The Journey of Three Self-Employed Women (Their First 1000 Days)

A wise man (who happens to be a tax accountant for expats and thus knows a lot on the subject) once said:

People don’t understand they need to be poor for 1000 days.

By “people” he means entrepreneurs, adventurers, expats, location independent modern nomads, and anyone who sets out to create a new enterprise and a new life.

The Tropical MBA puts it in business terms:

You’ll be doing worse than you were at your job for 1000 days after you start your muse business. For many of us it’s been almost exactly those 1000 days it took for us to get back to the level of income we enjoyed in our corporate days.

When we, as self-employed women, make the leap into our new careers, it takes time for things to get off the ground and go smoothly on a regular basis. In the beginning, there may be periods when you have lots of business, but it becomes too much, or no business, which creates too much financial strain. But it takes 1000 days for those cycles to even out and become sustainable.

What Are the 1000 Days?

The days process out into four main periods:

  • The Yearning: Pre-1000 DaysDuring this period, you may think you’re “working” on your business, but you’re really preparing to work on your business, saving money and/or quitting your job, pouring lots of time and money into learning, and chasing down different ideas.
  • The Great Hope: Days 1-333When you stop planning and start doing, taking on your first clients, making sales calls and start surrounding yourself with like-minded people. This is also when most people quit.
  • The Grind: Days 333-666You start feeling like a self-employed businessperson, but you’re constantly stressed because you’ve either taken on too much work or find yourself suddenly with none. You bid on some big clients or projects and get considered, but you’re not quite “there” yet. For some, the high stress and uncertainty is too much and they quit just on the horizon of….
  • The Sunrise: Days 664-1000Some people call this the “middle class problem” phase. You’ve got business, you’re cash flow is mostly under control, you’re subcontracting, and your family and friends finally seem to realize that you are running a business rather, not out of a job.

The Real Life First 1000 Days of Three Self-Employed Women

As we walk through our live case-study with our FreelanceMom Heather Holtschlag, the themes of the 1000 days and the journey to successful self-employment have come up a lot.

Especially the fact that it is easy to lose hope.

When support from family falters or the flow of clients—or paid invoices —seems to dry up, it is very easy to say, “This isn’t working.”

So take a look at the journeys of these three women who have made it in one way or another, whether in small ways, such as one travel writer finally getting the magazine and newspaper assignments she’s always wanted, or reaching the heights of a national TV show, like Pioneer Woman Ree Drummond, whose success we’ll examine in another upcoming case study.


Penelope Trunk, Small Business Owner

Though she’s a serial entrepreneur and former executive in a Fortune 100 company, Penelope tried her hand at country life when she married her current husband and settled on a cattle farm in Wisconsin.
The Yearning: Pre-1000 Days

  • Penelope spiraled through hundreds of small business ideas in her head, on paper, in discussions with her husband, confidants, and even with potential investors.
  • In the meantime, she tried to find new ways for her blog to make money, including coaching and webinars.
  • Though both offerings were very exclusively priced, Penelope’s large following allowed her to gain a lot of interest and traction in these services, leading to her idea for…

The Great Hope: Days 1-333

  • Quietly, without announcing it to her followers, the press, or many people in her network, Penelope began to put together Quistic, a company that trains people in the skills they need to develop great careers—a natural extension of her blog and previous web-based company, The Brazen Careerist.
  • Taking the feedback she’d received about the video seminars she ran on her blog, she fashioned evening courses that were more like meet-ups. “I know how to make online learning feel like a party instead of a lecture, [so] I decided to make a company out of it,” she says.
  • To create her team, Penelope tapped her best coaching clients. She figured, “I already know all their secrets because I coached them, and they already know all my secrets because they read my blog, so I have a company with no BS because we have nothing to hide.”

The Grind: Days 333-666

  • To continue to gauge interest, Penelope asked her online marketing friends to sell her seminars to their communities.
  • Even without a consumer-facing website up, she sold seminars and other online events to companies, creating a steady income stream.
  • When she was stalling on the official launch of Quistic, her supportive team encouraged her to get over her fears and get it out there. The post garnered 101 enthusiastic comments.

The Sunrise: Days 664-1000

  • She’s just starting to get here!

Linda McCormick 1000 days

Linda McCormick, Eco Traveller Guide

While traveling Linda became more and more aware of the various negative impacts of globetrotting and the importance of ecotourism and responsible travel, and knew that she wanted to be a resource for people to incorporate responsible travel into their plans even after the green trend hype died down.
The Yearning: Pre-1000 Days

  • In 2009, Linda struck out as a freelance writer, but wrote primarily about personal finance. She struggled to find outlets that paid for travel writing, particularly ecotravel.
  • From 2007 to 2009, Linda worked for ecotravel and environmental websites, but someone else always owned the copyright to her work. She yearned to create the ecotravel guide that she had in mind, without corporate oversight.

The Great Hope: Days 1-333

The Grind: Days 333-666

  • Just after the one-year anniversary of creating her blog, Linda upped the ante to take her site from one person’s thoughts to an ecotourism resource: hiring a stable of outside writers. Many fell off at the beginning, delivering low-quality work or nothing at all, and the management process took a lot of the time she expected to gain by hiring new writers. Instead of creating travel guides as she expected, she became a full-time editor!
  • A number of personal issues created huge set backs for her business, from moving to a new house with no internet for over a month to several incidents of death and cancer in her close family.
  • While content for the site was produced by new writers, Linda struggled with fitting in her other work (writing personal finance and occasionally also travel articles), the blog, and her two daughters, who were only in daycare a few days a week.

The Sunrise: Days 664-1000

  • In many ways, Linda still feels like she’s in the grind but the community she has created says otherwise. Even though Linda isn’t posting as regularly as she would like because she is prioritizing family time, every post she puts up is greeted with thoughtful comments right away. Her blog has been promoted on many other sites and publications, including the Britain Tourism Guide, where she placed an article.
  • Linda and her team—now three regular contributors—regularly receive invites on free ecotravel trips from tourism boards, tour companies, and individual eco-friendly hotels. More trips than they can possibly go on!
  • Her site is ranked 284,021 in the U.S. and 638,232 in the world on Alexa. (It seems like a big number, but one blog I know with similar traffic is ranked 8.5 million worldwide! (Even National Geographic is only #500.) Over the years she has gotten up 180 posts, and with her team and network, she is poised to expand her blog into a business when her family situation permits.

erin raub

Erin Raub, The Travel Copywriter

Erin had been freelance writing since 2007, dabbling in this, that, and the other thing, but mostly, she felt like she was slaving away for peanuts, working for clients she didn’t love.
The Yearning: Pre-1000 Days

  • Erin says, “It lasted years, not days! I juggled many ideas to grow my business, but had never identified one that both played to my passions and had a good chance of succeeding.
  • She was waking up at 3 a.m to do her writing., because she didn’t make enough to pay for childcare. She fit her writing into the early-morning hours and played full-time mom during the day.
  • It took months of serious brainstorming before she finally hit on the idea of The Travel Copywriter, combining her love of travel writing with a lucrative writing niche, copywriting.

The Great Hope: Days 1-333

  • For two months, she devoted all her free time to The Travel Copywriter. She hired a web designer while she wrote the copy, and she read absolutely everything about travel & tourism marketing, re-reading her favorite copywriting books and subscribing to dozens of industry blogs.
  • Before even her site design was ready, she had popped onto page 2 of Google search results for “travel copywriter,” then page 1, when her site was a white background with basic copy – nowhere near finished. When her first potential client emailed, based off that barren website, she realized she had to kick it into high gear.
  • She struggled to fulfill her regular work obligations while building her new business. There was a lot of work, but she loved her new clients.

The Grind: Days 333-666

  • Erin credits her fast luck to her Google ranking. She says, “Clients began contacting me. Suddenly, I had a full plate. Sometimes, it felt a little too full.”
  • She sent her son to preschool with her new income, buying herself more work hours – and, even more importantly, reasonable work hours, changing her work rapidly and for the better.
  • Slowly, she closed out her contracts with previous clients. Her schedule was full of inspiring hotels, vacation rentals, and travel agencies. Her dream clients.

The Sunrise: Days 664-1000

  • Erin’s client list grows every month, full of clients paying high, professional rates.
  • She’s financially prepared for any lulls, which would really mean free time and to check items off her to-do list like improving her website, networking, and growing her business.
  • ”I can see myself doing this for decades to come,” she says.

How has your journey been different?

ABOUT THE AUTHOR: Lisa Stein owns, is a college business professor and a mom to Gabriela and Elle. Lisa is dedicated to playing a part in helping women and moms run a business they love, help support themselves and their family and create a flexible lifestyle. You can find her online on Facebook and Twitter or at home burning something in the kitchen.