I CAN'T BELIEVE WHAT I NOW THINK ABOUT LATE PAYMENTS TO FREELANCERS
- Jason Hewett

- Nov 25, 2025
- 4 min read
Apparently agencies face the same problem with late payments as we freelancers do, but the way some approach collecting payment is different—perhaps better than how I used to approach getting paid as a freelancer.
THE BOOK THAT CHANGED MY PERSPECTIVE ABOUT GETTING PAID ON TIME
I read a book called The Art of Client Service by Robert Solomon (I wish I read it sooner) which in my understanding recommends anticipating and budgeting for scope creep and late payments.
This concept was interesting to me, as a freelancer I’m right there with everyone else demanding to be paid on time. We absolutely SHOULD be paid on time. We absolutely ARE worth being treated with dignity and respect. And yet... it happens.
So much that I feel like I might as well tell the ocean I deserve not to drown in the same breath that I say freelancers should be paid on time.
WHY AREN'T FREELANCERS PAID ON TIME?
In my experience it didn’t matter what the project was or who the client was, late payments are basically inevitable--having been client-side myself, I now understand it's not so much human carelessness as much as it is levels of approval:
Sometimes involving board of director levels of approval.
Sometimes involving government regulation.
Sometimes involving oops we actually need to background check this person who wrote a $100 article before we pay them.
Usually in my experience, there's some sort of bureaucratic formality that nobody knew about upfront.
HOW COULD FREELANCERS AVOID LATE PAYMENTS?
Well, maybe the answer is... we don't?
In his book, Solomon advocates for maintaining trust with clients above all else, and finding compromise when it comes to collection—you budget for late payments and scope creep and other expenses as part of your quoted fees. That way you have flexibility without keeping score in order to sustain the relationship long-term.
If the problems persist over time, you might decide to cut your losses and work with other clients, or you can deal with it and not be in starvation mode until you do find better clients.
While I personally could get behind the idea that everyone has a moral obligation to pay bills on time, I also advise any freelancer or business owner create incentives for timely payment rather than make demands, as demands don’t compensate you for time asking to be paid.
And I think making demands of the ocean not to drown me might not work as well as wearing a life jacket.
BUT THEN HOW CAN YOU FREELANCE IF YOU AREN'T GETTING PAID
I feel like this is like asking how do you go sailing if you aren't finding fish on time to eat. And how are you going to make it if you keep struggling to fish, and you think you get a bite on your line and the ocean keeps ghosting you. Dude. Just bring snacks.
For some reason when I started freelancing, I didn't think about funding or a line of credit, which are common ways that legitimate businesses and startups "keep the lights on" regardless of how many customers are showing up.
As a freelancer relying on paying clients, my literal life depended on getting paid on time, because as I ran out of funds, there was no clear way for me to buy insulin and supplies that my life as a diabetic depends on. And as much as I agree that insulin is a human right and we should all have unrestricted access to it, we don't.
So now what? Well, I stopped freelancing full-time. In theory it's possible to freelance full-time as a diabetic and ration medication and wait until you get paid--and in practice people have died doing that. So now I wonder how is it actually possible to have the freedom to setting my own schedule choosing my own clients etc. The answer seems to be get funding, take a more calculated risk, and set myself up for actual success. Explorers didn't go to Antarctica expecting to just find food from the land--they brought provisions. And they got funding so that they could stock up on provisions, and fuel, and warm clothing. What do we do freelancing besides "taking the plunge" and eventually "changing our mindset" to just quit a job and figure things out because we're so miserable--that's reckless. I was reckless. As soon as I got health insurance and started seeing a doctor, I got a colonoscopy which removed some polyps that could have been cancer. My A1C and blood sugars improved to record levels. I am as frustrated as any American with our healthcare system and I feel like life, liberty, and pursuit of happiness can't be guaranteed without some sort of access to affordable healthcare for all of us. In a sense, I might as well be just as frustrated that I can't just sail around the world and explore Antarctica without stocking up on provisions. I could try, but that would be pretty reckless. But it's not (as) reckless if you were to go to explore Antarctica well-prepared to sustain yourself, defend yourself, and get yourself out of there if things take a turn for the worse. Why don't we approach freelancing like that?
Sailors know to prepare for storms, droughts, getting lost--what are we preparing for as freelancers? The reality is we won't always get paid on time, and the ocean won't always avoid wrecking ships. So whether the strategy is charge late fees, roll with it and sustain yourself with a line of credit, a combination of both, getting paid upfront--or whatever the strategy is--I think it's important to have one rather than making demands. Because one day you might go camping for a weekend where there's no service and your fucking payment method declines over the weekend and your freelancer doesn't get paid on time.




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