Welcome to the Design Your Dream Life Series!

If you’re new here, this is a series where I interview people who have designed their dream life. You can find all the interviews here on the Design Your Dream Life Page.

I’m so happy and excited to have Jocelyn Paonita Pearson share her story today!

To give you some context, Jocelyn’s bio reads: Jocelyn Paonita Pearson is a Best-Selling Author, TEDx Speaker, and Founder of The Scholarship System, an online program to teach families how to pay for college with scholarships and avoid student loan debt. While building her own online business, Jocelyn gained over 3 years of experience in creating profitable funnels and now coaches others to do the same. Today, she continues to run her business while enjoying location-freedom, living on a small island in the Caribbean with her husband and their pleasantly plump dog.

Here’s my interview with Jocelyn…

Jocelyn Paonita Pearson


Finish the sentence “I knew I was living my dream life when…”

I moved to an island in the Caribbean with my husband and was able to grow my business from here.


What was your life like before all this that led you to make a change?

Starting The Scholarship System was somewhat of an accident. When I was in college, I had the belief that “I wasn’t creative enough” to be an entrepreneur.

I had a lot of friends quitting their jobs or leaving college to start an online business and thought it was a neat idea but it wouldn’t work for me. My plan was to work in a leadership program with a well-known company and slowly move up the ranks to C-Suite. Never did I even consider following in their footsteps!

And then someone told me, “You don’t have to be creative to be an entrepreneur. You just have to listen to people b*tch and solve their problem.” (Sorry for the vulgarity here but that was truly what the speaker said).

I thought to myself, “I think I can do that?” and talked to Donny, my then boyfriend, now husband, about what they said. We started brainstorming all the ways people complain to us in our day-to-day lives. Donny was a personal trainer at the time and told me how much time he wastes doing paperwork between training sessions. And so began our first startup – a tech startup to make gyms paperless.

I was a fish out of water when it came to the start-up. I had no idea what to do, where to begin, and had zero skills when it came to building anything online… it was kind of a mess. And this was back in 2012 so, honestly, there weren’t many Amy Porterfields or Natalie Bacons sharing their secrets just yet. 😉

We were staying in on weekends and cranking away for an entire year. We gained a little bit of traction but still, in the end, we realized our hearts just weren’t in it and ended up shutting it down.

I have a hard time with failure so it took me a while to really accept that we weren’t going to do anything with it. Little did I know, this “failure” would catapult my next business.

This was all while I worked in corporate finance.

Even though I had planned on sticking to the corporate world, I was really a black sheep. I always wanted to innovate, change processes, make them more efficient, go against the normal way of doing things. I always received high marks on my reviews but what kept popping up was “entrepreneurial” in the comments (which is funny now but back then, I didn’t think anything of it).

I wanted the “safety” of a corporate job, consistency when it came to income and honestly didn’t believe I’d have the ability to build my own business (even as we were trying to build our tech startup). Perhaps that’s part of the reason it failed? I didn’t have faith in myself back then.

But, while we intentionally sought out our first startup, The Scholarship System really just fell in my lap. More on that in a bit!


What’s your lifestyle like now?

Donny and I live in Curacao, an island down in the Caribbean.

I am currently sitting on our balcony overlooking the water as I write this. I do have an office space here but I only go there a few days per week. It’s hard to stay concentrated when you’re surrounded by such beauty and have nice weather 365 days out of the year!

I try to stay relatively disciplined with work because I have a small team that depends on me so that office space helps. Still, we frequently take an afternoon or morning off to go kiteboarding, snorkeling, grab lunch with friends, etc. I can honestly say that I’ve never “played” so much in my life and yet we just had our biggest month yet for the business!

I wouldn’t even say it’s work hard, play hard. It’s more like making play part of my regular routine.

Jocelyn Pearson

How many hours per week do you work?

I’ve used Toggl to track my time ever since the beginning and it’s eye-opening! When I first quit my job, I felt like I was working all the time but tracking my time made me realize how much waste was in there.

Now I try to clock 30 productive hours on there each week. I know I can usually accomplish what I need to accomplish in that time. If done sooner, great! The key here is only clocking productive hours though – which means I turn off the timer when I grab a cup of coffee or a bite to eat, bathroom breaks, scrolling through Instagram, etc.  We use this tool with my team as well.


How do you make money?

The Scholarship System is my primary focus where we teach families how to pay for college without student loan debt.

It started off as a book sold through Amazon, then grew into speaking and an online course, and now has slowly added other revenue streams. We have a few affiliate products we promote to our audience, ad revenue on our blog, a few sponsored posts and a membership that we just launched as well. Still, our online course is our flagship product as we’ve had many years to perfect that.

I also now coach others who want to create online passive income. Having done this for 3+ years now (longer if you include our original startup), I’ve had my fair share of experience in online marketing and product creation and truly love it. This isn’t something I will ever turn into a full-time thing but I love the change of pace when working with my clients. It keeps me sharp and there is nothing more rewarding than to see someone successfully launch their first product!


How did you get started?

A friend of mine had published a book through Amazon and was turning it into an online business. At this time, I had just graduated college debt-free after securing 6-figures in scholarships and had tons of people asking how I pulled it off. That’s when I realized I could easily write a book on it as well. It wasn’t meant to be a big “money maker” since my plan was to remain in the corporate world, but instead a way to help the masses when it came to avoiding student loan debt.

I hustled and wrote my book in the morning between 5 and 7 AM and then headed to work for the rest of the day. Luckily, my friend had suggested putting a lead magnet inside the book in case I ever did want to make a business out of it. It wasn’t until nearly a year later that I actually started doing anything with the emails I was collecting!

After watching my book sales grow every month (without doing any marketing), I realized this was a need. There were enough people with this problem and I knew I had the solution. So I asked myself, “How can I get this in front of more people?”

That’s when I decided to turn the book into an online course for families.

My first “launch” was in July 2015. I am actually extremely risk-averse, so I wanted to know that this was something people would pay for before quitting my comfy corporate job.

I honestly can’t remember how I came up with the idea of a webinar but that’s what I did. I put together the most awful sign up page and my sales page was basically a headline with a Paypal button. I then emailed my list of less than 1,000 people and had about 50 registrants.

I recapped the lessons from my book for the few people that attended and pitched them a live version of a course based on those lessons (that I had yet to create) for $47.

I got 8 customers, put in my 2-week notice that Monday and haven’t looked back.

Leaving the corporate world was a major relief mostly because I could finally make my own decisions and dictate the path of whatever it was I was working on. It drove me crazy when people stuck to the “old way of doing things” and I was TERRIBLE at playing corporate politics (still am…) I actually didn’t mind the work hours though I did find it difficult to stick within the allotted vacation days (Donny and I love to travel).

I wanted to help as many people as possible and do so on my own terms. The best way to do that, I realized, was to start my own business.


How long did it take for you to make $1k per month?

I had to dig up the old spreadsheets for this one! My book sales were regularly $500 or so per month so that was a decent base. Between book sales, speaking, and my mini launch, I’d say I made about $5,500-$6,000 in a matter of 3 months or so which would average to more than $1k/month.

Still, if I removed speaking, I’d say our consistent course revenue kicked in by October so that was 3 months into the business.


How long did it take for you to make six figures per year?

We were on track for 6-figures within 6 months of consistently promoting our course, 9 months from quitting my job.

It was kind of surreal and honestly, I was always waiting for the carpet to be ripped out from under me. I regularly thought “Is this real? Are we really doing this?” I had a little bit of impostor syndrome, but we’ve been able to maintain it. Nowadays I realize we are changing lives and that our earnings are tied to the value we are bringing to families and students around the country so I no longer feel guilty about it.

There is nothing more rewarding than an email or excited Facebook message that a family received thousands of dollars in scholarships – that’s when I know we are in the right place.

Scholarship System

What do you wish you knew when you were starting out that you know now?

Oh goodness. So many things! I probably would have started blogging right from the beginning. We didn’t start consistently blogging until over a year in to business which is crazy! We’ve had a lot of growth with our blog but I can’t even imagine where we’d be if we started from the beginning.

I also recently learned of Stu McLaren’s framework of using a “success path” in your content so that members and customers know exactly where they are now, where you are taking them, and the milestones they need to follow to get there. I wish I had this back when I first created my course! We’ve updated it a few times since the beginning but now I am thinking a complete overhaul is in the near future!


What advice would you give to someone who is starting out and wants to design her dream life?

For some of us risk-averse people, it can be challenging and scary to make the leap and pursue a more flexible path. For me, I made this possible by stashing away 6-months of expenses and validating my idea ahead of time. I personally believe in validation before committing 100% to something. I never put a ton of time into a product until I’ve already sold it. There are many ways you can do that so here is a checklist of ideas on how to test your idea before launching.

My second suggestion is to really perfect one product before moving onto the next. I have so many ideas of different ways we can help families, however, I once heard from Amy Porterfield that you should give a product 6-12 months before moving onto the next. I think focusing on our flagship course, and only the course, is why we experienced growth relatively quickly.

So I personally would test out an idea, see if the market is open to it and focus on that ONE idea.


Where can people find you if they want more?


A Final Note!

There is sooooo much I connect with in this interview that I truly had a hard time picking out my favorite parts. If you didn’t read every single word, go back and reread it. There is gold in this interview.

Jocelyn gets it. She gets it on a level that’s hard to explain… but I’ll try!

Jocelyn is focused on providing value to her target market. She understands her money is directly tied to the value she gives to the world.

Jocelyn gets that it’s about what the target customer wants and not what she wants (this is why she’s so focused on validation prior to going all in). It reminds me of Dan Sullivan’s advice that you should never fall in love with an idea before you have market proof it’s a good one. This is so important to making money from a business.

Jocelyn understands productivity, time management, and cranking (my all time favorite word for describing what it takes to produce massive results – any time someone uses this word, I know they get it). She understands commitment, hustle, and decisiveness, which is why she’s now living in the Caribbean living her dream.

A huge thank you to Jocelyn for providing so much value in this interview. I’m so thankful to her that I get to share this with you. 

P.s. Here’s a pic of Jocelyn and me speaking together on a panel at FinCon from my About Page!

Are you inspired by Jocelyn?! Let her know in the comments!

P.s. If you want to start an online business, I highly recommend joining me in Online Business For Her!