Ben Franklin ain’t having it son.

Freelancing Is All About The Benjamins.

Take the cash seriously. You can’t pay your bills with fuzzy feelings.

Being a freelancer is going to suck. Being a small business owner is going to suck. Running a startup is going to suck.

They’re all going to suck because nobody wants to pay you. No matter how good your work is, or how far you’ve bent over and twisted and contorted yourself to meet the needs of your customers, they won’t want to give you money.

It will happen time and time again. It will happen with clients you trust, who have always paid in the past. It will happen with new clients who come recommended. It will happen with your best friends and your family, if you’re gullible enough to work for them.

It will happen with enterprise clients who love your software. It will happen with musicians who love your production. It will happen with cafes who want you to paint a fucking mural on their wall.

Oh, they’ll come up with all kinds of different ways to avoid paying. Maybe you missed their monthly invoicing cycle and gosh darn it, it’s just against their company policy to pay you outside of it there pal.

Or maybe they’ve hit a snag. They can’t get a manager to sign off. They “lost” your invoice. The bank “lost” their transaction. You must have given them the wrong account details. It’s been put through, but it’ll take a week to show up.

Whatever bullshit excuse they give you, no matter how much they ask you to trust them — you’re fucked. The chances of you being paid are excruciatingly low. And if you do get paid, it’ll only be after dancing with them for months on end.

Fuck it. It’s enough to destroy anyone. I was forced to shut down my first marketing company because of it. I still wake up sweating thinking about chasing those invoices.

Freelancing and entrepreneurship is all about the Benjamins. So what’s the solution? How the fuck do you get around it all? How do you get paid?


1. Talk money early, and talk it hard.

When someone asks you for a service or a product, or they want your startup to implement some of the software you’ve slaved over, you talk money. Early in the conversation, you highlight what the cost is going to be and explain that nothing happens without money.

You’ll be surprised how many people will accept your fees without too much complaint if you make it clear that you take them seriously. You don’t have to be a dick about it — just be up front and honest.

That kind of information can’t be delayed, because yours fees set the tone of the entire conversation or negotiation. And yeah, feel free to negotiate, and discuss the fees, but don’t back down from demanding them.

You deserve to get paid; don’t be too embarrassed to tell people that.

2. Don’t lift a finger without down-payment.

Did that conversation go well? Yeah, I’ll bet it did. They want you to start right away. They can’t wait to see you work. They think the project will be awesome. They understand and accept your fee schedule. They’ll pay you in full on completion. Right?

WRONG.
They will not pay you in full on completion. They will pay you half now and half when you deliver. This is non-negotiable. You need to make sure they are invested in what you’re offering. If they haven’t given you a cent up-front, they have no motivation to see your work through.

There’s a very good chance you’ll be left out in the cold with months of work behind you and jack shit to show for it when the bell rings. So get a percentage in down payment and don’t lift a finger until you do.

3. Get yourself a safety net.

I hate doing this, but it is a must. Do not start any business or offer any service unless you have a safety net. Here’s some options:

  • A credit card that you haven’t maxed out buying leopard skin laptop bags on electronic bay dot com.
  • A backer who is prepared to buy out invoices if they’ve been outstanding for a certain length of time.
  • A professional invoice purchasing company who can handle your invoices for you, in exchange for a percentage.
  • …Or a healthy savings account.

You’re going to have to be creative, but the end goal is always going to be this. Have a back up plan for when people don’t pay. You need to keep the lights on, the bills paid and the staff happy, and a safety net is the only way to guarantee that.

If you can’t manage any of the above as a small freelancer, there’s no shame in maintaining one or two days of fixed work per week to fall back on when invoices are late. That’s a strategy I wish I’d followed.

4. Hire an asshole.

Every company needs an asshole. Someone who isn’t around to make friends and doesn’t have a problem with putting the boot in every now and then. That’s a must. You need to be able to count on having a team member who can get tough on clients and won’t feel bad about it.

I outsource this to a young lawyer who has a tough streak and likes making a little money outside of her full time job. She’s professional, polite but always firm, and if I need an invoice chased up she handles it perfectly. I call her The Sheriff.

It’s more about trusting someone to be persistent without worrying about ruining your relationship with a client. Having someone dedicated to handling late invoices who won’t back down means you can keep on being the nice one and let them handle the tough situations.

You have to stay in the loop though — ensure you’re aware of all the communications and you are happy with the level of pressure your sheriff is applying and the way she approaches clients.

5. Keep records of everything.

I’m serious. Everything. Every email, every invoice, every remit notice, every receipt, every call log. You want to have the information you need at your fingertips so you can constantly refer to it as needed.

It’s partly to safeguard yourself, so you can prove what was said and when. It’s partly to ensure you’re monitoring the financial situation of every single client or contract and not letting any information fall through the cracks.

Don’t lose yourself in a complicated filing system either. That’s going to waste time. Take photos or scan your records and save everything to Dropbox, OneNote, Evernote, Google Drive, whatever the fuck you want. But save it. Tag it. Make it searchable.

6. Communicate professionally.

Don’t text your clients. Don’t snapchat them. Don’t do deals through a chat program. Don’t rely on a phone call. You need to make sure that all your communication goes through provable, traceable professional channels.

Make sure you’re using emails, you’re using contracts and letters of agreement and proper proposals. Don’t screw around, crack a lot of jokes and act too casual.

You want every single interaction with your client to be professional and be suitable to use if you ever need to show a record of your relationship with them in order to secure payment and get them to stick to their word.

7. Use the right software.

Don’t try and run a business using a spreadsheet. That’s asking for trouble, and it’s asking for information to get completely lost. Use invoicing and accounting software to make sure your payment processes are clear, automated and controlled.

If you don’t do that, you’re giving your clients a bullshit reason to avoid paying you, and trust me — they have enough personal days, elderly relatives, sick pets, deadlines, staffing problems and emails that get magically lost. They don’t need you to give them any more excuses.

I fucking love Xero. It does everything I need, when I need it. But Zoho Invoices works too, and there are probably a dozen other top notch accounting packages that you can easily use to keep the invoices going out and the money coming in.

8. Don’t make exceptions.

Nobody gets to avoid paying. Not your friends, and not your relatives. Not even Shauna from Super Big Corporation X who promises that you’ll gain exposure and market positioning.

Everyone pays. Everyone follows your rules. When you make one exception, you’re committing to making one hundred. That’s just the way people work.

No matter what they offer, or what excuse they come up with, don’t walk away without your money. I once chased an invoice for $300 for 18 months. Believe me, I got my cash. And I got a story out of it that I tell every client.

It helps them to understand just how persistent I will be.


It’s not a game. Work, business, contracts — you have to take them seriously, and you can’t let anyone get away with not paying you. At the end of the day, your cashflow is what allows you to stay in business, and going soft on it means you will shut down.

You will go bust. You will end up looking back and wishing you’d kept your shit together.

When you’re freelancing, or being an entrepreneur, no matter if you work in comic art or quilt making or software development, the most important part of what you do will always be getting paid. If it’s not, I have news for you.

This ain’t your job. It’s your hobby.

It’s all about the fucking Benjamins. Are you?


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Thanks for reading — I’m Jon Westenberg. I’m a writer, critic, creative & digital evangelist. Since 2012, I’ve been helping people make things and find an audience. You can ask me to work with you, invite me to speak at your event, or set up a conversation on your podcast. I’m excited to hear from you!

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