Before You Quit Your 9–5: Brutally Honest Freelancing Truths

If this thought keeps lingering in your mind:

“So… should I quit?”

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Think more.
And more.

If you’ve found yourself Googling “How to quit my job and freelance full-time” at 2 AM, this post is for you.

Here’s the brutal truth no one really talks about.

The Fantasy vs. The Reality

I get it.

On Instagram, freelancing looks like client calls from a Bali villa, midday matcha breaks, and logging off at 2 PM to chase waterfalls.

Sometimes, it is like that.

But most days? It’s eight client deadlines, a moody Airbnb Wi-Fi, a backup connection staging the same drama, and you — curse (loudly and often), lose your sanity, and send invoices at midnight because… timezone math loves chaos.

Freedom is real. So are the challenges.

3 Hard Truths About Quitting Your 9–5

1. Your Paycheck Safety Net Will Disappear

That steady deposit every 15th and 30th? Gone.

As a freelancer, you are the boss, CEO, COO, sales team, accountant, and customer service rep.

You don’t just do the work.
You find the work.

If the thought of chasing clients makes you break out in hives, it’s not the right time to quit yet.

2. Your Workload Might Double at First (Even triple or quadruple)

When I started, I thought freelancing would mean fewer hours.

Wrong.

Building your client base while delivering quality work often means longer hours upfront, and I mean loooongerrrr hours.

Especially if you become in-demand and every startup wants you on their team.

We’re talking about:

12-hour workdays, Monday to Friday
8 hours on Saturday
3 hours on Sunday (the rest of Sunday becomes your actual freedom)
It’s like pushing a boulder uphill, but once momentum kicks in, things get easier.

Now? I choose my clients, projects, and work hours. But that didn’t happen overnight.

3. Loneliness Is Real

No coworkers.
No watercooler talk.

Just you, your laptop, and maybe a dog.

Freelancing can get isolating.

That’s why I intentionally built a support network: freelancer friends, online community groups, and even co-working spaces when I travel.

When Not to Quit (Yet)

You don’t have 3–6 months of savings
You’ve never landed a freelance client
You hate marketing or selling yourself
You’re still unclear on what services you’ll offer

If you checked any of these, hit pause. Freelance as a side hustle first.

That’s what I did, and it saved me from burning out and going broke.

When You Might Be Ready

You have repeat clients or strong leads
You’ve replaced at least 60–80% of your salary
You have systems for outreach, invoicing, and time management
You’re comfortable with uncertainty (because feast and drought cycles will happen)

If this is you?

It might be time to take the leap.

My Final Advice

Quitting your 9–5 is a huge decision.

Don’t do it because you hate your boss.
Don’t do it because you’re chasing Instagram’s version of freelancing.

Do it when you’ve built the skills, systems, structures, and mindset to survive and thrive in the freelance world.

Freedom is so worth it. But only if you’re prepared.

Want more real talk on freelancing and remote work? Follow my journey @jen.traveltales!