How do I know when it's time to make the leap?

Going from full time to freelance - my experience.

This week I’m addressing a question I get asked often: how do you know when you can ditch the day job and go full time creative? It’s a tricky question because it involves math, knowing your stress tolerance, and — full disclosure — I’m not yet fully freelance myself. So proceed with care.

About a year ago, I went part-time at my design job. The plan was to slowly tip the scale toward illustration. Logical mid-step, right? But that wasn’t actually my leap moment.

My real leap moment happened when I did the math.

For months I was clinging to my day job because — let’s be honest — I love security. I’m not the math person in my family¹ (that would be my kid, currently destroying calculus with a 95% average 🧮), but even I could see what was happening.

My day job, even part-time, was costing me money².

I was making more per hour freelancing than I was at my “stable” 15-hours-a-week design job. Every hour I spent on website maintenance was an hour I couldn’t bill at a higher rate elsewhere. And then last January, my freelance income exceeded my entire monthly wage.

On top of that: I was bored. Frustrated with the tasks. Working weekends and nights just to keep up with deadlines — not for my own clients, but for someone else’s.

All of that together was finally enough to outweigh the security blanket.

What is a leap moment?

It’s the moment you let go of the knowable universe and jump. There’s a hopeful energy in it — a trust in yourself and in a better future. It’s the tipping point when that trust finally outweighs the fear.

The thing that is a bit woo-woo in my case is that once I decided to quit the day job and told my boss, three projects landed in my inbox. Coincidence? Of course it is. But there’s something poetic in the fact that once I was brave enough to fully embrace my dream, the universe provided. Make of that what you will. ✨

The math — what numbers actually matter

Every financial “expert”³ will tell you the same thing: you need 3-6 months of saved income before even thinking about going freelance. That’s somewhat true — but the real number is your number. Know your monthly expenses (personal AND business), and having at least 3 months of savings as a buffer is genuinely non-negotiable (in my case anyway).

This is where your family situation, your debt load, your stress tolerance and your financial literacy all matter enormously. There’s no universal formula — only an honest conversation with yourself.

I freelanced for 15-ish years before COVID hit. Here’s what I learned the hard way:

1. Freelance income is irregular. In publishing especially, there are long stretches of working without seeing a cent. Plan for the gaps, not just the good months.

2. Taxes don’t pay themselves. I’m in Canada, so I do my income tax once a year — which means a percentage of every freelance payment goes straight into a can’t-touch-this savings account. Non-negotiable.

3. Freelancing requires business skills, not just creative ones. Cash flow, quotes, negotiating, invoicing — you need a basic handle on all of it before you leap.

4. Financial habits matter more than financial knowledge. Do you overspend? Carry debt? Skip saving for retirement? I did — all of it. I don’t anymore. Starting freelance on a solid financial foundation made everything less terrifying.

The honest complications

As I said at the start — my situation is not yours.

I have a partner with a steady job. My kid is 17. We own our house, close to the sea. I’m 47, which comes with knowledge, experience, and a drive fueled by equal parts ADHD and perimenopause. 🔥

Oh, and this is my second time going freelance.

If your situation is harder — you’re the sole income, you have young kids who won’t nap, you’re carrying debt, or you’re just a big bowl of anxiety terrified of making the leap — I want to be clear: freelancing is still doable. A creative freelance career is genuinely possible. It just requires more preparation before you jump.

Here’s what I’d want in place before ditching the day job:

• A clear understanding of my financial situation (all of it, no hiding)

• A plan to reach 3+ months of saved expenses

• At least 2 recurring paying clients (I currently have 3)

• Contingency plans for the slow months

• Business skills — or a mentor, or a support community

• Clarity on what you will actually do, sell, and offer

That last one matters more than people think. Leaping into “freelance creative work” is terrifying. Leaping into “I illustrate children’s books for these specific publishers and I have a system for finding them” is a plan.

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So… how do I know?

Start with these five questions:

• Is your freelance hourly rate higher than your day job hourly rate?

• Do you have at least 2 clients you didn’t have to chase?

• Are you working nights and weekends for your day job — or for yourself?

• Does your day job still excite you, or is it just the paycheque?

• If your biggest client called tomorrow with a large project, could you say yes?

If you answered “yes” to most of these — your gut already knows. The math just needs to catch up.

Next, audit your finances. All of it — expenses, debt, savings, monthly burn rate. No hiding. Once you have the full picture, you can build your cubicle-exit strategy:

• How do I finance the switch? (That 3-month expense buffer)

• Can I direct all current freelance income toward that goal?

• Can I transition to part-time first? Or could my current employer hire me as a freelancer at a proper hourly rate?

• Where do I build the business skills I’m missing?

• And — don’t forget — keep your family informed and involved. This affects them too.

Then it’s just a matter of working the plan until Jour J. Mine is June 30th. 🗓️

Final note

Late-bloomers: you didn’t get here by accident. Every project, every client, every skill you built while holding down a day job was preparation. The leap isn’t a leap into the unknown — it’s a leap into everything you’ve already built.

Nobody is ever fully ready. But there’s a difference between not ready and not yet. Do the math, make the plan, and trust yourself enough to jump when the numbers say go go go!

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If one of the things standing between you and your leap is clarity on what you’ll actually offer — what you do, who it’s for, and why clients should choose you — that’s exactly what the Brand Foundation Workshop builds. Six weeks, starting May 12th. Join the waitlist here → [link] for early bird pricing.

And if you want to start right now, the Portfolio Gut-Check will tell you in 10 minutes whether your portfolio is ready to support that leap. Grab it here → [link]

Now tell me in the comments: where are you in the journey? Day job and dreaming, one foot out the door, or already mid-leap? What do you feel is missing in order for you to go 100% freelance?👇

See you next week!

Valerie xo
Website | Instagram | LinkedIn

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2. hypothetical one, to be clear!

3. Defining expert super loosely here!