'It's OK not to want to "go freelance" in midlife!'

Midlifer and coach Jenny Stallard on why wanting to stay in a ‘real job’ is perfectly acceptable.

Freelance, self-employed, small business owner, entrepreneur… whichever word you use, working for yourself can seem like a perfect career pivot for midlifers. From Sara Davies and Deborah Meaden showing us how it’s done on Dragon’s Den, to Holly Tucker and, of course, Noon’s Eleanor Mills.

Going it alone can seem empowering, exciting and autonomous. And if often is, of course.

As someone who, at 44, has now been freelance three times (I call myself a threelancer”!), I know the push and pull of so-called “real jobs”. Staff jobs, with a contract and holiday pay, can seem dull compared to the whirlwind of “squiggly careers” and the stories we read in glossy magazines about women who began an empire from the kitchen table.

And then enters the FOMO. A friend, or a former colleague, perhaps, goes freelance. They quit, with great fanfare, and declare they are now self-employed. The grass looks oh-so-greener.

We should celebrate steady jobs in midlife

If you are a midlifer who feels lacking because you haven’t made The Leap, and don’t want to, I would like to offer reassurance and comfort. It might not always feel like it, but wanting – or wanting to keep – a steady job is nothing to be ashamed of.

Arguably, with the approach of midlife, it might be just what you need to keep your sanity in check.

You see, while ditching the “day job” might seem glamorous, there is a lot to be done behind the scenes, as well as huge challenges to your mental health. Freelancing is not, despite the shiny adverts on the tube, all about being a superhero who works from cute coffee shops in hipster clothing.

Things to love about office jobs

It could be that you enjoy the commute, now that offices are open again, taking time to read or listen to podcasts. Perhaps you love the moment you book a week’s holiday, and then when you come back, telling everyone about it. For you, the biggest thrill might just be (and I’m jealous of this one the most), a regular payday.

Working from home during the pandemic and lockdowns gave everyone – freelance or not – a taste of working from home full-time. As freelancers, we don’t tend to do that. Our days might be spent in client offices, at co-working spaces or even in coffee shops (ok, so yes, we do that sometimes!) as well as our home office. And that home office is often the corner of a spare room or doubling up as a playroom. Perfect, it is not. I found working from home 24/7 very challenging as a freelancer, and it made me realise just how much we rely on the human element of being in a dedicated workspace.

Why one Queenager chose a staff job over freelance

While often tempted, I am now committed to freelancing for life. But I hear daily of freelancers who decide to move back to contract or full-time work. One once-freelance friend of mine, Heidi, took a “real job” a while ago, and I asked her how she feels about moving away from being freelance. She told me: “Self-employment was the holy grail for the early years of parenthood for me – writing during nap times and in the evenings meant I had the best of both worlds, getting to be at home full-time with all three of my kids before the school years without sacrificing my career or ambition.

And while I never anticipated returning to employment, I’ve discovered that I actually love it as much as I loved freelancing – in part because it suits the stage of life I’m at so well. I don’t need the flexibility of freelancing now that my children are older, whereas finishing work at (roughly!) the same time each day and getting my evenings to myself (now that I don’t spend them on the bedtime routine) is a real bonus in midlife.”

Are you freelance curious or do you want a staff job?

She went on: “While I loved the autonomy of self-employment when I was establishing and growing my freelance career, I get a real buzz from bringing my skills and expertise to bear on a much bigger creative project now. I loved the cut and thrust of freelance life but I also love the dynamism of being part of a staff team. And yes, sick pay, annual leave, healthcare and pension contributions all matter much more to me in my mid-40s than they did in my late 20s. I used to think that giving up self-employment would be selling out. But the workplace is a much better place to be than when I left it 17 years ago and getting a permanent job offer actually felt like a validation of everything I had achieved during my self-employed years. Employment, it turns out, is the holy grail for this chapter of my working life.”

‘Sick pay, annual leave, healthcare and pension contributions all matter much more to me in my mid-40s than they did in my late 20s.’

As Queenagers, we know that midlife is a mixture of challenges, good and bad. There are the moments we want to run away and join the circus, other times we wish we just had something, one thing that was stable and we could rely on. We are often torn between different scenarios, and comparison is the place they meet. We see different women in different roles, and can’t help but ponder whether that would be right for us.

I’ve done this throughout my career, and, while freelancing won out ultimately, the security and reliability of a full-time role, from the team and the office to the is something I often miss when sitting at my desk in my home office.

Staff job as support system

In fact, a staff job can be a real support in midlife. Instead of the stresses of self-employment, having a job and boss you can trust can be something that gets you through the more difficult midlife challenges. I know the challenges of being self-employed, and it was my own mental health struggles which led to me setting up my well-being platform, Freelance Feels. I have spoken to countless people who are what I now call ‘Freelance Curious’ – they see the self-employed life and wonder if it’s for them. But it’s not, and knowing that has an amazing power to it.

I was amazed to find out a friend recently celebrated her 20-year work anniversary. Much like with friends who have 18-year-old children, or even 11-year-olds, I felt a pang of regret. I would never know that longevity in a role, and I wondered how it felt to be my career ‘opposite’. Her response will reassure all readers who are feeling like they should be more “adventurous” with their next steps.

She told me: “The thought of going freelance, aged 47, is probably my worst nightmare! I think what’s good is having a secure job, particularly at the moment, is that it’s exactly that – secure. The cost of living, energy prices… if you know you’ve got a wage coming in that you don’t have to ‘hustle’ for, that’s very reassuring. The thought of going out and trying to find clients, to pitch to people, is completely exhausting.”

Sarah adds: “There’s no need to turn your life upside down if you don’t need to. If you sit back and look at what you’ve got, from paid holiday to sick leave, if you’ve been in a job for two decades, actually it’s as flexible as working for yourself. People trust you; you can log on early, or work later, and your employers trust you to get the job done because you’ve been there so long and got so much experience.”

If closest you ever want to get to Dragon’s Den is watching it on the TV with a glass of wine after a day at work, then don’t be afraid to say “I’m in”. 

Jenny Stallard

Thinking of going freelance?

Jenny Stallard is a coach and podcaster, and founder of Freelance Feels, a well-being platform for the self-employed and “freelance curious”. Follow her on Instagram @freelance_feels and find blogs, coaching and podcast info at www.freelancefeels.com.



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