How to break through income plateaus in your freelancing business
Your strategy matters less than you might think — here's how to actually get to the next level.
Me, grinding through those early freelancing days. Figuring it out one article at a time.
In 2019, I was stuck at a certain income level in my business. I really wanted to hit six figures, but I couldn’t seem to get past about $5,000 a month, and even that was usually a stretch. There were a few reasons for this. Most of my work came from one-off jobs, so I was constantly starting over from scratch each month. I thought I wanted my niche to be finance writing, but because I was doing a lot of random jobs writing about everything, I didn’t have a lot of great samples to show potential clients.
At that point, I was offered a job writing daily articles for a personal finance site, and honestly, I really didn’t want to take it. The pay was just okay, the articles took me a long time to write, and when I was done writing them, I had to format them in the company’s CMS.
I wrote the first article, and was considering telling my editor I couldn’t do any more work for them. I just couldn’t see how this writing job would help me reach my goal. Then suddenly, I had this moment where I thought, Do you want to earn $100,000 or not? The job wasn’t perfect, but it was recurring work, which I really needed. So I grudgingly took it.
What I didn’t realize was that this publication syndicated its articles to sites like Yahoo Finance and Business Insider. So without even realizing it, I landed myself a bunch of really great bylines I could show personal finance clients. This led to a writing gig with GoBankingRates, and the work only improved from there.
I didn’t hit $100K in 2019, but I did get to about $90K, which was double what I’d earned the year before. I reached $100K in 2020, and I’ve earned over $100K every year since.
Income plateaus can be so frustrating because it’s not just a strategy problem — it’s mental, too. How do you believe you can earn an amount of money you’ve never earned before? Here are a few tips that helped me get through it.
Pick a goal that actually motivates you
I think the biggest mistake people make is picking an income goal they think is realistic. You can mentally work out how to get there, which makes it feel doable, but realistic goals aren’t usually very exciting. For example, I could have made my goal to go from $5,000 per month to $5,500, but that’s not really what I wanted.
The problem is, there’s no checklist for going from $45,000 per year to $100,000 per year. But I think the fact that I was really excited and energized by that goal gave me energy and motivation to keep trying things and failing until I eventually figured out what worked.
Ask yourself if you really want it
I love those beginning stages of starting a new project when it’s exciting and you’re full of energy. But inevitably, the motivation fades, and life starts putting obstacles in your path.
Honestly, this has happened to me recently with Substack. My first couple articles came to me really easily, and I was really motivated and excited to grow my subscribers. But I also have two kids and a full time job freelancing which pays for said kids. I started to find that it wasn’t so easy to work on Substack posts after a full day of client work.
I skipped a couple of weeks and was feeling guilty about it, so I started to rehash my list of reasons for why it was just too difficult. Then I had to stop and ask myself, “Do you want to do this?” If not, that’s okay — I’m an adult, and I can quit any unpaid hobbies I feel like. But if I do, then I need to quit complaining and figure out how to make it work.
Do something
When I find myself getting stuck in my business, the only way out is through some kind of action. Unfortunately, you just can’t think your way into more clients or more money — believe me, if there was a way, I would have found it.
In 2020, I sold a course teaching people how to make their first $1,000 as a freelance writer. At the time, my advice was to find your first few clients on Upwork, and it was always so interesting how people responded to that advice. Inevitably, people would come back to me with a long list of reasons why that would never work.
Upwork is full of scammers and low-paying clients. The fees are too high. There’s too much competition. It’s too hard to get hired if you don’t have any reviews.
And here’s the thing — all of that is true to some extent. But what strikes me is how much time and energy people invest in arguing against a strategy rather than spending even ten seconds considering how it might work for them. There’s something powerful about being willing to try something even if you aren’t sure it’s going to work for you.
The truth is, the tactics matter a lot less than you might think. What matters more is whether you actually want the thing you say you want, and whether you’re willing to take imperfect action to get there.