From Side Hustle to Something More: On Knowing When It’s Time to Step Away From the Day Job
- Rebecca Cook

- 17 minutes ago
- 4 min read
There comes a moment in many careers when you start wondering if it’s time to leave the day job and finally give your side hustle the space it’s been asking for. Not in a dramatic “quit your job” way, but in a quiet, persistent way — the kind that makes you question whether the work you do on the side is actually the work you want to build a life around. I’ve been pondering that question for a while now, balancing the security of a stable job with the pull of something more meaningful, more creative, and more aligned with who I am.
Years ago, I was a project manager. On paper, it was fine. In reality, it was a loop of requirements → build → test → fail → redefine → repeat. Deadlines slipped. Vendors promised the earth and delivered something… smaller.
We waited for fixes that didn’t quite hit the mark.
Every week felt like déjà vu: “We’re still not live.”
It wasn’t anyone’s fault. It was just the nature of the work. But it chipped away at me. I felt responsible for outcomes I couldn’t control, and powerless to change the things that mattered.
And in the middle of all that frustration, I baked.
Not elaborate celebration cakes — the team never got those. More often it was a traybake, or something simple and comforting. But it brought lift. It brought a moment of “oh, this is nice” into a room full of people who were tired of waiting for systems to behave. And it reminded me that I could still create something that worked, even when everything else felt stuck.
But baking has been more than a counterbalance to work frustration. It has been the thread that has held me together through some of the hardest chapters of my life.
When Abigail was diagnosed with type 1 diabetes, I baked. It steadied me when everything felt uncertain. (And yes — before anyone asks — you can be type 1 and still eat cake. Sometimes it’s the only thing that keeps you out of hospital.)
When my grandad died, I started Becca’s Bouqcakes — not because I was honouring him through beauty, but because losing him made me realise life is short, and I needed to start building towards the dream I kept postponing.
And when my mum died unexpectedly at a relatively young age, I created again. I made a floral display of cakes for her wake — something that rivalled the real flowers, made from the recipe she passed down to me. It gave me purpose when I felt hollow. It reflected the values she instilled in me: show up for people, even when you’re hurting.
So when I talk about boundaries, pricing, and not giving away your creativity for free, this is why. Baking has sustained me through grief, frustration, and identity knocks.
It deserves to be protected.
And so do the people who create — especially when that creativity comes from a place of love, resilience, and meaning.
Some people know me only as the baker.
Others know I also have a full‑time job.
I’ve never hidden it — it’s just that different parts of my world show up in different places.
And I’m privileged enough to be able to do both.
I’m also someone who is always on the go, who pushes herself, who rarely feels she is “enough.”
I’m not looking for labels, but I know that busyness has been both my coping mechanism and my camouflage.
And now I’m at a crossroads.
I love what I’ve built. I love teaching. I love creating. I love bringing joy to people’s days. I love watching someone realise they can pipe a flower they never thought they could. I love the community that has grown around this work.
And I’m starting to wonder whether it’s time to step away from the day job and step fully into the thing that aligns with my values.
But it’s not a simple decision.
My biggest fear?
Financial instability.
Losing joy in the creativity when it becomes the one thing that pays the bill.
The increased washing up.
The increased anxiety — the mental load of being your own boss, the not‑knowing where the next payday is coming from.
And the risk that the sanctuary becomes the stressor.
My biggest hope? That I can finally spend my days doing work that feels like me.
That I can be creative.
That I can bring more joy into my own life and into other people’s.
That I can teach, inspire, and support others to grow.
That I can build something rooted in purpose, not politics.
And if you’re wondering why I haven’t stepped away before, the answer is simple: life.
Abigail’s diagnosis.
Losing my grandad.
Losing my mum unexpectedly at a relatively young age.
My own health challenges.
I needed stability while everything else was shifting.
The day job wasn’t fulfilling, but it was steady — and sometimes steady is the only thing that keeps you upright.
So how will I know if it’s the right time now?
I think it’s when the reason to stay (security) no longer outweighs the reason to go (alignment). When the fear of losing joy is matched by the fear of wasting years in misalignment.
When the next curveball doesn’t feel like a reason to delay, but a reminder that life is short.
When the numbers don’t have to be perfect — just possible.
Because curveballs will always come.
Life will always be unpredictable.
There will never be a moment where everything is calm and tidy and perfectly aligned.
The real question is whether I want to meet the next curveball from a place of exhaustion or a place of purpose.
I don’t know exactly when I’ll step away. But I do know this: the work that has carried me deserves to be treated with respect — and that starts with me respecting myself.
Does any of this resonate with you?
Are you standing at a similar crossroads?
And if you are — do you feel like you’re respecting yourself and your craft in the process?
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