5 "Tough Love" Lessons That Grew My Freelance Business

Let's hope they save you years of struggle

Author

Diana Kelly Levey
July 30, 2025 • Estimated Reading Time: 9 minutes

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I didn’t learn these freelance business lessons the easy way. Most came from messing up, figuring it out, talking too much (!) and promising myself I’d do better next time.

If you’re a freelance writer trying to grow your business and stop working for pennies, keep reading to discover lessons that help me move toward a six-figure freelance business.

1. Rejection Isn’t Personal

If you haven’t been rejected yet, you’re not pitching enough.

Clients say no. Editors ghost you. Ideas fall flat. It sucks, but it’s normal. Thick skin helps. So does understanding that a “no” could just mean “not now.” I’ve had editors pass on an idea and assign something totally different six months later, eight months, or even a year later.

Pitch anyway. Follow up. Pitch someone else. Keep it moving.

2. The Magic Is in the Follow-Up

Some editors won’t see your first email. Or your second. That doesn’t mean you’re annoying. It means they’re busy.

I’ve had article pitches accepted only after the third follow-up. I’ve also ignored pitches as an editor and then assigned something when the writer circled back. It happens.

Track your emails. Reevaluate. Follow up like it’s your job—because it is.

3. Stay in Touch (Seriously.)

Check in.

Congratulate them on a new role.

Comment on their LinkedIn posts.

Tell them that you saw a good article written up about their company and link it.

I once reached out to a former editor just to say congrats, and ended up landing over $10,000 in freelance work.

People hire people they remember. So stay on their radar.

4. Your Time = Real Money

When I was writing $200 press releases on weekends in my 20s, I learned that speed improves with experience. But faster doesn’t mean cheaper.

Now, I avoid hourly rates when I can. If I deliver better work faster, I shouldn’t be paid less. That’s why I prefer flat rates or scoped projects.

Want to earn more per hour? Get faster.

Then charge by the project. You can still earn over $100 an hour freelancing without telling clients that’s what your internal rate is.

5. Say Your Rate—Then Zip It

Quoting a rate? Say the number. Then stop talking.

Don’t rush to justify it. Don’t fill the silence.

I know it feels awkward.

But let them respond. I’ve quoted higher than I thought they’d go, and they just said yes. You don’t need to explain your worth.

Quiet confidence beats out nervous rambling.

Thinking your freelance article pitches could use some finessing?

Check out this guide of 12+ freelance article pitches that turned into paid assignments.

“This guide is filled with practical information on pitching. Its case-study format basically shares 12 actual pitches to editors, along with comments received by the editors. The pitches span a variety of writing topics and serve as great examples of concise templates that writers can use as models for their own pitches. This is especially well suited to new writers who want guidance on targeted pitching, but will also suit any writer who just wants to tighten up their own pitching style!” ~Nicola Parry, Medical Writer

Thank you for reading.

Diana

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What I’m Reading / Listening to / Doing / Publishing

No jobs this week. On vacation

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