Going Freelance: The Journey So Far

9 months in, I break down what’s going to plan, the feelings and anxieties, and finding my place in the world of freelancing.

Olly Browning
5 min readJul 18, 2019

For someone who gets anxious pretty easily, going freelance and starting a company certainly hasn’t been the easiest (or necessarily the smartest) challenge of my career. Despite what I’m about to share, please know that working for yourself absolutely is exciting and worth all the risks you hear about: I love the way I work now and the focus it’s given me on the actual work and deliverables — rather than the sometimes toxic feelings of hour-filling or ‘work hard play hard’ like I’ve experienced grafting in big ad agencies. I feel like my knowledge and experience is appreciated more. I adore the brand I’m building and the work I’ve done under it. And I’m sure The Good Bits are something I’ll write about more in future, but right now, I wanted to focus on sharing the bits of freelancing I hadn’t expected, so whether you work for yourself, are planning to, or just curious about it, we can all start being more honest and transparent about our careers and ambitions.

I’ll also admit: I’m not in my chirpiest place personally right now. Financially and operationally things at the company are fine & dandy, but from one day to the next I seem to oscillate between feeling [and pick any of the following here]: depressed, elated, smart, foolish, wealthy, penniless, motivated and bored. I’m particularly in the ‘bored’ subset right now, and I think I’ve landed on the reasons for why.

1. Overambition, imposter syndrome and creative frustration.

I’d always intended for going freelance to be a chance to explore my other ambitions under the ‘creative’ banner — not just graphic design but also more writing and more media work. I’ve also always known that Mighty Oak wouldn’t just be ‘a creative agency’, but a production house and a home for all of the weird ideas I get — because I know, somehow and at some point, they’ll add value for someone.

The problem is, these new avenues don’t always pay… yet… nor do they pay big. I’ve often found myself getting frustrated that “x hasn’t happened yet” or feeling like I’m resting on my laurels by not taking more risks. Which is when I have to step back and remind myself: it has only been 9 months — it’s unrealistic to think my career is going to change in that time. Sometimes, sticking to what you know isn’t always the most fun route, but it’s also the route that pays the bills. And that’s no bad thing, as long as you’re conscious of it.

On the other hand, it’s also where the imposter syndrome kicks in. “Well, I’ve never been a staff writer before, so I’m anxious about pitching this editor.” “I’ve had a killer idea for X brand but I’m afraid to pitch it because I’ve not done a massive campaign under Mighty Oak yet”. “I’ve never been quiet about the fact it’s just me in the company, but does that mean I don’t deserve to work with big clients?”. Even writing this article triggered a bunch of anxieties: am I publishing it in the right place? Is it going to be too long? Too personal? Too cynical? I don’t know. But what I am learning, is:

Done is better than perfect. I say it a lot and I believe it entirely… it’s just really hard to follow through with it sometimes, especially when you’re a perfectionist.

2. Charging too little.

Not going to linger on this one too much because I think EVERYONE starts out cheaper than they should be. I know it’s partially because you want to get clients through the door, but it’s also (as we’ve discussed) out of… fear.

When I started out, I had the (maybe naïve) idea that I would give every client the same fixed day rate. No project pricing, no hourly rates, just one price for as long as you needed my help. It was my way of being as democratic as possible: a fixed day rate both startups and big businesses could afford, and as long as I filled up my calendar every month I could cover my costs and pay myself okay. It didn’t work like that. Firstly, I love project pricing now (it gets both you and the client on the same page, focusing on the deliverable), and I’ve learnt no two businesses are the same: startups might need more support writing a communication, and big corporates might just want to get something out the door — treating it like it’s the same thing, or something you can just fix by prescribing time to it isn’t the right way to think about it — for either you or the client.

Also, you’re not always going to fill your calendar. That’s just the reality of freelancing. You spend more time than you think writing lovely emails to clients, invoicing, accounting, and coming up with all the ideas in the first place, and that’s something you deserve to compensate yourself for too. I’m now learning to really objectively think about the task/s at hand, my relationship with the client, and the value I’ll be delivering for them — and when I frame it like that, I suddenly feel a lot less vulnerable and a lot more secure in the rate I charge: no big-agency bucks, but a fair market price that’s enough for me not just to cover my costs, but earn a living from and grow personally. Charging too little or ‘just making enough’ is devaluing your work and punishing yourself for doing the work that you love.

RELATED READ: Hourly Billing Is Nuts by Jonathan Stark, a great eBook to get you thinking about how you value your work, recommended to me by the ace

. Link here.

3. Holidays=necessary

Finally, since going freelance, I’ve been a lot more reluctant to grant myself and my brain any time off — I made myself believe it was unproductive and too expensive to allow myself any sort of extended break.

I’ve since learnt that holidays are NECESSARY for that exact reason; sometimes “not having to think” is a good enough excuse to blow everything else off. So I’m really glad I recently booked myself an impromptu trip to Seattle; I was feeling burnt out with work, the flights dropped in price, and I was lucky enough to have a great friend I could crash with, so it all felt rather impromptu but also quite necessary.

Going away didn’t quite give me the career focus I was hoping for, but it certainly taught me to start worrying less, apologising less (no more “sorry to chase you!” emails), and forgiving myself for taking time out. I still miss Seattle and the incredible breakfasts I had in America, but I can tell you that booking a holiday was 100% worth it and hugely recommended — even if it’s just an escape to the country or something.

I’ve come to the conclusion that choosing to be a freelancer is choosing to enter a life of double-edged swords. Sticking to what you know vs. being too ambitious. Having faith in your work vs. second-guessing your skills. Desperately wanting to do some work vs. pitching for it in the first place.

And that’s no bad thing. I just think it’s one we’re better navigating together and being more open about. Onwards and upwards.



Olly Browning

A freelance writer and graphic designer in London. Follow me on Twitter @yourolly.