To hell with clickbait. This, right here, is an old-school, comprehensive, in-depth feature article, based on a whole bunch of hard-earned experience. SEO be damned. This is actually intended to benefit mankind.

Going solo in the Creative Industries (advertising, editorial, TV production, web design, video editing, whatever) is a dream for many of us “creatives*”. Freedom from office hours, status meetings, meetings about meetings and, of course, traffic**!  The freedom to work when you want, to manage your own time and to pursue those fulfilling creative projects of your own… Bliss!

Or, you could face the other side of the freelance coin, which involves uncertainty as to whether the next month’s bills will be paid, no paid sick days, working your arse off trying to get work, and having to chase down every cent you’re owed, sometimes for months.

This is not clickbait. Or I would have divided it into a series of 5 articles, with each tip as a separate page. And, I would have made the ideas insultingly simple, practically useless and as pseudo-motivational as possible. I’ve been happily consulting for more than a year now. My second foray into freelancing. This time has been awesome. The first time (in 2011) sucked, big time. Here are the lessons I have learned…

1. Have agency experience

Whether it’s on a news desk, in a production company, as a photographer’s assistant or (especially) in advertising, it’s important to have worked inside the industry for a year or two at least, before you can serve that industry from the outside. Not only because you need to get to know good people (see the next point) but also to learn industry jargon, internal processes and understand the everyday stresses that you will be called upon to face and/or solve.

Probably the main difference between this time around and my first attempt at freelancing, is having worked in an ad agency. It allows me to work in the ad industry, in TV and radio production, and not just the editorial world, which was my original background.

2. …and make friends.

Before you can go solo, you need to build up a network of allies. As a habit, always stay in touch with good people, even if they’re a lighting-guy you used once for a shoot in another country, a client of a previous agency, or a talented colleague you worked alongside, back in the day. Even if freelance is “just something you’d maybe like to try one day in the future”, start building a list of contacts who can give you work, refer you, or just keep you on their radar for the future.

In short: Be cool. Make friends.

3. Prepare before you leap

Unless you have a large windfall of cash set aside – and you’re prepared to spend it – do not “go freelance” as a result of suddenly resigning in a knee-jerk hissy fit. Firstly, because it’s a lifestyle-change that really benefits from being approached with positive energy and an optimistic outlook. Secondly, because that final pay-cheque will run out just as quickly as those good ol’ debits arrive, bang on time.

Plan the plunge for several months, at least. Start saving. Buy equipment. Chat to potential clients. And, importantly…

4. Talk to those who’ve done it

If you know people who work for themselves – even in industries completely different than yours – pick their brains. Ask for advice, learnings, useful tricks, and stories of triumph and failure. You’ll be surprised how many people are willing to share their story. I’ve told mine in detail to two former colleagues who’ve since gone solo, and some of their questions surprised me in that I’d learned to take the answers for granted. Tax, for example, often features as an intimidating and bewildering “perceived obstacle.”

Like everything in this world, though; once you understand it, it’s fairly easy.

5. Open a second bank account

Before your colleagues even throw you that bitter-sweet, boozy, Friday-afternoon send-off, open a second bank account. You will use this to receive payments, to pay yourself a salary, pay work-related expenses and to keep perspective on how much money you actually have in the pipeline. Not using the new account for day-to-day life transactions will also make any forensic book-keeping a lot easier if, down the line, if you need to go and figure out who paid you for something (or didn’t), and when. Most importantly, this is the account from which you will…

6. Pay yourself a salary

Strict discipline is required here, especially in the beginning. Once you’re established, this needs to have become a non-negotiable habit.
Work out the minimum amount you will initially need every month in order to survive with some level of dignity and a semblance of security. Be realistic, but not greedy. Pay this amount – on payday and not a day sooner – into your regular, good ol’ transitional account (the one your old salary used to land in every month) and do not dip into your business account’s surplus (when indeed you get to the point of having one) no matter how tempting it may seem.

Mark my words: If you try to receive payments from clients, pay your debits, indulge in extras, buy groceries, pay for a night out, pay for a sudden car repair or doctor’s visit (or whatever unexpected costs arise) all from one account, your life will descend into chaos. You will lose track of who owes you and whom you owe. And, suddenly a miscalculation will result in overwhelming stress about how you’re gonna pay rent and medical aid this month. Then you fall behind, and the Cycle of Chaos begins.

7. Start two months ahead

As I’ve mentioned already, you need to properly plan for this lifestyle change. One of the first things you should do is to start squirrelling away money, until you have two months’ of your newly calculated salary-need (see above) set aside. Save this money separately from whatever existing savings, nest-eggs or or investments you may already have. It is its own, separate-entity buffer to start you off. An investment in yourself. If you don’t have the discipline and means to set this aside over time, it’s not a good indicator for managing yourself as a business going forward.

It will, in all likelihood, take at least two months for your client-base to grow sufficiently to meet your initial salary targets (possibly longer), and for the first of your invoices at the end of Month One to start landing in your business account. Some will take longer as a matter of process. Others, because people are often very slow to pay. Be prepared for this or it will ruin your life. Or, less dramatically, just make it stressful and angry all the time. If you’re not at least getting near to your salary targets after two full months, it may be time to re-evaluate your lifestyle decision. At least you won’t have starved in the meantime.

8. Stay two months ahead

This one’s a little personal challenge I set myself. I treat it like an ongoing “video game.” In trying times, it’s a self-preservation mechanism. In times of plenty, it’s kind of… fun. Make it your determined mission to get – and keep – your cashflow two months ahead of your the next payday. In other words, if you’re paying yourself your salary tomorrow, have all of next months’ salary and most (if not, all) of the following month’s arriving, or invoiced out and due.

It’s tricky to get right, it seldom lasts more than a week or two, but it prevents cashflow panic, gives you a feeling of achievement when you’re in the green and (here’s the fun bit) lets you know when you can go and splurge – guilt free – on a pair of Nike Airmax Ones, a bicycle, a unicorn, or – if you’re very responsible – make a nice cash deposit into your unit trust or boob-job/lasik-surgery savings fund. Or whatever. Conversely, when you’ve fallen to only one month ahead (or even less) you know it’s time to knuckle down, tighten the belt and start urgently following up your outstanding invoices.

This one sounds like a big ask, but it’s actually not asking the world. The pay-off is terrific peace of mind and a real barometer for how well you’re doing as a business.

It’s tempting to spend the extra cash, but if you can just get yourself two months ahead, and then spend (or invest) anything above that, your life becomes an exciting, secure place, rich with prospects. All it takes is two months’ worth of discipline and extra-hard work.

9. Live in the green

A quick addendum to the above point: stay away from credit. Well, at least in as much as you presently do, anyways. It’s not my place or business to pontificate about how to manage your credit card/s. Just treat it as you probably presently should – as a buffer against your regular, on-the-25th, monthly salary. Don’t use it to bankroll clients who are late for paying you, to pay your fixed life expenses because you’ve fallen behind the salary buffer or – worst of all – to live off permanently with your incoming payments merely servicing a permanent, negative cashflow.

I tend to use my credit card to occasionally make up a four or five-day cash shortfall at the end of each month, when my day-to-day account hits zero. I then pay it back on payday, from my salary. I could just use my business account to “lend” myself money when I fall short, I suppose. My way works much better for me psychologically, though. See, I’m not some super-responsible, financial Bhuddist or anything. I’ve just done it the wrong way before and suffered the endless cycle of misery and worry. This approach makes my life suck less. A lot less. Plus, this way, your emergency credit is actually there in the event of a real emergency.

Freelancers should, the vast majority of the time, rely on less on credit than employed people. Not more.

10. Have a routine

So far, I’ve focused a lot on preparing for “the change”. Then I shared my methods of managing the financial differences. Now, I’ll look at some of the lifestyle leanings that have benefited me. Or bitten me in the ass, as the case may be…

Yes, working for yourself should mean having a bit more flexibility, time-wise. You wanna work until 3am and then sleep in until 11 the next morning? More power to you. But it really helps if you find a ritual you can stick to nine working days out of ten. It keeps you in sync with the rest of the world and the rest of your industry. It gives you a sense of organisation, purpose, and direction. Descending into what feels like a “permanent holiday” quickly leads to self-loathing, inertia and financial panic.

Even if it involves catching the morning sports highlights on Blitz every day, checking through 9Gag and then reading the news headlines online before sending out emails, have a more-or-less consistent expectation as to what tomorrow’s flow will be like. Remember; your job is to be executing work. Or, looking for it. It’s fine for a day or two after a series of intense (and ideally, lucrative) deadlines, to park off and feel good about your life.

But, generally speaking, having nothing to do is the last reason you should have for doing nothing.

11. (Physically) Go somewhere

This one really helps me. Staying cooped up inside the home office can do your head in. You end up spending days in your pyjamas, living in a very small, isolated world. My work sometimes has me in my home office at length. Usually, I’m fortunate enough to regularly revolve around a few other clients’ premises with people I know that work there. But, whatever happens, I get up, go to gym, dress for facing the public (as I would have done at my old job) and then come home or head out into the world.

Maybe going to the nearby coffee shop for an orange juice and a toasted sandwich is more your speed. Great. Just add to your day, a place where someone will notice if you don’t arrive for a while. Even if you just leave for half an hour and then go back home again to work.

12. Don’t be a slob

A follow-on to the point above… Grooming and general upkeep is not just about impressing others, it’s also for the benefit of your own self-esteem. Plus, freelancing means clients, who will often require meetings – in person or on Skype. Be presentable. If you – like me – are not the typical “corporate-looking” professional, that’s fine. I have a million tattoos (many of them of skulls with stuff carved into their heads) and I dress a bit like a white rapper with a sneaker fetish. I’m not rocking ties and chinos. But, my clothes are always clean and pressed, my hair is always neat and my sneakers usually match my shirt. Helps me walk into a room (even if it’s my own home office) with my head held high. And that’s half of any battle won, right there.

Don’t look like a stoner student unless you’re happy to be treated like one.

13. Get the best Internet you can afford

You should be able to run a relatively lean shop as a freelancer. Whatever equipment you need (more for photographers than art directors, more for art directors than copywriters, and so on) will require a capital outlay. Obviously you need a premises. After that, though, your overheads should be low and you should try to keep them that way.

With that in mind, don’t skimp on your internet. Get the best damn internet you can afford. For the sake of your sanity, your quality of life outside of work (“needing” good Internet is a perk unto itself)  and, especially, Skyping and sharing large files. The difference between a 4mb line and a 10mb is a few hundred bucks. And, a great deal of happiness. Plus, if that expense the difference between sink or swim, you have bigger problems than download speeds.

PS, also try have a back up. A dongle and a small data bundle is super-useful if you work on the road or you ADSL goes down.

14. Do not fear learning

The more you widen your skill-set, the more employable you become. Working in and around different offices with different staff members will mean exposure to different methods and talents. If you’re asked to join for a presentation, go. Watch how different seniors handle presentations. Pay attention to how different clients brief you. Who does it well and who doesn’t. Keep an eye on the parts of jobs you’re not executing. Pick things up and make mental (or actual) notes of them.

You’re probably going to see a lot more people do their jobs than you would in an agency. Learn from the good ones and the weak ones alike.

15. Don’t be enslaved by your specialisation.

In big agencies, people are often placed at a desk, set to a task, and “shielded” from other aspects of the process. The logic is something along the lines of, “You just sit there and focus on what you’re good at, and don’t bother with all that other ‘business’ stuff… We’ll take care of that.” The other way to look at it is, “You just sit there on your conveyor belt, and get better at that one thing, churning it out until you hate it, but become dependent on it as the only thing you can do.

You’re creative. Good at it. But you also exist in a business context. A “suit” cannot learn creativity. But anyone can learn basic billing, client service and traffic. I mean, literally anyone.

The difference between those creatives that become all-powerful bosses and designers (etc) who just design forever? Learning to understand the other junk.

16. Be a solution

You’re there to solve a client’s problem, not to add new ones by pointing out all the problems with their situation and the turn-around. They wouldn’t have called on you if they could handle it in-house or the job was simple. If the job is too big (or the pay too small), say no. Otherwise, get them what they need, when they need it, and do it well. Take the job in your stride, or make it look like you did. That way, the client will mark you as the solution to their problem and continue to call upon you in future. Problem solved!

As my friend and former CD Mike Cook (now co-owner of Workbench – check them out, they’re awesome) once taught me, “Understand their stress.” All a client wants from you is something they no longer have to worry about. Don’t be difficult… Be a solution.

17. Be available

When I started out, a very clever dude called Brad Dessington (head honcho at Rogue Agency and, incidentally, husband of my awesome former work partner and current Art Director of preference, Beth Dessington) took the time to give me some advice from the perspective of a person who frequently hires freelancers. One thing in particular stood out to me. “Be available.”

What he meant was, either take a job and say thank you, or – if you really can’t manage it – politely decline. Don’t accept it, but then go on about what a nightmare turnaround it is for you, how busy you are, and how “helping them out” is a huge ball-ache. That’s why they’re calling on you; to relieve their pressure, usually in a hurry. Plus, they really don’t care. If you can do it, just do it. That way, after eleven jobs, when you do eventually have to explain that you legitimately can’t meet their deadline this time, they might find the extra two days you need because
(A) you don’t bitch for nothing, and
(B) you’re their go-to guy and they’ve come to depend on you.

18. Clients = good

Here’s something that will blow your mind if you’ve done time in a big agency… clients are good! They mean income, relationships, new leads and – if you make them happy – more work! In an agency, you have to do whatever comes your way and you get paid the same every month. Of course you’re going to hate the committee of accountants that want you to make the logo bigger.

You’re no longer going to be fed work that more or less suits your skillset on a steady basis. Now, you must seek work out. When you find it, present as much value as you can. If you hear your client mention a challenge or a need that you can help with, say so. If you spot a place where the campaign can be better, politely suggest some ideas. If clients like you, you get work. If they don’t, you don’t.

Plus, when you go in with a smile, you’ll find they’re usually just pleasant-enough people. Looking for someone to smooth something over for them. Be that guy.

19. Retainer up!

The principle behind finding a good retainer is a little like dating someone with whom you have really good electricity, but without having to live together, nor commit to any of that pesky monogamy business. If you find that one specific client keeps you nicely busy, treats you well and has come to depend on your because you do a good job, strike up a retainer. They commit to a set amount of pay each month, you commit to a certain amount of work. If they don’t have quite enough for you in a given month… goodie for you! If it’s slightly more work now and then, take it on the chin (erm, I’m no longer referring to the dating metaphor, btw) and do them a solid. When it’s considerably more work, you agree on a pro-rata rate that benefits everyone.

In an ideal world, a good retainer client should bring you at least half your required income in one third of your available time, or less. Then, you can roll the dice with the rest of your time, knowing that the rent, medical aid and cat food will at least be covered each month. For freelancers who prefer security, two or three manageable retainers can mean a greater income than full-time employment, with a similar workload, minus the 8am status meetings.

20. Market yourself (I): be a brand

Build a website. Design (or commission) a decent CI. Make up an impressive-sounding title and get some business cards professionally printed on decent paper. Write articles and blogs on your field of expertise. Post your work online. Make a fancy-looking email signature for your non-schmoe email address.

It’s a mission once. Then you look legit forever. Be your first client. Take the brief seriously.

Then, mail your network of friends, former colleagues and clients and let them know you’re available and, critically, what it is exactly that you do. Include a call to action asking when it would be convenient to meet or Skype. Then follow up. A face-to-face is so much more effective than a lone mail. My CI was designed by Denton Pretorius at Indent.
Hint: when you do talk to your client, ask them all about what they’re working on. They’ll talk. You’ll learn. Boom! A relationship!

21. Market yourself (II): reach out daily

Felix Kessel is a very clever man. He once told me, “No matter how much or how little time you have, do something to market yourself every single day. If you’ve got some time, put together a presentation or create new content for your website. If you’ve got no time, send out one introductory email to one potential client.”

Spread the word far and wide. If no one knows you’re out there, no one will hire you. Simple as that.

22. Try to agree on per-project fees

Per-hour billing is the industry norm. And, while you can take every measure possible to be as ethical and accurate as possible, someone’s always going to lose out. You, or the client. If you have to stare at a wall stressing your tits off because you can’t crack a brief, only to crack it ten minutes before you present, why should that cost the client more? If you crack it with the best idea you’ve ever had within minutes of taking the brief, why should that pay you less?

Try to agree on a project fee upfront for the work to be delivered. Base this fee on an hourly-rate estimate, if that makes the client happy. Give yourself a little wriggle room without ripping the client off. Then, if you work extra-fast, good for you. If you end up pulling a week of all-nighters, not the client’s problem. You have a deadline, you know what needs to be done by that time, and you know what you’re going to earn. Easy peasy.

23. Learn tax

Tax, like everything else in this life, is only complicated until you understand it. Then it’s simple. Anyone capable of doing any kind of quality freelance work is, by default, competent enough to handle the fundamentals of income tax. I used to be terrified of it. then I had to learn it. Now I wonder what the fuss was about.

Get a good tax person to do your returns each year (should cost you less than ZAR1000 each year) after you hand over all your expenses. It’s simple. Basically, you pay income tax on whatever you earn, minus whatever it cost you to make. As a freelancer, there are loads of things you can claim as an expense to lower the amount of income you pay tax on. Restaurants, computer stuff, travel… heck, even rent if you work at home.

Do it. It’s money you don’t pay the government. How can that not be awesome?

24. Hook your homies up

Throughout your career, you’ll meet and get to know people who are rad and talented. When you need a contributor or collaborator, or one of your clients is looking for a good person to do something that isn’t your territory, you’re too busy, or it’s dog work that you don’t want (but a promising junior you know could really use) hook them up. It builds networks, makes you a valuable source of resources to your clients and, importantly, comes back to you eventually.

People remember your vibe far longer than their (or your) jobs last.

25. Skype

Have a decent internet connection and get on Skype. It makes long-distance meetings far more personal than the phone, and enables you to work with clients far away. Use it, get your clients onto it, make it part of your life. It’s also great for combatting work-at-home cabin fever.

26. Follow up

Such a simple thing that makes such a difference. When a job is done, mail your client a week later and ask how it went. Ask how their other accounts are doing, how they’re doing, and send them a useful link to an online story you saw that made you think of them. Think of it like dating; don’t just get what you want and disappear. Between delivering work and chasing up your money, check in with your clients. Being top-of-mind and building relationships is worth the effort.

27. Charge what you’re worth

Too many freelancers make the mistake of trying to build up a client base by taking work on risk, undercutting their fees or agreeing on whatever is offered, no matter how insulting.

You sell time and expertise. And no amount of the latter creates more of the former.

You’re worth what you say you’re worth. Clients will never pay you more tomorrow because you worked for less today. Don’t make the mistake of charging the minimum amount per hour that you need in order to just scrape by if you’re working 14 paying hours a day, 31 days a month. Because you won’t be. And even if you do, it will kill you.

Being cheap doesn’t make you desirable. It makes you cheap.

28. Never work for free

An add-on to the point above: Doing work “because it will lead to more work later” is not a good strategy. It’s insulting. It’s exploitation. It’s even theft. It’s why there’s so much garbage work out there and so many garbage creatives undercutting everyone else’s prices.

If you want to work for free so you can “grow”, do yourself, the Industry and the world a favour and go get an internship somewhere that will teach you a great deal.

29. Reverts

Agree upfront on a number of reverts with your client. My brilliant friend and long-time collaborator Beth Dessington (check out her magnificent Art Direction stuff here) taught me this one. We offer clients a two-revert system, which we stipulate in the brief. It goes like this…

When you present your idea and plan to your client, they must sign the plan off. Then, you start on it, mock it all up and show them your direction. They can make changes in direction at this stage (that’s Revert One). Then, when it’s done, they get to look at it and make changes (as long as it’s not stuff they previously signed off – no “changing their minds”) again (that’s Revert Two). Then you hand the work over.

Any additional changes beyond these reverts (or “mind changing”) are requoted and treated as a new job, with new fees.

30. Be a team player

Going solo does not necessarily mean working solo. Of course, there will be long hours of solitude. But, you might find yourself working with more people than before, as you move between and touch base with a greater number of businesses and their internal teams. Be helpful, be friendly, be social. Don’t sweat the small stuff or count the minutes when it comes to your regular clients. They don’t “own” you like they would a salaried staff member. That doesn’t mean, though, that you shouldn’t go the extra mile or take the odd one for the team.

31. Invoice. Hard.

I’m crap at this, still. But I’ve devised a system. You need to invoice for the work you’ve done quickly and systematically. It feels a little needy to invoice the second you hand over your work. Put a reminder in your calendar to invoice for a job one week after it’s done, and then do it. Otherwise, you’ll put it off until you badly need the money for the work you’ve done, at which point you’ll send the invoice and immediately become needy and irritating about trying to expedite payment.

Companies usually 4 – 8 weeks to pay. Sometimes longer. Deal with it.

32. Timesheets

The very mention of the word draws the kind of hatred and seething disgust from a creative that is usually reserved for kiddy-fiddlers and bank managers only. I’m not saying you should install Chase onto your computer and spend hours a month trying to account for all the hours you spend working, but keep a list.

Write down what you did, for how long, for whom, and when. Otherwise, when you get behind on your invoicing (which you will) trying to forensically figure out what you were doing a month ago will not only be  pain in the arse, it’ll also jeopardise your ability to be honest and fair and, with that, potentially ruin relationships.

33. Lists win wars

There is nothing more powerful in the freelancer’s life than a regularly updated (and then mercilessly whittled-down) list.

There is great joy in being free of nagging account managers and soulless traffic drones, but there is also a great potential for chaos.

Do what’s important, and what might feel like it isn’t. Set a to-do list. Allocate time periods to the things in it. Do them on time. Work late if you don’t. Then have a good think before making another list. Lists win wars. It’s that simple.

34. Have background projects

What’s the point of struggling for your freedom if you’re not going to have time to do some things that you love? Agencies will always tell their creatives to enrich themselves creatively with outside projects, then keep the same people chained to their desks until whatever-o’-clock every day.

Allocate time to yourself. Create. Make stuff. Have fun. Go to galleries. Sing songs. Spray-paint trains. Whatever. Doing what you love is the whole point. Give yourself the occasional brief and then see it through.

I for example, like writing really long, overly detailed articles…

[THE END]

*I hate the term because it uses an adjective as a noun and is inherently poncy, but I have conceded that it’s a battle I shall not win. Sigh.

**Those readers in advertising will shudder at the mention of the word. For the rest of you, suffice it to say, it’s an agency thing; even worse than the kind you get on the N1 Johannesburg between 7 and 9am.

For more articles dealing with freelancing tips and advice, try:
– How to Work Out What You Should Charge as a Freelancer
– 8 Little Things That Keep Your Clients Loving You
– Hiring Independent Consultants: Skip the Hive & Go Straight to the Honey
– Tips for Unblocking Writer’s Block (from a Guy Who Writes a Lot)

A little bit about my experience with this subject…
(I tucked this bit away at the end, in case no one cares)

I’ve taken the freelance plunge. Twice. The first time was when I left FHM at the end of 2010, after 8 years there. My first and only job from my varsity internship until I was 29. For all intents and purposes; a lifetime.

Going freelance was essentially an experiment to see how slowly I could whittle away all my meagre savings, while working harder than I’d ever worked. Most of the time, in a gruelling, ironic effort, trying to “earn” paying work. It lasted about 14 months and was, in retrospect, the most stressed I’ve ever been in my life, even if my friend Dale Imerman and I did make some work I’m pretty proud of on our website, Mojodojo. Check it out here. When I was offered an out-of-the-blue  job at an ad agency called Owen Kessel, I took it.

There, I was a senior copywriter. Soon, a Creative Group Head and, ultimately, a Creative Director. A rich but punishing experience, packed with learning and some wonderful people. But I never quite got used to having my diary managed (and not always efficiently) by someone else. I just don’t like office hours – especially the advertising variety.

Early in 2014 I quit my job and became a Creative Consultant. A fancy way of saying, “I went freelance.” And it’s been great.

The article above is about some of the things I’ve learned along the way, that have made all the difference between 2011’s nightmare and 2014/15’s far more successful incarnation.