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

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I started freelancing full-time in July 2019. Here’s an overview 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, a normal month of work brought in about $9,000 last year. Let me toot my own horn for a moment – I’m damn proud of it.

According to the most desirable indicator (income), “I succeeded”. Or at least I’m financially stable. That said, if I could sum up everything I learned into an oversimplified lesson, it would be this: don’t glamorize the future.

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

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

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

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 cushion for procrastination that I once unconsciously had, which means I have to operate with urgency and avoid distractions. It’s a different kind of stress.

Rate hikes are another example. Money is a tricky subject. Asking clients for more money for the same services? It’s almost wrong.

With plenty of “uncomfortable” conversations under my belt, I feel confident and justified in charging higher prices, but still—negotiation is a delicate challenge that I’ve expressed before.

Maybe this is just my opinion, but compared to building a six-figure freelancer, I think it’s a much more daunting task to build an audience and then develop and sell compelling products. I’ve seen others succeed in the creative arena, but the dedication it takes to shake off months of negligible sales and unlivable earnings? Sheeshit’s difficult.

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

Am I happier than when I was in banking? Yes.

Am I happier than when I first started freelancing and living from invoice to invoice? Marginally.

Although I am much closer to being satisfied and fulfilled with my work, it could be a never-ending quest. I’ve learned that it’s more valuable to enjoy the process.

When I first switched to freelancing full-time, 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 that thrifty decision, because otherwise, who knows if I would have lasted long enough to experience that spike in hockey stick income.

Besides, it helped to form good habits. Three and a half years later, I’m still pretty darn close to following my self-imposed spending limit; with the exception of higher rent (something out of my control), my expenses haven’t really changed.

Your rates are yours rates, but someone has to be willing to pay them. Every time you raise your price, you drain a little water from the pool of potential clients. In my opinion, it is far easier to increase profits by outsourcing and focusing on default 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 network with other freelancers. You never know, you might find someone whose prices fit the client’s budget while still allowing you to generate semi-passive income.

I like the ass-to-fire approach. That’s what freelancing is all about at the end of the day: we are directly and solely responsible for supporting ourselves financially. If we don’t work, we don’t earn.

However, I find it just as easy to procrastinate today as I did three years ago. The difference is that I know my triggers — my phone (which should be either on do not disturb mode or out of my reach), heavy food, and noise.

Freelancing is such a volatile line of work that it’s difficult to feel as if we are progressing.

In the fall of 2020, I had a few well-paying copywriting gigs that helped me surpass my monthly income from banking back when I was a corporate drone. I remember thinking, “I made it, I finally turned the corner.

And then they forced me.

One company turned around and fired my primary contact (I only found out after messaging them on LinkedIn two months later). Others cut ties with their freelancers and hired an in-house team (same as before, I only found this out by proactively asking around on LinkedIn).

I was at that time crushed. My earnings plummeted, and I was back to living invoice after invoice.

But looking back, it was still progress – I had new pieces for my portfolio that I would eventually use to land even better clients.

Metaphorically speaking, you need to take an elevator ride into the clouds, look at your business from a 30,000-foot perspective, and ask a simple but important 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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