Freelancers Tips and Tricks

For all the wonderful aspects of freelancing life, there are just as many challenges: getting paid on time, dealing with difficult clients, navigating your own health insurance, and more. Here are some tips and tricks from some of our members who freelance.

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Tips for invoicing and payment:


Use Retainers:

"I always get a retainer, unless the client is a close friend. The retainer generally covers most of the work until the first invoice - and means they have some skin in the game. If they are unable to cut a check for the retainer with the signed proposal, it's usually a sign that they are non-serious."


Bill in phases:

"I prefer to invoice by phase so there is a clear deliverable at the end of the phase, though that is not always possible for long-running projects. If the project gets delayed at that point, the deliverable means there is a clear stopping point in the process, and makes things easier to pick up again."


On not getting paid:

"My husband taught a course on small claims ages ago, just after college, and so I have a process whereby if someone doesn't pay, I take steps with certified letters cc'd to an attorney to make sure I get paid, and set myself up for filing in small claims if I need to do. Thankfully (knock wood) it's never gone that far -- a terse certified letter usually does the trick."


Use an invoicing system:

“I use an invoice system that sends automated reminders. That way I don't have to feel guilty sending a reminder because I don't even know it is happening!"

“I agree with  [the above poster] about an invoicing service -- I use Harvest. It also looks more professional, I think. Also, I don't like keeping up with tracking and spreadsheets. Harvest and similar services take care of that, I can download simple spreadsheets for an accountant at the end of the year. And I will happily pay $10/month to have something else track it all for me.”


Spell out payment terms in the contract:

“I always have a contract that details the work to be done and payment terms. On top of this, when I’m dealing with someone for the first time I always have an introductory email explaining the workflow, payment terms and what to expect in friendly/professional terms. Also, I always get 1/2 to book and final half due with deliverables. If I’m ever dealing with a client who I know can be forgetful with payments I just send the invoice right before I’m delivering the final product and basically make it tough for them to forget, haha.”


Send your invoices from the billing department:

"At another meetup someone mentioned creating a separate email address (e.g., This email address is being protected from spambots. You need JavaScript enabled to view it.) and sending emails from THAT address when sending invoices rather than the one you use for client/project interactions. It adds a sense of distance with your clients so you don’t feel like Oliver saying, “please may I have my pay” since that can feel weird. You can send any “your payment is past due” from that billing address and it doesn’t feel so much like you’re jeopardizing your relationship with the client by asking for the money they owe you. Many of us are so much better advocating for their kids, friends, or family members than they are for ourselves. We’ve gotta be better at advocating for ourselves."


Advice from an accountant:

“ Hi fellow freelancers,    I provide freelance bookkeeping so I’m usually also the person on the other side making sure that I get paid.   
It’s a simple suggestion but so often freelancers submit invoices without W9’s and this can definitely delay payment especially if the organization you are billing only has monthly bookkeeping. I work under an LLC and I print my tax ID at the bottom of my invoices as well as always send a W9 with my first invoice for a new client.    Also I have found with some clients, being able to accept credit card payments really speeds things up a lot. I know that Quickbooks has a feature to accept credit card payments directly through your invoice but there are fees involved. I accept payments through Venmo which I have a separate account linked to my business checking. I also print this info on my invoice and usually include it in the note I send with my invoice.   
Having a second voice asking for payments does help get stuck invoices unstuck. I know freelancers that buddy up and write collection emails for each other. I have written some for my husband’s freelance work. Usually I try to tie it into some sort of deadline, for example “We’re wrapping the books up for the year/quarter and wanted to follow up on this invoice.” This creates some sort of an illusion of a deadline.”


Making use of the “Freelance isn’t Free Act”:

"There’s a new Freelance isn’t Free Act that was passed in May 2017 that you should know about. It requires a written contract (an email is fine, but there are also templates), timely and full payment, and protection from retaliation. So if you’re getting ready to take on a freelance project, you’re required to put something in writing."

“Regarding the "Freelance isn't free Act," I always include a little blurb at the bottom of my invoices that says "In accordance with the Freelance Isn't Free Act" passed on blah blah date, please remit payment within 30 days of receipt of invoice."  Technically, at least for voiceovers, it's not binding in certain areas - but it seems to get people's attention and make them a little more responsive.”


Useful reading from around the web:

“After becoming frustrated with my online invoicing platform (freshbooks- basic plan limits 10 clients and no way to take deposit + payments for 1 invoice), I found this article with other options for time tracking and invoicing specifically for small businesses.   I am trying out two of the services and so far much happier. Give a read if looking to try new platforms if the tried and true format isnt working for you anymore. I am of the camp that this part of freelancing should be on auto pilot as much as possible.


Related PSP articles:

How to Deal with a Deliquent Client

How to connect your way into your next job