?) as performer at the award-winning Ice Castles. Photo courtesy of Patrick Sarson.


1) What do you do?

I currently juggle the arts of tattooing and outdoor educator/guide.

About a year and a half ago I decided to commit to a career as a tattoo artist.

When I’m not making income through art, I work my other passion in the outdoor industry. I serve as a guide, trainer and course director for outdoor organizations. 


2) How did you learn about outdoor education and tattooing?

Outdoor Educator: I began to learn what it meant to be an outdoor educator six years ago when I began as an intern for the Mid-Atlantic Outward Bound. I decided to use creativity to explore group dynamics, facilitate challenge, and connect the public to outdoor spaces through the skill sets of climbing, backpacking, and sea kayaking.

Tattooing: I’ve known since I was fourteen years old that I wanted to be a tattoo artist. I had a friend who made a tattoo machine from scratch out of a toy car motor, pen ink, and a sewing needle and asked me to “draw on him.” I suppose that’s what originally put the idea in my head.


“I pursue careers where I feel like I have the highest yield of positive impact on people.”


3) What are some of the perks of the job?

I love what I do every single day.

Outdoor Ed: My office is enviable. I have had the pleasure and privilege of spending weeks at a time working and living in places such as Joshua Tree, Yosemite, Sequoia Kings Canyon, etc.

The experiences of living with groups in the wilderness are incredibly impactful, but mostly indescribable. 

Tattooing: I get to be creative and meet rad people.

“Fox hobbit. This was so fun!” Photo courtesy of Amy.


4) What are some of the challenges?

The challenges are:

WORK
LIFE
BALANCE

(Editor’s Note: Amy’s emphasis)

Outdoor Ed: Working long format courses for several weeks/months at a time in the wilderness can stress relationships outside of the outdoor industry. It can even be difficult to connect to cultural events if they occurred while you were away for a month and a half, unplugged from wifi, phones and television.

The world doesn’t wait to change while you’re blissed out in the mountains.

Tattooing: Tattooing has humbled me because of how incredibly harsh it can be on the body. Transitioning between careers where I am constantly hiking/climbing/paddling/moving to sitting still for hours is cruxy.


“Success is not an accident, and failure is the most effective facilitator of discovery. So set a goal and go for it.”


5) What motivated you to pursue these paths?

I pursue careers where I feel like I have the highest yield of positive impact on people.

My role in facilitation, or “activating space” for someone else to experience a little bit of magic, is the reason why I love my careers. 

Outdoor Ed: I enjoy observing people open to new ways of thinking. Working outdoors with youth and adult groups provides space for people to empower themselves.

When someone tries something new, whether it be a social role (such as leadership/followership) or takes appropriate risks (navigates off-trail/asks for help), this person creates a “schema” for themselves. And this schema, or conceptual framework for how they navigate an experience, can later be transferred to life at home. This process of thought-work is very compatible with the outdoor classroom.

Tattooing: The art of tattooing allows people access and permission to explore ideas. Many people come in without the words to express memories or thoughts they want, or sometimes need, to process.

I know something really cool has happened in the studio when people come back to me and tell me that the tattoo has allowed them to access the feelings or closure they were having trouble finding when we first spoke about the idea. 

“More than just create an image, I try my best to listen, ask curious questions and facilitate story telling through artistic process… Through intentional conversations we were able to collect the information necessary for this piece. I am so fortunate to be able to work in a field that allows me to build connections and share meaning with others in this way.” Photo courtesy of Amy.


6) How has your life changed since you started these jobs?

Outdoor Ed: My ability to give and receive feedback based on personal growth and technical performance has enabled me to take career risks and connect with people in ways I previously did not have the capacity for.

Tattooing: The ability to reconnect with friends/family, think about the future, and pursue making a livelihood from creating.


7) How do these jobs allow you to travel and climb?

Outdoor Ed: This can provide a great opportunity for climbing/traveling when there are contract agreements. Contracts bind people for a certain number of courses or days of expected work, and the rest of the time is free to make climbing trips! 

Tattooing: Build a mutually respectful relationship with your mentor or shop owner and prioritize communication. Make every moment in the shop count and pour your heart into your art, treat your clients well.


8) What does a “typical” week or month look like?

Outdoor Ed: 

Typical month:

  • 2-3 days prep
  • 14-30 days in [insert name of epic course location]
  • 2 days debrief
  • CLIMB YOUR FACE OFF UNTIL NEXT COURSE
  • Repeat

“El Cap sticking its Nose out. View from the last pitch of East Buttress on Middle Cathedral.” Photo courtesy of Amy.


Tattooing: 

Typical week:

  • Basecamp: New England!
  • Work 4 days a week. Occasionally glance at large El Cap route map in studio to stay motivated
  • Stay fit around Cathedral Ledge, Cannon, Rumney and occasional Maine trip 


9) What do you wish you knew when first starting out?

Outdoor Ed: Open up a Roth IRA and make a retirement plan as soon as possible. We don’t do this gig for the money!

Tattooing: Learn the body mechanics of sitting or overuse of certain muscle groups can creep into climbing and tattoo performance in unpleasant ways! 


10) What is one lesson learned from your journey so far?

Success is not an accident, and failure is the most effective facilitator of discovery. So set a goal and go for it.

Thanks, Amy!

“Endless starry nights to white noise and city lights. It feels like different worlds. But I dream of one world, connected.” Photo courtesy of Amy.


You can see more of Amy’s tattoo artistry on instagram: @amy.wildhand



Feature photo courtesy of Adam Nawrot

Jobs for the Traveling Climber: Niche Blogger

In this interview series we talk with people who spend their time traveling and climbing, while still holding down a steady income. From nurses to coders, writers to outdoor guides, we want to show that you don’t have to go full dirtbag to live the itinerant life. Because contributing to your 401k while seeing the world doesn’t sound so bad.

Name: Jacob Bushmaker

Job: Blogger


Editor’s note:

I came across Jacob’s blog, The Wandering Climber, earlier this year when I was researching cheaper travel/ climbing destinations in South America. There were surprisingly few resources, but I eventually landed on TWC’s The Top 6 Rock Climbing Towns in South America – Why Should You Go?. It was great! I quickly dove into the rest of his pieces on Peru, Bolivia, Ecuador, Colombia, and others. His articles are well written and full of useful bits.


1) What do you do?

I currently have two jobs.

1) I work as a sales agent for a company called Unbundled Attorney, where we connect people with lawyers who are looking for affordable legal representation.

2) I run a blog called The Wandering Climber, which focuses on providing climbers with beta on the world’s best rock climbing destinations [Editor’s note: Typically lesser known places].

I’ll be answering the questions in respect to my work with TWC. 

A view from Freedom Bar, aka “the office,” in Tonsai. Photo courtesy of Jacob Bushmaker


2) What are some of the perks of the job?

A few things. Probably the most notable is it is completely remote, meaning that I can work from just about anywhere in the world. This is pretty much a necessity for anyone who wants to travel long term… unless you have some other source of income!! 

Second is that I’m my own boss. I don’t have any set hours, deadlines or anyone to “answer” to. 

It is also great to be creating something. It has its own intrinsic value which is sort of hard to explain. [I like to be able to] look back and be like, “yea, I did that.”

Lastly, this is a way for me to give back to the rock climbing community with my unique experiences and knowledge. This is a perk of the job I really didn’t anticipate, but it has been awesome to get so much positive feedback from people who have read my blog and used it. 


“The only people who think this is easy are ones who haven’t done it before.”


3) What are some of the challenges?

There are a lot of challenges with running a blog as a business.

The only people who think this is easy are ones who haven’t done it before.

With the incredible freedom which comes from being your own boss comes the pretty obvious drawback that there is absolutely no one keeping you accountable.

This is particularly difficult when you’re posted up in one of the world’s top climbing destinations. As you might imagine, these environments aren’t exactly conducive to “hard work.”

Also, it is always an ongoing challenge that I have to learn how to do things on my own. I have never had a “teacher” [for this stuff]. At times things can be super frustrating.


4) What motivated you to pursue this path?

The whole journey started when I read the 4 Hour Workweek by Tim Ferris. It really opened my eyes to what was out there and has fundamentally changed my life in just about every sense imaginable. 

I went from a 9-5 office job (I was a Civil Engineer) to working remote, visiting about 30 countries in 4 continents, and living abroad in South America. 

There were the obvious perks of living abroad, such as learning another culture/ language and meeting new people/ traveling which appealed to me.

In addition, there are also some financial benefits of working abroad which don’t get mentioned as much, such as having a huge reduced cost of living.

One Of Hatun Machay’s Mega Classics Highballs: The Rhino (v4). Photo courtesy of Jacob Bushmaker


5) How does this job allow you to travel and climb?

If I was just doing one of the two jobs, I would have plenty of time to dirtbag. I did so for about 2-3 years, but there sort of came a point where I started taking work more seriously again. 

Over the past six months I have been much more “buckled down,” you might say.

The site launched in February of this year, and [so far] I’ve always had another full time job which takes up a ton of time. If all goes well, within the next 6 months to a year, I’ll be able to comfortably support myself with the income earned off the blog. [At that point] I’ll be able to make the decision whether I’d like to pursue it full time or not. 

Right now, I work more than full time between my two jobs, probably in the 50-60 hours a week range.


“Travel and being an entrepreneur is romanticised, but I’m here to tell you that sometimes it just sucks.”


6) What do you wish you knew when first starting out?

The hardest thing about this lifestyle has always been things I left behind when I was an engineer: The “steady” job, “good” career, friends, family and security were all sort of thrown aside to live the dream. 

Travel and being an entrepreneur is romanticised, but I’m here to tell you that sometimes it just sucks. 

On Top of El Filo la Lete de Tiburon (5.10+) in Cochamo Valley (Valle Cochamó), Chile. Photo courtesy of Jacob Bushmaker


7) What is one lesson learned from your journey so far?

It is better to focus on the process than the goal.

Once you get going it just becomes another day in the life, and before you know it your on your way. 


8) Anything else you’d like to add?

You overestimate what you can do in a year, but underestimate what you can do in five.

My point: Just get started now, be patient and incredibly persistent! 

Thanks, Jacob!

You can learn more about Jacob, his work, and his travels:

Jobs for the Traveling Climber: Freelance Front-End Web Developer

In this interview series we talk with people who spend their time traveling and climbing, while still holding down a steady income. From nurses to coders, writers to outdoor guides, we want to show that you don’t have to go full dirtbag to live the itinerant life. Because contributing to your 401k while seeing the world doesn’t sound so bad.

Name: Jack Lyons

Job: Front End Web Developer


1) What do you do?

I’m a front-end web developer. That means I write code for basically anything you see and interact with on a web page.

Working on the front-end is fun because it’s really easy to impact the look and feel of a page just by changing a few lines of code. It feels more artistic because you literally start with a blank canvas with every new page you build.

Currently I work as a freelancer and have a variety of clients located all around the world. Every day is filled with different challenges and I like being able to switch between client projects whenever I like.


2) How did you learn about web development?

Back in 2014/15 I was travelling in China, teaching English in Hangzhou, a city just west of Shanghai. I was pretty miserable with my current situation: Teaching English wasn’t as fun as I thought, mainly because the working conditions were brutal. I really wanted to make a change.

The only reason I was in China was so I could climb at the infamous crags of Yangshuo (hands down, some of the best climbing in the world). After a few months of teaching, I quickly realised that it wasn’t a sustainable way to work and travel and so I started researching other options.

That’s when I stumbled upon the whole “digital nomad” scene. I would read blogs and follow all the cool kids online who were “living the dream” with just a backpack and a laptop.

I got chatting  with a colleague at my English school who had a background in IT. Funnily enough, he had a big fat book Chinese/English book on HTML and CSS. He let me borrow it and I immediately devoured it. For the next 6-12 months I just totally immersed myself in learning to code because I knew it would allow me the chance to create the lifestyle I always wanted: To work and travel on my own terms and without burning a hole in my savings.

Climbing “The First Full Moon,” 7a in Bali, Indonesia. Photo courtesy of Jack Lyons.


3) What are some of the perks?

For starters, I get to create my own schedule. I can work early, late, from a cafe, at home, on the couch, at the library…

What’s more, I can pick who I want to work with and what I want to work on. I use a freelancing platform called Upwork that allows me to have a profile and be contacted by potential clients who need help. This means that the work literally comes to me and I don’t have to lift a finger to find new work. 

And lastly, I can save money even while traveling. This is huge for me, because I can take my remote career seriously and contribute to my pension, as well as personal savings and investments.

4) What are some of the challenges?

I know this sounds like a “first world problem,” but traveling in developing countries or rural areas means little to no wifi. While this makes for a relaxing getaway for most, this can be a seriously frustrating experience when I’ve got deadlines to meet.

Other than that, all general travel issues apply. Being flexible comes at a price.

5) What motivated you to pursue this path?

My dream has always been to be financially free and able to live and work wherever I want. Second to that, I love rock climbing and want to spend my days out at the crag rather than in the office.

I wanted a career where I could climb by day and work at night, or just take a day off whenever and make up my hours later.

To me, it only made sense that I’d need to find a job that would be online. Coding suited my personality well but I certainly could have gone down the path of a blogger / copywriter / online marketer and gotten the same results.

Jack and his wife in the famous bouldering area of Castle Hill, New Zealand. Photo courtesy of Jack Lyons.


6) How has your life changed since you started this?

Well, for starters, I no longer have to go to an office from 9 – 5 every day. I don’t really have a boss and I can charge whatever rate I feel is acceptable based on the project at hand.

I love the fact that I am able to see so much of the world and still have money left over. I thoroughly enjoy my work and need to pinch myself most days. I’ve lived in Europe, USA, Asia and travelled to over 30 countries. I’ve climbed in some of the most beautiful places in the world ( Greece, China, Austria, Germany, Croatia, Slovenia, USA, Thailand, New Zealand, Australia).

7) What does a “typical” week or month look like?

It depends where I am. Currently I’m based in Boulder, Colorado. It’s nice to have a home base because it gives you time to decompress from all the travel. It also allows you to get settled and lock in when you’ve got some serious deadlines or big projects to tackle. 

When traveling or on a climbing trip I try to scale back my work commitments because I know how demanding and exhausting it can be. For example, currently I am on a two week road trip with my wife in Alaska. I decided to take the entire time off, which is very rare for me to do, but it was absolutely necessary because I had  been working on some big projects over the last couple of months. I needed some time out to recharge.

Coding is really, really mentally taxing. It requires a lot of brainpower. It’s hard to stay focused when your work environment keeps on changing. So I prefer to plan out my work schedule depending on where we will be and when.

Climbing in Moon Hill, Yangshuo. Photo courtesy of Jack Lyons.

8) What do you wish you knew when first starting out?

The matter of fact is this: Coding is hard and takes so so so soooooo many hours of dedication, practice and patience. It’s not for everyone and it can be an incredibly frustrating profession.

I think one of the best ways to accelerate your web development journey would be to sign up for a coding bootcamp (bonus points for an exotic location somewhere in the world). This won’t make you a coding wizard but it will help lay a solid foundation, to meet like-minded peers, and to have dedicated help from a mentor. 

Having a mentor helps a lot but you have to realise that no one is going to hold your hand out in the “real world.” You’ve gotta have grit and figure things out for yourself.

Know that there will be roadblocks, bugs, meltdowns and disasters – it’s going to be how you react to them that makes the difference. Keep calm, and know that you will figure it out. Just learn to do whatever it takes to get unstuck – even if it means paying an expert for their time. You’ll learn from your mistakes and grow rapidly if you have the right mindset.

9) What is one lesson learned from your journey so far?

Patience is an important “skill” that can be developed throughout difficult situations under high stress, commonly known as “stress inoculation.”

I’ve had so many moments where I just wanted to smash my computer and curse my code for not working. But over the years I’ve learned to channel this into a more relaxed state where I can work through the problems in a calm and focused manner (sometimes).

10) Anything else you’d like to add?

Yeah! If you’re interested in becoming a digital dirtbag then check out my blog over at Medium: Adventure In My Veins.

There I interview other wanderlusting climbers who have built a lifestyle and a living around their digital skills. If you know anyone who you’d describe as a “digital dirtbag,” then please get in touch!

Thanks, Jack!

You can learn more about Jack, his work, and his travels: