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February 2026 marks 13 years of running a full-time freelance business and 20 years of freelance writing, starting as a side hustle.

A few years ago, I almost hit that $100,000 salary ($96,000 gross PAID that year while waiting on a few invoices that trickled in January so, yea, I’m rounding up). It was a 30% jump from the year before so I wanted to take note and see what I did.

These are the habits that helped my freelance income grow.

Borrow what makes sense for you.

Best practices that can drive a freelance income up.

I didn’t try to do everything myself all day every day.

I invested in:

I unsubscribed from things that weren’t driving results and doubled down on tools that saved time or led to better-paying work.

I didn’t just post on DianaKelly.com’s freelance writing blog “when I felt inspired.”

I set a reminder.
I published weekly.
I kept a running list of blog ideas in my phone.

And knowing my newsletter went out every Wednesday kept me accountable.

In 2018, I joined ASJA. (American Society of Journalists and Authors). I’m not still a member in 2026 but I am part of the American Society of Business Publication Editors.

That year, I went to a conference, which led to thousands of dollars in work over the next few years from editors I met there.

These days, I try to stay active with freelance communities as well as small businesses. I still believe that attending in-person events can result in leads.

We shared:

I passed on work I couldn’t take.
They sent work my way.

Freelancing tends to be a lonely career path but you can forge online relationships, schedule virtual coffee chats, and stay in touch on LinkedIn.

This one matters a lot.

I tracked article pitches.
I followed up politely.
I checked in with past editors.

One follow-up turned into $10,000 the following year.

Most people don’t follow up. Be the freelancer that does and you’ll reap the financial benefits.

Especially when I was busy.

New clients made up 40 to 50% of my income some years of freelancing.

I also shifted niches over time:

Higher-paying niches = higher ceiling.

This part is uncomfortable.
And necessary at times.

I raised rates.
I explained the value.
Some clients couldn’t swing it.

That freed up time to land better-paying “anchor clients,” which meant I wasn’t working as many hours.

Not everything was exciting.

Some SEO projects.
Some editing work.
Some were topics that I thought, “OMG, I need to clear my search history after working on these articles.”

Together?
About $8,200 I was glad I didn’t turn down.

Freelancing is a business.
Not every assignment will be fun, creative, and ones you’ll talk about at parties.

I wish I’d done this sooner. I used a simple Google Sheet.

It helped me:

This was eye-opening.

I realized:

I also tracked non-billable time:

What I’m reading: She Didn’t See It Coming by Shari Lapena (Thriller), The Automatic Millionaire by David Bach (money/personal finance read about paying yourself first!)

What I’m listening to: How to Build $100K in Five Years by Nicole Lapin

What I’m reading online: The Marketing Talent AI Impact Report from the Marketing AI Institute

What I published for on the blog: How to Balance Parenting and Running a Business (without Burnout)

What I’m watching: ‘Platonic’ on Apple TV (kinda dark, definitely funny) and ‘Landman’ on Paramount+

If you found something valuable in this newsletter, I hope you’ll spread the word to your community or friends.

Forward it to a friend and encourage them to sign up using this link. You’ll get a helpful freelance resource PDF as a thank you when a few people sign up using your link.

Big Desk Energy: A newsletter from Beehiiv’s founder, Tyler Denk, which includes startup stories and relevant industry news

Kaitlyn Arford’s Freelance Opportunities: Kaitlyn does the hard work of sourcing WAY more jobs than I do and sends them out a few times a week. Hopefully you’ll find some gigs between her newsletter or mine.

Here’s a roundup of creative, full-time, part-time, freelance, remote, and hybrid jobs in the editorial, copywriting, content writing, and creative fields. Good luck.

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