How I Started An Online Business That Actually Pays the Bills
Woooo buddy, this post is a LONG time coming. Like LONG TIME. I haven’t ever sat down and spilled the twists and turns of my career story in one place. So, sister, grab a cup of something warm (almond milk latte for me!) and get ready for the FULL version of how I dropped out of grad school to run my online businesses.
Before we get rolling, let’s talk about my motives here. WHY AM I SHARING MY LONG, VERY MESSY STORY WITH YOU?
Because I want you to know that it’s okay if you don’t have it all figured out right this very second.
It’s okay to explore.
To try something. Hate it.
Try something else.
I didn’t wake up when I was a kid and declare that I wanted to write books (okay maybe I did declare this part lol), create digital organizational/mindfulness tools, design t-shirts, write blog posts, coach women through time management programs, host a podcast (coming soon!), etc.
NO! I uncovered one piece at a time. Finding your passion(s) is like a scavenger hunt. You uncover one thing and it leads you to the next, and then to the next, and then to the next.
So girl, if you’re unsure of what the heck your “thing” is, I really recommend that you do a little bit of heart work so you can get clear and stop putting so much pressure on yourself.
And guess what? I have JUST the tool that you need to do this. Best part? It’s free. I put together a 3-day video email series where I give you worksheets to help you do some sifting and get some clarity. I made these worksheets for some of my clients and they’ve helped so many of them so I just HAD to share them with the rest of the world.
Before I get into the details of my career story, I want to give you a timeline:
2008: I graduated from high school with a few different career path options in mind: I wanted to either be an author, work for a magazine, work as a wedding planner, or be an elementary school teacher.
2009: Worked my first job in retail as an assistant store manager (started out as a sales associate).
2010: Started working in the office at my family’s air conditioning company doing the billing while in college.
2012: Graduated from The University of South Florida with a bachelor’s degree in Mass Communications - Public Relations. Completed an internship at an event production company.
2013: Became a National Academy of Sports Medicine Certified Personal Trainer and started my first online business, Glisten Fit.
2015: Decided to go back to school to pursue speech-language pathology.
2017: Graduated with a second bachelor’s degree from the University of South Florida in Communication Sciences and Disorders - Language, Speech, and Hearing. Started graduate school at Florida State University for Speech-Language Pathology. Worked as a speech-language pathology assistant at a private school. Became a distributor of Young Living. Started The Social Speechie.
2018: Started Hustle Sanely in September, while still in grad school.
2019: Decided to leave grad school in January to pursue Hustle Sanely full time.
Okay now that you have a timeline to follow, let’s get into the juicy details, shall we?
As a little girl, it was always my dream to be an author. But I wasn’t really committed to the dream itself. I was more committed to my love for books. I was the type of kid who got in trouble for staying up past her bedtime, because I was crouched under my blanket with a flashlight trying to get through one more chapter. Books have always been my happy place, my safe place.
Fast forward to high school and I was on the yearbook staff. Being in this kind of environment really sold me on the idea of wanting to work for a big, fancy magazine. I pictured myself writing articles that changed the lives of the people who read them.
I also toyed around with the idea of becoming a wedding planner, because on the weekends, I was working on the setup team at an events venue. I loved helping make a bride’s wedding day dreams come true. Plus, organization was my love language (still is, lol).
Toward the end of high school, it started to dawn on me that I “should” desire to have a “safe and responsible” dream job. That’s when I thought that maybe teaching could be a good fit. I volunteered in the kid’s department at my church and I’d be able to work with books every day if I was a teacher (my love for books didn’t fade as I got older). I’d have a stable job with good benefits. Plus summers off...okay, I was sold.
Then I got to college and realized that education majors had to complete full-time, unpaid internships and that wasn’t going to work for me - I had bills to pay and was working full-time as an assistant store manager at my local mall.
You guys I changed my major SIX times. SIX. I started out as a business administration major. Then I hopped on over to marketing. Business calc scared the bejesus out of me so I decided to go back to pursuing elementary education and try to figure out a way to make it work. I just couldn't swing the the internship so I decided to give advertising a try. That was a big NO for me.
By this point, I had started getting into fitness and eating healthy. I decided to look into majoring in something nutrition-based. The science classes scared me so I was back to the drawing board.
I was running out of time to pick a major because my junior year was quickly approaching. I met with my advisor and shot it to her straight, “What major can I choose that is going to make sure that I’m out of here within 4 years of starting and requires close to no math?” Public Relations was the answer I got so Public Relations was the path that I took.
In hindsight, haphazardly choosing public relations actually changed my life. During my senior year of college, I needed an elective credit to graduate. The only course that was available online that fulfilled that elective credit was Intro to Blogging.
Little did I know that I would fall absolutely in love with connecting with people online. Being the Enneagram 3 that I am, I spent all of my winter break before my final semester of college building my blog, Lovely Little Things. I thought that I would need a semi-established blog going into the course, and I didn’t want to be behind. Turns out that the entire course was structured around building a blog from scratch SO I had already completed the entire semester’s coursework before day 1...lol. So I spent that semester exploring blogging more and more. I built this community of women who cared about what I was writing about. It was honestly the coolest feeling.
I never thought about potentially making a career out of blogging - it honestly seemed too good to be true.
Fast forward to the end of that semester and I was walking out of USF with my first bachelor’s degree, still unsure of where I was heading.
I was still toying around with my high school wedding planning dreams so I decided to apply for an internship at an event production company. Y’all I’m gonna be real: it was intense. The hours were long (I’m talking 14 hour long Saturdays) and I got paid a whopping 0 dollars. Fun fact, though: my blog was brought up in my interview and actually helped me get the job. I am thankful that I did this internship, because it made me realize that I actually really disliked the schedule of someone who works in the event industry. I was able to cross that off my list.
For the rest of 2012, I worked at my office job that I started when I was 19 (the A/C billing job) full time. I loathed going to work every day, and I just knew that there was something else that I was called to do.
I started getting the itch to try the teacher route again so I applied for a Masters of Art in Teaching program and got accepted. Before starting the program, I decided that it would be a good idea to go shadow a local elementary teacher to see what it’s really like. So I cold-emailed a few schools and was able to shadow a few teachers. Seeing the reality of being a teacher was totally eye-opening to me (aka it wasn’t just writing pretty notes on a whiteboard and reading stories to kids lol imagine that) and I knew that it just wouldn’t be a good fit so I declined my seat in that graduate program and moved on.
My friends and family urged me to get my personal training certification since I really loved working out and eating healthy. It made sense, so I did it. In early 2013, I became a certified personal trainer through the National Academy of Sports Medicine.
Working as a personal trainer taught me how much I loved helping people work toward their goals. I started an online fitness brand for women called Glisten Fit. I retired my first blog, Lovely Little Things, and dove head first into all things health and fitness.
I wrote weekly blog posts for Glisten Fit, had one-on-one virtual clients, created workout e-books, and started an online gym (my first monthly membership program) where I filmed real-time workouts and shared them in a members only portal.
Glisten Fit is when I was bit by the entrepreneur bug and whether I wanted to admit it or not, I was hooked. I learned how to build an online biz from the ground up with the help of Google and a lot of prayer, lol. This business taught me how to film and edit videos, create branded content, and build out systems that allowed me to work with clients seamlessly.
In January of 2014, I decided to work a few days a week at a local gym for some human interaction. I was training clients one-on-one as well as teaching a few HIIT group fitness classes.
So I was running Glisten Fit, working at the gym, and STILL doing the billing for the A/C company. As I’m sure you can imagine, I burnt myself out QUICK. Being a first time business owner was exhausting on its own, but add in 2 other part-time jobs on top of that and I was toast mentally.
I was constantly on the verge of a mental breakdown.
I was so unhealthy mentally.
I knew something had to change. I started to lose my passion for health and fitness because of the intensity of this burn out and I was NOT okay with this because my daily workouts had always been my way to clear my head and fill my cup. I wasn’t willing to sacrifice my personal love of working out to continue pursuing fitness as a career.
In 2015, I closed the doors on Glisten Fit and left the gym that I was working at.
I felt like I was back at square one. I was 25 years old and had no idea what I wanted to be when I grew up.
I continued working at my office job, miserable and lacking direction.
I honestly spent my free time Googling careers. I stumbled upon something called Speech-Language Pathology and was intrigued. It seemed SORT OF similar to the parts of teaching that appealed to me. So what did I do? Cold-emailed local SLPs to shadow, of course!
I shadowed 2 SLPs and was sold. They had “safe/good” jobs that seemed fulfilling and like they paid pretty well. They seemed happy and to really enjoy their jobs.
In August 2015, I started working toward a second bachelor’s degree in Communication Sciences and Disorders while still working my office job, except now that I was back in school, my family let me leave the office and work remotely, which was an incredible blessing.
I spent my days working and going to class and my nights studying.
During this time, I was scouring the Internet for any and all advice about getting into Speech-Language Pathology graduate programs. But I couldn’t find any relevant/updated information. I promised myself that if I did manage to get into grad school, that I would create a brand that was dedicated to providing SLP undergrad students with tips on how to get into grad school.
In May of 2017, I finished my second bachelor’s degree and found out that I had been accepted into a few SLP master’s programs....I was STOKED! And got right on creating that brand that I talked about before. The grad school application process was so intimidating and I wanted to ease that stress for as many people as possible.
During the summer of 2017, I created an Instagram account called The Social Speechie. It was through TSS that I started creating digital resources for other people to use to organize their work flows and schedules. I started a Teachers Pay Teachers store and started selling my planning tools and lesson plans that I was creating for my students.
Wait, what students you ask?
I accepted a job to work as a Speech-Language Pathology Assistant (SLPA) that coming fall so during the summer, I was getting down and dirty with creating lesson plans for my future students. I watched SO many tutorials and read SO many blog posts about how to create digital resources.
As I progressed through my graduate program, The Social Speechie was growing faster than I ever could’ve imagined. People were asking me to share more of my planning resources - except now, people who weren’t teachers and did not have access to my Teachers Pay Teachers store wanted in on the goods.
So in September 2018, I started my Etsy Shop, Hustle Sanely, and my website, jessicamassey.com.
I had absolutely no idea that they would take off the way that they did. All I know is women were DMing me on Instagram, asking if I would please share my digital planner with them so sure enough I Googled my way through starting an Etsy shop. Because I wanted to help these women. I STILL didn’t know that this is what I wanted to do long term. I was so focused on serving and meeting the needs of the people around me that I was too busy to be striving toward trying to make this thing happen.
In August of 2018, I started sharing heartfelt captions on my personal Instagram page that really resonated with people. My personal brand was growing and by December, I was at a fork in the road. I could either continue on with pursuing my SLP master’s degree or I could jump full force into pursuing Hustle Sanely. Which to be honest, I didn’t really know what that entailed. And it scared the absolute crap out of me because it involved a lot of unknowns. But what I did know is that I couldn’t fall asleep at night because I was SO excited to wake up and create products to share with these women who I was connecting with on Instagram. I didn’t know someone could be SO excited about….work.
In January 2019, after MANY conversations with my husband and family (and after a few glasses of really great wine at a winery in Blue Ridge, Georgia with one of my best friends...now virtual assistant which is WILD) I decided that I was going to drop out of school and see where this digital planning biz took me.
It’s almost July 2019 when I’m writing this and my business has evolved so much in 10 months.
I released a digital mindfulness journal in February.
I started designing and selling t-shirts, prints, and totes in March.
My very first program is launching in 3 days: The Hustle Sanely Lifestyle Coaching program, where I teach women how to ditch doubt and create a schedule that allows them to go after their dreams without sacrificing their mental health or relationships. Aka teaching them what took me years of trial and error to figure out.
I’m releasing my 3rd-5th digital planners within the next 4 weeks.
I have a podcast launching in September.
And plans to write my first book within the next 3 years.
WHAT A TURN OF EVENTS, PEOPLE!
Plus, I’m leaving my A/C billing job in September, because thanks be to Jesus, my business is thriving.
Aka September will be the first time in over 10 years that I have worked ONE job and not been in school. HALLELUJAH.
But remember, I didn’t just wake up one day and know that I wanted to be doing all of this. I served people with one thing at a time. That led to another. And another. And another.
So if you’re still here (I wish I could high five you through the screen honestly because I know that was A LOT lol), the 2 biggest things that I’ve learned over this long, messy career journey of mine:
When you spend your energy serving instead of striving, you will find your calling.
When you are led by love instead of pushed by fear when it comes to making decisions, things tend to work themselves out.
Don’t spend your time and energy trying to frantically figure out what you want to do. Spend your time and energy doing things that light you up (for me that was helping people get organized) and figure out how you can serve people through that.
It’s okay if it takes you awhile to figure it out - I was 29 years old when I figured out what I wanted to be when I grew up!
P.S. I don’t want to leave out my favorite part of the story.
When I was in high school, I was at a church conference and I will never forget a prophet telling me that he saw me surrounded by flags from countries all over the world. 17 year old me thought:
#1 he was wild and
#2 cool, I guess I’ll be a world traveller or something.
What I didn’t know is that one day I’d be sitting behind my computer screen getting messages from women ALL OVER THE WORLD thanking me for encouraging them and being a light in their life. God is really, really cool.