The Entrepreneurial Journey — Swim, Don’t Sink By Heeding These Dozen Lessons Learned

Rachel Strella
4 min readAug 12, 2018

I was recently asked to share my business success story for inclusion in an entrepreneurial publication.

Entrepreneurship is a topic I have much passion for, but I’m always hesitant to share sure-fire “success”-related advice because anyone who walks the path of entrepreneurship knows that success has ebb and flow moments — akin to a wave crashing over your face.

I started like many other people do in business — I wanted something different, and I was determined to get it. At the time, my expectations of what business ownership would be like were in many ways different from what it is.

Here’s the reality: Entrepreneurship is a rocky journey full of learning lessons that never seem to end.

So, when asked to share my success journey for that publication, I shared my lessons learned instead in hopes of helping others learn how to ride the tumultuous waves of business ownership.

My Top 12 Entrepreneurship Lessons Learned

Lesson #1 — The freedom to be your own boss and set your own hours are relative.

While you will have more control over when and how you work than you did when employed by someone else, you will (to some degree) have to plan your schedule around your clients’ availability and deadlines.

Lesson #2 — Success is not a straight line.

Revenue and profitability may not follow a flawless upward trajectory because many factors affect business growth. The goal is to see overall progress, so don’t get discouraged if results take a few steps back before they move forward again.

Lesson #3 — The people you hire will never be YOU.

End of story.

Lesson #4 — You still can’t do it alone.

To grow and sustain your business, you will need to find capable individuals with the right skills and work ethic to handle tasks and assume responsibility for different aspects of your business. It can be challenging to let go and delegate, but it’s essential. “Delegation is the skill that makes remarkable success possible.

Lesson #5 — If your heart isn’t in it, you’re not going to be successful.

Starting and building a business isn’t for sissies or the half-hearted. Unless you’re genuinely committed to making a go of it, you won’t have the drive to put in the hard work needed to push through the challenges.

Lesson #6 — The unexpected is what’s for breakfast, lunch, and dinner.

When you’re a small business owner who is heavily involved in the day-to-day activities of running your business, you will encounter surprises at every turn.

From technology failures to rush projects from clients to tricky staffing situations, and more — unanticipated circumstances happen. Prepare to be nimble when facing the unexpected!

Lesson #7 — Owning a business is not how it’s portrayed in get-rich books.

If only there were a magic formula for running a business! However, there is not. A single “system” or “process” that works for everyone is baloney.

Lesson #8 — You’re still not the boss.

Even as a business owner, you need to follow rules (legal, accounting, industry regulations, etc.) and answer to people (your customers, government authorities, etc.).

Lesson #9 — “Making money” is relative.

Revenue growth often comes at additional cost. To make more money, you may face added expenses, such as the costs of hiring, inventory, and higher taxes. More money does not always equal “more profit.”

Lesson #10 — It’s lonely at the top.

Sometimes, you might feel somewhat isolated and alone. Your friends and family members — unless they, too, have had the experience of starting a business — will likely not understand what you’re dealing with and the pressure you’re under.

Lesson #11 — You have no idea where the day goes.

Seriously, time will fly. That’s why it’s critical to set priorities and schedule your to-dos.

Lesson #12 — Everyone will have an opinion about what you do.

Trust me on this: People who don’t work in your industry or run their own businesses can’t understand how you spend your time or what your responsibilities are. Many people think I play on Facebook and Twitter all day; that couldn’t be farther from the truth!

Final Thoughts Before You Dive In

Running a business is a constant lesson in survival. Successful leaders are the ones who are hungry enough for it, and they accept that it will never be easy. However, it does get easier as you learn from the difficulties you encounter and develop your business acumen. Also, I believe succeeding in business involves taking calculated risks — but never blind dives. Carefully evaluated risks have allowed me to leave my comfort zone without betting it all.

Throughout my entrepreneurial journey, I have learned that business success is cyclic. When times are good, we must strive to be better so that we can ride the wave as long as possible. When times are not so good, we need to adjust our bearings, and adapt.

I’m still here, and I’m still profitable after riding many a wave. I consider that a success. But, ask me again next year!

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Rachel Strella

Owner of #Strella Social Media, Writer, Entrepreneur, Social Media Manager, Social Media Strategist, and Chronic Multi-tasker! High-D Personality!