Freelancing vs. Remote Job: What’s Better After 50?

Through my daily 9-to-5 grind and the commute to and from the office, I discovered a desire for freedom. That’s what nudged me toward exploring the idea of working remotely while travelling. While thinking through this life-changing decision, I realized there was a big decision to make: 

Should I go freelance or look for a remote job?

It wasn’t an easy decision.

One promised independence, the other offered stability. At this stage of life—when energy is valuable and peace of mind matters more than ever—it felt like more than just a career move. 

It was a lifestyle decision.

That’s what led me to dig deep into the question: Freelancing vs. Remote Job: What’s Better After 50?

I decided to become a freelancer while working full-time.

This would allow me to clear my debt more quickly and save more money for the day when I decide to quit my job and employer of 24 years. I felt this would give me a comparison between the two.

Freelancing: Full Control, Full Responsibility

When I first went freelance, I loved the thrill of it. No one is telling me when to work. No boss. No micromanagement. 

Just me and my clients. I picked the projects I wanted. I worked in the evening and on weekends. I took time off from my full-time job and visited other cities while working in coffee shops to gain a firsthand experience of what it could be like. 

Here’s the truth: freelancing isn’t just freedom—it’s also a grind. You’re not just doing the work; you’re finding the work. You’re sending proposals, chasing invoices, marketing yourself, and building systems. 

It can be lonely too. There’s no built-in team, no office chat. You have to create your own structure, your own momentum. 

How I Decided Between the Two

After 18 months of freelancing while working full-time employment—continuously trying to find new clients, chasing invoices, and honestly having no idea when the next payment would arrive in my bank, I decided that freelancing was not for me. 

I craved freedom, but with consistency, less stress, and a remote job that met that need. While traveling, I didn’t want to be continuously worrying about when clients would process my invoices. 

Spending time working out the pros and cons of freelancing vs. a remote job really helped me make the right decision for me.

Even with savings, my concern would be that money would run out much quicker as a freelancer, as it would not be a consistent income. 

Of course, I never ruled out freelancing completely; if my remote job came to an end, then it would be an option in the interim. 

There was another option, though, that would give me more freedom and also a regular income. I discovered that I could have remote employment as an international contractor, which meant working for companies on short-to-medium term contracts and getting paid every single month.  

Initially, I worked full-time, but over time, I transitioned to part-time to achieve the perfect work-life balance. 

I’ll discuss this further in another post. 

Remote Job: Stability Without the Office

Finding a remote job was not easy, and at first, I worried it would feel like a regular job in disguise. I imagined endless Zoom calls and rigid hours. 

Thankfully, that wasn’t the case. What I found was a new kind of stability: predictable income, a team I could collaborate and communicate with online through channels like Slack. 

The best part? I still had flexibility. I worked from wherever I wanted—Malaysia, Spain, South Korea. As long as I met my deadlines and stayed communicative, nobody cared where I logged in from.

Having a work routine made it easier to plan my life. I could take a weekend trip without stressing about missing a new client lead. I wasn’t constantly promoting myself or switching between hats. 

I just did my job, logged off, and enjoyed my time off. For someone like me—who still values freedom but also appreciates a bit of calm—it felt like a great middle ground.

Freelancing vs. Remote Job: What’s Better After 50?

So here’s the big question again—Freelancing vs. Remote Job: What’s Better After 50? The answer? It depends on how you want to live your life. We all react differently to situations, and for me, I stress about money, so I needed to focus on enjoying the experience; otherwise, I might as well be working in the office.

If you’re looking for independence, flexibility, and the chance to shape your own work day from the ground up, freelancing might be your path. 

If you want the freedom to work from anywhere without the stress of constant client hunting, a remote job is what you need.

Neither one is “better”—they’re just different kinds of freedom.

If you had no past job title, no pressure to prove anything to anyone, and could start your work life fresh today, what kind of structure would actually support the way you want to live?

That’s the real question behind all of this. 

It’s not just “what should I do?” It’s: What kind of life do I want to wake up to every morning from here on out? Whatever your answer is, there’s a path for it. You just have to take the first step.