Why I Quit A High-Paying Job at Apple to Travel and Live Out of a Backpack

My name is Tom Wahlin and I’m a front-end designer, digital nomad, and entrepreneur. I spent about a year and a half traveling around the world living out of a 30L backpack, and that experience plus my love for design culminated in my current endeavor, Pack Hacker, where my team and I review travel gear. We do video and written reviews for everything from backpacks to t-shirts to nail clippers, in order to help people choose the right gear for traveling.

There was quite a bit of work & exploration leading up to today. At one point I was working at Apple and people still seem to be obsessed with the fact that I quit my job there. I see where they’re coming from—it was a “dream job”—but there’s certainly a lot more to my life than just my time spent there. It took a long time and a lot of hustling to get to Apple, and the decision to depart was not one I simply made on a whim.

Once I did quit I was able to start this digital nomad lifestyle that I have since fallen in love with. It ended up working out really well in the end because I was able to achieve the lifestyle I wanted and start something of my own in the process.

But in order to get into all of that, we should probably start from the beginning…

The Hustle

Most of my life has been spent working and just—for lack of a better word—hustling. Not like “selling drugs on the street” hustling, but just putting my head down and getting shit done. For a long time I was always putting my career first and I had a pretty set path that I was following with a lot of goals along the way.

I guess it started in college (or even high school, but I won’t bore you with those details). I graduated college in three years by taking classes year round and I started working as a front-end engineer in Minneapolis (where I’m from) two weeks after graduation. It was fairly simple stuff—chopping up photoshop documents for websites & developing them.

Eventually, I was hired as a junior designer at another firm. I was starting to do more creative work there, which was great. I’ve always been a creative type—not like an artist per se, but I have what you could call a “design mindset” and I’ve always been a curious thinker. This job was definitely a step in the right direction and I was starting to really enjoy the work I was doing.

They soon moved me to NYC, which was quite a change from Minneapolis. I was actually the first of my family to move out of Minneapolis, so I had kind of become the black sheep at this point. “There goes Tom, doing his crazy computer thing in the big city!” (half-joking)

From there, it was great to experience the culture & hustle in the city—working with agencies & startups, and generally soaking in everything the city had to offer.

The “Dream Job”

At this point I had really put my dues in, so to speak. I had been doing the grind for 7 years now, and it all sort of culminated with an offer to go work at Apple.

It’s funny, most people would think that as soon as you get an offer from Apple you just immediately take it, right? That is definitely the goal for some people in the industry—and it did fit in with my goals, for sure. But I was somewhat reluctant.

I had been living in this startup world for a while now and that sort of all-encompassing corporate nature of Apple was pretty intimidating. I wasn’t entirely sure if I was up for it, but I figured it would be a good place to work and when it came down to it, it was “an offer I couldn’t refuse.”

I mean, it’s Apple. Come on. I’m not just going to say no.

So I took the job and was brought in as a design lead. The first six months I just worked my ass off. I literally didn’t take a lunch break during those six months—I would drink Soylent at my desk while all my co-workers took an hour for lunch. I used that time to work and learn the systems and intricacies of life at Apple.

This worked well and I advanced quickly—I was promoted to a design manager position after those six months (and I did start eating solid lunches at this point). Life was pretty good at Apple, as far as the day-to-day went. I mean, the stories are all true—they treat you really well and you’re working with some of the best people in the business. But still, something wasn’t quite right.

Life Post Apple

I knew this was a dream job and I should be psyched about it, but it was strange for me because I had actually achieved my goal. There was nowhere left to go. I think that naturally progressed into me wanting some more autonomy—I wanted to create something on my own instead of just living this cozy life at Apple.The company was going to survive no matter what I did, so there wasn’t much in it for me. I wanted to build a rocketship versus riding the the Apple ship.

I will also say that my life at Apple was not exactly “cozy.” While full of amenities and nice stuff, I was working crazy hours. I was working with teams in Australia, London, NYC and California.

If you didn’t catch that, those locations span every time zone. I was getting blasted with emails every couple minutes with people needing my attention throughout the day and night. It was definitely a ton of work just keeping up to date on email.

My job was mostly communication, email, and meetings which didn’t fully scratch the design itch. Sure, we worked on some incredible projects with some very smart people, but in the corporate world, there’s a lot more red tape around projects when compared to the startup world where you just kind of “get it done” and then figure it out later.

I do love managing and helping people develop their skills, but I miss the act of design and creation. Maybe there’s some irony in that—like I had the Steve Wozniak sort of mindset where I wanted to keep designing instead of going “full-blown-manager.”

So I quit.

The Aftermath

Quitting a job at Apple definitely raises some eyebrows. I guess that’s part of the reason why I’m writing this article, after all…

A lot of people were surprised when I made the decision to quit. My parents were a bit confused as to why I would want to leave that job, and they didn’t fully understand what I was doing. It was pretty easy for my parents to talk about my job—when you say your son works at Apple, everyone understands and their ears kind of perk up—so funnily enough, I think they were a bit let down that they couldn’t talk about how their kid was a designer at Apple anymore.

But they certainly understood my reasoning and where I was coming from. They know me pretty well, after all. They have always been in full support of me following my “path.”

I got a part time gig as the creative director at The Infatuation—a restaurant review site that just purchase Zagat. This was a great job, I was working in their office in NYC and then started to have the ability to work remotely.

The remote nature of the job definitely opened up a lot of possibilities for me. This was at a time when the digital nomad lifestyle was becoming more viable for a lot of people. The concept of working from a laptop wasn’t so crazy anymore and you could live out of a backpack while still having a fairly normal lifestyle with most of the amenities you’d find at home.

I was curious about this whole digital nomad thing and had been reading up on it quite a bit. I watched tons of YouTube videos about the gear and all the necessities. I felt like I could make it happen, but it was just such a big decision to make. Pulling the trigger on something like that is easier said than done.

People talk about this digital nomad thing like you just wake up one day and think, “I’m gonna pack my entire life into a backpack and hit the airport around 4 o’clock.” I mean, how many times have you heard someone say, “You’ve just gotta DO it, man! Just pack your shit and GO!”

No one does that! That is terrible advice, you shouldn’t just “pack your shit” and go travel the world. You will not make it.

Packing your life into a backpack and traveling the world is not a simple task, and it’s a decision that shouldn’t be taken lightly. Not only is there a lot of preparation involved, but you’re about to cut yourself off from family and friends for very long periods of time. You’re not going to be able to come home and sleep in your own bed (you’ll probably sell your bed to some college kid on Craigslist) and you’re abandoning all those comforts of home that you may not even realize you need.

Taking all this into account, I did a trial run in The Dominican Republic. I packed my bag up like I would for perpetual travel and I spent a week in The DR, working remotely.

I loved it.

The Real Deal

After watching hours of YouTube videos and reading countless digital nomad blogs (including OWM!) I felt “prepared”.

I ended up Craigslisting everything in my apartment outside of what I could into a 40L backpack. The setup from my trial run was pretty good—I made a few tweaks by adding more serious “travel gear” to my loadout, but it was mostly ready to go.

Breaking the news to my family was certainly… interesting. They were surprised that I was making such a big change but I think they sort of understood where I was coming from. I guess it made sense that if anyone in the family was going to pull a stunt like this, it would be me.

My grandparents definitely took it the worst. I think they were just really worried about my safety. The whole thing was pretty nerve-racking for them, but I did my best to explain that I’d be safe and I kind of let on like I had more of a plan than I actually did. The thought of just moving from country to country on a whim is something that was pretty hard for them to wrap their head around.

At this point, I had decided to make my first stop in Northern Norway. Beyond that, I didn’t really have a clue as to where I’d go next. I had my little “travel office setup” with me and I was putting in like twenty hours a week, so I was really mobile. I could pretty much work wherever and whenever I wanted, so I never felt like I had to plan things out far in advance.

The First Stop

That first stop in Norway was something else. I had been spending so much of my time stressing out about work and dealing with emails and issues every few minutes, it felt like I hadn’t had time to stop and take a breath in years.

I took a lot of breaths in Norway–specifically, Lofoten.

I spent a lot of my time there hiking and just “decompressing.” I definitely felt a little lost, which is something I think a lot of nomads can relate to. Up until that point my life was very strictly regimented and having this total change where I had almost no schedule was kind of unnerving in a good way, if that makes sense?

My plan for that year was to make no plans. I had spent the last ten years making plans and I had barely had time to breathe since I went to college—which, to be fair, was mostly self-induced. For that entire year, I never booked any accommodations for more than a week at a time.

Because I was traveling with just one carry-on sized bag it was ridiculously easy for me to move around. Sometimes I’d wake up in the morning and decide I didn’t want to be in a certain country anymore. That was totally fine—I’d just leave. It was so easy.

From Norway I went to Sweden. Then to Denmark. Then Germany. Then the UK. Then I hit Poland and jetted over to Japan. From Japan, a quick trip back to the US, then back across the Pacific to Thailand. From here it starts to become a bit of a blur. Vietnam, Australia, New Zealand, The Philippines, Malaysia, a few trips back to the US…

It was a fun, slightly crazy time in my life that I will never forget. But keeping up with work during all this was becoming a challenge, especially because I was one of the only remote employees at my gig. It’s hard when everyone on a team is in one location while I was off on my own.

With the actual design work, it’s pretty easy to work asynchronously. Someone would need a design, I’d work on it, send it back to them, they’d give me feedback, etc. But when it comes to actually managing people and projects, it can get pretty tricky—especially if the entire team isn’t remote or, like in my case, you’re the only remote employee.

Around this time, I decided to really drill into the goal of starting something for myself.

The Side Hustle Turned Full Hustle

This was something that had certainly come up before. I wanted that freedom and autonomy to make something for myself—to build the rocketship. It was in Mui Ne, Vietnam, that Pack Hacker was born.

It started out as a side project and then quickly morphed into a full-time gig. I started reviewing tons of backpacks and bringing on contributors, video editors, writers—the whole nine yards. It has since expanded to well beyond backpacks, including everything from toiletries to t-shirts to rain jackets, but all with a specific focus on one bag travel.

The main goal was to test a lot of this stuff in the real world—in an actual travel setting—so that people can know how their stuff will hold up over the course of their trip(s). Having a piece of gear break when you’re in another country and don’t speak the language really sucks, so I wanted to help people avoid that in the first place. We’re always looking for awesome, durable gear that one bag travelers can get behind.

Nowadays, I’m leading a slightly more sedentary lifestyle in order to keep all of the gear centralized (I’ve set up shop in Detroit) but I’m still traveling a good bit and reviewing gear like it’s my job… because it is. When I’m not traveling I can at least live vicariously through all the contributors we have around the globe, most of whom are living the one bag digital nomad lifestyle.