In an interview on In Good Company, author Otegha Uwgba’s culture and ideas podcast, Ann Friedman, a pioneer of the digital newsletter and one half of the wildly popular podcast Call Your Girlfriend, talked about her freelance career having different stages.
She described what she called her “flailing years” where she hadn’t found her feet and was without focus, before she became a Limited Company and started perceiving herself as a business. Next up she tried different things, wrote for different people, worked with brands, jumped on the very lucrative American speakers circuit, and most recently she co-wrote a book. Now she’s back to streamlining her efforts into fewer directions.
The conversation made me consider the stages of my own four years of freelancing, which, if I’m honest, still feels like “flailing” (a feeling, I’m convinced, that never truly goes away). Yet listening to Friedman helped clarify something. I realised that it was precisely the different phases of my freelance career that had kept my freelance candle burning. And I was particularly struck by the idea that I wished someone had made that clear to me when I started out, that someone could have dropped this podcast into my lap four years ago. And so I’m hoping to share hard-earned lessons with as many people as possible.
When I left a staff job as a senior editor on a woman’s content website, I thought I was a one-trick pony. In fact, I only wanted to be a one-trick pony. I wanted to write about women. And nothing else. But this tunnel vision was naive and unhelpful. I have learned, embarrassingly late in the game, that agility, developing new skills, entering new stages and broadening your business offer is essential to a happy, healthy and secure freelance life (and I still get to write about women).
A former colleague once said to me that to succeed in the internet era, we need to be more like Madonna – a reinvention machine. I don’t think that you need to reinvent yourself, but you do need to expand your empire, find those other strings to your bow, be ready to jump when the next stage presents itself, and in a Madonna-esque way, learn how to keep you and your skills relevant.
So, how?
- Try things you think you can’t do – you probably can
2020 ushered my freelance career into a new stage. When journalism budgets were slashed, I reached out to a charity I had a relationship with. Soon I was writing their reports and consulting on communications. I only did this because the pandemic forced me into a corner, but I had long thought about potentially pursuing this line of work. I hadn’t done so previously because I hadn’t needed to, and, more honestly, I had doubted I could. Don’t make my mistake: tell those questioning voices in your head to pipe down and don’t wait til your back is up against the wall. Think of satellite sectors of your own; industries which demand the same skillset or speak to another line of your interests and start reaching out now. The more connections you make, the easier it will be to find a way in.
- Do things you think you don’t want to do – you might be surprised.
Reality checks are important, not least when embarking on a freelance career, and especially with so many Insta lifestyle accounts making the whole process look so easy. For the majority of freelancers, behind whatever they’re showing off on social media, there is bread and butter work that pays the bills. No, it may not be what you spent three years at art school for, but having a source of income that takes away financial stress can be the most reliable ticket to having the capacity to do the work you love. Besides, you might surprise yourself. Even the most soulless of jobs I’ve taken on have proved useful in some ways, forcing me to think differently, make a new connection, or understand a different sector.
- Nothing is forever
That dream client of yours, the one who is giving you all that nicely-paid regular work, could call time on the project tomorrow (it happens, trust me). Equally, when you take on bread and butter work you’re not completely sure of, and definitely not proud of, don’t feel that this is an all-defining career move. It’s simply a side step, or even a building block to strengthen your offering in the long term. It doesn’t mean you’ve given up on your dream. It means you’re working hard to keep that dream alive.
- Sell your skills, not your passion
My freelance career went from flailing to a steady trot when I sold myself not by my passion (women’s rights) but my skills – writer, copywriter, and communications expert. This means I can approach numerous sectors for work. If you’ve already built up connections in your chosen area, start thinking about your skill set and how to get more experience of the same skill but in different sectors. Pitch or apply for things that may seem out of your comfort zone. (See 1 & 2)
- Invest in your mindset
A crucial way of accessing the next phase of your career is shifting your mindset. Friedman spoke at length of how the sense of ownership of her career altered how she worked, taking her from failing freelancer to self-employed professional. My freelance career got much steadier when I accepted that other types of work didn’t change my identity or negate from my career path to date. If you want to attract more clients, start thinking like a business. If you want to broaden your network, start pressing send on emails you hadn’t dared to before. Plan for your stages. Consider what you’d like them to be. Review them. Update yourself on your progress. I’ve started having business development meetings with myself, and lo and behold, I’ve had a good stream of business lately.
Understanding that a freelance career may not be a linear trajectory, focusing on just one area of expertise, is crucial because it will help you lay foundations for a healthy, steadier and more robust freelancing future. Embracing different phases, and preparing for the next, will also help you focus on where you need to put your time and energy in the short-term to achieve those long term goals.
