Mistakes in your freelance business are inevitable and while, hopefully, you learn something along the way, it’s better to learn from someone else’s mistakes.
Here are five of the biggest mistakes I’ve made in my career as a freelance writer and how I learned to deal with them.
Mistake #1: Being complacent when times are good.
A rookie mistake for freelancer workers is to wait until the current project ends before looking for the next one. This is how you wind up with time where you don’t have any work. You should always aim to have your next project lined up well before the current one ends.
In fact, a portion of EVERY week should be spent looking for new clients. It’s an obvious strategy, but the first time that business booms and every day is filled with client work, it’s easy to let this slide.
While that may seem simple, what isn’t so straightforward is when you start working on long-term retainers.
As long as you have availability, you’ll naturally keep hunting for work to fill up that bandwidth. But once you get enough retainers to fill ALL of your working time, and you have to start turning work away, that’s when complacency can start to kick in.
A nice collection of retainers can result in months or even years going by without ever needing to sign on new clients. It’s a nice position to be in but,after a while, it can start to feel like it’s never going to end. Your clients love your work, the money’s rolling in every month like clockwork. What could possibly go wrong?
All kinds of things…
A client gets sick and closes their business. The project you’re working on comes to an end and the client no longer needs you. Or the economy tanks and a client has to make cutbacks.
I’m not suggesting the life of a freelancer is one of constant fatalistic gloom, but it must be acknowledged that occasionally even the most dependable of clients fall away for some reason. And if it’s been a while since you had to find a new client, it’s like a bucket of cold water over your head.
The first time this happened to me, I had no plans. I was deluded enough to think that the project I was working on would run for decades. When it didn’t, I spent a couple of months performing a highly-realistic headless chicken impression.
If you’ve been squirreling some money away, you’ll have plenty of time to find something to fill a newly-created hole in your client list. But the most important way to minimize the fallout from this kind of event is to avoid becoming complacent in the first place.
When you have a full roster of clients, enjoy it but don’t let it stop you from continuing your networking activities. You may not be in a position to look for additional work, but there’s nothing to stop you from periodically emailing existing contacts and just reminding them of your existence.
Something like this…
This touch base email accomplishes two important things. First, it helps your former clients, prospects and industry colleagues remember you. Second, it stops you from looking like the kind of person that only reaches out when they’re looking for work. When you do contact people in your network to enquire about available work, you’ll find it much easier for having maintained the relationship, even if it’s only with a light touch.
And it is very much a casual process. Don’t feel like you need to email everyone you know, week in, week out. When you have plenty of work, and you’re just maintaining your network, I find that reaching out once or twice a year is sufficient.
It’s also a subtle way of letting people know that you’re in demand, without making you sound like a braggart.
This is an important part of establishing your professional credentials. It means that, when you do have availability, your prospects will know that they only have a limited window to obtain your services before you’re snapped up.
The last time I needed to find a new client I was able to truthfully say that it was the first time I’d had availability in over two years. There’s nothing like a little scarcity to cajole people into action.
Of course, you can perform similar activities on social media but, on these platforms, you’re just another face in the crowd. An email is more personal and more impactful.
Attending real-world events connected to your preferred industry is also a smart use of your time. This is something I haven’t done enough recently, but in the early part of my career, it was critical to making new contacts and forging closer relationships with existing friends.
However, you go about it, this is all about maintaining a presence in your industry. Don’t get so wrapped up in the work of just a handful of projects that, when you need to find a new client, you find yourself having to start your networking process again from scratch.
Mistake #2: Ignoring the dangers of working for a single client.
My first long-term retainer was sizeable enough that I didn’t have a lot of bandwidth available for additional work. For a couple of years, this was my only significant project.
When it ended, suddenly and unexpectedly, I had no choice but to live off my reserves until I could find something else. I burned through virtually every last cent and came within a couple of weeks of having to close my business. I even began applying for local jobs, just in case no new clients turned up.
Fortunately, a couple of short-term projects arrived to keep me going and, within a few months, I had landed two retainers. Shortly after that, I added a third.
That’s when I realized how much safer it was to have several small or medium retainers, as opposed to one epic project. When I was only working for one client, I was only one terminated retainer away from having absolutely no work. But maintaining several clients meant that losing one piece of business only resulted in a moderate dip in income.
There is always the possibility that all my clients will disappear at the same time. But, obviously, this is unlikely. And to date, it’s never happened.
At my peak, I’ve had six different projects on the go for five different clients. It takes some juggling, but it provides plenty of variety and adds some security to my regular income.
None of which is to say that you should turn down an offer for a sizeable retainer that will preclude other work. But be sure that the income from that job is enough to allow you to put some money away.
And be mindful of maintaining your networking, no matter how secure the work may seem.
Mistake #3: Thinking prompt payers will always be prompt payers.
When a retained client comes to you and says they’re terminating your contract for financial reasons, shrug your shoulders, wish them well and start looking for a replacement.
It’s always a shame when it happens, but there’s nothing to be done but move on. Simple.
But what do you do if a client says they’re having financial difficulties and ask if they can delay their payment?
Now it’s complicated…
It could be a good client. Someone you’ve worked with for a long time. Someone with whom you have a good rapport. The last thing you want to do is play hardball and sour the relationship.
Then again… you can’t be expected to work for free.
The obvious solution is to pause your work for your client and resume once they catch up with their payments. But what if your work is critical to their business? Stopping work will only make it harder for your client to recover.
Needless to say, this is not a fun quandary. And if you’re not prepared for it, anxiety over what to do will shred your nerves.
In many ways, it’s easier just to quickly acquiesce and allow your client to pay late. Which is fine if they catch up quickly. But I’ve been in this situation and, before I could blink, wound up with a client that owed three months of payments. Suddenly I was in a position where I couldn’t pay the freelancers working for me.
When you’re in this situation, there’s no easy fix. I suggest treating each instance individually and trying to find a balance between being helpful to your client while not neglecting your own business interests.
But there is one solution that can eliminate this problem almost 100% of the time, before it ever becomes an issue…
Always require payment upfront, in full.
The first time you explain to a new client that these are your terms, you may feel a little light-headed. I’ll freely admit it took some courage for me to make this shift. And yet, as it turned out, most of my clients accepted this without even blinking.
In fact, the only person who’s ever made a fuss turned out to be one of the worst clients I’ve ever had the misfortune of working with (we’re talking broken contracts, vile language and threats).
If the project cost is large, I might agree to a series of staged payments, but I avoid starting work until the first payment has arrived.
This doesn’t prevent the scenario where a client asks for a delay in payment later on a retained project, but it helps massively with cash flow and it’s rare that I have to chase payments.
Mistake #4: Counting my clients before they’ve hatched.
This scenario is almost worse than losing a valued, long-term client. I’m talking about that moment when a prospect comes within a whisker of being the most lucrative client you’ve ever had, only for everything to unexpectedly fall apart at the last minute.
Substantial retainers, by their very nature, take time to discuss and agree and it can easily be a number of weeks between first contact and signed agreement. The mistake that is so easy to make is assuming that the money is in the bank before… well… the money is in the bank.
On one occasion, I almost landed an editing job with a brand-new print magazine only to see it fall apart at an advanced stage. The prospect (whom I found on a freelance auction site) liked my portfolio, was impressed with my experience and seemed excited by the ideas I had for developing the project. But after asking me about my usual payment procedures, they inexplicably reported me to the freelance site administrators, claiming that I was trying to get them to pay offsite.
The freelance site immediately locked my account. I managed to convince the customer service department that I’d been slandered, but by then the project was dead. This is, by the way, another reason why I grew to detest freelance sites.
On another occasion, I had an agreement to create ten pieces of work at $1k each. But after completing two of them, the client ignored my invoices, stopped replying to my messages, and the project died.
In the world of freelancing, sometimes things fall apart. It can’t be helped. But the one thing you cannot afford to do is bank on promised income before an agreement is signed and the money is deposited in your account.
More damaging than the disappointment is the wasted time on project planning that goes nowhere.
The answer is to take a realistic view of your work, not to make any assumptions and NEVER to spend expected money before it arrives.
Asking for a payment upfront, as already discussed, is a protection. But you should also continue to look for new clients right up until the moment that your current prospect pays their deposit and signs on the bottom line.
Don’t allow weeks to go by without networking and client-hunting because you’re convinced that nothing can go wrong with your current negotiations.
Mistake #5: Indulging the hagglers.
I touched on this already in an earlier article but it bears repeating.
For whatever reason, as a general rule, the less a client is paying me, the more likely they are to be difficult to work for (and the reverse is true – my most lucrative clients have always provided the most enjoyable and stress-free working experiences).
So, beware of prospects that want to haggle.
I’m not saying you should be suspicious of everyone who asks you to move a little on your prices. But if someone is trying to drive you down by 30, 40, even 50%, right from the opening conversation, be on your guard.
It’s tempting to allow your financial needs to push you into agreeing to unusually low rates, but the stress that comes from a difficult or overly-demanding client will cost you far more than if you’d turned the work away in the first place.
Offer a 10-20% discount if you think it’s worth it, but I would avoid going lower without very good reason.
And, in case you were wondering, the nightmare client I mentioned earlier spent weeks haggling me down before work began.
In my experience, not every haggler becomes a problem client, but every problem client started out as a haggler.
Here’s the summary of my advice here…
Get paid upfront and never stop networking.
Your freelance career will always have difficulties and challenges. But follow those two simple tenets and you’ll save yourself a world of trouble.
Do you have questions about working as a freelancer? Post them in the comments below and I’ll cover them in a future article.
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