I’d love to go freelance but is this the worst possible time?
This post is part of THE DEEP STUFF — reflective answers to the questions senior creatives ask when confidence and direction start to shift.
I write these pieces as a coach and a former creative director. I work with experienced creative leaders who are navigating confidence loss, change, and the pressure to stay relevant. No platitudes. No fridge magnet philosophy. Just saying what I hear.
(For context this question came from a senior creative as part of bigger conversation about the quality of the briefs that the agency was getting.)
So you reckon you could do better creatively than the scope you are being given, but the thought of going off the payroll feels scary.
Let’s be honest, economically, culturally, politically -it does feel like a terrible moment to take a risk.
But is there ever a safe time to go freelance?
And the truth is no. There is no objectively “safe” time.
Every single generation of freelancers (myself included) can point to recessions, industry disruption, technological change, shrinking budgets.
And yet people still go freelance - not because conditions are perfect, but because the internal cost of staying starts to outweigh the external risk of leaving.
Senior creatives feel this more sharply because by this point you’re not chasing experience, you’re looking for more control over work that respects your thinking.
Going freelance is about curation. Getting to choose where you put your energy. Even if you do have to makes some compromises and take some cash cow briefs.
The thing to remember is that going freelance doesn’t have to be a dramatic leap. I see more transitions that are grounded and planned rather than reckless. They involve testing the market, doing the maths and more critically giving space to notice whether this is about briefs or something deeper.
It almost certainly means having braver conversations around your relationship with uncertainty and confidence.
And that isn’t asking “Is it safe to go freelance?”
If you like this mini series and have a question you don’t mind being answered publicly (no names obvs) get in touch by email jude@theshapeshifter.co.uk
Discover more thinking from THE DEEP STUFF — the real questions senior creatives ask.