Speak Softly and Carry a Big Stick

My daughter’s in the thick of GCSE revision at the moment. The other evening we ended up talking about former US presidents — as you do — and Theodore Roosevelt came up. It reminded me of a quote of his.

Roosevelt claimed it was a West African proverb, though there’s no real evidence of that. He probably made it up. Doesn’t matter. The principle is sound. And he later expanded on it, which is the bit people tend to miss: “If you simply speak softly, the other man will bully you. If you leave your stick at home, you will find the other man did not.”

I’m currently going through a situation with a former client who refused to pay for work that was completed. I’m not going to get into the specifics — it’s ongoing, and there’s a long road ahead. But I can talk about what it’s taught me, and what I wish someone had told me earlier in my career.

Because the uncomfortable truth is this: most freelancers don’t carry a big stick. They speak softly — politely, professionally, patiently — and when someone decides not to pay, they’ve got nothing behind the words except frustration and a sense of injustice.

Frustration doesn’t get invoices paid.

Here’s the thing that nobody wants to say out loud: some clients will try it on. Not all of them. Not even most of them. But enough that it’s statistically guaranteed to happen to you at some point. Over half of all freelancers have experienced non-payment. In the UK, 62% of small businesses report being owed money, with the average debt sitting at around £21,400. Late payments cost SMEs an estimated £22,000 a year and 56 million hours in lost productivity.

This isn’t a fringe problem. It’s the norm. And yet most freelancers go into client relationships with nothing more than a handshake, a PDF proposal, and a vague hope that everyone will be decent about it.

Hope is not a business strategy. It’s barely even a coping mechanism.

Your terms are your stick

The single most useful thing I’ve done in the last few years is rewrite my business terms from scratch. Not the template I downloaded in 2014 and never read properly. Actual terms. Written clearly, in plain English, covering what happens at every stage — including when things go wrong.

A few examples of what I mean by “carrying a stick.”

Copyright of everything I create remains with me until the client has paid in full. Not after delivery. After payment. That means if someone ghosts an invoice, they don’t just owe me money — they’re using work they don’t legally own. That’s not a threat. It’s just how it works, and it’s written down before we start.

All projects require up to 50% upfront, with the balance due on sign-off. If a project gets cancelled, at least 50% of the total estimated cost remains payable. That’s not punitive — it reflects the fact that I’ve blocked out time, turned down other work, and started thinking about their problem. Cancellation doesn’t undo that.

And here’s one that’s saved me more than once: if an invoice goes more than 45 days overdue, any discounted rate I’ve applied — whether that’s a project discount or a retainer rate — gets revoked. The invoice is recalculated at my standard hourly rate, and the revised total becomes payable. It’s a simple clause, but it reframes the dynamic entirely. A discount is a gesture of goodwill. Goodwill doesn’t survive non-payment.

I’ve also got an inactivity clause — if a client goes silent for 30 consecutive days, I can cancel the contract and bill for the full project fee. Because “we’ll get back to you” shouldn’t mean “we’ll leave you in limbo indefinitely while you keep the diary clear.”

None of this is aggressive. None of it is hidden in small print. Every client sees it before any work begins. That’s the “speak softly” part — being calm, being professional, being upfront about how this works.

The terms themselves are the stick.

When a client disputes an invoice now, I don’t have to get emotional about it. I don’t have to argue. I just point to the document they agreed to. It’s boring. It’s procedural. And it works far better than a heated email written at midnight.

If you’re freelancing without proper terms, you’re walking into every engagement unarmed and hoping nobody notices. You can read mine at j-kindred.com/terms — not because you should copy them, but because seeing how someone else has structured theirs might help you think about your own.

Insurance is the stick you pray you never swing

Insurance has always been one of the first things I sort out when setting up a business. Not the exciting bit. Not the bit you tell people about at the pub. But the foundation everything else sits on. There’s a difference between testing an idea — seeing if something has legs — and actually selling a product or service. The moment you cross that line and start taking money, you need to be covered. That’s not caution. That’s just building on solid ground.

And I’m profoundly grateful I did, because I’ve needed it.

Professional indemnity insurance and legal expenses cover aren’t glamorous. Nobody’s posting about them on LinkedIn with a fire emoji. But when a client refuses to pay and you’re staring down the barrel of legal proceedings, knowing you’ve got cover behind you changes everything. It changes your posture. It changes your decision-making. It means you can pursue what you’re owed without the fear that the process itself will bankrupt you.

The cost of not having it isn’t just financial. It’s the moment where you know you’re in the right, but you can’t afford to prove it — so you walk away. And the client learns that not paying works.

Don’t teach them that lesson.

Protecting your head

This is the bit that doesn’t make it into the business advice threads. The mental health cost of a payment dispute is brutal.

It sits in your chest. It’s the first thing you think about in the morning and the last thing at night. It bleeds into other client relationships — you start reading bad faith into innocuous emails. You second-guess your own value. You wonder if it’s even worth the fight, or if the stress alone has already cost you more than the invoice was ever worth.

I’ve had to be very deliberate about protecting my headspace through this. Not in a “practise gratitude and journal” way — in a practical, structural way. Setting boundaries around when I deal with the legal admin. Not checking emails about it after a certain time. Talking to people who understand the situation rather than letting it fester.

The measured approach isn’t just better strategy. It’s self-preservation. Getting angry feels righteous, but it costs you twice — once when the client doesn’t pay, and again when the stress of chasing it affects the rest of your work and your life.

Speak softly. Not because you’re weak. Because losing your composure is expensive in ways that don’t show up on an invoice.

The freelancer’s Big Three

If I could go back and give myself three pieces of advice before taking on my first client, they’d be these.

Get your terms right. Not a template. Not something you copied from someone else’s website. Terms that you’ve actually thought about, that reflect how you work, that cover you when things go sideways. Have a solicitor look at them. It’ll cost you a few hundred quid. It’s worth every penny.

Get insured. Professional indemnity. Legal expenses. Whatever is appropriate for your trade. Pay the monthly premium and forget about it until the day you need it — and then be profoundly grateful you did.

Guard your energy. Not every battle needs to consume you. Build systems — in your contracts, in your process, in your routine — that let you deal with the hard stuff without it eating you alive. The clients who don’t pay aren’t worth your health. But the ones who do are worth protecting your ability to keep showing up for.

Roosevelt was talking about international diplomacy. But the principle scales down perfectly well to a freelancer in Suffolk trying to get paid for work they’ve already done.

You don’t need to be confrontational. You don’t need to threaten. You don’t need to match anyone’s aggression.

You just need to make sure that when you walk into the room, you’re carrying the stick. And that the other person knows it’s there.

Hi! I'm James Kindred. I wrote this!

With over 25 years in design, branding and startups, I help businesses craft compelling identities, develop engaging assets, and build results-focused growth plans. I am AuDHD and bring my unique thought process to every project, ensuring that your brand is more than a logo. It's a reason to believe.