Lessons Learned After A Client Skipped Out On An $8,000 Invoice

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Kaitlyn Arford never intended to be a freelancer, but an opportunity came from her network for a side hustle that turned into full-time freelancing. Now she loves the control over her own schedule and the ability to work remotely. However, it’s not all roses. In this Q&A interview, Kaitlyn shares her worst client experience and the lessons she learned. Further, she shares her top tips and resources for freelance business growth.

How did you get into freelancing?

I never intended to become a freelancer! I got offered the opportunity as a freelance technical writer working on a few articles each week from a college friend who knew I was looking for writing opportunities. (One reason why it’s good to let people you know that you’re looking for work!) 

That’s how I discovered that I loved working remotely on my own schedule. I started looking into how to build this side gig of mine into a career.

How are you adjusting your freelance work lately?

I’m a full-time freelancer. I’m still working on diversifying my income but my freelance work can be divided up into the following:

  • 55% Content marketing for companies
  • 20% Subcontracting work for another freelancer
  • 15% Reading and reviewing ebooks
  • 10% Occasional pet sitting and walking

With that said, 2020 has really taught me the importance of diversifying my income, so I’m actively working to create templates to sell in the future.

I started recently working as a subcontractor for another freelancer, which has been really fun! I think if other freelancers have the opportunity, they should work with other freelancers and learn from them.

One of my favorite projects is writing the monthly Dog Athlete of the Month feature for the American Kennel Club. I get to interview people who compete in dog sports, which is deeply delightful.

I’m most active on Twitter sharing freelancing advice and opportunities, but you can also catch me on Instagram. I’m slowly but surely pulling together a blog filled with freelancing advice.

What’s your favorite thing about freelancing?

I love the flexibility freelancing gives me. When a family member died last year (pre-pandemic), I was immediately able to head home without asking for permission from a boss. I wouldn’t trade the flexibility of freelancing for anything.

What’s your freelancer tech stack?

I could not live without Marijana Kay’s freelance project planner. I started using it this year and it’s helped me know what my income will be and plan out which projects to take on and when to take time off.

On a technical note, I use Grammarly, ProWritingAid, and Hemingway Editor for editing. Using Descript to transcribe my many interviews has saved me so much time. And if you’re looking for more helpful tools, I’ve got a whole list.

What’s one pitfall of freelancing that every freelancer should be aware of? How can they avoid it?

I think at some point every freelancer is going to experience burnout. Honestly, it’s inevitable: either you’re going to take on too much at one time or you’re going to just get overwhelmed and tired of your work.

If you get burned out, don’t try to work your way through it. Schedule time for yourself away from your work. 

What are your best strategies for maintaining mental and physical health? What’s your routine?

It’s so easy to get wrapped up in the hustle of freelancing and overwork yourself. Rest is sometimes the most productive thing you can do. Give yourself permission to rest.

Accept that some days will be harder than others. To get motivated and focused, I recommend starting with a project that will give you a positive response to start the day on the right foot.

Personally, I make a point of taking time for myself in the outdoors every day. Daily walks help me center myself, forces me to exercise, and keeps me away from my computer. I also like reading Fiza Pirani’s newsletter. It’s always filled with great tips!

What was the worst client experience you’ve ever had?

I think every freelancer has a horror story

I worked with one client for a few years as a freelance writer and eventually became a freelance editor with them. I had enjoyed working with them, but when the company was acquired, things started going downhill.

It got to the point where my invoices were not paid in net-30. When I was laid off, they owed me $8,000 from two months of work.

Thinking back, there’s a lot of mistakes I made (that I’ve now learned from!):

  • Continuing to submit work even when they owed me money.
  • Ignoring red flags (like other freelancers reporting they were paid late, repeated promises that the company would start paying on time).
  • Not updating my contract with them after switching into an editorial role.
  • Not charging a late fee for repeated late payments.
  • Not pursuing double damages through the Freelance Isn’t Free law.

What book, blog, or longform article has been impactful for you as a freelance entrepreneur?

I’m a huge reader so I turn to books for wisdom. Jane Friedman’s The Business of Being a Writer is so helpful for creating a business mindset for writing and helped me set realistic expectations. When I first started freelancing, Zachary Petit’s The Essential Guide to Freelance Writing was basically my guidebook for sending pitches, building a brand, and managing freelancing.

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