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My biggest lesson from being an underpaid freelance writer

Eleanor Beaton

When I was 22 and still employed full-time in advertising, I started the first iteration of my first business: I became a freelance writer.

I didn’t do any of the time-wasting things people generally recommend you start with. I did no real market research to expose “needs”, “wants” and “gaps.” 

(Micro-Rant: The only type of market research worth doing is selling. It’s not that I’m anti-research — I have done my share of sUrVeYs and un-focus groups, but they are no substitute for actually trying to sell the simplest possible version of your offer. Come on people it’s not that hard.)

Anyway, someone told me that magazines buy articles from freelance writers. So I read two articles about how to do this, then followed the straightforward instructions.

I came up with story ideas, matched them to publications I thought would buy them, framed said ideas in a way that would appeal to the publication in question, put it into a pitch letter, emailed them off and did one round of follow-up.


At my peak, I batted about 50% and was usually paid the princely sum of anywhere from 5 cents per word to $2 per word.

I was earning $35K a year in my agency job at the time so this felt like big money. The natural conclusion I drew from this was that I needed to go “all in” on freelancing, which I did, shortly after getting married and being a dairy farmer for all of 5 minutes, but this is another story, for another time, and that time is called… NEVAH, DON’T EVER ASK ME ABOUT IT HAHAHAHA).

Freelance writing for magazines is a harrowing business and my relatives warned me against it. Why? Because it’s hard! You have to come up with an awesome idea, research a bunch of magazines to pitch it to, personalize and tailor each pitch into a piece of fabulous writing, submit the pitch with high hopes, hear a lot of silence a lot of the time (until you establish a reputation) and basically deal with mucho rejection to make what will most likely only ever be a modest salary. 

But I am so glad I didn’t listen to the people who attempted to warn me off it because…

Freelancing taught me the single most important skill any entrepreneur must master if you want to have a snowball’s chance in HAIL of building a lucrative business.

Freelancing taught me how to sell.

If I didn’t come up with great story ideas (i.e. compelling offers) I didn’t eat.

If I didn’t pitch these ideas WEEKLY, I didn’t eat.

In short, I learned the habit of SELLING.

If you are an entrepreneur and you are not ACTIVELY SELLING — whether through sales calls, proposals, webinars, challenges, in your store, on your computer, on a stage, over the phone, by yourself, with a team, to one person, to many people at once, whatevs…

You will not eat.

How I think about and execute selling has changed dramatically over the years. But the basic habit of daily or weekly selling has never left me. 

If you aren’t generating the revenue you want, 70% of the time (rough estimate) it’s because you are acting like a delusional trust fund entrepreneur.

There’s a business. There’s you. But there’s no trust fund. And there’s not NEARLY enough selling. Hence, delusional trust fund entrepreneur.

I am being harsh I know. But in a couple of weeks, I will give you a free sales resource that I SHOULD be charging for but will not because I just can’t take this habit of women not selling. When I provide that resource I will be much kinder and empathetic but for now, I just need to be straight with you.

If you are NOT making the volume of cash you desire, I am asking that you ovary up, accept my challenge and go sell your amazing work every day for 30 days straight and see what happens.

You are welcome.


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