Freelance Work Vs a Remote Job – The Pros And Cons

I get this question a lot from clients: should I go freelance or find a remote job with a company? Both paths help you escape the office. Past that, they are very different ways of working, and picking the wrong one costs you money and time you don’t get back.

I’ve done both. For two years before quitting my office job of 24 years, I freelanced in the evenings and weekends to save money so I could escape the office and start my new journey as a remote worker. When I did finally quit the office job, I continued freelancing for six months.

Experiencing both freelancing and being employed in a remote job taught me more about the real pros and cons, so the advice in this guide comes from my own experiences, not something made up for clicks.

What Freelancing Actually Gives You

You set your own hours. You decide your rate and who you work with, and that is the ultimate in flexibility. We are all the most productive at different times of the day, and freelancing gives you the power to choose. It also offers genuine location freedom.

Take the work to an island with slow WiFi for a week if you want; that’s fine, provided the client work still lands on deadline. Before you leap into a remote or freelance job, it’s worth asking yourself which of these you actually want, rather than which one sounds better.

What Freelancing Actually Costs You

Here’s what most freelance advice skips: you spend more time chasing invoices than you do working on projects. Clients pay late. Sometimes they forget entirely, and you’re the one who has to ask twice. Sometimes you have no choice but to take them to small-claims court to get your money paid.

I once had a client who sat on an invoice for six weeks. It was a slow month, so panic set in when flights had to be booked because my visa was coming to an end.

You’ll also need to save for taxes yourself, and cover your own health insurance and pension, because none of that comes bundled with the work. Take a week of vacation, and that week earns nothing.

Depending on the type of freelance work that you offer clients, it’s also possible that you will have to pay for freelancer insurance so that you are financially protected should you find yourself in legal situations.

What an Employer Remote Job Gives You Instead

This assumes the remote job is with an employer, not contracting. Contracting carries the same tradeoffs as freelancing, just with steadier, monthly pay. A regular salary makes life less stressful. Sick pay, vacation pay, a pension, health coverage, the safety net freelancing doesn’t offer.

You also feel less disconnected because you’re working with a remote company and a distributed team who are based all over the world: regular video calls, stand-ups, async communication on Slack.

What an Employer Remote Job Costs You Instead

The big tradeoff is flexibility. Most employers expect a specific shift and time zone, which can mean working unsociable hours. I live in Asia, and most of my team is based in Europe and the USA.

So, my working hours are in the evening, sometimes past midnight if there are urgent deadlines or meetings to attend. Still, during the day, I choose when and where I work on my coaching business.

Reliable internet stops being optional because a dropped call mid-meeting, a slow connection right as your manager messages you, or buffering during a stand-up all read the same way to an employer: you weren’t available when it mattered. That’s the risk, not the WiFi itself.

Why I Ended Up Doing Both

Both paths get you the same: no commute, more time with the people you actually want to see, room to work on something that’s yours.

There’s a third option worth naming directly: do both part-time. For over 4 years, I worked as a freelancer for 20 hours a week and also had a remote job for 20 hours a week. It was a challenge to juggle both a client and an employer, but it is possible if you are organized and maintain a routine in your working week. It was the best of both, though.

Right now, I work 30 hours a week as an employee for a US-based remote company and 15-20 hours a week running my coaching business, the Remote Hive. That split means I still receive a monthly salary without stressing if business is slow.

None of the cons above are dealbreakers on their own, but they’re not nothing either.

If you land on the employer route, the next decision is which kind of remote role actually fits how you like to work, since not every remote job listing means the same thing day to day. My guide on how to choose the right remote job when you’ve never worked remotely walks through that next.