7 Hard-to-Swallow Lessons From My $90,000 Year of Freelancing | by Carter Kilmann | Jan, 2023

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I started freelancing full-time in July 2019. Here’s a breakdown of my annual earnings since then.

  • 2019: $8,314 (five months)
  • 2020: $35,479
  • 2021: $31,464
  • 2022: $90,565

Factoring in holidays and vacations, a normal working month brought in about $9,000 last year. Let me honk for a second – I’m damn proud of that.

According to the most coveted measure (income), I have “succeeded”. Or, I’m financially stable at least. That said, if I could condense everything I’ve learned into one oversimplified lesson, it’s this: do not glorify the future.

Here are some potentially hard-to-swallow lessons I learned building a (nearly) six-figure writing business.

Problem number one when I started my freelance career: making money.

Translation: finding clients willing to pay me for a service that I was relatively inexperienced with. After three and a half years and hundreds of missions, I no longer have this problem. But a steady income doesn’t mean I can turn on cruise control and just vibrate.

Other issues arose as I scaled my business.

For example, it’s nice to have a longer client list, but I don’t have the same cushion for procrastination as before, which means I have to operate urgently and avoid distractions. It is another type of stress.

Raising rates is another example. Money is a tricky subject as it is. Asking customers more money for the same services? It’s almost wrong.

With many “uncomfortable” conversations under my belt, I feel confident and justified in charging higher rates, but still – negotiation is a tricky challenge that has backfired on me before.

This may just be my opinion, but compared to building a six-figure independent business, I think it’s a much more daunting task to build an audience and then develop and sell products. attractive. I’ve seen others succeed in the creative arena, but the dedication it takes to drain months of negligible sales and unlivable revenue? Sheeshit’s hard.

I wish my personal projects would support me financially, but I barely make enough from selling Medium and books each month to cover my internet bill. (My other creative endeavors don’t even generate income.)

Am I happier than when I was in the bank? Yes.

Am I happier than when I started freelancing and lived from bill to bill? Marginally.

Although I am much closer to being satisfied and fulfilled by my work, it may very well be a never-ending pursuit. I learned that it is more valuable to enjoy the process.

During my first transition to full-time self-employment, I reduced my monthly budget by 32%. I had to — I wasn’t making enough money to continue my previous lifestyle.

And I attribute my current success to that frugal decision because, otherwise, who knows if I would have lasted long enough to experience this sudden growth in hockey stick revenue.

Plus, it helped instill good habits. Three and a half years later, I’m still close to hitting my self-imposed spending limit; except for higher rent (a little out of my control), my expenses haven’t really changed.

Your rates are your tariffs, but someone has to be prepared to pay them. Every time you raise your price, you drain some water from the pool of potential customers. In my opinion, it is much easier to increase profits by outsourcing and focusing on implicit hourly rates. Your time is your most valuable currency.

Of course, finding reliable freelancers is easier said than done. But that’s one more reason to network with other freelancers. You never know, you may find someone you trust whose rates fit a client’s budget while allowing you to generate semi-passive income.

I like the ass to fire approach. That’s what freelancing is after all: we are directly and solely responsible for our financial sustenance. If we don’t work, we don’t earn anything.

That said, it’s just as easy for me to procrastinate today as it was three years ago. The difference is that I know my triggers – my phone (which needs to be on do not disturb or out of my reach), heavy food, and noise.

Freelance work is such a volatile line of work that it is difficult to to feel as if we were progressing.

In the fall of 2020, I landed a few high-paying writing gigs, which helped me exceed my monthly banking income back when I was a corporate drone. I remember thinking “I did, I finally turned the corner.

And then they ghosted me.

A company pivoted and fired my key points of contact (I only found out after I messaged them on LinkedIn two months later). The others have cut ties with their freelancers and hired an in-house team (as before, I only found out by proactively interviewing on LinkedIn).

At the time I was crushed. My income dropped and I went back to bill on bill.

But, looking back, it was still progress – I had new elements for my portfolio that I would eventually leverage to attract even better clients.

Metaphorically speaking, you need to take an elevator into the clouds, look at your business from a 30,000 foot vantage point, and ask a simple but relevant question: Am I closer to my goals than when I started?

It may not look like it, but progress is being made.