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10 Life & Career Lessons I Learned From Being A Nearly-Failed Freelancer

When embarking on a freelance writing career for the first time six months ago, I had grand delusions of how I would structure my working day. With the freedom of not having to rush in the morning, I’d rise early, exercise, meditate, eat a healthy breakfast, stroll to a café to collect my morning coffee, then sit at my tidy desk and tap away on my laptop for the next eight hours.

Instead, I found myself binging on Netflix well into the night; scheduling unnecessary “meetings” throughout the week; snoozing well into the mid-morning; sitting on Facebook for hours; moving between cafes, libraries, co-working studios and my home office to find the “perfect” working environment (and never finding anything “just right”). The few deadlines I had were met, but this meant that a typical week would consist of, at most, fifteen hours of actual work. Luckily, due to having no mortgage, dependents, or financial strains, it was enough to just get by and pay my rent, but deadline-less self-initiated work — the very reason I quit my full-time job in the first place — fell by the wayside.

I felt like the very worst freelancer. That is, until I started talking and listening to other freelancers in a range of industries and income brackets who also felt as if they weren’t working hard enough, long enough, focussed enough. It struck me that we had all fallen into the trap of applying the flawed 9-5 measures of productivity to freelancing.

In the “real” working world, a typical day in the office is buffered with unnecessary meetings, coffee breaks, and plenty of “busy work,” and faffing is validated by being around colleagues who are also faffing. Speaking to friends in full-time jobs in publishing, public relations, agencies, and similar work environments, many if not all reported they only spend 1-3 hours actually working. If this is commonly the case, why are freelancers so hard on themselves for not filling each hour of the day with productivity?

We all have natural ebbs and flows to our energy, it’s just that working for an organization with set hours and salary means we are somewhat protected from those whims. When you work for yourself, there are no benchmarks for how much work you should be doing — you don’t get paid at the end of each week like you do as an employee. When each hour is billable, procrastinating on Facebook suddenly holds more weight.

It turns out, most freelancers feel like they are the worst freelancer. But comparing our productivity to other people’s (perceived) output without really knowing what’s going on behind the scenes is a recipe for guilt and shame about our own. To banish the smoke and mirrors, I reached out to a handful of experienced writers, publicists and illustrators to uncover the common challenges that are often kept hush-hush, and reveal the lessons that come from the struggle of learning how to best work for yourself. 

1. Take time to adjust

As freelancers, we can be so hard on ourselves, as illustrator Gorkie points out. But really, we need to be comfortable with floundering for a long time. “In any other job, we give ourselves a set time to adjust — reminding ourselves it’s okay, as I’m only in my first six months, or I’m just a graduate. But with freelancing, we expect to hit the ground running and never trip up…But the first year or two is floundering. And necessarily so. You’ve got to give yourself permission to hit dead ends and waste money and be inefficient. You only earn hindsight afterwards. I think in freelancing, we want our hindsight first.”

2. Work smarter, not harder

The trickiest part about being a freelancer is defining your own work hours. As freelance writer and editor of Vault magazine, Neha Kale explains:

The best thing about freelancing full-time — which is the ability to be completely in charge of your working life as well as your creative output — can also be the worst thing. There’s no boss to tell you to take time off to rest, there’s no project manager to anticipate clashes in your schedule and there’s no accounts department chasing invoices so that you can make rent.

But it’s possible to work smarter, not harder. In his book The Productivity Project, Chris Bailey explores what happens to his energy and attention when he works short hours. Turns out your “guilt” is all in your head. “In the middle of my twenty-hour weeks, I couldn’t help but feel guilty that I wasn’t as busy as I thought I should be…even though I was spending a ton of energy and focus on what I had to get done, and I was accomplishing about the same amount of work.”

The lesson? Do your work when you have the most focus and attention. “Learn to invest more energy and attention into your work, so you can get the same amount done in a fraction of the time,” writes Bailey.

3. Have an off-day plan

At a salaried job with vacation days and sick leave, you’ll get paid regardless of whether you took the day off. Freelancing, however, is far more entangled with your level of energy. Fiona Killackey knows too well how this can fluctuate. “I have days when everything feels like I’m pushing peanut butter through a sieve and then other days when work is like water and I’m ticking off every item on the to-do list — and loving it. I’m slowly learning to, where possible, go with my energy.”

On the days her energy is not there, Killackey has a plan: “I figure out three things that must get done, do them and set an alarm so it’s all within the first hours of the day. Then I might take the dog for a walk, go to the gym, do some life admin, or invest in ‘learning,’ which is usually an online course, podcast binge or reading a book in my industry.”

4. Give yourself more time than you need

It’s tempting to set KPIs for yourself as if you were still in the workplace, but didn’t you become a freelancer to escape all of that? Learn to respect your own working pace and the amount of time you need for a task.

“I’ve learnt to accept the fact that my writing work just takes me a lot of time,” says Kale.

“Although I’m still working on this one — not always easy when you’re juggling writing deadlines, editing responsibilities and client stuff — I’ve really been trying to not to overpack my schedule and give myself a buffer so I can really establish the direction of a piece. There’s nothing worse than feeling like you’re on a hamster wheel, rushing from deadline to deadline — although sometimes that’s unavoidable,” she adds.

5. Beware of time vacuums

Freelancers must be weary of a variety of time vacuums, and one such hazard is the internet and social media. Consider switching your phone to airplane mode and turn off social media alerts when you need to focus.

Another time vacuum can be meetings — especially if you have a large commute or find they can be draining on your mental energy. Fiona Killackey suggests setting Skype meetings. “I used to go meet potential clients or collaborators for coffees all the time and it just chews up your day. I now restrict how many of those I’ll do in person and usually ask people to chat over Skype instead. Saves me the transport and parking time and it’s easier to conclude at exactly thirty minutes.”

6. Give yourself permission not to work

Working project to project, or even juggling multiple briefs means that it’s especially important to conserve your energy as a freelancer, explains writer Emily Weekes. “Coming to terms with my own limits and being okay with the fact that I’ll probably never have it totally figured out has been a really lovely thing…Especially after a long project, it can be hard to muster the same flow of energy. Admitting that you’re feeling drained is much healthier and more productive than sitting exhausted at the computer. But then, you have to be able to give yourself permission not to work, which is tricky. I’m still figuring this out.”

Neha Kale agrees. “In the last year or so, I’ve really made an effort to avoid weekend work and allow myself the luxury of being unproductive. It doesn’t come easy to me, and it’s probably made worse by this weird obsession our culture has with being crazy-busy and prolific, especially if you’re a creative person.”

7. Understand the power of a deadline

The adage if you want something done, ask a busy person may ring true for freelancers, explains writer and journalist Annabel Ross. “I find that the busier I am, the more productive I tend to be — I’m sure it’s similar for most but there’s nothing like a deadline, or multiple deadlines, to get me focused and pumping out the work…It can be too easy to bend the rules, whether that’s sleeping in, having lunch with a friend when you really should be working through, or not putting in enough hours.”

8. Remember learning is still working

When you’re working in a company, even a small one, you are automatically learning from those around you — even if it’s learning who you don’t want to be like! “That can slow down when you’re working for yourself, especially if working from home. I put aside an amount of money each month to spend on my own learning, whether it’s a book, course, seminar, documentary bought on iTunes, whatever. You need to keep challenging yourself,” says Killackey.

Allow yourself time to just be in your head, adds Kale. “Whether it’s working on a piece of writing or editing a piece, so much of my creative process involves giving myself the time and space just to read and absorb things — whether it’s magazines, books, art, or the world around me.”

9. Make some financial decisions

When you’re able to scale your income depending on how many clients you take on, or pitches you make, it can be difficult to determine if you are doing enough. Set an income target can be a useful guide, explains Killackey.

“I left a pretty well paid job to go out on my own and I am fortunate to have an amazing partner who encouraged this. That said, I didn’t want to put my family at risk or feel like my decision would leave us struggling financially. I have a 12-month excel sheet with a weekly projected income for myself so I know exactly how I’m tracking week to week and where I need to pick up more work.”

10. Know you’re doing better than you think

Know that you’re most likely working harder than you think. “Most freelancers I know work much harder than they give themselves credit for. They’re always thinking of solutions or coming up with new ideas. That’s half the fun too!” says Emily Weekes.

Know that you’ll simultaneously feel like freelancing is the best and worst job in the world. “Feel like sleeping in a little after having a few too many wines the night before? No problem! But expect a big fat serving of guilt to come with that, and prepare yourself for the icky feeling of chasing your own tail when you let your routine slide,” says Annabel Ross. “When you’re organized, busy, and motivated — as I am occasionally — it’s brilliant.”

Know it’s important to make friends with other freelancers who are the worst. Be good to each other, and be good to yourself. And finally, don’t underestimate the power of a good nap. In the words of Tom Hodgkinson: “A nap is a perfect pleasure and it’s useful, too. It splits the day into two halves, making each half more manageable and enjoyable.”

Madeleine Dore is a freelancer writer and founder of the interview project Extraordinary Routines. She regularly shares interviews, experiments, and articles exploring creativity and everyday life in her weekly newsletter.

  • Tori Dunlap

    This is such an important article, thank you for sharing! Even though I have a 9-5, I freelance on the side, and have felt every single on of these things. As someone who dreams of freelancing full-time eventually, this was a great piece to read.

  • Kate

    Madeleine, seriously, this post is so perfectly timed for me. I left my FT job 4 months ago to pursue consulting/freelancing. I am having great success but continuously think I am never doing enough/being product enough/and that my well will “dry up” very soon. You gave great advice and insight from other freelancers. it’s a HUGE relief to know I am not alone in feeling this way. Thank you, thank you. Would love more posts like this!!!

  • Natasha

    I do volunteer work online and away from home in order to make myself feel like I’m doing my part to better the world and feel like I’m making a more honest effort.

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