Looking Back on 2 Years of Freelancing

It all started with an invoice for $41.66

Today’s edition of Wishful Working is a 3 minute read.

On March 30, 2022, I received the first payment of my freelance journey — $41.66, ⅓ of the total $125 invoice from a project almost 9 years earlier, during a brief and ill-fated foray into freelancing after college. 

It’s a long story that involves a cheapskate bossbabe and a sketchy MLM smoothie shop. Anyway.

After that day, I buried the proverbial hatchet and looked toward what I hoped would be a bright future of freelancing.

Nearly two years later, I can confidently say things are going well! And I’ve gotten to work with some awesome clients that have more than make up for that post-college nightmare project that left a bad taste in my mouth. 🙌

I thought it would be fun to reflect on the last two years by sharing some some big and small moments from my freelancing journey: 

March 2022 - First invoice! Woohoo! I’ve considered putting that $41.66 toward this flag that says “Good work isn’t cheap, cheap work isn’t good,” to hang in my office. Too petty?

April 2022 - After two Upwork projects, I get my first non-Upwork client — Yay! The rate is $50 per blog, which isn’t great, but I’m thrilled about this first client nonetheless. 

May 2022 - I stumble upon an awesome opportunity in a newsletter I still swear by — WriteJobsPlus. The rate is much better than $50/blog, and the relationship has resulted in ongoing work.

August 2022 - The stars (or invoice due dates) align, and I have a $10k month. Worth noting: I have not had one since. Pretty fun though. I got to help pay for our new air conditioner that summer. 🥵

September 2022 - I realize I do not have enough structure in place to manage my workload, and I am very stressed. My new therapist suggests I buy a planner. Lol. 🤯

December 2022 - I wrap up the year having matched my former full-time salary in just 9 months of freelancing.

January 2023 - I make a goal to meet fellow freelancers for short video chats because freelancing can be so lonely sometimes! I do pretty well with this goal in 2023, but I want to get back to it. (Lmk if you want to chat sometime!)

April 2023 - I celebrate my first freelance anniversary by filing taxes as a self-employed person for the first time and paying a relatively giant bill because I underpaid on my quarterly payments. 🆒

August 2023 - The idea for Wishful Working is born, but I catch a bad case of imposter syndrome (among other excuses), and the project stalls for several months. 😅

December 2023 - I take a break from client work for the entire month and find my business doesn’t come crashing down in my absence. All in all, a good year.

Also December 2023 - I finally launch the newsletter you’re reading right now!

February 2024 - I take a 12-day dream vacation to Ireland and England with my husband and 3 friends — funded with freelance income/savings.

Also February 2024 - On the heels of that vacation, I have my lowest income month since my first month. I try not to panic.

Yesterday - I buy myself a little treat to celebrate two years of freelancing, but I choose something that qualifies as a business expense so it’s also tax deductible. 🧠

I’m so grateful for my freelance journey so far, and I’m looking forward to many, many more years of working for myself. Thanks so much for reading, and please reach out if you have any questions or just want to say “hey”!

See you next week,

Kara