What I wish I knew before I started freelancing


Hello Reader!

I started freelancing back in the Dark Ages—you know, back when people rented books from the library to learn how to do new things. Back when the iPhone was barely new. Back. In. The. Day.

(Shush! I'm not old. YOU ARE!)

Anyway, how I wish I had someone to sit me down and tell me what I'm about to tell you. Here's everything I wish I knew back when I got started:

1/ Your business entity matters (at least for US workers. I know nothing about the UK, India, Canada, Australia, etc).

When you get started, it's tempting to just register as an individual entrepreneur and call it a day.

This is NOT the way to go.

It took me 13 years and a discussion with my accountant and Lettuce (see below) to realize I was losing THOUSANDS by not registering as an S-corp.

Do yourself a favor and hire an accountant, or make your life easier by signing up for a service like Lettuce.

2/ You need a contract.

There are a few reasons to have a contract in place (BTW, I hired a lawyer to create a customizable contract that all freelancers/solos can use).

The reasons:

  • Clients don't always know how to work with freelancers. You can make it easy for them by setting legal expectations up front.
  • You have what you get paid, and when locked in a contract, so you don't have to chase down invoices.
  • It makes you look even more professional than you already are. You have your business *ish together and clients like that.
  • Here are 8 minutes of other reasons from my friend and lawyer, Nanette:
video preview

3/ You gotta get good at business.

You may be the best writer/strategist/editor/content pro in the whole world, but if you don't learn how to run a business, everything will be...not impossible... but more challenging.

Here's what this means:

  • Hire an accountant and bookkeeper
  • Invest in a contract (don't have AI write you one, unless you like legal challenges)
  • Get consulting on health insurance, life insurance, and retirement. You don't have an employer who matches your 401 (k) contributions every month. But you still want to be rich when you grow up.
  • Learn how to sell yourself, or hire someone to do it for you.
  • Market yourself. This means you need a website, social media accounts, and a consistent outreach strategy. I'd suggest following Georgia Darling and Lizzie Davey to learn how they do this.

4/ Don't be afraid to charge your clients.

It took me a lot of time to learn that what felt like a lot of money to me isn't a lot of money to a company.

It also took me a long time to realize that there are additional expenses involved in running a solo business.

And it took me some time to realize I was undervaluing myself and the value my work brings to a company.

Here's one little example from a client. I work on a team of 7 people and this is what we've done in a year:

I promise you, they don't pay the 7 of us a combined $20 million, but that is what we do for them.

For context, this is what I think the MINIMUMS (why does this word look weird? Did I spell this right? What is happening to my brain?) for certain content should be:

  • Long-form content: $1,000
  • Case study: $1,500
  • Ebook: $2,000
  • Ad copy: $1,000
  • Editing: $100/hour

I don't care how long you've been doing this, where you're located, what your native language is... If you can bring monetary value to a company, charge them for your work. You deserve it!

5/ Prepare for burnout.

It is physically impossible to engage in a cognitively demanding task (writing, editing, creating, etc) for 40 hours a week.

Guys/gals/pals, it's literally science.

You'll have tons of creative days.

You'll also have tons of days where you think the word MINIMUM looks weird and your brain won't function.

Your brain is a muscle, and like EVERY MUSCLE in the body, it needs rest.

So here are some rules to follow so you don't burn out:

  • Don't partner with clients that expect you to pump out 40 hours of content a week. Those are nightmare clients.
  • Plan downtime to do what energizes you. For me, this is being outside with my family and traveling.
  • Don't overschedule yourself. Leave 4-5 days of nothing on your calendar at the beginning of the month.
  • Learn what you need to stay creative without burning out. For me, I try to only work in the mornings. Once I'm done, the computer goes far, far away. I spend purposeful time consuming nature and art. I plan regular travel.

6/ Learn everything you need to know to get results for your clients.

I'm primarily a content writer in the SaaS niche. But that encompasses a lot more than just putting pen to paper. It also means I know:

  • Content strategy
  • Research
  • SEO/AEO
  • AI
  • Industry trends
  • Subject matter experts to interview

If the job were just writing, we'd all probably write beach reads or something cool like that.

Words aren't the only part of the job. The job is bringing value to your clients, getting them visibility across platforms where people search, and writing in a voice that makes their content super interesting. Yay!

I call this the 3V content marketing framework. Learn more here.

7/ Find a niche you like

It's really hard to churn out content every week for an industry that bores you to tears.

If you need to pivot, do it.

We spend a huge portion of our lives working. Yes, it's work. But it can be fun.

Okay, that's what I have for you.

Have a good week,

Ashley R. Cummings

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Partner | Lettuce

The Lettuce Solo Summit is a free, one-day virtual conference on May 14th, where every session is a working masterclass, and every attendee leaves with something they can use that day.

We surveyed 600+ solopreneurs and found a clear pattern: the ones who grow aren't more talented, they're more intentional. They've each found their version of what works. This Summit helps you find yours. Sessions include a financial framework from a CPA who strategizes for solos, a positioning statement that makes you the obvious choice, an AI critique of your LinkedIn visuals, and a partner strategy to turn your existing network into a real pipeline.

Two tracks. Eleven sessions. All led by experts who know what it takes to make the climb.


Must-Read Industry Content

Think smarter, faster: Each week, I share the articles that are shaping where content marketing is going, so you don’t have to dig.

1/ The 2026 AI Index Report

2/ The Voice That Got Away: AI, Authenticity, and the Slow Death of Your Writing Voice

3/ The Content Cultures That Last Have One Thing in Common


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