So, last week, I did it. I quit my job. The email I’d been considering for nearly a year went in – “please accept this as formal notice of my resignation…”. I actually left employment to start freelancing. Well, technically, actually, if you’re splitting hairs, I just triggered my three months’ notice, but the key point is – what happens next is a huge unknown. I’m leaving a steady well-paid job, regular wages, pension contributions, friends and colleagues and a whole host of other benefits to try myself out as an employer for a while. Early onset on midlife crisis? Maybe. But will I wake up later in life disappointed I never gave it a go? Definitely.
So what got me to this point? Why take the plunge now, particularly in this slightly-new-post-pandemic world, with uncertain global relations and the cost of living spiralling? And what exactly am I going to try?
One – New Challenges
First up, itchy feet. I’ve been having itchy feet for a while now. You know, that feeling you get when you need a new challenge. I’d accidentally stayed in an organisation for nearly 8 years and while I’d held two roles and had my two kids (and two maternity leaves) during that time, it felt like the time was right to look for something new to take on. Which begged the question of “to do what?” and endlessly scrolling through vacancies, I struggled to find anything that lit that fire of “I’d LOVE to do that!” And I can’t lie, my heart always sank at the pages of application forms, the relisting of qualifications, digging out job dates etc. A number of unsuccessful applications made me stop and think maybe my heart just wasn’t in it.
Two – Entrepreneurial Ideas
For years I’ve had all sorts of business ideas, from the genius to the outright bonkers but I’ve never quite had enough confidence to push forward with any. And that feeling of being excited and energised over a new idea was always quickly followed by deflation as I overthought it, found strong competition, believed it won’t pay etc. But what it did make me realise is somewhere deep down I’ve got an entrepreneurial spirit, and recognising that felt half the battle. It’s the competition with my risk-averse nature/upbringing that’s hard to resolve – how to tackle that voice that constantly nags “but what if I fail?” and “how will I pay the bills?”
Three – Self Employed Possibilities
My husband took his own leap about two years ago and started working for himself. At the time, it felt terrifying and full of “what-ifs” but seeing how it’s worked for him has been really inspiring. He’s been able to choose who he works with, set his own rates and also has more flexibility than he’s ever done with days and hours, which is a massive help with school and nursery runs.
Four – A Book
I must have rambled on enough about the possibility of maybe, somehow, someday, doing something about this seed of an idea because my sister bought me a book (Be a Free Range Human by Marianne Cantwell) to help nudge me over the line. It talks about what can be achieved by breaking away from the traditional 9-5, and that the world had shifted significantly from the days of needing to find and keep employment with a single organisation. It gave a load of inspiring stories about people who had used their skills and determination to build their own businesses. I loved it.
Five – Work/Life Balance
And let’s be honest – what doesn’t appeal about that? Finding something you’re passionate about, that you can be the driving force behind, the ability to choose how and when you work as well as who with, and the possibility (apparently) of making more than in employment? The dream! I’ve worked some long hours, particularly this last year, and I’ve found myself, way too often, working while kids are napping, answering emails in the park or back on the laptop in the evening. Doing a condensed work pattern has been worthwhile financially (particularly for fewer days’ nursery costs) but mentally it’s been exhausting. I’ve been force-fitting two days of childcare and four days of work into a five day week – no wonder I’m constantly behind on my life admin, the house is always a bit of a mess and there’s always a huge to-do list whirling round my head. The idea of stepping back, breathing a bit and trying to recalibrate that balance really appeals, not least because our youngest is only little and I appreciate now how quickly this time will go.
And has anyone really sat down and thought about how absolutely insane these last two years have been? If anything is going to make you re-evaluate life and consider a new direction, a global pandemic will definitely help you down that road.
Six – Use What I Know
So here’s the thing. I read that amazing book and felt fired up. I went back to my list of business ideas and realised that I was trying too hard to invent something or be something completely new. I realised maybe I was overlooking some of the fundamentals. That I’ve got a great range of skills from my roles so far, and that I don’t have to be the best out there or totally unique. I just need to understand my niche. And I’ve *loved* some of the work I’ve done over the years, working with non-profits. What about pulling out the best bits of the work I’ve done so far and trying to run with those?
While I’ve been asked to take on one-off freelance pieces a number of times over the last decade, I’d never really clocked what that meant – that people thought I had skills/knowledge/experience that are worth paying for! The other thing is that without being in the right headspace of considering freelance as an actual job, I’d always seen all the opportunities just as “extra work” on top of an existing job and I just couldn’t work out how to fit them in, however interesting. Finally, where I’ve had some of those natural frustrations over the years with the decisions-by-committee mentality or the time taken to get things off the ground aspects of being in an organisation, I realised freelance was potentially a way of converting my completer-finisher personality into a strength.
Anyone seen that Venn diagram on finding your sweet spot in life? It’s a good really way to challenge yourself on trying to link together what you enjoy, with what you actually are any good at, plus whether there’s a market for it, and whether its something that will actually pay your bills. So perhaps the answer (or at least part of it) was staring at me in the face all this time.

Image credit: Women@NASA Blog
Seven – Freelance Community
Honestly, I don’t think I believe in fate, but then the world delivered me two chance encounters that pushed my seed of an idea into a reality. One was falling into step with someone in with my running club one weekend, who not only turned out to be a consultant, but almost the exact type I aspired to be, and she was completely lovely, grounded and normal and she was making it work in reality. We had a great chat about generalities as well as practicalities and she invited me to an online group of freelancers who share opportunities, collaborate and generally act as a supportive community for one another. What were the chances?!
Eight – My Kind of Freelancer
Then a few weeks later, another chance encounter, this time on an evening out, with someone who’d freelanced for years but taken a break into employment to support getting a mortgage. As a local fellow mum with a child in reception, it was another lived experience example I needed to hear. Not only of someone achieving something I was trying to, but someone who almost was me – balancing young kids and all the challenges and compromises that involves. It felt like a giant dose of “this might be possible.”
Nine – Securing Work
And then finally in the freelance group, in between the big-budget-big-team-needing projects, a couple of small charities popped up needing things that were entirely my world – evaluation of some funded advice work and some facilitation work for a staff group. Arguably small contracts and lower-end budgets compared to some of what’s posted but perfect for what I needed right now, which was a foot in the door and a test of whether this could actually be a thing.
So I spent waaaaaay too many hours writing proposals, deliberating over every aspect – from not knowing how much things cost, to whether I’d be taken seriously with my background, from how on earth I’d fit the work in to whether to should set up company. And you know what? I got both.
Ten – If Not Now, When?
Ever have one of those moments where the radio seems to play the exact song for your situation/headspace right now? I was driving home from work after a long day and MPeople (remember them?!)’s “Proud” played.
“What have you done today to make you feel proud?
It’s never too late to try
What have you done today to make you feel proud?
You could be so many people
If you make that break for freedom
What have you done today to make you feel proud?
Everything about it resonated, and especially that challenge of – why not now? Why keep doing the same thing? And that, finally, was my lightbulb moment. What else needs to happen to convince me? The conditions are never going to be perfect, but sometimes you have to be brave.
So here I am. Taking a terrifying leap of faith into the world of freelance. I’ve taken stock, and my stock consists of three months’ pay during my notice period (until mid Aug), income from my first two contracts adding on two months (mid Oct), and absolute worst case scenario I have savings to get us into the new year. And so my experiment begins – freelancing into the unknown.