Leadership

The accidental entrepreneur

Embracing spontaneity, opportunity and the unexpected

Headshot of Caitlyn Scaggs
Caitlyn ScaggsJanuary 15, 2025
A young person riding a bicycle, smiling and holding a smartphone, featured on a magazine cover with the "Digital Entrepreneur" logo.

There is so much value in being a highly strategic entrepreneur with a firm business plan, clear goals and a clear strategy. Meanwhile, some of us look back on the entrepreneurial journey and realize much of it was unexpected and unintended, yet–against all odds–it came together. While the “accidental entrepreneurship” journey can feel reckless, it does invite spontaneity, opportunity and as a result, immense joy.

Take good care of people and the rest will take care of itself.

My entrepreneurial journey began completely organically because I love people and I loved what I was doing. I had transitioned from a career in law enforcement as a patrol officer on midnight shift into the dynamic world of marketing and communications. I found a whole playground of professional fun that I didn’t know was possible. As my passion for my work grew, word spread within the local business community. I was asked to join panels and I found myself winning awards for the work I was doing for my employer.

I was having fun, and the increasing publicity around my work led to business leaders asking me to meet over coffee and share more of what I know. That was another thrilling win for me—an opportunity to help others while pursuing something I was truly passionate about. At one of those early coffee meetings, someone asked me what my hourly rate was. At that time, with a non-traditional business background, I never considered I could monetize my knowledge and passion.

Yes, you can laugh–I still chuckle about it to this day.

My lunch-time consulting meetings soon turned into consultations outside of my day job. I was helping small and local businesses find their footing and voice on social media platforms. At that time, businesses were new to using social media as a marketing tool. They felt overwhelmed by the growing need for social media and the steep learning curve. I came in and provided clarity, enthusiasm and seamless execution of social media strategies. What was overwhelming to them was exhilarating to me.

Word of mouth spread about my great work in marketing and communications, and as a result, demand for my time and services was growing. I maintained this side-hustle for a couple of years before realizing that I could no longer work full-time for my employer, maintain my at-home responsibilities as a wife and mother and keep pace with my side-business.

It was time to choose, and I decided to go all-in with my business, Blue Mobius Marketing.

It wasn’t an easy decision, but I found myself drawn to the qualities of entrepreneurship. Autonomy, flexibility and the freedom to chart my own path painted entrepreneurship as an exhilarating prospect– one I believed could be lucrative for my family.

It felt like a choose-your-own-adventure novel brought to life.

I had intended to keep my business a solo endeavor, but within 16 months I hired employees and rented an office space to keep up with the demand for our services.

It was fast, it was exciting and it was an unexpected journey filled with lessons I’m ready to share–and apply to my next business.

Lessons learned from an accidental entrepreneur

I know that the work I put in long before starting a business helped me to prepare for success–even if I wasn’t sure what I was preparing for. I built a strong foundation that drove rapid growth in a short time and ultimately led me to sell my business to a local design firm.

Above all, I found joy in my entrepreneurial journey, and that helped me attract success in many ways.

Nourish yourself

I felt ready for entrepreneurship because I’d been actively seeking out professional content and growth opportunities.

I didn’t have a formal business degree, but I’m an avid reader, and I dug into works by authors like Dan and Chip Heath, Simon Sinek, Carol Dweck and Brené Brown. Their brilliant insights reshaped my mindset, giving me practical strategies I was eager to put into action when I launched my own venture.

I purposely write all over my books. I treat them like a journal, textbook and conversation wrapped in one. I make sure my books are never too far away because when I remember an idea or need a little guidance, I want to be able to quickly grab the book, flip through it and find the answer. I encourage you to read books that are relevant to where you are today. It’s just as important to explore ones that challenge your perspective or lie just outside your immediate focus. These diverse perspectives will give you an arsenal of tools and knowledge to draw from as you face the challenges of entrepreneurship.

John Warrillow’s “Built to Sell” was particularly critical to my journey. My dad, a fellow entrepreneur, was reading the book because he was preparing to sell the business he had grown over a 30-year period. I enjoyed reading the book alongside him, and it helped me see business from a different perspective–the idea of building something you could one day step away from intrigued me.

When it came time to move from coffee meetings to consultations, I carried the insights of seasoned leaders in my mind as I tackled challenges and made key decisions. For example, I structured my business in many of the ways Warrillow had suggested.

One key approach I implemented was treating services like a product line. By doing so, I created systems that prevented the success of our service-driven organization from relying on any single individual. Treating services like a product line helps make success repeatable as a team grows and also ensures there is something tangible to sell.

It really comes down to turning what some folks think is a "secret sauce" or "x-factor" into a repeatable process–and that’s the core theme in Warrilow’s book and the real reason I could sell my business. At one point, the buying agency even asked, "How will we maintain success after you’re gone? Aren't you the secret sauce to the whole thing?" I could honestly say I had created a way for others to continue delivering the same great work I did. Yes, they had to hire the right creative minds, but it was entirely possible to repeat the great work well into the future.

Hold space for spontaneity

Even the best-laid plans may need a pivot. As an entrepreneur, you have goals to achieve, customers to answer to, and a profit and loss statement to monitor. Absolutely, manage all of those expectations and needs! But, don’t cling so tightly to plans and performance outcomes that you put on blinders to the opportunities around you.

A critical part of my success as an entrepreneur was that I created time and space to reflect, which allowed me to recognize a good opportunity when it came my way.

Instead of being relentless in what I thought the growth trajectory should be, I was open to what the business community most needed from me. I listened to my customers, and that’s how my niche revealed itself. I took a chance and allowed my customers and stakeholders to directly inform the direction of my business. It's easier to sell what people need and want, not what I think they need and want.

It can be challenging to slow down and listen to what the community is saying and sharing. One tactic I used was to host free marketing workshops. At the workshops, I paid careful attention to the questions people asked and the challenges participants named. Their feedback revealed the opportunities.

Are you allowing yourself the breathing room you need to explore unexpected opportunities? Or have you gotten so wrapped up in putting out the day-to-day fires that you’ve forgotten to include space for dreaming and reflecting?

Once an opportunity or challenge emerges, consider how you can adjust course. You don’t need to take drastic or immediate action, but allow yourself space to reflect and iterate.

Establish your non-negotiables

When I realized that I was going to be all-in with my business I quickly developed some boundaries and non-negotiables that would guide me. While I was totally comfortable with spontaneity and a go-with-the-flow mentality, I knew it needed to be tempered with some hard-and-fast rules.

My core rule for the business was, “Take good care of people and the rest will take care of itself.” That mantra held so much and was how I checked myself on decisions, especially the hard ones.

Early on, I had to release our biggest client–some might call it firing them. This client was consistently mistreating my employees and creating unsafe conditions. I knew that to continue operating my business with integrity, and in alignment with my core rule, the client had to go. The decision wasn’t easy but I knew it was the right one for my business and my team. It did create temporary financial hardship, but I quickly on-boarded another client who aligned with our values.

One way to decide on your boundaries and non-negotiables is to determine the business legacy you wish to leave and how you want to be remembered as an entrepreneur or employer. Don’t let your journey get so spontaneous that you lose yourself–and your integrity–in the process.

Enjoy the adventure!

Just for a moment, I want you to pause, take a deep breath and consider the fantastic journey you're on. I imagine it is a journey with ups and downs, twists and turns, challenges and victories. That is what makes it worth doing.

While you’re with me in this moment of reflection, think about everything you've accomplished so far. They might be big or small, but they’re yours, and they’re worth celebrating. That’s one way to tap into the joy of the work we do.

I’m certain you have plenty of goals, and it may seem like insurmountable challenges are blocking those goals.

By acknowledging and celebrating what you’ve accomplished so far, you can give that inner critic a break. It’s also a good reminder that you’re pursuing your dream, something many people never muster the courage to do. You're a member of a community of brave souls who have taken that entrepreneurial leap of faith. That’s worth celebrating, too.

As you find meaning and joy in your journey, you’ll discover that you'll attract colleagues, clients and team members who share that same sense of zest for the work. When you allow yourself to let go of the need to be in ultra-control, and instead allow yourself to be just a little spontaneous, a world of entrepreneurial adventure awaits.

Maybe you aren’t exactly an accidental entrepreneur like me–but I hope you’ll choose to be an adventurous entrepreneur who fully embraces the journey.

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Headshot of Caitlyn Scaggs
Caitlyn Scaggs

Caitlyn Scaggs, M.S., is an entrepreneur, author, and keynote speaker based in Virginia. As a former police officer, Caitlyn has enjoyed a dynamic career that includes delivering a TEDx talk, publishing a women’s empowerment book, and serving as a top administrator for a mid-sized university. Currently, she equips other organizations for increased impact through her business, Connect 936.