business travel

How to Build a Business While Traveling – Entrepreneur Interview with Jason Lengstorf

Do you dream of a location independent business?

Jason Lengstorf is a speaker, author, and consultant. He is a location independent entrepreneur who makes a living building web apps for clients, including Playstation, Intel, and Precision Nutrition. In 2014, Jason sold everything he owned and started traveling the world while running his business. Jason blogs at lengstorf.com. Check out Jason’s book Untethered: Tips and Gear for Travelers Who Want to Worry Less and Experience More, Collected By a Long-Term Traveler.

SUCCESS HARBOR: YOU ARE MAKING A LIVING BUILDING WEB APPS FOR CLIENTS INCLUDING PLAYSTATION, INTEL, AND PRECISION NUTRITION. WHAT ADVICE DO YOU HAVE FOR ENTREPRENEURS TO LAND THESE TYPES OF CLIENTS?

Jason Lengstorf: My strategy for growing my client list was to try and raise awareness in the community about what I’m capable of doing. I wrote tutorials, I submitted conference talk proposals, and I showed up and local code meetups.

One of my early tutorials was really popular, and it was on a really popular site (CSS-Tricks.com). Thanks to its success, I got an offer from Apress Publishing to write a book — which is actually pretty easy to do if you’re a competent writer and developer — and leveraged that to get more prominent guest posts and speaking gigs.

Through local networking at meetups, I met the people who worked at local design agencies, and I learned that many design agencies don’t actually have Python developers on staff; almost all of their interactive work is subcontracted out.

I made sure they knew I was capable of handling the kinds of projects they were selling — the tutorials and books lend me a lot of authority in Google search results — and that put me on their shortlist of contractors. It saved me the stress of bidding against agencies for the same projects and offloaded the client management to the agency, which made my job much easier.

It was kind of an end-around strategy, but it worked for me.

SUCCESS HARBOR: HOW DID YOU COME TO THE DECISION TO SELL EVERYTHING TO TRAVEL THE WORLD WHILE RUNNING YOUR BUSINESS?

Jason Lengstorf: In 2013, I was killing myself working. It got so bad that at one point, my beard died and fell out.

After that, I took a hard look at what I was doing and realized I was on a success treadmill: I thought I was working for “a better life,” but I was actually making my life worse so that I could work harder (ostensibly so I could achieve more “success”). My priorities were f*cked, and it was taking a major mental and physical toll on me.

In early 2014, I found myself grappling with what “work” meant to me, and then my relationship at the time came to an end. I was at a clean break, and I could either do something different or slowly drift back toward what I’d always done.

I decided to do something drastic and booked a one-way ticket to Europe.

SUCCESS HARBOR: YOU HAVE BEEN ON THE ROAD SINCE 2014. HOW DO YOU STAY FOCUSED ON THE PROJECTS YOU ARE WORKING ON WHILE ON THE ROAD?

Jason Lengstorf: Because I’m so concerned with keeping my work in balance with the rest of my life, I take productivity and focus very seriously.

As a result, I’ve done a lot of self-experimentation to find out what works for me. Out of that experimentation, I built a general framework that keeps me productive enough to complete a full-time workload in roughly 25–30 hours each week, so I have plenty of time to explore the places I’m living.

The two biggest players in keeping my focus high are:

  1. Scheduling for maximum productivity using context-based task groups.
  2. Working with willpower instead of against it to build productive habits.

The elevator pitch is to stop multitasking, eliminate all distractions, and do the important things first. Everything else I do is a strategy to make that happen.

SUCCESS HARBOR: WHAT ARE THE GREATEST CHALLENGES TO RUN A BUSINESS WHILE ON THE ROAD?

Jason Lengstorf: The hardest part about running a business is dealing with timezones and making sales. I don’t get to spend a lot of time face-to-face with prospective clients, which is my preferred method of selling. I also have to take a lot of calls late at night, which makes it challenging to operate at 100% — I’m always sharper early in the day, so I have to really focus hard to stay on top of a 9pm meeting.

However, the trade-offs are few and far between. Compared to the upside, they’re barely worth mentioning.

SUCCESS HARBOR: HOW HAS YOUR LIFE CHANGED SINCE YOU HAVE BEEN RUNNING YOUR BUSINESS WHILE TRAVELLING?

Jason Lengstorf: I’ve developed a lot of empathy since leaving the States. At home, I’m a great communicator, and I use that to get the things that I want.

Abroad, I lose that: I barely speak enough of the local language to order food — and even that doesn’t always work out without playing charades.

As a result, I’ve spent a lot of time frustrated because I knew exactly what I meant, but I couldn’t get anyone to understand. It’s been a huge wake-up call to me, not only with regards to the language barrier but with people back in the States who are more introverted or less comfortable speaking their mind.

It’s also been wonderful to see that everywhere in the world is full of good people. Mass media paints up the rest of the world as a warzone, and portrays anyone foreign as a threat — and that couldn’t be further from the truth.

I’ve been met with nothing but kindness and smiles everywhere I’ve gone in the world. I’ve never felt endangered, unwelcome, or anything other than just another person in a crowd full of people.

SUCCESS HARBOR: AS YOU ARE BUILDING YOUR BUSINESS HOW DO YOU MEASURE SUCCESS?

Jason Lengstorf: As a part of my transition from workaholism to my current lifestyle, I had to think pretty hard on what “success” meant to me.

I used to think success was more press, more money, higher-profile projects. It made me crazy because every accomplishment was immediately overshadowed by the next step — you can never be the “most successful” person, so framing success as an end in itself is an endless, frustrating pursuit.

Instead, I think of success like this: if I can wake up without an alarm, do work that challenges me and makes me feel like I’m putting something good into the world, and always have the freedom to accept an invitation to spend time with a friend or family member, I’m pretty damn successful.

It changes the focus: success isn’t money or recognition or prestige; success is the freedom to live life on your own terms. You need to make money to have that freedom, of course, but that makes money a tool, not a goal.

Making that distinction saved my life. And I’m pretty sure I mean that literally.

SUCCESS HARBOR: WHAT ARE THE MOST IMPORTANT KEY PERFORMANCE INDICATORS IN YOUR BUSINESS?

Jason Lengstorf: My primary focus is to spend less than 40 hours each week on the computer. That means I need to be extremely productive if I’m going to get enough work done to support my lifestyle.

I need to make enough money to cover my expenses, plus what I want to put into savings each month — which, thanks to the surprisingly low cost of living abroad, isn’t all that much. This keeps me on the road and prevents me from stressing about income.

I need to dedicate at least 60 minutes a day, 5–6 days a week to grow my business: that means writing, developing new ideas, staying active in the community, and keeping up with clients. This is how I keep the business running, so it’s critical.

I need to take at least one day each week completely off. No screens at all. It keeps me excited about work and prevents burnout.

SUCCESS HARBOR: WHAT ARE THE MOST EFFECTIVE WAYS FOR YOU TO BRING IN NEW CLIENTS?

Jason Lengstorf: Right now, I’m in a long-term contract, so new clients aren’t a priority. However, I know that all contracts eventually end, so I do a lot of content marketing and speaking to stay on the radar with people who hire folks to do what I do.

I network as often as I can, but that’s less because I want new business and more because one of my favorite pastimes is talking shop with smart people. New business is just a pleasant side effect.

SUCCESS HARBOR: WHAT MISTAKES DO YOU SEE ENTREPRENEURS OR THOSE WHO ARE IN THE PROCESS OF STARTING A BUSINESS MAKE?

Jason Lengstorf: Where I cringe the most is when I see people who try to go freelance or start a business, and they assume their skills will carry them to fortune.

Unfortunately, 100% of making it as a freelancer is selling. A product locked in a backroom will never sell because no one will ever know it’s there. In the same way, an excellent freelancer who never promotes their business will starve because clients never know they’re available.

I also see a lot of people chasing funding. And, look, I know that this probably isn’t a popular opinion, but why the f*ck would I — an entrepreneur, who spurns the corporate world and talks about freedom and being my own boss — trade control and autonomy for a bucket of cash?

There are definitely cases where investors are necessary to grow a business, but again: don’t chase funding unless you actually need it. Keep control of your business, your time, and your freedom for as long as possible. When your business really needs funding to scale, you should find yourself with an awful lot of leverage to maintain control.

SUCCESS HARBOR: WHAT ARE THE TOP TWO-THREE THINGS YOU WISH SOMEONE HAD TOLD YOU BEFORE YOU STARTED YOUR OWN BUSINESS?

Jason Lengstorf: First, I really wish I would have listened to all the people who told me to put myself on payroll instead of spending what the company made as it came in. I spent a lot of hungry months after I blew all the surplus from a good month on vacation. When I fixed that by giving myself a set paycheck each month, I never had to deal with the “feast or famine” problem again.

Second, I wish I would have had someone to show me that the real point of starting a business is to become the master of your own destiny. I let my business become my boss, and it took total control of everything in my life. A business is a tool we use to create a better life for ourselves, and we should treat it as such.

Third, I wish I would have waited before hiring employees. I didn’t have processes in place; I thought I was spending money to save time, but without systems, I ended up spending more time to make sure my money wasn’t wasted. Systems first, then scale.

SUCCESS HARBOR: WHERE ARE YOU NOW, WHERE HAVE YOU BEEN RECENTLY, AND WHERE ARE YOU GOING NEXT?

Jason Lengstorf: Right now, I’m in Thailand. Next up, I’m headed to Vietnam. Next year I’m tentatively planning to hit Japan, Croatia, and Spain early on. After that, no plans; we’ll see what happens.

The following two tabs change content below.
George Meszaros is the editor and co-founder of Success Harbor where entrepreneurs learn about building successful companies. Success Harbor is dedicated to document the entrepreneurial journey through interviews, original research, and unique content. George Meszaros is also co-founder of Webene, a web design and digital marketing agency.