1 Year of Remote Freelancing: Lessons Learned

Apr 29 · 5 min read
Prague, Czech Republic (April 2019)

Exactly a year ago, when I was just starting out as an independent freelancer, I read Brad Haynes’ post about his first year of freelancing. Now that I’m exactly one year into my own freelancing journey, I’m inspired to share my own thoughts about lessons learned along the way, especially as a fully remote freelancer traveling the world.

Here are the top lessons I’ve learned as a remote freelancer over the past year:

1. Perception is everything

Because I’m never in the same room as my clients, all of my work is done virtually, which means the only time my clients see me working is when we’re on Slack and Google Hangouts video calls. This can be troublesome, especially if the client already has some hesitation towards remote freelancers.

Perception is everything. If your client sees that you’re working or not working, they’re right. As a remote freelancer, one of the worst things that can happen is that you’re putting in the hours and producing quality work, but because the client doesn’t see your efforts, you don’t get recognized for it, and they end the contract under the misassumption that you’re not productive.

To avoid this potentially hazardous situation, it’s important to demonstrate that you’re producing work during the agreed upon hours. This means being online and available for regular check-ins, handing over deliverables, and answering questions during the hours you’re expected to. This guideline applies to most industries, but especially as a remote freelancer, the lack of face time can create uncertainty and doubt that requires extra attention.

This doesn’t mean you should only work for the purpose of being recognized and slack off during the hours you’re not on a call. It’s important to do good work at all times.

When in doubt, always over-communicate

2. It’s all about relationships

A year ago, when I quit my full-time job with no offers or consulting opportunities lined up, I was scared. My biggest worry was that I wouldn’t be able to close any clients in time, run out of money, and eventually have to go back to applying for full-time jobs.

Fortunately, having been in the tech startup industry for five years, my professional relationships have led me to all of my clients to date. In the past year, I’ve had the fortune of working with incredibly talented startups from Y Combinator alumni (Universe) to high-growth startups (Hims and Life360).

Networking is powerful. Whatever industry you’re in, establish connections with influential people, ask the right questions, and make sure to thank them for their time. I’ve found that 1:1 coffee chats are far more effective than surface-level networking events. You’re more likely to make an impact, and you’re more likely to have in-depth, engaging conversations.

Just always remember to pay it forward and help others.

Networking is a two-way street: help others as much as they’ve helped you, even if it doesn’t benefit you in any way.

I made it a point to network as much as possible before I took off to travel the world last October. I met with influential founders, investors, VC firms, and recruiters to get my name out there and make it known that I was available for consulting work. These relationships have paid dividends when I’m traveling because it’s difficult to sell a potential client when there’s no face time. Companies often want to meet in person several times before feeling comfortable engaging in consulting services. Fortunately, I have tremendous investors and recruiters who pitch my professional services on my behalf.

3. Clearly define time commitments and availabilities

When I first started freelancing, I made the mistake of always being available for all of my clients at all times throughout the week. This meant that on any given day, I was on Slack/email for multiple clients, oftentimes jumping back and forth between concurrent conversations with clients. As you can imagine, this burned me out pretty quickly.

Having learned my lessons, I now block off 4-hour work blocks each day, and I focus exclusively on one client per work block. This allows me to focus on one project and team at a time, thus increasing my productivity and output. I also avoid the risk of sending the wrong deliverables to the wrong client (almost happened one time).

4. Build a consistent daily routine

Over the last six months, I traveled all over Southeast Asia and Australia/New Zealand. I moved around a lot, but I didn’t consider myself to be “backpacking”. I stayed in each location anywhere from 2 to 4 weeks at a time, so I could build a consistent daily routine like I had back home in the US.

When you’re simultaneously working and traveling abroad, it is so important to build a steady routine that you could stick to every day. I woke up at the same time I did back home, I had a normal gym routine, and I dedicated afternoons and/or evenings to work. Like I did back home, I had a few hours of free time each day, but instead of staying home and watching Netflix (which I would often do in the US), I would go out and explore the city.

If I didn’t build a consistent routine, it would’ve been easy for me to slip into “vacation mode” and not focus on producing good work. As you can imagine, every city comes with new experiences, and along with it, a new wave of excitement to explore it all. It was a challenging but fun exercise to learn how to control the excitement and balance work and play.

5. Find like-minded individuals and communities

When you’re traveling and working alone most of the time, it can get lonely. That’s why I found it extremely helpful to find like-minded individuals who were on similar journeys as solo travelers, freelancers, digital nomads, and online entrepreneurs.

Bali is universally known as the biggest digital nomad hub in the world. In Bali, there are dozens of coworking spaces and shared villas, filled with inspiring people from all around the world. Specifically, Dojo Bali is a 24-hour, 7-days a week coworking space that has daily workshops/events, speaker series, holiday parties, weekly Friday happy hours, and an outdoor swimming pool.

When I showed up for the first time, I felt like a wide-eyed freshman on the first day of school, in awe at how developed the community was.

Every day, I worked next to someone new. Throughout the day, the space was very quiet, and you could visibly see how focused everyone was on their work. This was incredibly encouraging and motivating to feel a shared sense of “we’re all in this together” attitude.

In other cities, I would frequently rotate between working out of coworking spaces, cafes/coffee shops, public libraries, and my Airbnbs to keep things fresh and change my scenery every day.


It’s crazy to think that I’ve only been on this journey for a year because I’ve learned more about myself in the last year than I have in the last five. If you’re interested in traveling the world and making an income at the same time, I encourage exploring the possibility of a remote freelancing lifestyle. Find a niche, develop valuable skillsets, network, and start selling clients.

The future of work will bring about more independent freelancers who choose where they work and how they live their lives.

Johnny Chen

Written by

Product & growth consultant traveling the world since October 2018. Follow my adventures at instagram.com/johnnychen0

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