Next week, the Freelancers Union will mark a major milestone: We’re turning the big 3-0.

Obviously, the world is much different than it was 30 years ago, and by extension, so is the business of freelancing. Freelancers are nimble by nature, and just as the last three decades have forced freelancers to navigate a constantly shifting media, tech, and economic landscape, the Freelancers Union, too, has grown and changed.

In the spirit of navigating change and getting back up again, even after you’ve been knocked down, we asked freelancers to share some of the “mistakes” they’ve made over the course of their freelance careers.

Our members kindly shared their stories, as seen below, that will both give you some pointers of things to consider in your own freelance career, as well as a reminder that lessons learned don’t break a career, but help build one.

“I’ve made the mistake multiple times of working before a contract or deal memo was issued. Each time, surprise, the company wanted to pay much less than what I quoted.” - Khalil

"I continued to take on work from a client for a few months or so after invoices were not being paid, all the while with the client thanking me and heaping praise, telling me such things as "You are G-O-O-D!" and joking about going to Vegas with my paycheck (not kidding). Because of the nature of my work transcribing medicological reports, I felt that I couldn't possibly not take work and thereby jeopardize patient care and safety. My husband at the time finally insisted that I stop taking work.

Once I did that and didn't hear back from the client after repeated attempts at contacting her, I took her to small claims court but had to travel to the state in which the client lived in order to do so. I was lucky enough at the time that my husband had the ability to pay for our travel expenses and accompany me to court, and I won, but had I been doing that completely on my own, I would have had to mostly eat those travel expenses (other than itemize them as business expenses), as well as losing money with time lost from work, as well as tackling the whole ordeal by myself without any moral support. And there was a second mistake along with this one: I accidentally transposed some of the numbers in the amount that I was requesting be compensated, so that I received $2,580 vs. $2,850 - a big brain cramp there for sure! I realized my error after the adjudication but before leaving the courtroom, so I asked the judge if I could change that number to the correct amount, but he deemed that, unfortunately, a no-go. A bit embarrassing being in a profession in which accuracy is of utmost importance. So, lesson learned there, too!" - T.

“A mistake I made more than once was doing a big job with payment only at the end. I learned to state in advance, in writing, that I would need one-third or one-half of the payment after finishing that portion of the job. I always got paid, even when I made that mistake, but I had to do a lot more nagging to get the money if I waited till the end. I also learned to be very specific about what my work would entail — one read or two reads, for instance, no re-reading if the author or business decided to revise something after my work was done unless I was paid extra for that, and so on.” - Peggy

“The one mistake I continue to make is to set a fee that's too low. I've made progress over the years, and lately I've been charging more and feeling good about that. One mistake from years ago that sticks with me is that I let myself be pushed around by a couple of art directors at a financial magazine. They asked for a chart that looked shiny and gold, with drop shadows and reflections, against a green background. It looked terrible in the end, and I told myself I'd never create work I don't like at least a little bit. I'm happy to collaborate, but this wasn't a healthy collaboration.” - Haisam

“Where do I start? I just retired from about 35 years of freelancing, writing and consulting in persuasive communications, mostly for architects. That gave me a great deal of time and many opportunities for mistakes. But let me offer one that may be helpful to other freelancers, whatever their specialty may be.

A number of times, I made the mistake of hiring the wrong client, the result of not asking the right questions. This has been a particular issue when I was enlisted to help an architect with a submission for Fellowship in the AIA College of Fellows. It's an extraordinarily complicated and lengthy process, and I've worked on more than 40 of them.

Mistake #1: Every once in a while, I've been approached by an architect who simply is not a good candidate. I should decline to take them on, but it's hard to tell someone ‘You don't got the goods.’ Working with someone who isn't a good candidate is a miserable chore. When they also refuse to understand what the AIA is looking for, it's a head-banging time.

Mistake #2: Early on, I wasn't clear enough about the tasks I don’t take on. 

Mistake #2a: I sometimes failed to ask detailed questions about who the client is using for graphic design. I should never have taken on an assignment with the wrong designer — but on occasion I did.

Mistake #2b: There's a great deal of nit-picking, irritating, often nonsensical rules in a Fellowship submission. I should always have been clear not only that I don't do these, but also that the candidate needs to appoint someone in-house who understands all of this, especially all the electronic stuff.

Mistake 3: I should have been emphatic about the need for a team and the absolute requirement that the candidate be directly involved. Some candidates seem to think that, having retained me, they can go off and sketch a super-tall building. It's important to make any client understand that they're not buying a piece of furniture to be delivered.

And, finally, a suggestion: Although the kind of work I've mostly done has an obvious objective, for other kinds of projects it can be really helpful to ask, before taking on an assignment, ‘How will I know when you think I've succeeded?’ If you're in public relations, and the client's response is ‘When I'm on the cover of [choose the publication],’ run away.” - Erika

“I dealt with a woman who delayed and delayed turning in my (and a colleague's) invoices to the point where I had trouble paying my bills on time. It caused me no end of grief. I should have gone over her head to whomever was her supervisor after it happened twice. Prior to her coming aboard, I worked for someone else at the same company who always put them in promptly. I would never let someone get away with that again.” - Anonymous

“Here is a list of the mistakes which are at top of mind:

• Did not save $ for quarterly taxes.
• Did not have a friend sign a contract for a job. 
• I have worked for and with people I distrust. Never again.” - Anonymous

“I am relatively new to freelancing but I have found that at the onset, I have given away too much information — so much so, that they did not need to hire me. I should have charged for the initial consultation but instead told them if I was aware of the project, I would add that time in.” - Anonymous

“I discovered that I wasn’t charging my clients enough for my work. I started making incremental additions to my fees, and my clients didn’t complain.” - Anonymous

“Hands down, the worst mistake I made was leaving freelance/fractional work and rejoining a corporation. I made more as a freelancer, but I needed healthcare, and the idea of benefits was attractive. I also tended to compare my trajectory with my friends ' titles, salaries, vs. control over my life. Huge mistake.

My second mistake that I'm working on developing into a strength was trying to follow the market.When tech became all the rage, I migrated to UX research. While the pivots were valuable, the market is flooded with researchers with limited bootcamp training who believe they know more than they do.

My third mistake was questioning myself. As a freelancer, you often lack access to information that can be crucial for your recommendations. Being sensitive to this, I indulged in self-protection. I felt that flying below the radar was safer than going head-to-head when that was necessary.” - Anonymous

“I did a lot of work for people who never paid me what was agreed upon as a final payment. I just expected my client to be honest and responsible enough to eventually pay me my just deserves. I needed to learn about keeping better records of sales and completed work and transactional payment history.

Researching how to run a more organized business is next on my to do list.” - Siregar

“Earlier in my career, I was not diligent about following up with clients on past-due invoices. Many editorial clients had a net 60-day term, but everyone was still always late. To compound this, I didn’t want to appear desperate or difficult, so I would foolishly grant a grace period. Sometimes invoices were ‘never received’ by the correct department and were relegated to the back of the line for a new 60-day term. After a high-profile music mag (now defunct) gave me the runaround for 6 months, I received a bankruptcy notice and never got paid a dime. I took the next late client to a collections agency when 90 days turned into 4 months. Eventually, I received payment, but it was only for a partial amount. The lesson learned was that it’s more than okay to be diligent. It’s professional and it’s necessary. 

Now, my invoices have a net 30-day term, and I often receive payments within 20 days. I ask clients to ‘Confirm the invoice has been received and is in line for processing.’ I follow up if I don’t hear back, and I mark the due date on a calendar. I don’t just assume my contact will send the invoice to the correct department. I kindly ask them to confirm it at the time the invoice is sent.” - Jay

“As soon as you start spending or making money in your business, have a good accountant lined up and also a good bookkeeper. At least note the basic rules and you could find all that now easily with AI – but you still need a professional.

Get written agreements for anything you’re hired for.  A contract is best but even an email specifying overtime for instance has saved my butt with clients who wanted to change the terms after the work was done.

Don’t fall into the trap of obsessing about gear because what’s important is what you do with it, not having the latest tools.

I tell myself all the time that ‘Nothing good ever happened to me when I was sitting alone on the sofa,’ so it’s good to be out there meeting people. A corollary to that first statement is ‘Any good thing that ever happened to me in my career came through with another person.’

Related to that last statement is something I’ve told many sound guys I’ve trained earlier in their careers: Be at least competent in your trade, show up on time, and don’t be an asshole and you’re 80% of the way towards success.” - Ed

“I haven't been paying my quarterly taxes and it has been the worst snowball effect.” - Anonymous

“My mistake was in not staying in my lane. Coming from a corporate background, I started out focused on LinkedIn connections and marketing. I also sought out local companies in the industries I was most familiar with. But when I started working with (very) small business owner friends whose clients were local businesses, my ADHD brain shifted away from where I needed to be as I tried to help them.

It didn't occur to me until years later that I could've had a tier of pricing based on the type and size of business (or individual) I was targeting. Doing so would've allowed me to market to both B2B and B2C.” - Roxanne