The 24 Most Important Things I’ve Learned in 24 Years as a Solopreneur

Matthew Fenton
Winning Solo
Published in
11 min readJun 16, 2021

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On June 16, 1997, at age 27, I placed a bet on myself, eliminated my steady paycheck, and hung out my shingle as a positioning and strategy consultant.

My employment record at that time included nearly five years as a marketer manager at Van Melle, where I launched products like White Mystery Airheads and the Airheads 6-bar pack. It was an outstanding crash-course in both positioning and the art of doing more with less. We racked up some impressive numbers and had plenty of laughs.

I then joined a Fortune 200 company as a Group Brand Manager. I resigned that position after nine weeks. Miserable as I was during that brief time, it also provided the motivation to go solo.

I made the decision to launch my consultancy in a single day, and without a formal plan. I was brimming with both enthusiasm and naivete.

I’ve avoided the deepest ditches and I’ve gotten some things right. But I’ve also made plenty of mistakes. Here are the 24 most important things I’ve learned about consulting, freelancing and self-employment. I hope they may be of value to those of you who have made the leap, or are considering it.

1. The Primary Reason for Your Business to Exist Is to Meet Your Needs.

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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/