Case Study: How Jo took a series of “baby” steps to become the CEO of her life

Ramit Sethi

Over the course of creating Earn1K 2.0, we discovered some fascinating insights about people and money.

In order to create the second version of my flagship course on earning money on the side, I collected over 100,000 data points. That’s surveys, emails, phone calls, 1-on-1s, and Earn1K 1.0 student feedback.

Here are two of the most interesting barriers we discovered:

“I can’t start earning money until I get all of my finances in order…I need to get business cards, a website, Twitter…then I’ll take this course.”

Then we discovered this:

“I can’t be an entrepreneur. That’s for people who quit their job and start a company. I don’t know anything about that.”

After we heard those the 650th time, we began to craft a response.

The truth is that aiming for perfection is a great way to do nothing. How many of us are guilty of that?

Instead, I always push for a series of Quick Wins and Big Wins.

Quick Wins: Focus on getting immediate positive feedback. This is critical to ongoing motivation and helps get you over the initial hump of starting out.

Big Wins: Instead of worrying about saving a few bucks here or there, or setting up a useless blog that nobody reads, identify the 2-3 things that would get you DISPROPORTIONATE rewards. Spend your time there.

As a result, in Earn1K, we are ruthless about showing people a series of baby steps to get 3 paying clients and earn $1,000/month…and then far, far more.

Today, I’d like to share a story of one of my students: Jo.

You’ll notice that in her story, she doesn’t “boil the ocean,” a term that describes doing something earth-shattering (usually used derisively since it’s an impossibly large goal).

Instead, she takes a series of BABY STEPS that continually keep her moving.

Sometimes she might make a bad decision, but at least she’s moving — and smart people can correct their course.

The result?.

Well, within a few months of Earn1K, here’s an exact quote she got: “They wanted to hire me,” Jo said, “but by then they couldn’t afford me.”

If you’re nervous about quitting your day job and making the leap to working for yourself full-time, I think you’ll enjoy Jo’s story.

“I didn’t want to work for a corporation anymore.”

Jo is no stranger to hard work.

For years she had spent 60-70 grueling hours a week racing deadlines and fighting budgets as a manager for an enterprise-level project management software company. And while she still loved computers and technology, her heart just wasn’t in the work anymore.

“It was a hard time,” recalls Jo. “I’m very loyal, very hardworking. But because our system was so large and custom, any changes meant a lot of rework. My mother had just died. I didn’t like living in Las Vegas. And the work and the bureaucracy was killing me. I didn’t want to work for a corporation anymore. I wanted to work for myself.”

That’s when she stumbled across I Will Teach You To Be Rich.

“Ramit is one of the most relentless people I’ve ever met.”

An avid reader, Jo gobbled up Ramit’s book. That lead her to his blog. From there, eager to learn more, Jo signed up for Ramit’s mailing list.

“Ramit cuts to the chase. I like him a lot. He doesn’t tolerate a lot of slack and bullshit. I’m not quite as ruthless as he is,” Jo laughed, “but I’m also cut to the chase. People either have the chops or they don’t to be an entrepreneur. And until you figure that out you’ll never be successful.”

Ready to figure out if she could turn her software management skills into a lucrative and reliable consulting career, Jo signed up for Earn1K.

Jo had read plenty of books about starting a business and changing her life, but none of them were near as systematic in breaking down the exact steps to take (and avoid) to earn money on the side. “If you actually work through the exercises in Earn1K, you start to figure out who you are and what you can do. That builds your confidence that you can be successful by implementing what the course teaches – using the skills you have to earn money, how to crush the psychological barriers all entrepreneurs have to face, how to structure your time, what employers are looking for.”

Jo’s favorite lesson?

A 65-minute video Master Class with the super-successful lawyer, pundit and serial entrepreneur Alexis Martin Neely. “Alexis explains exactly how she raises her rates $500 every time she gets five new clients. That blew me away!” Included with the video is a worksheet breaking down Alexis’ six step process for creating your own Money Map and a bonus worksheet showing you how to maximize your rates.

Jo was hooked. She completed the course on top of her 60-70 hour workweeks. It was time to put it all into action.

Making the leap to full-time consulting

The phone rang. It was a construction company in Minnesota. They were interested in paying Jo $5,000 for a three month contract. Jo knew this could launch her consulting career, but three months?

“I said no. I said it would not be worth it to quit my regular job for a three month contract.” The company was still interested in either a longer contract or hiring Jo as a full-time, regular employee.

That’s when Jo applied the tactics from the final lesson in Earn1K, a 39-minute video on how to make the leap to full-time freelancing. She decided to take a close look at exactly how much she needed to quit her job. If she could calculate her expenses and strike a better deal, Jo knew she could overcome her fear of quitting.

“I negotiated for a flat rate contract which paid enough to match my salary and cover medical, dental, and vision insurance, 401k, life insurance, travel, accounting and legal costs. I spelled all of that out to my client so they would understand how I was calculating my rate.” Literally. Jo compiled all of the numbers in a spreadsheet and presented it to the company. Take it or leave it.

“They said six months. I said okay.”

Jo attributes her success to Earn1K. “The course taught me how to be the CEO of my own life. I’m in charge of my life. It doesn’t matter who I’m working for. I can’t begin to explain how helpful that confidence was. When we started talking money, I didn’t blink or flinch. These people really understood the consulting world. If they had sensed the littlest bit of weakness, they would have brought me down on the price. But it wasn’t there.”

Jo got her six month contract, $5,000 a week and all her benefits. She was officially working for herself.

Six months later…

Her contract was about to expire. The company called her into the office. “They wanted to hire me,” Jo smiled, “but by then they couldn’t afford me.” They did the next best thing and extended her contract.

In the meantime, Jo landed a second client and hired two subcontractors to manage that while she focused on the construction company. Her consulting business was growing. And for the first time, Jo realized that instead of living where she found work, she could find work where she wanted to live. Where did she want to go next?

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  1. Nick Fox

    “They wanted to hire me,” Jo smiled, “but by then they couldn’t afford me.”

    WOW! I think that about sums up my feelings right there.

    It’s great to see someone who opened herself up to reasonable uncertainty long enough to get some quick wins in…and then used those quick wins to build towards some MASSIVE wins.

    I think if we could all open ourselves up to a reasonable amount of uncertainty, we’d all see our success rates go up.

    You don’t have to know every detail of what you’re about to do. Sometimes when it comes to just getting things started, close enough is good enough.

  2. STRONGside

    I love the concept of raising your rates after every 5 new clients. I recently did this with my wedding photography business. We recently attended a bridal Show and signed 7 contracts out of the show. We quickly realized our rates were way below the competition, and so we priced them accordingly.

  3. Yes I Am Cheap

    It requires grit & determination to achieve your dreams. Patience & perseverance are also important. It’s always great to be an entrepreneur but you have to face a lot of challenges before you become a successful one.

  4. Agota

    What’s the reason I can’t see the video in the private list area?

    Don’t laugh from me, my hair is getting blonde in summer 😀

  5. peterxyz

    Agota – you’re not the only one – I’ve spent 10 minutes clicking and can’t see it

  6. Greg Miliates

    Consistent baby steps are the key to moving forward and eventually achieving your goals, no matter how big the changes seem. By breaking down seemingly-huge, daunting tasks into tiny, actionable steps, you make the big goal doable.

    Set up systems to keep yourself on track so you’ll be less likely to slack off. Keep a daily journal of your progress. Get an accountability buddy. Create a small group of like-minded people who are making similar changes.

    Create an environment that won’t let you fail. I’ve done it, and I know it’s possible for others.

    One more piece of advice: don’t be squeamish about your rate. At first, you’ll feel like you’re gouging your clients–even if you’re charging the prevailing market rate. Get over it. A low rate makes you look cheap, unprofessional, and maybe even incompetent. A higher rate can give the appearance that you’re an expert (you are, right?) whose skills and experience demands a premium.

  7. Tracey

    Wow, that’s a great story. Well done Jo!

    I so agree that the perfectionist attitude stops too many people from achieving their potential. The problem is that being ‘perfect’ is highly overrated. It’s the people willing to take a chance and put in the work that succeed, just like Jo has done.


  8. Juliana

    Where did you go, Ramit?

  9. Erika Awakening

    Wow, I really enjoyed Jo’s inspirational story, and I love how you broke it down into these steps, Ramit.

    One of my coaching clients recommended your website to me (he posted it on my Facebook wall). He said some of my emails to my list sounded like yours to your list (tough love), lol, so I wanted to connect with you somehow.

    I used to be a lawyer. I was so scared of being an entrepreneur that for years I never even realized I wanted to be one! No joke. I dated entrepreneurs instead, living vicariously. Not fully satisfying by any means.

    But then I discovered my true life passion (facilitating transformation and connection), and suddenly what seemed previously impossible now seemed so compelling that somehow I started a business while still working full-time as a lawyer. It’s too long of a story for a blog comment. Suffice to say, now I am CEO of my life. 🙂

    Thanks for making the world a better place, Ramit. I will be back here again soon.

    Erika Awakening

  10. Darren

    Inspiring article. I think alot of people don’t take the plunge into self-employment because of the fear of uncertainty, you no longer get a steady paycheck and if you have a mortgage, you know you must pay those bills every month or else trouble!

    However, you will never create the life you want unless you put fear aside and go for it. A good way to gain confidence is to not worry too much about the outcome, but instead gauge your success by the actions you take. So as long as you are taking positive actions to create your business, then you are successful.

  11. Mary


    I think this guy must be a subscriber. Look at his quote.

    Good on him for finding his thing & making a little cash doing it.

  12. Natalie @ Mango

    “Baby steps” are important to remember with any seemingly “impossible” obstacle in life. Just do one little thing at a time, and before you know it, you’re at the top of the mountain! Okay, no more metaphors, I promise. I work at Mango Money and we have a great series of post about switching jobs– check it out if you’re like Jo and needing a change.
    Also, I came across a post on Moolanomy the other day about starting your own business, which you guys might find helpful too. For all of you Jos out there!

  13. Maddie

    I actually couldn’t get access to the Master class listed above either. Any suggestions? I signed in, and found a lot of other great material, but not that one.

  14. Dennis van der Heijden

    This is how I started my first company, step by step taking a day extra for the ‘baby’ me and my wife had, while actually building a lead generation company on the side. Before I knew I was asked by my boss if I could stay for at least two days a week in the company. They realized that I had outgrown the company but did not want to let me go. Now what a great feeling was that.

  15. sarena


  16. Gerard

    Interesting post, but it seems as a consultant, she still has to deal with the bureaucracy, the tight deadlines and all.
    She may now have more freedom, but in the end whether you work for an idiot or you consult to one, the idiot is still an idiot.

  17. Bharath

    Very inspiring. And detailed enough that I got a good look at what’s involved in moving from a full-time gig into free-lancing. All the best Jo!