When Should You Go "All-In" on Freelancing?
- Kyle Prinsloo
- Feb 6
- 5 min read
Quitting your job to go all-in on freelancing is an exciting but nerve-wracking decision.
The idea of working for yourself, setting your own hours, and making money on your terms sounds great.
But the transition from employee to full-time freelancer isn’t as simple as just handing in your resignation.
In this article, I’ll walk you through the key factors that determine when it’s the right time to go all-in.
…so you can make the leap with confidence.
I'll cover:
Let’s get into it!
How Much Cash Do You Need To Go "All-In" On Freelancing
Money is the biggest safety net when you’re transitioning into freelancing.
Without a financial cushion, the pressure to land clients quickly can push you into taking bad deals or making rushed decisions.
For more insights on financial management as a freelancer, check out this guide.
The Ideal Savings Buffer
✅ Three months of expenses saved up (at the very least). Six months is even better.
✅ This buffer helps you avoid stress, allowing you to focus on growing your business instead of scrambling for survival gigs.
✅ Consider personal expenses, taxes, and any unexpected costs that may come up.
✅ Also factor in health insurance and emergency funds—unlike a full-time job, freelancing doesn’t come with built-in benefits.
If you don’t have enough savings yet, it might be worth delaying your exit while you build up a financial safety net.
How Much Freelance Income Should You Have Before Quitting?
Freelancing as a side hustle before going full-time gives you a significant advantage.
If you're new to freelancing, start by reading this comprehensive guide.
It allows you to test your business model, gain clients, and understand your earning potential before taking the plunge.
A Good Rule of Thumb
✅ You should be making at least 50% of your full-time salary from freelancing before quitting.
✅ This proves there is demand for your services and shows that you can realistically replace your income.
✅ If you’re consistently landing clients and managing projects successfully, that’s a strong sign that you can scale up once you have more time.
✅ Consider contract-based work—longer-term projects or retainers provide more stability compared to one-off gigs.
Personally, I matched (and eventually exceeded) my full-time salary within a year of freelancing on the side. At that point, I knew it was time to go all-in.
Do You Have the Time and Energy to Scale?
Freelancing isn’t just a job replacement—it’s building a business. And businesses take time to grow.
Things to Consider
✅ Do you have the mental bandwidth to handle client work, marketing, admin, and learning new skills?
✅ Are you comfortable with irregular income?
Freelance income fluctuates, and handling slow months requires discipline and planning.
✅ Are you ready to put in the extra effort to network and find clients?
Unlike a job, there’s no HR department sending you work—you’re responsible for everything.
Getting clients is a big topic - watch this:
✅ Are you managing your workload efficiently?
Poor time management can lead to burnout and instability.
✅ Are you consistently generating leads?
Without a steady pipeline, income fluctuations can be hard to handle.
If you’re already struggling to balance freelancing with a full-time job, it’s worth analyzing whether you’ll have the stamina to go all-in.
The ‘Soft’ Factors That Matter
Beyond financial security and workload, your personality, mindset, and risk tolerance play a huge role in whether you should quit your job.
Ask yourself:
Are you okay with uncertainty?
Clients come and go. Are you adaptable enough to handle ups and downs?
Do you have the skills to compete?
Are your skills strong enough to justify your pricing and attract clients?
Do you have the discipline to stay productive without a boss?
Self-motivation is crucial in freelancing.
Are you willing to continuously learn and adapt?
Industries evolve, and so should your skills.
Stay ahead by understanding the latest web design trends for 2025.
Do you have a backup plan
It’s smart to have a fallback option if things don’t go as planned.
There’s no right or wrong way—just the way that works for you.
Additional Tips for a Smoother Transition
To make your move into full-time freelancing easier, here are a few additional strategies:
For a deep dive into building a strong freelance business, read this guide.
✅ Build a strong personal brand
Start sharing your expertise through social media, blogs, or YouTube to establish credibility.
✅ Diversify your income sources
Don’t rely on one big client. Work with multiple clients and consider passive income streams.
✅ Network strategically
Connect with others in your industry through LinkedIn, Twitter, and online communities.
✅ Invest in tools & software
Project management tools, accounting software, and automation tools can streamline your workflow.
✅ Work on your mindset
Shifting from an employee mindset to an entrepreneurial one is crucial for long-term success.
✅ Set realistic expectations
Freelancing isn’t a get-rich-quick scheme. It takes time, patience, and persistence.
Common Mistakes to Avoid When Going Full-Time
When transitioning to full-time freelancing, many people make costly mistakes that could have been avoided. Here are some of the most common ones:
Lack of a Financial Plan
Many freelancers quit too soon without a solid financial plan.
Learn how to set up a financial buffer by following this detailed guide. Make sure you have savings and a clear strategy for managing your expenses.
Underpricing Your Services
New freelancers often undervalue their work.
Master value-based pricing to charge what you're worth.
Set competitive rates that reflect your skills, experience, and the value you bring to clients.
Pricing is also big topic, watch this:
Ignoring Contracts
Freelancers must always use contracts to protect themselves from scope creep, late payments, and disputes.
Poor Time Management
Without a structured schedule, it’s easy to get overwhelmed.
Create a daily routine and set clear work hours to stay productive.
Relying on One Client
Having a single high-paying client might seem great—until they disappear. Always work on diversifying your client base to ensure long-term stability.
Watch this video on getting clients from Google Maps
Final Thoughts
So, when should you go all-in on freelancing?
It depends. 🙂
On your finances. Your freelance income. Your mindset. Your tolerance for uncertainty.
If you’ve got three months (or more) of savings, a steady freelance income covering at least 50% of your salary, and the time and energy to scale, you’re in a strong position to make the leap.
If not, there’s no shame in waiting a little longer while you build a stronger foundation. Freelancing is a marathon, not a sprint.
Whenever you decide to go all-in, make sure you’re jumping with confidence, not just wishful thinking.