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Three Freelancing Models

Thoughts on a few ways to make a living for yourself.
Jun | 4 | 2024


Jun | 4 | 2024
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Starting in my late twenties, I started doing freelance consulting work. Since that time, I’ve hopped in and out of full-time gigs—most recently as a college professor. Even then, I kept a few side hustles going. My prior employer allowed it then and still does now.

These days, I pay my bills by speaking, writing, and consulting. Book sales don’t hurt, either. #passiveincome Although the type of work I do differs compared to when I started, I still work on a discrete or project basis. Nothing is guaranteed. The fleas come with the dog.

In today’s post, I’ll describe three different freelance models and their advantages and disadvantages.

Model 1: The Big Fish

The idea here is simple, even if its execution isn’t: Find a single, lucrative, and long-term client. That person or organization may, in fact, represent your primary one. In the extreme, it’s your exclusive one—at least for the duration of the project.

In 2008, I chose this model—or, rather, it chose me.1 Although only two clients paid me during those 12 months, they did so for 51 weeks of the year. That year, I earned more than I ever had in my life. Color me lucky, considering the housing crisis was unfolding at the time.


The sense of stability of working on only two major projects set me at ease. What’s more, I didn’t have to scramble to find other gigs. Although my clients could be demanding, at least I knew where my bread was buttered. I enjoyed a sense of clarity in knowing that you need to placate a single person or group of people at any given time.


Nate Silver has famously said, “Trust the process—not the outcome.”

Tru dat.

Despite my best results, my approach was risky. Losing one would mean a big financial hit.

At any point, one of my few large clients could have decided that it didn’t want to keep paying me or couldn’t afford to do so. As a result, despite making the most I’d made in my life, this approach was risky. Losing one would represent a big financial hit. It’s also challenging to find new work when you’re effectively unavailable for most of the day.

Pro tip if you’re deciding to freelance: Ensure that your savings allows you to cover all of your expenses for at least six months.

Model 2: Guppies

This is the antithesis of the first model. In it, hedge your bets by signing up a series of small to mid-ranged clients—each of whom will pay you a fraction of what a large one would.


If you sport a dozen small clients, you’re far more insulated if one or two go away. In the early 2010s, I made most of my money via writing. I booked anywhere from $1,000 to $4,000 per month from about five different clients. When (as expected) one ended its engagement with contributors like me, the hit wasn’t particularly devastating.


This approach inheres far less risk than number one. Concurrently, though, there’s less clarity. That is, you’ll have to simultaneously please multiple masters and use different tools. With respect to the latter, some of my clients preferred using Slack and Google Docs. Others explicitly prohibited it. (Maybe that’s why I’ve learned how to use so many productivity and collaboration applications. I’ve had to adapt to my clients’ needs.)

There was also the administrative tax. I had to submit a boatload of forms to my clients from the get-go; they had to set me up in their systems to remit payment. Income tax prep wasn’t exactly easy.

Model 3: Hybrid/Flagship

Lastly, you can mix and match. You might land a flagship client and several smaller ones. Since leaving academia a smidge more than four years ago, I’ve done a good number of speaking gigs and plenty of ghostwriting. Still, meeting the intermittent needs of a five- or six-figure client leaves plenty of time for smaller-scale work.


In theory, you’ve minimized your risk. You lock in large monthly payments, and smaller ones hit your bank account. Even if the big fish gets away, your income doesn’t drop to zero.


If your primary client needs you at the same time as one of your secondary ones does, you’ll be tempted to satisfy the former at the expense of the latter. That conflict can cause you agita. Ideally, though, all of your clients—regardless of size—respect the fact that your relationship with them isn’t monogamous.


What say you?


Icons courtesy of The Noun Project.


  1. It’s silly to think that you always get to decide how you work as a freelancer.

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