7 Hard-to-Swallow Lessons From My $90,000 Year of Self-Employment | by Carter Kellman | January 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

Adjusting for holidays and vacations, the average month of work brought in about $9,000 last year. Let me blow my horn for a moment – I’m very proud of that.

According to the most requested metric (income), “I made it.” Or, at least I’m financially stable. Having said that, if I can condense everything I learned into a simplified lesson, this is it: Do not exaggerate the future.

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

The number one problem when I started my career: making money.

Translation: Find clients who are willing to pay you for a service you are relatively inexperienced in providing. After three and a half years and hundreds of assignments, I no longer have this problem. But fixed income doesn’t mean I can only turn on cruise control and dynamism.

Other problems arose as I developed my business.

For example, it’s great to have a longer client list, but I don’t have the same facility for unintentionally procrastinating that I once had, which means I need to work with urgency and avoid distractions. It’s a different kind of stress.

Raising prices is another example. Money is such an embarrassing topic. Are you asking customers for more money for the same services? It is almost wrong.

With so many “uncomfortable” conversations under my belt, I feel confident and justified in charging higher prices, but still – negotiating is a delicate challenge that has backfired for me before.

Maybe it’s just my opinion, but compared to building a six-figure indie company, I think it’s a much more difficult task to build an audience then develop and sell compelling products. I’ve seen others succeed in the creative arena, but the dedication it takes to make months of meager sales and non-livable profits? Sheeshthat’s hard.

I’d like my personal projects to support me financially, but I barely earn enough from Medium and book sales each month to cover my internet bill. (My other creative endeavors don’t even generate revenue.)

Am I happier than when I worked in banks? yes.

Am I happier than when I first started freelancing and lived bill to bill? Marginal.

Although I am closer to satisfaction and fulfillment in my work, this may be an endless pursuit. I’ve learned it’s best to enjoy the process.

When I first transitioned to full-time freelancing, I cut my monthly budget by 32%. I had to – I didn’t make enough money to continue my previous lifestyle.

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

In addition, it has helped inculcate good habits. Three and a half years later, I’m still very close to following my self-imposed spending limit; Except for the rent hike (somewhat beyond my control), my expenses haven’t really changed.

Your prices are for you Prices, but someone has to be willing to pay them. Every time you raise your price, you drain a little water from your pool of leads. In my opinion, it is much easier to increase profits by outsourcing and focusing on implied hourly rates. Your time is your most valuable currency.

Of course, finding reliable freelancers is easier said than done. But that’s all the more reason to connect with other freelancers. You never know, you might find someone whose pricing fits within a client’s budget and still allows you to generate some semi-passive income.

I love the ass-to-the-fire style. This is self-employment at the end of the day: we are directly and solely responsible for providing for ourselves financially. If we don’t work, we won’t win.

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 should either be on Do Not Disturb or out of my reach), heavy foods, and noise.

Freelancing is a fickle type of work that is hard to do feelings It’s like we’re moving forward.

In the fall of 2020, I landed a couple of high-paying copywriting gigs, helping me outpace my monthly bank income back when I was working as a corproate drone. I remember thinking,You did it, you finally turned the corner.

And then they shadowed me.

A company rotated and fired my primary touch points (I found out after messaging them on LinkedIn just a couple of months later). Others have cut ties with freelancers and hired an in-house team (as before, I only learned this through a proactive ask on LinkedIn).

At that time, I was crushed. My earnings went down, and I’m back on the living bill.

But, looking back, it was still progress — I had new pieces of portfolio that I could eventually leverage to get better clients.

Metaphorically speaking, you have to ride an elevator to the clouds, look at your work from a 30,000-foot perspective, and ask a simple but salient question: Am I closer to my goals than when I started?

It may not seem like it, but progress is happening.

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