Should you quit your job to pursue remote work?

I hate this question.

So much.

Yeah, there, I said it. If you have ever asked me this, I thought you should know. But, trust me, it has nothing to do with you. It has everything to do with me. I struggle with answering this question because I feel like I never have a straightforward answer to it.

When people hear my story of how I left my corporate banking job 11 years ago, I think they assume I was over the moon about it.

Newsflash!

I was not. I was terrified. I was relieved. I was scared of what could possibly happen or not happen. I was scared of failing. I was scared of leaving the comfort of a salary, medical aid, fuel and all the perks that came with the job and going back to having to figure out how to recharge my phone with a juice card. Tjo!

I was afraid of running out of money (which I quickly did) and just struggling.

Yet. I still made the decision to quit my job with all of these things in sight.

Why? Well, my life was honestly set up differently then. I was in my 20s and living with my parents for starters and I had managed to convince myself that if it didn’t work out within x number of months, I would just go and look for job in corporate.

And guess what? It didn’t quite work out especially in that first year but I found the highs of remote and flexible work so thrilling, I decided, “A luta continua!” and continue I did.

Fast forward to today, my life is set up different. I don’t live with my parents anymore and I’m actually a parent myself. Would I make the same decision? Maybe yes. Maybe no. You see why I hate this question? Because it all depends on the circumstances. It depends on what’s at stake. Is it my child’s welfare? Is it my mental state? Is there something at stake?

Because if my child’s welfare is at stake if I stay in an in-person job, maybe I work long hours or I don’t have childcare, I’m likely going to quit and look for flexible options. If my mental health is at stake if I stay in this in-person job, I may choose to stay and engage a therapist as a start or, if my savings permit, wave my colleagues goodbye.

What am I saying? I am not in a position in my life where I would just choose instability or uncertainty without just cause. And yes, sometimes my mental health is just cause. Sometimes my child is just cause.

Now, maybe you are asking yourself this question. You are probably burnt out in your job or fed up with your bosses or colleagues. What should you do?

I would say pick whatever decision you like and be prepared to live with it.

This is why…

You have to own your decision. You can’t make it based on vibes, or because someone else seems to be thriving remotely, or because you saw a TikTok about working on a beach in Bali. You have to make it based on your own situation, your values, your goals, and what you’re willing (or not willing) to risk.

Remote work is not a magic fix. It’s not always a better alternative. It’s just different. It has perks. Oh yes, it has perks! But it also comes with its own challenges. You might get flexibility, but you’ll also need discipline. Do you have it? You might get freedom, but you might also feel isolated. Can you stand loneliness? You might escape a toxic workplace, only to realise that you miss the energy of being around people.

And if you’re thinking of quitting your in-person job to find a remote job, that’s another layer to consider. Remote jobs are so competitive. Are you ready to compete at the level they demand? Remote jobs also don’t always pay as well at the beginning, especially if you’re making a pivot. They can take time to find. Are you okay with that time gap? Do you have savings? A support system? A plan B or C?

This is not to scare you. It’s to ground you.

Quitting isn’t failure. Staying isn’t weakness. Choosing stability isn’t being boring. Chasing freedom isn’t being reckless. It all depends on why you’re making the decision and what you need right now.

So, should you quit your in-person job to pursue remote work?

Only you can really answer that. But here’s what I would say:

Make sure you’re running towards something, not just running away from something. Make sure you’re aware of what you’re giving up, just as much as what you’re gaining. And whatever you choose, stand ten toes down in that decision. Learn from it. Pivot if you need to. You’re allowed to change your mind.

I don’t have a straight answer. I never have.

But I do know this: your life, your season and your priorities matter. Let them guide you

Before you make the leap, ask yourself: What matters most to me right now? What am I willing to risk, and what do I want to protect?

Let your answers (not fear, not pressure, not Instagram posts or a TikTok or YouTube influencer) lead the way.