Chapter 1: The Hard Truth About Entrepreneurship

Writing about my experiences is not something I initially wanted to do, but I believe it's essential to share my story. Not everyone is suited to be their own boss. Even those who may seem destined for it face significant challenges along the way.

I worked as a freelance marketing manager, and after a challenging stint with a difficult employer, I embraced the freelance lifestyle, which felt liberating. However, after five years of building my business from scratch, everything collapsed around me. As you'll see, my foundation was not as solid as I had thought.

Here are three crucial lessons I learned from this painful experience.

> Note: For more insights, check out this video: How I almost lost my business. It delves into my experiences and the lessons I learned.

Takeaway #1: Recognizing People-Pleasing Tendencies

I've always had a tendency to please others, not out of genuine kindness, but because of my nature as a people-pleaser. My struggles with imposter syndrome can be traced back to my childhood, and despite running my own business, I found myself lacking confidence.

While some clients were respectful and supportive, I also encountered those who took advantage of my accommodating nature. Late payments, rushed deadlines, and a lack of mutual respect were common in some of my client relationships. I should have ended those partnerships sooner, but my inclination to please others kept me from doing so.

My advice is not just about following up on invoices; it’s about ensuring you can stand your ground when necessary. Constantly going against your nature is challenging, and this conflict ultimately led to my downfall.

Takeaway #2: The Dangers of Overcommitment

They often say, "give the people what they want," and I certainly did. However, deep down, I knew that cramming my calendar with one-on-one work was unsustainable. I needed to reduce this workload and offer scalable solutions, like a course or a book, but I struggled to implement these changes.

Though I did create a marketing course and a companion book as a lead magnet, I couldn't resist the urge to say yes to every one-on-one request. The gratitude I felt for being sought after made it difficult for me to decline, revealing my imposter syndrome yet again.

Ultimately, my inability to draw the line led to burnout, leaving me drained and unprepared for the challenges that arose during the pandemic.

Takeaway #3: The Importance of Adaptability

When COVID-19 hit, my business began a slow decline. The small businesses I served could no longer afford my services, even at a low rate. This was the moment I should have pivoted, but I didn’t know how. I clung to my familiar small business clientele, which proved disastrous.

The lesson here is to recognize when it's time to adapt. Don't ignore the signs of impending trouble. If you sense a crisis approaching, actively seek alternative paths.

While sharing this experience has been difficult, it was necessary for me to release the guilt of losing my business. If you find yourself struggling, let my story serve as a wake-up call. Be proactive, listen to your instincts, and make the necessary changes before it’s too late.

Additional Resources

For further insights on navigating business challenges, watch this video: I Lost my Dream Job and Started My Own Business | How to Pivot After a Loss.