Lessons From a Failed Entrepreneur: What I Wish I Had Known Sooner

For as long as I can remember, I’ve always wanted to be my own boss. Not for the glamor of saying I owned a business, but because I longed to work somewhere—or for something—that valued me.

Something that saw me. That desire led me to try and build my own businesses, not once or twice, but multiple times, even while I was employed full-time in the corporate world.

I’ve worked in various industries over the span of twenty years—retail, law, and auto insurance—with roles including general sales clerk, legal secretary, and auto insurance underwriter.

While the salaries were stable and I had some genuinely kind bosses (one like a second mother to me), I never truly felt fulfilled. I never felt I belonged.

The 7:30 AM starts, the long hours past 7:00 PM, working on Saturdays, the constant burnout—I did it all because I had bills to pay and responsibilities at home. But it never lit me up inside. It drained me.

And oddly enough, I became the person who left her job five times—only to return each time. It was the only work I knew. And thankfully, my employer always welcomed me back.

But deep down, I knew I wanted something different. Something more aligned. So, I started a few business ventures—most of which failed. Here’s a snapshot of those endeavors and what I’ve learned along the way.

The Ventures That Didn't Work Out

Editorial Services Business

I’ve always loved writing, so this seemed like the perfect fit. However the business partnership I entered into was poorly matched. Trust was broken. Money got messy. And without even putting up a fight, I walked away losing $40,000 in the process.

Make Peace With Money Coaching Service

In 2021, I registered a business rooted in my personal money story—how I lost my first million before 35 due to poor spending habits and a toxic mindset. I created digital products, secured a space, and built out social media. But the business never officially launched. Though it’s still registered, it’s yet to come to life.

Destination Wine Nuptials

Inspired by my love for tropical fruit wine and my high school best friend who’s a winemaker, I dreamed up a coaching service for wine-inspired destination weddings. I reached out to others, pitched the idea, and even enrolled in a government-funded diploma in event management to help me bring it to life. But I realized—logistics weren't my strong suit. And the dream began to slip.

Reality Check: What I’ve Learned

Despite pouring over $120,000 into these ventures, none flourished. At least not in the way I’d hoped. I faced exhaustion, disappointment, and eventually burnout. And now, as I complete my diploma in Event Management Services & Planning (ending September 2025), I find myself asking: What’s next?

Am I a failed entrepreneur? Or am I just someone who took the scenic route to discover her purpose?

7 Hard Lessons I Wish I Knew When I Started

Validate Your Idea

Passion isn't enough. You must research, test your concept, and understand the needs of the people you're hoping to serve. Most of my ventures were built around me—my passions, my stories—without ensuring there was a real need in the market.

Passion Must Meet Purpose

I love writing, blogging, and journaling. But not all writing sets me on fire. The editorial business didn’t align with my voice or purpose—it was profit-driven, not purpose-fueled. When your passion fuels your work, it becomes your anchor in tough times.

Choose Partners Carefully

Friendship does not equal business compatibility. Money and outside opinions can change people. My first business failed because of a breakdown in trust and boundaries. If you're starting a business with someone else, vet their values as much as their skills.

Find Your Niche

I wanted to do it all—coaching, events, content, writing. But without focus, your brand becomes diluted. Now, I’ve realized that my sweet spot is in eco-conscious and sustainable event storytelling and content creation—writing, photography, and one day, videography.

Not Everyone Is Your Client

Some people will love your message. Others won’t get it. And some will want free rides. Defining your ideal client—and knowing who’s not—is critical to business growth and sanity.

Stick With One Thing Long Enough to Grow It

A tree doesn’t grow overnight. It needs watering, light, and care. The same goes for a business. I changed my business identity so often that followers were confused. One even emailed me, bluntly saying: “I wouldn’t refer anyone to you—I don’t know who you are.” That hit hard. But it was the wake-up call I needed.

Failure Is Not Final

Fear of failure led me to quit too soon, too often. But now, I understand that failure is part of the journey. It's painful—but it teaches resilience, clarity, and courage.

So, What’s Next?

Right now, I’m choosing to shift—not quit. I’ve realized I don’t love the logistics of planning events, but I adore the storytelling, the visuals, the experience. I see myself more in eco-conscious storytelling and sustainable content creation—photography, writing, and one day, videography.

I still believe in sustainable event coaching—but perhaps my strength lies in the content side: helping eco-conscious brands, tourism boards, and event hosts share their stories powerfully through words and visuals.

So, whether I step into the role of a sustainable event content strategist, an eco storyteller, or a visual creative—whatever comes next will come from purpose, not pressure. From alignment, not fear.

Final Thoughts

I’m not where I want to be—but I’m not where I used to be either. I’ve made mistakes, yes. But I’ve also grown in ways I never imagined. And if my story helps even one aspiring entrepreneur navigate their path with a little more wisdom and grace, then maybe none of it was in vain.

Here’s to new beginnings—from a place of fullness, not scarcity.