Want to Earn Six Figures In Your Pajamas? These Freelancers Will Show You How

Pajamas are comfortable.

They also have hella sexy patterns.

And today, making six figures while freelancing in your pajamas is a reality.

Just ask Holly Johnson.

In 2016, Johnson earned a massive $225,000 from her freelance writing alone. “I barely got dressed, choosing to spend most work days in my pajamas on my couch,” she says.

That’s pretty dang awesome.

Pajamas aside, freelancers now make up 35% of the U.S. workforce and collectively earned $1 trillion in 2016.

That’s a lot of money on the table.

And it’s not just the number of freelancers that’s growing, but the amount they’re earning.

In 2016, nearly half of all freelancers raised their rates and saw an increase in demand for their services. And, more than half of freelancers expected to raise their rates the following year.

But here’s the really fun part.

About one-fifth of U.S. freelancers are making at least $100,000 per year.

So, how do you go from being paid $15 for a logo on Upwork, to raking in your six-figure share of a $1 trillion dollar pie?

Here, five six-figure freelancers share their top tips to help you make it rain.

Holly Johnson


Before she began her career as a freelance writer, Holly Johnson worked a stressful job that consumed nearly every waking hour of her life — and all for $38,000 per year.

“I schlepped into the office for long hours, weekends and holidays, with little time left for ‘real living’ after taking care of laundry and other chores. And, did I mention I had two small kids? I had them, but I rarely saw them. Basically, my life sucked.”

But in 2016, Johnson earned $225,000 from her freelance gigs alone — earning another $45,000 from her blog, Club Thrifty.

Still, she was probably stressed out and barely slept, right? Nope.

“I went on 11 vacations … barely got dressed, choosing to spend most work days in my pajamas on my couch. Best of all, I put my kids on the bus at 8 a.m. each morning and stood smiling at the bus stop at 3:40 p.m. each day.”

I know what you’re thinking: “How can I do that too?!”

So how does Johnson do it?

“Limit distractions and you’ll make more money … A lot of writers I know want to make more money but really suck with their time. They secretly hope to boost their incomes, they say, but they also spend little time actually working.

If you want to make money, you have to enjoy freedom in moderation and work like your income depends on it. Because it does!

… you will earn more money if you create a set work schedule and stick to it. My kids go to school from 8 a.m. until 3:40 p.m., so this is when I work. And no, I don’t go out to lunch, hit up Hobby Lobby at noon or sip fancy drinks at Starbucks all day.”

What do limiting distractions and sticking to a work schedule have in common? They both enable you to spend more of your time actually working.

This is crucial.

Especially when in an eight-hour workday, the average worker is productive for only two hours and 53 minutes.

Johnson also recommends that you avoid bidding sites.

“Clients who use bidding sites care more about cheap labor than quality work. While it is possible to run into the occasional client you may want to keep, these sites will most likely use you and abuse you.”

Also, bidding sites are often a race to the bottom, charge hefty fees and prevent you from owning the client relationship.


Blog Post: If You’re On Upwork, You’re Not Really Freelancing


Johnson also highlights that you won’t always be working on projects you’re passionate about:

“Freelancing isn’t always glamorous. Many writers wish to pen bestselling novels. Yet, the most lucrative writing jobs you’ll find on the web may not excite you nearly as much.

Personally, I’ve written hundreds of articles on topics I couldn’t care less about. As a writer, you’ll be able to write about things you love some of the time…but you’ll need to broaden your horizons if you want to earn a real income.”

Key Takeaways:

  • Limit distractions.
  • Set a work schedule and stick to it.
  • Avoid bidding sites.
  • Accept that you won’t always be working on passion projects.

Kelly James-Enger


When it comes to six-figure freelancing, Kelly James-Enger wrote the book.


In her book, “Six-Figure Freelancing: The Writer’s Guide to Making More Money,” James-Enger shares:

“Mindset. Efficiency. Connections. That’s how I built my freelance business.

You too can make a good living as a freelancer if you’re willing to treat your writing like a business, work as efficiently as possible, research and contact potential markets, and develop and cultivate relationships with other pros.”

Self-belief is paramount to success. If you don’t believe you’re the right person for the job, why should anyone else?

“I became successful because I believed I could become successful,” says James-Enger. But still, “your mindset and office setup can only take you so far. It’s your work habits (or, sadly, lack of same) that will largely determine your success as a freelancer.”

Although talent and skills are important, without treating freelancing as a proper business, it’ll be hard to get far.

“No doubt there are millions of nonfiction writers out there who are more talented, more creative, and way more gifted than I am. But unlike many of them, I’ve figured out how to run my writing business—and it is a business.

It wasn’t talent that transformed me into a six-figure freelancer. It was my attitude, my approach to my writing career, and my drive to succeed.”

In another of her books, “Writer for Hire: 101 Secrets to Freelance Success,” James-Enger shares her zeal for marketing:

“When you think successful freelancer, what skill first comes to mind? If you said writing, you’re wrong. It’s selling … If you can’t sell your writing, you won’t succeed as a freelancer.

I know–you hate cold calls. Most writers do. But your willingness to make them may make the difference between a full plate of work and struggling to pay your bills each month.

Make sure you follow up on every query … Following up isn’t being a pest; it’s being professional.”

Without marketing your freelancing services it’ll be next-to-impossible to find the right clients to catapult your business into six-figures.


Blog Post: The 3 Step “CGF” Method For Getting Freelancing Clients On Demand

But when it comes to your marketing strategy, think quality over quantity.

“It’s natural to want to approach as many markets and clients as possible. It’s more effective, however, to look for a smaller stable of clients—but those who will give you steady work.”

Remember, you only need 5 clients to give you $2,000 of work each month to hit $120,000 per year.

Key Takeaways:

  • Focus on improving your mindset.
  • Treat freelancing like the business it is.
  • Market your socks off, always.

Lisa Kaneff


Lisa Kaneff quit her job as a senior marketing consultant at an agency to start freelancing.

Today, she spends most of her time crafting digital fundraising campaigns for progressive nonprofits.

Although Kaneff has grown her freelancing business to over six figures a year, she prefers to focus on the many other benefits her new career provides:

“The value I’ve gotten goes well beyond the money I’m making. I can give back to the community more. I’m healthier. I’m happier.”

And that’s the point isn’t it? Earning more money is great, but not at the expense of your well-being and fulfillment.

So how do you build a lucrative and fulfilling business?

Kaneff recommends that you invest:

“One of the things I tell people who want to become freelancers is to invest in yourself and your business the way you would want an employer to invest. I pay for things that will help me be successful. It’s the infrastructure that my company would pay for that I now need to pay for myself.

Think about what you need to build your business.

Perhaps you need a new laptop or a dedicated workspace. Kaneff says, “Join a coworking space-it’s a worthwhile investment.”

Having used coworking spaces for two years now, I couldn’t agree more! Despite what many people think, freelancing doesn’t have to be lonely.


Blog Post: 4 Truths About Freelancing Your Boss Doesn’t Want You To Know


And as great as it can be, there are some mundane aspects of running a freelancing business:

“I don’t have an accounting department looking over my shoulder,” says Kaneff, so she uses the online accounting tool Freshbooks, to keep track of her time and finances.

“Get Legal. Know legally what you need to do to become a business in the town that you live. Business license, taxes etc.”

Lastly, Kaneff recommends that you find ways to keep growing. (If you’re on this blog, you’re off to a good start!)

One of her best investments was hiring a coach to help her improve her business skills.

“I needed someone to be the boss–give me the wisdom and confidence of a senior coworker, a manager or business owner. He was instrumental in helping me find my voice and my confidence for helping me understand my value.”

Marshall Goldsmith said, “What got you here, won’t get you there.”

So if you want to keep developing your business, you need to keep developing your skills and business acumen.

Reading, attending webinars, taking a course, or hiring a coach are all ways to take your business to the next level.

Key Takeaways:

  • Build a business that’s good for your life and not just your bank balance.
  • Invest in yourself and your business.
  • Don’t neglect the administrative side of your business.
  • Find ways to keep growing.

Carol Tice


Carol Tice has been a six-figure writer since 2011, when she hit that number solely from her freelance gigs.

On her blog, Tice shares some key insights into her experience as a six-figure freelancer:

“I’ve never met a six-fig freelance writer who doesn’t work a *ton* of hours. Work, work, work. We get up before our kids wake, or work after they sleep, we work on Sunday— often, we also work while on vacation.”

Once more, the need for consistent marketing becomes clear:

“It’s tough to earn big if you’re in feast-and-famine mode. The only way to prevent that is constant marketing to ensure a steady stream of client leads and new work.

Having lots of offers is what drives your rates up and lets you pick and choose the best ones to grow your income.”

Tice also outlines the fact that to earn more, freelancers often choose the projects that pay, over the projects they love:

“Often, the best-paying gigs aren’t your dream topic or magazine — but you take them for the money. ‘I’m like a machine, stamping out hamburgers,’ one well-paid writer-friend once told me, as she turned in yet another arcane trade-publication article on new refrigeration technology for convenience stores.”

The fact is, business needs don’t always align with what your heart wants.

Key Takeaways:

  • Put the time in. Your freelancing business won’t build itself.
  • Constantly market your services.
  • Compromise on passion in exchange for pay.

Jennifer Goforth Gregory


Jennifer Goforth Gregory hit six figures in 2015.

Once again, having only a few, high-value clients is key:

“I had fewer clients … When you work on small to medium projects for many different clients, you lose productivity because the first few projects always take longer as you learn the client’s expectations, tone and topics.

Having long-term clients also decreases your marketing time and downtime, which also dramatically increases your income.”

Remember, by taking on only a few clients, you’re able to serve each of them better.

Gregory also highlights how finding a small niche and specializing helped her increase her rates:

“I developed a high paying and in demand niche. I thought that I had a great niche with personal finance and technology, but this year I took it a step further and developed a niche in big data analytics.

My income increased dramatically because it is an in-demand niche with very few qualified writers. Another benefit is that when you are very familiar with a topic, you can write high quality articles in a very short amount of time so you end up with a high hourly rate.”

Also, when you specialize, your marketing becomes much easier because your target client group becomes more specific.

Remember, a trap freelancers often fall into is undervaluing their services.

One of the simplest ways to earn more money as a freelancer is to negotiate a higher rate that more accurately reflects the value you can bring to the table.

“I learned to be a better negotiator. I’m a people pleaser and want everyone to like me. While this trait has been great for developing long term client relationships, it has also caused me to significantly underprice myself on many occasions.

The first step for me was to realize this about myself and be aware that my initial instinct for pricing was most likely too low.”


Blog Post: Are You Making These Mistakes When Pricing Freelancing Projects


Lastly, Gregory explains the need to choose the people you work with carefully.

“I only worked with nice people. I am sensitive … and find it very stressful to work with jerky people. … When I work with people that I really enjoy and feel a part of a team, my productivity is off the chart.

I started to not only turn down clients that were not very nice, but actually try to only work with clients whose work style and personality brought out the best in me.”

Key Takeaways:

  • Only take on a few, high-value clients.
  • Find a niche and specialize in it.
  • Work only with people who bring out the best in you.


Final Thoughts

Are you fired up yet?!

Each of the freelancers above have their own personal priorities when it comes to crafting the life and career they want for themselves.

Still, there are similarities in the way they approach their businesses. Let’s run through the key takeaways once more with a 15-point checklist:

  1. Limit distractions.
  2. Create a work schedule and stick to it.
  3. Believe in yourself—you can do this.
  4. Treat freelancing like the business it is.
  5. Avoid bidding sites.
  6. Constantly market your services.
  7. Invest in yourself and your business.
  8. Find ways to keep growing.
  9. Don’t neglect the administrative side of your business.
  10. Find a niche and specialize in it.
  11. Put the time in. Your freelancing business won’t build itself.
  12. Only take on a few, high-value clients.
  13. Work with people who bring out the best in you.
  14. Compromise on passion in exchange for pay.
  15. Build a business that’s good for your bank balance and your life.

If you’re feeling overwhelmed, that’s okay.

Keep it simple. Pick one thing off the list and think about how you can improve it or make it happen.

To accomplish your freelancing goals, you just need to take one step at a time.

That, and some hella sexy pajamas.