What I learned in my third year as a freelancer

LauraOliver
5 min readNov 15, 2019
A trip to Beijing with the Thomson Foundation was a highlight of my third year.

I left my last staff job in mid-2016; September 2019 marked the end of my third year as a freelance journalist. Reflecting on my first year, the power of my network, learning to be my own boss and surviving vs strategy were the most important lessons, but what did year three teach me?

  1. Saying yes — and no — for the right reasons

“The right client isn’t the right client just because they came to you.”

This piece of advice overheard in a co-working space has stuck with me all year. I think it reflects the eternal dilemma of freelancing: whether to take work when offered to you because you never know when your next dry spell will be; versus refusing a work approach because it doesn’t meet your goals and the inevitable guilt of turning down £s that follows.

I’m always grateful for commissions and work inquiries that come straight to me, and often they are a really good fit, but in my third year I’ve learned to take a breath before replying: “Yes, YES, a thousand times, yes.” My knee-jerk response is usually driven by financial fears and a misguided sense that a freelancer should never say no if the price is right. I now try to ask a series of questions before making an immediate response:

  • Will this commission/project/part-time role help me achieve goals beyond the purely financial?
  • Will accepting it cost me other work opportunities or time that could be better spent on other projects?
  • What’s my heart (and not just my head) saying?

That last point is an important one for me — there have been projects I’ve taken on where I knew early on or even before I started that they weren’t a good fit, but my head made me take it on. In the end, my heart was right every time. The stress and difficulties I experienced on some of these projects far outweighed the discomfort I would have felt turning them down in the first place. I could have saved valuable time and energy and put this towards finding something more suitable.

2. Remember your experience and take a leap

One of my biggest pieces of work in my third year — and one of my proudest achievements — was taking on a maternity cover contract for Conde Nast International. For six months, I was lucky enough to take care of the excellent audience growth team that Sarah Marshall has built there. I hadn’t managed a team for a couple of years or been working in an office environment in a regular capacity for a year or so when I first discussed the contract. This made me doubt myself. I was worried that I’d lose other clients I’d built up as a freelancer by not being available for half a year and I was anxious that I’d have somehow forgotten to lead a team or take on a senior role again.

I am very glad I didn’t let my inner critic take over. I learned so much on that contract, loved being part of a team and office again and reminded myself that I can work as a lone, remote worker and as a senior leader. I’m very grateful to CNI for the opportunity and all the staffers who welcomed this freelancer as she dipped back into office life. (Having a proper Christmas party was pretty nice too.)

Taking on a longer, but still short-term, contract taught me a lot about managing client relationships and boosted my confidence and skills in team management — an area where I have previous experience but which I’d inadvertently neglected as a freelancer.

3. Invest in the plan

This is something I’ve learned as I’ve moved from reflecting on year three to planning for year four. Three years of working for myself have taught me a great deal about my working habits, how to hustle, how to build networks and my professional value. But as hinted at in lesson #1, I’m very susceptible to panic if I haven’t filled every minute of my working week with an assignment or project. While this is good for keeping money worries at bay, it has also meant I rarely step away from the hamster wheel to consider if I’m travelling in the right direction. As I mentioned, focusing on finding enough work can obscure finding the right work.

Thanks to a career development course I’m currently taking called My So-Called Career, I’ve spent some time recently thinking about longer-term career goals. If I don’t make time to invest in these goals, they’re never going to happen. It’s up to me.

This is blindingly obvious, but until now taking an afternoon to work out how I might make one of these goals happen or organising a week according to these ambitions never happened. Three years of freelancing has, I hope, proved I can survive and that’s a lot, but I want year four to be about more. That means setting goals and investing time and energy in meeting them, returning to them regularly and revising them if I need to, and measuring success in more than just financial targets.

It’s strange just how strange this feels, but until now I haven’t replaced the “career path” I was on in my last staff role or the sense of it. I’ve now got the chance to make that track whatever I want. For me, that’s going to involve pursuing some long-held ambitions around creative writing and different forms of storytelling (even writing that out loud feels like a good commitment), so if you are in that field and looking for someone to mentor, buddy up or share war stories with, let me know.

There are lots of people who have continued to be of great support and some specific tools and communities that are increasingly valuable to me:

If you’d like to talk to me about writing or editing commissions, or consultancy and training projects, please do get in touch. I hope this post is valuable to other freelancers — I’d love to hear what you’ve learned in the past year.

The wonderful animations are from ailadi.

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LauraOliver

Freelance journalist, consultant and trainer. Former head of social and community, the Guardian. @lauraoliver