$508,000 Worth of Business Advice for Freelance Writers

Lots of freelance writers start out following their passion and then try to make money. I’ve done the reverse. I started my career as a software sales rep and got into freelance writing partly because the money was good.

Earning a livable wage has freed me to explore my passion and given me a totally different view on building a freelance business.

Here are seven lessons I carried from sales to freelancing which made finding clients the easy part, and helped me clear $508,000 over the past several years.

Follow the money

The money is in writing for businesses that write for other businesses, known as the business to business (B2B) sector.

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Consumer topics like travel, entertainment, and news may be fun and approachable, but these industries are so inundated with writers that content mills can get away with paying them as little as $11 per article.

In B2B, you can’t pay just anyone to write believably about APIs or tech stacks. That work is only available to those who are qualified, which keeps rates high—usually $500 or more per article.

Marketers treasure a good B2B writer. Many are on a never-ending quest to find a writer who’s both talented and understands their space well enough to avoid obvious errors, like assuming their readers can directly purchase what they sell. (B2B sales cycles are more complex than that.)

Plus, the B2B industry has a secret: Once you break through these companies’ tech-focused, statistics-hardened exteriors, you’ll find that they crave the sort of stories you’d want to write for consumer publications.

Take a client of mine that sells chatbot software. They won’t hire you if you can’t talk about interactive voice recordings (IVRs), but once you’re accepted, they’ll want you to interview everyday people about things that frustrate them.

Another, Zendesk, has an entire publication about people’s lives.

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If you follow the money into B2B rather than pursue your passion outright, I have found, you’ll get both.

Be known

People don’t hire the best writer they know, they hire the only one they know. You’d be shocked at how many friends and colleagues want to refer you, but don’t know how.

Freelancing is, in large part, a game of overcoming your discomfort with talking about work. If you’re interested in it, others will be too, and everyone you know wants to help.

Plus, friends are the most credible people to promote you: referrals are responsible for 50 percent of all sales, and 90 percent of it happens in-person.

But don’t be too available

Cultivate a perception of having lots of work and it can become a self-fulfilling prophecy. Don’t lie about being busy, but don’t let people know how available you are either. When clients ask when you can have a call, don’t say, “anytime.”

Give them three specific time slots. When they ask about your availability for a project, tell them you’ll have to check your production calendar.

This telegraphs that you’re an in-demand writer and the same way Supreme clothing resells at ludicrous markups, people will want you because you’re wanted.

Conduct outbound sales weekly

The feast and famine of freelancing is real, and it happens because the best thing you can do for yourself once you get a new client is counterintuitive: Continue selling.

I find that it’s best to compartmentalize your time: Set a recurring reminder for two hours each Monday to create lists of prospects, reach out, and follow-up.

Tell prospects you might not be the right fit

It’s counterintuitive, but acknowledging that they might not want to buy from you is generous, honest, and builds trust. People generally dislike talking to salespeople because they know that the salesperson has an agenda and will try to sell them no matter what.

It puts prospects on the defensive and makes them uncomfortable. Diffuse all of this tension right up front by telling prospects that your first call is to figure out if you’re a good mutual fit—you might not be, and that’s okay.

If you realize that, you promise to tell them, and you hope they’ll tell you. Say this and you’ll often hear a big sigh of relief and get far more honest answers to your questions.

Clarify before you negotiate

Often, writers don’t know their worth. They offer discounts before the prospect has had an opportunity to respond and send proposals with language like, “this is negotiable.” If you say that, you are only negotiating with yourself.

Plus, too must discounting communicates that there may be something wrong with your work. It’s like a car salesman offering you 30 percent off if you promise not to look under the hood. How could you not wonder what’s wrong with the car?

If they ask for a discount, ask if that’s the only thing stopping them from signing. Often, it isn’t, and they have other objects unrelated to price. Maybe what they’re really unsure about is the quality of your work and you can make them comfortable by sending samples or talking them through a project.

If you must give that discount, only do it in return for something, like them signing right away, or them paying the full amount up-front.

Never stop selling

And by selling, I mean doing great work. Sales and finding new customers takes effort and the more any given customer buys from you, the better return you get on each sale. If it takes a week to find a client and you only get one week of work out of it, you may break even.

But if they love your writing and stay with you for a year, that same week of effort generates 52x the results. With good writing and clear communication, you can eventually develop a recurring stable of clients that frees you from having to conduct sales at all.

Follow good salespeople

The best way to get in a sales mindset is to follow real salespeople. Below are a few folks I recommend.

I hope you can take something from my experience and apply it to your business moving forward. All the best!


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