A Freelancer’s Top Five Priorities

Matthew Fenton
Winning Solo
Published in
14 min readApr 21, 2021

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“As a one-person operation, I can only do so many things to grow my business. So I need to choose wisely. But sometimes I’m paralyzed by the sheer number of options. How do I know which choices are best for me?”

I coach other freelancers, and that’s how I’d summarize one of the top struggles they report.

As an independent consultant myself for over 20 years, I’ve lived the struggle. It’s like standing before one of those endless Vegas buffets; how can you choose when you can’t even wrap your head around all the options?

This is the challenging flip-side of one of the wonderful things about freelancing: That we choose our own paths. We get to decide what we want our businesses to be, and how we’ll make them successful. And then we live with the outcomes of those decisions.

The purpose of this post is to make those decisions easier for you. I’ll identify the top five priorities of any freelancer, to make your consideration set more manageable. While I’m in no position to tell you what your best next step is — I don’t know enough about you to do that — I will endeavor to simplify the options and give you a framework for choosing.

Let’s dig in!

Preamble: What’s Our Freelance Objective?

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Matthew Fenton
Winning Solo

I write about brand strategy & freelancing. Ex-CMO. Music junkie. For brand leaders: https://matthew-fenton.com/ For freelancers: https://winningsolo.com/