Booking a one-way ticket to Croatia was the best career decision I ever made

1. Hey, can you please introduce yourself?

Well, hello there! My name is David. I am 29 (almost 30, yikes) years old. I am from a small town in Wisconsin called Beaver Dam. Over the past 40 months, I have been to over 40 countries, all while enjoying life from the road. I’m a big photography buff and love spy movies. I try to grow each day. If I am one percent better than I was yesterday, I triple my growth every year. Whether that’s physically, mentally, psychologically, academically, personally, or professionally, I try to improve every day.  

I believe that listening to stories is one of life’s most significant rewards. I’d much rather listen to the experiences of others than sharing my own. I started eight businesses, and seven failed. I hit the eighth right on the head. 

I pet stray dogs on the street. My favorite place is the Masai Mara Nature Reserve in Kenya. I love and live without fear.

I pet stray dogs on the street
I pet stray dogs on the street.

2. What motivated you to choose remote working?

I am a white male from white America. My hometown is 99 percent white. I am unbelievably fortunate to be born who I was, where I was, when I was. Growing up, I was sheltered. I didn’t know about other cultures, experiences, people, or ways of life. I thought I was the best person in the world, and in retrospect, I took life for granted. 

Up until the age of 23, I rarely left Wisconsin. Why should I? I had everything I needed there: Family, friends, food, and shelter. Life was good. After university, I got a job as a journalist in Wenatchee, Washington. I was moving halfway across the country. 

When I got there, I was hooked. I had never seen mountains, oceans, forests, or canyons before. The Pacific Northwest has all of that. Every single day I wasn’t in the office, I was out exploring. First, I explored the city and the west side of the mountains near Seattle. Then I branched out to all corners of the state. Within three months, I had taken my first west coast road trip through Oregon and California. Three years later, I’d visited 43/50 states. 

I knew then I was an explorer at heart. I realized then that I needed to see the world through my own eyes, to experience the sights, sounds, and smells of life outside the United States. I wanted to form my own opinion of the world instead of believing everything I heard on TV or read online. It was time to live my life with no regrets and experience it the way I wanted to. 

I had quit my job as a journalist a few months previously and was now working as a travel agent booking cruises and all-inclusive vacations for older folks when it hit me. I needed to find a way to lose the office and make money from the road. There had to be a way. I watched the beautiful summer days pass me by through my office’s tiny window, which looked out into the parking lot. 

About 10 minutes later, I quit. It was a Tuesday afternoon.  

I didn’t have any money. I no longer had a job. I didn’t have anything but a car, a computer, a camera, a phone, and a cat (her name is Willow, bless her heart). I drove back home to my parents’ house and started the job hunt. 

3. What were your initial months like? Did it live up to your expectations?

Pure bliss. 

I hit the jackpot with my first remote role. I became a content editor for a hyperlocal news aggregate service called Hoodline out of San Francisco. Years later, it was purchased by Nextdoor, which you might have heard of by now because of its gaining popularity. I was one of the first content editors hired. 

I was paid about $25/hour, $11/hour more than I was getting at the travel agency. Without a specific amount of money going out the window for rent, I made more money than I ever had before. Oh, and I can work from anywhere I want as long as I hit my deadlines? Deal. 

I circled the country in my car three times, just exploring. I would drive near to somewhere that interested me and grab a cheap hotel/Airbnb for a night or a week. I’d explore in the early sunrise hours at some nature reserve or underrated state park, work in the middle of the day, take a nap, and check out the sunset from the Pacific Ocean, Grand Canyon, or the Great Smokies. 

Like I said, pure bliss. 

4. How did you find remote working roles?

Like I mentioned above, I hit the jackpot with my first role. It was the second job I applied for once I got back to Wisconsin. It was on Indeed. I quite literally typed in “remote journalist” and saw Hoodline had an opening for a content editor. 

Over the past 40 months, I have been to over 40 countries, all while enjoying life from the road
Over the past 40 months, I have been to over 40 countries, all while enjoying life from the road

The interview took about 10 minutes. I told the hiring manager that I was a journalist and had been working with AP style for about five years (including college, of course), and was willing and able to work as many hours as necessary. I completed a writing test and a probationary period of three weeks and was in. 

More than two years later, in the summer of 2019, the number of hours I was getting at Hoodline decreased, so I decided to take on a second part-time job. I found a job planning trips at a startup called Jubel on AngelList. 

This job interview process was much more detailed and in-depth and took about three months for me to be offered the position. 

5. What have been the best, good and worst aspects of remote working for you?

Best – I have to say the best part of remote working has been location independence. I’m a roamer at heart… a wanderer. A wanderluster… an explorer. Being able to see the Taj Mahal at sunrise and finish your work later that day is an unbelievable perk. 

Up until the age of 23, I rarely left Wisconsin. Why should I? I had everything I needed there: Family, friends, food, and shelter.
Up until the age of 23, I rarely left Wisconsin. Why should I? I had everything I needed there: Family, friends, food, and shelter.

One time, I finished some Hoodline articles Friday morning, slept in the Sahara Desert on Saturday and Sunday night, then came back and finished Monday articles on Monday afternoon. I did all of this without taking time off, and continued to maximize my earnings. Imagine that. 

Good – I’m always a day ahead. I’ve found that most of the remote work I do is project-based. This means you don’t have to change your schedule to hit meeting after meeting in a different time zone. No matter where you are, you can work ahead and stay ahead of the game. 

East of your place of employment? Do all the work before your team wakes up. West of your place of employment? Work on Friday tasks on Thursday, so when your employer wakes up, the work is already done. 

Worst – Isolation. If you’re an extrovert and you don’t have a good group of friends, a co-working area, or something/someone to keep you occupied, life can get quite lonely. 

6. What tools do you swear by while working remotely?

Because I am mostly a writer, I don’t need as many tools as some other remote workers I have seen. Since I have recently launched my own small business, this has expanded a bit, but I will outline the top 4 tools I use every single day. 

Asana – My whole life is on Asana, and I feel it is one of the best project management softwares out there. It also helps with team coordination, as there are many options for integration. I have the free version and have for the last three years or so. 

Google – Oh, Google. How I love you. I use Google Drive, Docs, and Sheets every single day, and I love it. I’m writing on a Google Doc right now. 

Hubspot – A CRM is crucial for any small business but may not be applicable for many remote workers, so I’ll keep it brief. I like keeping all my contacts in one place, and in my opinion, Hubspot offers the best and easiest way to do that. 

Slack – I use Slack probably more than I would like to, but it is an easy and effective way to communicate with people on different teams. Hoodline had one, so did Jubel. In my opinion, Slack is kind of like a necessary evil. Pro tip: If you feel stressed out or anxious in your remote work arrangement, delete Slack for a few days. You’ll feel better. 

7. Your most exciting/ hilarious experience since you started working remotely.

The most exciting experience I’ve had since I started working remotely was waking up before dawn at the Masai Mara Nature Reserve in Kenya, driving through a thicket, and emerging to a complete lion family playing in a clearing. 

I’m a big photography buff and love spy movies.
I’m a big photography buff and love spy movies.

About five females, two males, and 12 cubs in the clearing, a full pride. The fathers slept barely in sight, and a pair of females made a sort of perimeter looking out for danger. The cubs took turns pouncing on each other, biting the female’s heads, and practicing their stalking technique. 

The two Masai tribesmen who were our safari guides for the week are still our friends today. They were in the front seat, my partner and I were in the back seat. The sun peeked over the horizon of the savannah, and the sky erupted a hue of pink. That morning is something I will not forget for the rest of my life, and remote work is the reason why I was able to do it. 

This was not a vacation. We worked every day in the Masai. This is my perfect example of an exciting life as a remote worker. 

8. What is your golden advice to a new remote worker?

Relax. Smile. Exercise.

If you are getting into remote working for the first time or were forced into it because of COVID-19, relax. Many people feel an obligation to work 60 hours a week to show their superiors they are doing the most and can be trusted. 

Don’t kill yourself. Work smarter, not harder. Work a day in advance like I tried to outline above. Remote work can be exciting, nerve-racking, and financially-fulfilling. But remember, your life and your job are separate. While you are remote working, those two lines can overlap. Make time for doing the things you like doing. 

Smile. Enjoy your new working arrangement. You’re lucky you have it! 

When you are working from home, sitting on your couch all day with a big tub of ice cream and Netflix in the comfiest clothes you can find is appealing. Exercise your body. Humans were not meant to be stagnant. You will get large if you don’t move your body. Join a gym. Walk around outside for an hour. Walk up the stairs. Anything! Don’t sacrifice your physical health for your new job. 

9. How do you see your career shaping up and your goals?

I am proud to say that I am the owner of a freelance copywriting business. Unfortunately, I lost both of my remote jobs due to COVID-19 in June. It was a struggle for quite a while. 

Finally, in October, I got a part-time remote job as a copywriter for an SEO company out of London. They liked my work so much that they put me on a long-term, project-based retainer instead of paying me by the hour. 

A little lightbulb went off in my head, and I combined my new copywriting work samples with thousands of other bylines sprinkled over the world wide web to make an appealing portfolio for other businesses in need of website copy, email sequences, or long-form blog posts. 

My goal is to automate my workflow with other writers, employees, and managers within five years. Right now, I am focusing on producing great work that people will appreciate and find value in. So far, the response has been overwhelmingly positive, and I’m thankful for that. 

10. How do you expect remote working to evolve in the future?

I think a majority of the world’s workforce will be either semi-remote or completely remote by 2025. The world now knows the general public can work from home for various professions. I believe that, for the most part, people like working remotely. They enjoy the freedom. 

Zoom calls might be a bit tiring, but I think that’s a small price to pay for all the other benefits that come along with remote work. Moms can be with their babies. Dogs get more exercise. Household chores don’t get put off. You can customize your home office any way you’d like. Your boss isn’t breathing down your neck every four minutes waiting for that report. 

If I were going to take a shot in the dark, I’d say productivity reports will show workers get just as much work done, if not more, from home than the office. The revolving door of “I can’t get a remote job because I haven’t had a remote job,” will cease to exist, and those people looking for remote work will be able to find it more manageable. 

11. Where can we follow you on?

If you would like to follow along with my journey, you can either follow me on Instagram or check out my brand new website.

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