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TAMPA BAY • FEBRUARY 23-24 2026

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High School And Starting An Online Business – The Connection

High school can be a wonderful experience where you create lasting memories.

Starting an online business can be a beautiful experience where you make connections, build relationships, and build your business.

High school can be scary if you’re entering in the last two years or if, as some children still do in Jamaica, for example, you have to attend a brand new school for an extra two years of advanced study.

Starting an online business can feel as scary as that high school experience.

Let’s see how.

Different ponds; different fish

It varies throughout the world, but here in the United States, many high school students have known each other at least from middle school. In middle school, you were the child who received the awards at the end of the school year for never missing a day from school.  You were on the Honor Roll, and during graduation, you received several Awards. Your teachers loved you and showered you with attention because you showed you were enthusiastic about learning. You Home Room teacher gave you special privileges because she could count on you to assist her and others.

You were a big fish in a little pond…

The big day arrives. It’s your first day of high school and you look around and see no one you know. No, wait! You see a girl from middle school. You eagerly walk up to her to check if you’ll be in the same classes. You’re not. In fact, she becomes a little distant when she discovers you’re taking all Honors Classes. It’s your first day yet the teacher barely glances up as she calls the seemingly endless list of names on the register. Seems there’s not too much interest in getting to know the students.

It suddenly dawns on you that you’re now a little fish in a big pond and you have to figure out things more independently. There is no one to show you the way, and if there is, you have not met them yet.

My Online Journey Begins

I started my online journey in the fall of 2008 with knowing only ONE thing.  I had taken a 6-week online training for Direct Sales Consultants of every type of business and at the end of the training, the presenter mentioned the opportunity to market your business to a larger audience online. Armed with that (theoretical) knowledge and nothing else, I went online.

I had no idea how I was going to market my products online but I was optimistic. 

After all, I was a high-achieving employee in different multi-national corporations, received many accolades and promotions.  I’d also owned and operated three off-line businesses. How hard could it be? As I tried to get my bearings, I felt just like the girl who entered high school in 11th grade where everyone knew each other and she knew no one. The other students had their rituals and understood their special language.  I felt as if I were going up and down hallways and could not find the hidden door to my classroom.

A Memory

One of my memories that still make me smile was connected to the first online class I took in November 2008.  Since I had a love for writing, I saw “somewhere” that a marketer was offering a course in Article Marketing.  I quickly signed up for the class as that was a good place to start. He told us that we should open accounts on Facebook, Twitter, and LinkedIn. I dutifully did but had no idea what to do. The funny part was when he told us that we needed to create a landing page with a free offer to “build a list.”  When I asked for a sample landing page (had no idea what he was talking about. And build a list?), he said to copy his.

Since I’d done some basic designing in college, I felt I could copy his page.  So after a few days, I felt pretty good about what I’d done…but it still looked homemade. Oh, but wait! How was I to get the landing page from my computer to the world wide web?  I had no clue and did not know whom to ask.

I somehow got introduced to Chris Farwell’s training where he took you by the hand, step by step, through videos.  I learned about FileZilla and FTP and things began to look a little more promising. Those were pretty tough times because all the confidence I had in my ability to quickly learn a new job and new skills went out the window. The online world was totally unchartered waters. I was spending a lot of money taking classes – some of which I was not ready for as the basic foundational pieces to build on were not there.  Some training was mere fluff, but I learned something from all. The worst part, I was not making money. As I learned more and gained confidence in some areas, another ‘ugly cousin’ reared its head.

The Ugly Cousin

My belief that everything had to be perfect almost paralyzed me as I created what would later be considered amazing products and courses, but never released them as I felt they were not perfect.

Are you holding yourself back with perfection analysis and perfection paralysis?

No one expects it of you!

No one wants you to be perfect! Imperfect people relate better to imperfect mentors and coaches.

Resolve and Determination

I was tenacious because I’d walked away from corporate America two years before and I’d resolved not to go back to work 9-5 five days each week! I was also determined to break through these barriers and succeed.

My Breakthrough

Happily, seven months after coming online I got connected with someone who’d be my mentor for the next three years. Through her mentoring, I began to get clarity and restored confidence so that I had my first affiliate sale through the articles I was writing on ezinearticles. I later went on to teach online marketing to newbies and later more advanced students.

My further journey would take me through positions as a Social Media Manager, Local Business Consultant, Mentoring, and Coaching.

If you’re new to online marketing, if you’re struggling and feel like you’re the new kid in school, you’re not alone. I share my journey of my first year online to help you appreciate that although it can be challenging to transfer your skills from the offline world online, you do not have to go it alone.  You can work with someone who has been there and avoids wasting the time of trial and error.

Your Turn to Seize the Opportunity

How would you like to join me on a complimentary “Double Your Results” coaching session?
Simply send me a message through my contact form and I’ll send you a link to my scheduler so you may schedule a time that works best for you.

If you’re working online, what were or are your three biggest challenges?  Please share in the comments.

Yvonne A. Jones
Yvonne A. Joneshttps://50andwisercoaching.com/
YVONNE is a Personal Business Coach | Relationship Marketing Strategist| Amazon Best-Selling Author| International Speaker. She is the Founder of the 50 and Wiser Community on Facebook – a Group of women who want to DO more, GIVE more, and BE more. As a certified Strategy and Accountability Coach, she helps Entrepreneurs, Coaches, Consultants, and Small Business Owners eliminate limiting beliefs, create a business they love, and have fun doing so. Her favorite client is a highly-motivated woman 50 and Wiser who has been in business for approximately one year and is ready to empower herself and move to the next level. Yvonne’s background is in banking, Human Resources, administration, and Customer Service. At 52 years she handed in her resignation and walked away from Corporate America to start her own business full-time. She has experienced the joys and challenges of owning multiple businesses. She was listed on HuffingtonPost.com as one of the “Top 100 Most Social Customer Service Pros on Twitter” and on GetApp.com: “One of the Top 15 Most Influential Customer Service Experts to Follow on Twitter.” Despite the recognition and promotions received while in corporate life in Jamaica and America, she now considers herself “unemployable” due to her love of being her own boss and inspiring others to pursue their passion and dreams. Yvonne’s mantra: “Focus on relationships; the money will follow.”

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2 CONVERSATIONS

  1. What a great article Yvonne. It really resonated with me because as an International Army Brat I was always starting new schools and always looking around to see if I knew ANYONE from ANYWHERE! Yes, we can become overachievers, often just to be seen and recognized in new environments, and can let that Overachievement-Mindset get in our way. Thanks for the tips on how to get past that.

    • Oh my! I can empathize with you moving from place to place and changing schools. Would you believe when I wrote the article I totally forgot that I had the exact experience?

      Switched from boarding school to another high school in the city with only two years of high school left. The illustration in the article was supposed to be hypothetical!

      That description-overachievement mindset-can definitely be both a blessing and a curse for adults.

      Thank you, Kat, for your insightful comments.

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