The Ultimate Guide To Freelancing

If you spend your days imagining elaborate ways you’d like to quit your job, it might be time to find a new way to channel that extra energy. One idea? Reimaging your career — and figuring out a way to become your own boss.
In the era of outsourcing and social media, there’s never been a better time to freelance. What’s more, the world of freelancing offers a heady mix of pleasures denied to the average 9-to-5er. Afternoon naps! PJs instead of suits! Off-peak gym membership! But, there are some downsides, too: struggling to maintain a work-life balance, a hermit-like existence, and that infernal tax-return form, to name a few. So, before you flounce out of the office Jerry Maguire-style (with or without Renée Zellweger in tow), we suggest you click through and read what the experts have to say.
We’ve asked seasoned freelancers and professional advisors to give us the skinny on what it takes to make it on your own. While being your own boss is tough, if you put in the research, time, and self-discipline, you might just make it work. Read on to find out how.
1 of 7
Felicity Duke, Luxury Travel PR

What do you need to consider before embarking on a freelance career?
“Do you have enough experience in your field? Will you be taken seriously if not under the banner of a bigger agency or corporation? It is important to be confident in your ability and self-motivated. Additionally, you need to be resilient and flexible if things don't work out quite as you planned.”

How can you protect yourself when you make the transition from full time to freelance?
“I would recommend making sure you have finances to support you through the first six months at least. Be patient and take on clients you feel you are genuinely interested in and feel you can do a great job. The easiest way to get new business is by personal recommendation, so always keep that in mind and don't be tempted to take less appealing jobs purely for the money.”

What are the toughest things about going it alone?
“Having no team to work with — both for brainstorming (and reassurance!) and administrative work. Admin is important to the running of a successful business, but it can get pushed aside in favour of more urgent client work. It can be lonely at times, but I try to arrange regular meetings. You have to make an extra effort to stay up to date with industry happenings.”

What is your best piece of advice for someone considering a career in freelance?
“Don't put too much pressure on yourself and enjoy the quieter moments in your projects and take time out! When you're busy you will happily work evenings and weekends, so take guilt-free advantage of quiet afternoons when you can. Whilst it's obviously advisable to have a rough year, two-year, and five-year plan, you do not have to have a firm business plan as a PR consultant. Do not spend too much time worrying about that and enjoy your freedom!”

What practical lessons have you learned?
“Be flexible and open-minded. Consider different projects and seemingly random meetings — you never know where they might lead.”

How do you achieve a work-life balance?
“Very easily! I have relished the shift to working from home. I have an office/shed in the garden, which gives me a sense of proper working space, and importantly, I can close the door on. I have two dogs and instead of a commute I take the dogs for a walk. Not only is it good exercise, but it clears my head and gets me out of the house and ready to start the working day.”
2 of 7

Jade Lisa, Photographer

What do you need to know before starting a freelance career?
“The most important consideration was 'can I afford to do this?' You definitely need to sit down and create a spreadsheet listing all of your monthly outgoings (bills, food, travel). Work out what you could live off, what you could sacrifice, and work out the bare minimum. Get your head around the numbers before you begin and it will make your life much easier! You also need to be good at time management (there is no boss to kick you into gear) and be able to work on your own without company.”

What’s the best thing about doing what you do?
“I absolutely love the freedom of being able to work for myself — I can choose my hours, have a day off whenever I like, and not worry about booking in holiday time off. The most important thing for me is the flexibility.”

Is there anything you miss about working in an office?
“The lack of company and general chit-chat is something that I miss. I've always enjoyed working by myself, but not having anyone to gossip or moan to face-to-face can be a bit of a downer. The amount of admin and paperwork that quickly builds up was also a shock! I didn't realise it would be so time-consuming being your own boss. My to-do tray is constantly full!”

Is there any advice you wish someone had told you before you became freelance?
“Don't get disheartened if you have a quiet period where you spend more time chasing for work then doing actual work. It can be easy to find yourself wallowing a little when work is quiet, and I know that I find myself getting a little self-critical during quieter weeks. It can be especially tough when you are on your own and don't have a team to lean on for support.”
3 of 7
Navaz Batliwalla, Freelance Fashion Editor and Blogger at Disneyrollergirl

What does it take to make it as a freelancer?
“I think you're either a freelance type or you're not. So, if you're someone who craves security and a regular paycheck, then freelancing might make you a neurotic mess. But, if you're a resourceful risk-taker then it can be seen as an exciting challenge. The first time I went freelance, I gave three-months notice so I could save up, put the word out, and get used to the change in my head. It's a whole different lifestyle, from managing your own hours to having to chase commissions and payments.”

What do you love about what you do?
“I love the freedom, flexibility, and autonomy. I combine blogging with freelance writing and styling, so it's very varied and I can switch things up if I find I'm doing too much of one thing than the other. Managing my own hours is a huge plus, as I'm an evening person so I don't have to deal with the morning commute. Being freelance has made me more proactive in approaching my contacts directly to make my own ideas happen. There's a sense that you never know what's around the corner and that's very motivating.”

What was the biggest shock?
“How long it can take to get paid. There will always be an invisible bubble with a few grand in it that you never get your hands on, as you're always waiting to be paid by someone. Freelancers are at the bottom of the food chain it seems!”

Is there any advice you wish someone had told you before you became freelance?
“The reality is that most of my commissions have come through people I know. Word of mouth is still the best method of recommendation, so it's important to put yourself out there and build on your contacts. I love Twitter and LinkedIn for maintaining work contacts, but you can't beat physical networking.”

How do you approach the money stuff?
“I've learned to pay myself a monthly wage and I set aside tax from that as soon as I get paid, so I don't dread getting my tax bill. I'm good with money anyway, but if you're not, getting an accountant will save a lot of grief. It's hard to know what's an allowable expense, but a good accountant who is familiar with your industry will deal with that headache for you.”

What else is important?
“Time management is another crucial skill. I've realised that everything takes twice as long as I think it will, so I now put fewer things on my to-do list, but do a better job of them.”
4 of 7
Kristina Ralph, Makeup Artist

What’s the most important thing you’ve learned during your time as a freelancer?
“You have to be driven and capable of motivating yourself as you really are a one-man band. If you don't get out there and PR yourself, no one else is doing it for you.”

What is the best thing about what you do?
“Working to your own schedule and making your job work for you are the best things about being freelance. Weekends are sometimes nonexistent for me, but I don't mind as I can then have three or four days off in a row. I also love that every job is different and I am constantly meeting and working with new and exciting people.”

…and the worst?
“Chasing invoices is the daily battle of every freelancer. Waiting months to be paid for a job can be frustrating, but this is just something you have to be prepared for and stay on top of.”

What’s the hardest piece of advice to remember?
“Enjoy the times when work is quiet. It will always get hectic again, and you'll wish you had made the most of it.”

How do you get the work-life balance right?
“It's probably not much of a balance! Most of my work is done out of the house, so I tend to be able to relax when I'm at home. I do prioritise work, but I think as a freelancer that's just part of the job. You need to take the opportunities when they present themselves.”

5 of 7
Chloë Carmichael, Forensic Accountant

What do you need to do before you start a career as a freelancer?
“Research your market. I work as a forensic accountant, which is a small world in the city. I knew a diverse set of people who were contractors and agents and I knew where there was work. If there's no freelance work knocking around in your market, you should question whether you can make it work. I set up lots of meetings beforehand and sent out my CV to gauge how I would get work.”

What else do you need to think about?
“What is the minimum salary you could work for to cover yourself? Does that fit with market rates? You’ll straight away get asked about your rate, so you need to have something in mind in advance. And, an eye on paying future bills is always helpful! Also, what level are you pitching yourself at, or are you happy to take whatever's going so you don't restrict yourself? While it's never fun doing a more junior role than you're used to, you might need the work.”

What are the best things about what you do?
“Being your own boss, having a variety of projects and mentors to learn from, and not feeling trapped if you hate it. I was slowly getting bored with my career but now that I'm working with new and different people at my own pace, I find I'm enjoying the work again.”

What are your biggest gripes?
“If you're a very work sociable person, then short-term project freelancing isn't for you, as you are not one of the office anymore. I don't mind it, although being in the office when the rest of the team was at a Christmas do in Miami was quite depressing!”

How do you make sure you’re not working all the time?
“Remember to be selfish. If you can't work a particular day or you need time off, do it — you're the boss. Your client will happily ditch you if they don't need you, so your loyalty should be with you. Also, after many years in the city, I know what ISN'T a work-life balance and I try to stay clear of going there again! Life's too short and precious to be stressed at work.”

6 of 7
Masha Karpushina, Illustrator

What personality traits are important for a freelancer to have?
“Confidence and persistence. But, you have to be realistic, as bills need to be paid. I've often had to take jobs in graphic design or photography to give me a bit more of a stable income, so I could continue to work within illustration. “

What’s the hard part of the job?
“Not having a stable income. Even when I had an agent, the jobs weren't always regular enough. It's good to have some regular gigs at magazines, for example, or having an extra other job within the creative sector.”

How do you make it work for you?
“Time management for me is the most important factor to consider. Without strict discipline, my world would collapse. It is a fine-tuned choreography. It’s about getting your priorities in order. You need to balance PR and networking and then manage the workload. I would say it’s better to do less, but at your best ability. The worst thing is to take on a job and run out of time. You name is on the line. Being loyal and honest is important to clients, but also you must stay curious and not forget that you are doing your dream job!”

How do you master work-life balance?
“It is important for me to be physically challenged, so I run three times a week, most often after I drop off my eldest son. It’s important to be in touch with what is happening in the creative world and to feel part of a community. I run with a group of people called Run Dem Crew. It’s a creative hub for runners, and it has changed my life for the better.”
7 of 7
Rosie Libell, Freelancing Union PCG

What are most important things to think about before making the leap to freelance?
“Freelancing can be risky for some because it doesn’t have the same security of a traditional 9-to-5 job. You also need a huge amount of motivation to put yourself out there, which can be difficult. But, if you are confident about your skills and learn the basics of promoting yourself, it will get much easier after a little practice.”

What are the most common issues that your members face?
“One problem that freelancers face is late payment. In the U.K., the government has recognised this issue and implemented a Prompt Payment Code. While it is progress, the scheme is only voluntary for big businesses to sign up to. A compulsory scheme would be much more effective. From a freelancer’s perspective, there is only a small amount you can do, such as make it clear that you need to be paid within 30 days.”

What are the best bits about freelancing?
“The best thing about being a freelancer is that you are your own boss. It offers total flexibility and you don’t have the restrictions of a traditional 9-to-5. You can decide on the work you choose, when you want to work, and where you work. Because you’re the boss, there’s no more asking for approval, and without the office, the worry around office politics is put to an end!”

What are the practical factors to consider before becoming freelance?
“Freelancing can be a risk, as there is no guarantee of a regular income. But, as long as people are prepared for this, it shouldn’t be a cause of huge concern. PCG would recommend networking on a regular basis as a way of building up your contacts. Also receiving a ‘no’ is not a knock back, and it shouldn’t affect your confidence in your expertise.”

Are there any secrets to getting an ideal work-life balance?
“You’re not restricted to a 9-to-5, so you can arrange your working day how you wish. For example, I recently spoke to a freelancer who enjoys running during the day, so she can schedule her work around her hobby.”

More from Work & Money


R29 Original Series