Journey From Side Hustle to Full-Time Entrepreneur

The Contents

If you are thinking of starting a business you have likely heard “Everyone’s path to entrepreneurship looks different”. Reading other entrepreneur’s journey stories or listening to How I Built This Podcast, it only highlights for true that sentiment is.

I am an organizer, process and category person to my core. So over the past few years when I was asked- “what do you do [for work]?” I struggled hard to find the right label because it was consistently evolving!

My journey started as a side-hustle and transitioned into third-shifting until I made the leap into full-time entrepreneurship! Looking back at 2018 when I started allowing myself to dream of Olive Fox Design I would not have predicted how this unfolded into where I am today.

Corporate Job Burnout – The Trigger

I was coming out of a particularly rough busy season as an auditor. Busy season for a CPA consists of a lot of late nights, balancing a number of client deadlines, working on the weekends. The years prior I did a much better job of taking care of myself- that last busy season I did not. I was going through the motions of attempting to set boundaries yet unsuccessful in executing on that thought. I was left craving feeling inspired and creating.

My (now) husband and I were engaged – I knew that my life would drastically change as a military spouse. This was also prompting a desire to connect with others outside of my sphere. My past as a business major likely colored my outlook because the only way I could see meeting all of these internal goals was to go down the path of entrepreneurship.

Gateway to Entrepreneurship – Etsy Shop

Walking through a local shop, I started to notice all off the prints that depicted the city. It got my thinking that shortly I will be moving around wehre the army sends me and calling a lot of places home. The idea to open an Etsy shop to sell military themed prints was born.

I spent the next few months laying the behind the scenes groundwork for my business (getting reacquainted with Adobe software, naming, branding, website, securing social media, designing shop items, etc). Then in September of 2017, I posted my first 20 listings to Etsy. Days later I had my first sale. I don’t have the perfect words to describe how much that $6 sale meant. It was proof that others appreciated my work and made me realize I had more to contribute to the economy than my accounting skills.

The holiday season was very good to me that year and I had over 100 ornament orders in a three week period. I like to think my supply chain/business processing professors would be incredibly proud of the workflow I built to handle this crazy influx and production of handmade custom orders.

Phase: Side Hustle

I classify the time period where I was building my Etsy shop as a side hustle. It was and still remains to be a good supplemental income. BUT realistically even applying full-time hours to this endeavor would not have been enough of a sustainable income. Therefore even in the dream world of unlimited resources, I would still limit the time and monetary investment being poured into this venture.

Exploration – Trying all the things

Alongside the Etsy shop, I dipped my toe into the social media realm (primarily with Instagram) and started to make some amazing connections within the military spouse community. Because I had a full-time job to provide the monetary support of my lifestyle- I could freely explore down a LOT of graphic design paths.

I went against a lot of common advice to say “no” while I was exploring to find my perfect fit. I said yes to everything from elopement invitations to custom lead magnet workbook design. [if you are curious to see some of these projects I use the color inspiration series to highlight various projects outside of brand design].

During this exploration, my brother asked me for my opinion on some Fiverr style logos for my sister-in-law’s new business. I died a little on the inside. While these logos are an incredibly inexpensive option, they lack the perfect reflection of a business that only custom design can provide. I ended up saying yes to creating her the logo + necessary brand elements for her practice and it opened up the world of brand design!

Finding my Perfect Space – Brand Strategist + Designer

Quickly after starting my first brand project, I dove into furthering my education in this specific space. From free podcasts and blog posts to paid courses about brand strategy best practices, I was absorbing it all like a sponge. I enjoyed building out the best workflow for my brand clients and diving into brand buildout projects.

In hindsight, it is so easy to see how brand strategy + design is the perfect fit for me. This combines my extensive business background with my creative side. BUT It took me quite some time to realize this. And even more, time to become more confident with saying no and limit the types of custom design work I take on.

Phase: Third-Shift Entrepreneurship

Once I was clear that brand strategy and design is my focus, my outlook towards my business began to shift. It clicked that with my new path I had moved from “side-hustler” into an entrepreneur. For me, the distinction between the two is in the potential. Could this venture realistically sustain my living with full-time hours? Yes.

With the understanding I was building something greater than a side-hustle, I worked on aligning my business goals. However, I still didn’t identify with the “entrepreneur” title, I fell somewhere in the middle.

When Todd Connor presented on the topic of third shift entrepreneurship at last year’s Military Influencer Conference, I finally felt like I found a label that fit my situation. The third shift concept helped me articulate how Olive Fox Design would fit in with my corporate accounting job and my home life.

Leaving the Full-Time Job

I continued with my third-shift entrepreneurship status for a year navigating handling work, Olive Fox, and home life. Depending on the day (heck even the hour) each bucket would take priority. After our cross country PCS (military move for those not familiar), it became more clear that third-shifting was not going to be sustainable for me much longer. Many hours of planning logistics and discussions with my husband, the wheels to leave my corporate job were set in motion.

I certainly had times of doubt. Leaving stable six-figure income for the uncertainty of entrepreneurship is not an easy mental hurdle to get over. But there were a good number of signs I noticed (and I’m betting a lot I missed).

One of those signs was during a conversation I had with my husband on the day of my CPA job compensation review. What he said to me hit like a ton of bricks –

“Tara, you just got a five-figure bonus and you sound more excited about booking a brand client and a $6 Etsy sale.”

It was absolutely true. I built a business that allowed me to live more in alignment with my priorities. Each sale reminds me of how much is possible. After that conversation, I walked a bit more confidently with the choice to walk away from steady and bet on me.

Phase: Entrepreneurship

On May 15th, I dropped the “third-shift” qualifier from my entrepreneur journey! I now am able to set my working hours and craft my days with a bit more intention. Some housekeeping items have been top of mind with this change! From working on revamping my welcome guide to editing my brand strategy and design timelines!

Next Chapter

In the accounting world that I had been a part of for over a decade, there is a very clear map of how to progress your career. Undergrad → Internship → Grad School → Full Time Job → CPA → Move Up Corporate Ladder

AND NOW… there are so many more directions I feel I can go. Am I terrified to get lost? Absolutely. But then I think about my favorite way to explore cities (you know when we could travel). Loosely research the must-sees and general area knowledge then set out and explore.

I am focused on doing the same with Olive Fox Design. I am getting a good sense of the overall direction while also letting the details be the adventure.

One thing I know that will continue to be central to Olive Fox Design is inspiring and supporting other ambitious entrepreneurs moving from the traditional workforce to building their own value-driven business.

Thank you for coming along with me!

Are you in the idea phase for your own venture? Working a W-2 job and side-hustle? Did you also take the leap into entrepreneurship? I’d love to hear about your journey to entrepreneurship in the comments below!

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