When I started freelancing, it just seemed so obvious.
Small businesses are everywhere – and most of them need things written. So start here, pay your dues to earn money and experience.
When you’re finally ready to go head to head with the top dogs and high rollers, you can step up to working with really big companies, where all the money and prestige is.
In the years since, I’ve written website content for everyone from global technology companies to solo tradesmen. It’s slowly dawned on me that this initial assumption wasn’t merely off base…it was totally, diametrically wrong.
I’m coming at this as a copywriter and content marketer. If you write something very different, like journalism or fiction, maybe not all of this will hold. I think this will be broadly similar for many of you though.
Here’s what I’ve worked out so far:
Smaller Doesn’t Mean Easier
When writing for small businesses, here are some of the colourful characters you can meet:
- Total Newbies: Small businesses often haven’t worked with writers much before. They’re coming in unprepared, aren’t sure what they want and don’t even know what it is they don’t know. This means they really benefit from working with someone who’s been around the block a bit, has the confidence of experience to take charge and lead, and has systems and processes set up and ready to go.
- Cheapskates: Some entrepreneurs go around lowballing freelancers when they really need the work of an agency.
They just don’t want to pay agency rates.
- Ambushers: New small business clients also come up with eleventh-hour plot twists, when you thought your work was nearly done.
They might at this point disappear from contact for several months, without explanation, regardless of whatever is in your agreement. One electrician once even told me he wasn’t sure he wanted to go ahead with the project, having totally forgotten that he’d already paid for it.
Or they might suddenly involve a relative, spouse or good friend who has a whole new set of requirements and a veto over the project. This person might not have actually done what you did before but is thought to be an authority on writing because they’re an aspiring novelist or an English teacher.
Somehow you have to defuse this without anyone losing face, without massively blowing out your hours, and without destroying the quality of the work. This requires every ounce of diplomacy.
- Diamonds: Along the way, you also find hugely talented entrepreneurs running small businesses who will set you up to do work you’re proud of, pay what you’re worth, and teach you things along the way worth even more than your fee.
The point here is not to trash talk small businesses or scare you away from working with them. Just stop seeing it as the only beginner option.
With big clients, you report to someone who has worked with writers before. It might be all they do. This means they have a much better idea of what to expect from a relationship, making it easier for you in turn know what to expect from them.
Bigger Businesses Give You Different Headaches
Larger businesses are easier overall, they do present difficulties all of their own.
When you’re dealing with a really large team, projects have a way of stalling while you wait for answers. Your contact person won’t always have everything at their fingertips and will need to liaise with their team or their client.
Project managers and marketing directors also don’t stay in their roles anywhere near as long as small business owners. You’re having to re-establish that working relationship all the more often. Sometimes this means a great client becomes just a good one. More often, it just means rehashing conversations you had six months ago.
Some non-disclosure agreements out there are very severe, to a point where you can’t tell anyone about the work you’re doing.
Finally, the size of the client doesn’t always correspond to the size of the payday. These much larger budgets have to be split in so many more ways. There’s still scope to write some big invoices, but it’s usually by putting in many hours to provide a volume of work.
Landing Big Clients is Actually Easy (With the Right Positioning)
With all the big agencies elbowing each other out of the way to handle big brands, how would little old me even be noticed?
It turns out that big clients don’t just launch large projects, they do lots of little ones all the time as well. On top of this, the big agencies who take on big jobs look for freelancers to fill in skill gaps too.
But here’s the thing: small businesses often seek freelance writers for fairly general requirements. They need a flyer written, or an email sequence, or better visibility on the search engines. Big businesses tend to be already able to handle all of that in-house or with existing relationships.
They’ll seek you out for much more specialised needs. They might want someone with a special understanding of a particular topic, audience or industry, or who really know how to work a particular platform, ad network or online community.
For me, big clients started sliding in my inbox far more often when I started properly positioning myself as a copywriter who understands computers. After adding this page to my website, the search engines did the rest.
You’re no doubt unique in a different way. Stop trying to be all things to all people, focus on the place where you add the best value, and they will come.
It’s usually no problem to get small businesses to sign a copywriting agreement (you do have an agreement, right?). On the rare instance they don’t, this is probably a cause for concern.
My agreement requires upfront payment before work starts, with the rest payable within 14 days of delivery. There’s also some wording in there to stop them from sitting on the revisions indefinitely. This is great for cash flow.
Some large businesses will sign this too. More often though, they have their own contract. You’re dancing to their tune.
When the pandemic hit, I got through much of it by writing for a large agency handling an even larger electronics giant. They offered 45-day terms, which isn’t great, but some places will say 90. Because I couldn’t invoice until after the work was accepted, 45-day terms mean it’s more like 60 days until you get paid.
Even worse, some big businesses see the terms they agree to more as a suggestion than a binding obligation. 45 or 90 days might just be how long you have to wait until you can start making a polite fuss and hearing excuses.
With this kind of terms on offer, if you don’t have a cash buffer, that’s months of belt-tightening, giving the credit card some exercise, and stressing out more than is ideal.
There’s also the maze of vendor portals and payment systems, each of which different enough that they have to be learned separately, and will then totally change in a couple of months.
For all these frustrations, I’ve never had a big client try to skip out on payment entirely. They always pay eventually.
Most small businesses are honourable too, but the other kinds do exist: the ones who go all quiet when it’s time to pay, and the charming sorts who use a stack of unpaid bills to get something more out of you.
For more, check out 5 Ways to Manage Freelance Billing Like a Professional.
Feast and Famine Cycles
All freelancers deal with lumpy income, being really reliant on a single large client can make this severe.
It all starts when you land a client who loves what you do, has a budget and wants as many hours as possible. Of course, you want to make them happy and make hay. You become very busy.
The first thing to go is whatever marketing activity you were engaged in. Whether that’s speaking at events, involving yourself in forums, SEO activities, whatever…it’s all on the backburner now. It feels easy to justify this because you’re busy already – perhaps too busy.
You’ve also got a lot more money coming in, so you start bringing forward all those expenses you’d been putting off.
But at some point, there’s no work left in the pipeline. The longer you went neglecting your visibility, the worse this is. It takes time to ramp things back up.
If another big client comes along in the meantime, you’ll likely latch on to it and do it all again. This is a cycle where you can grab a few big paydays every so often, but you never build beyond that.
Managing this is more a matter of maturity and emotional discipline than of any hard skill.
The rule I now follow is this: no matter how much client work I have, I will always set aside at least one half day per fortnight for some unpaid project that grows my business.
That’s not the only way to approach it. Just be sure you don’t become so busy working on your client’s business that you forget your own. Otherwise, you might as well be an employee.
Which is Right for You?
Large and small businesses present different opportunities and different challenges.
Big businesses tend to be easier to manage, can keep you busy for a while, and people seem to be impressed when you say you have done it.
Ultimately, though, you’re just another cog in a very big machine. No matter how well you write something, it’s probably not going to add 50% to an already gargantuan business.
Small businesses force you to be good at much more than writing, and you will need to manage many more relationships. If you can make this work, though, this can be where you build your biggest success stories and most devoted fans.
James Mawson is a freelance copywriter and content marketer from Australia with a special interest in making technology more human. Find out more at his website or on Twitter.
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