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Lessons from My Business Failures

by | Feb 27, 2025 | Next Level Thinking Newsletter

Jaye Lee

Jaye Lee

Business Strategist for Therapists & Coaches | Scaled 3 Startups | ICF PCC | EMCC ESIA Supervisor & EIA SP | CEO Whisperer for the Helping Professions

Lessons from My Business Failures

Lessons from My Business Failures (That I Wish I Knew Sooner)

Jaye Lee

Jaye Lee

Business Strategist for Therapists & Coaches | ICF PCC | Scaled 3 Startups | Certified Mentor Coach & Supervisor | CEO Whisperer for the Helping Professions

The Brutal Truth About Failure: It’s a Better Teacher Than Success

Nobody starts a business thinking, Wow, I can’t wait to fail spectacularly!

Failure is inevitable.

The trick isn’t to avoid it! it’s to survive it and come out smarter. I’ve had my fair share of palm face in the business world.

One of my most humbling experiences? Running my own dental clinic. And not just any clinic. I am never medically trained but I leaped on the opportunity to craft the setup. I tweaked the business model into a braces niche for teenagers, where customer experience was a top priority, both externally and internally. I thought I had it all figured out: a great location (facing directly the exit of a high-traffic flow supermarket), highly skilled dentists, and a chic cozy waiting area that practically screamed “experience.”

What I didn’t account for was the fact that business isn’t just about having a solid service. It’s about knowing how to market, price, and manage people. Patients loved us, but our cash flow told a different story. By the time I realized we were overspending on luxury (Yes, I purchased that SGD$45,000 dentist chair) but underspending on visibility, we were already bleeding financially. The horror story? I only have cash flow that lasts me for a month from opening. I literally prayed every day prior to opening for the booking calendar to be filled.

That business taught me more about pricing psychology, consumer behaviour, and financial discipline than any textbook ever could.


1. Never Assume Customers Will Just “Find” You

I used to believe that if you offer a stellar product or service, customers will naturally gravitate toward you. Turns out, that’s a lie. In my dental clinic days, I relied on word-of-mouth and the assumption that “everyone needs a dentist.”

Here’s what actually happened: we got lost in a sea of competitors who were louder, more visible, and dare I say; less qualified. The lesson? Marketing isn’t a luxury; it’s oxygen.

Actionable Strategy: Never rely on organic reach alone. Leverage digital marketing, strategic partnerships, and referral incentives to stay top of mind.


2. Cash Flow is King (and Ignoring It is a Fast-Track to Disaster)

In the early days of my clinic, I focused on providing top-tier service, which meant hiring highly skilled staff, investing in premium decor, and ensuring that every patient felt like royalty. What did I fail to do? Keep a tight grip on cash flow. We have been bringing in revenue since Day 1 of operation, but expenses were eating it up just as fast. Before I knew it, I was playing financial Jenga; pulling funds from here to cover there, hoping the whole thing wouldn’t collapse.

Actionable Strategy: Understand your numbers. Profit doesn’t mean anything if your cash flow is negative. Keep a pulse on revenue, costs, and margins.


3. Pricing is a Psychological Game

I priced our dental services based on costs and market standards, thinking logic would drive customer decisions. Reality check: People don’t buy based on logic, they buy based on perceived value. One small pricing tweak (bundling high-ticket procedures with routine checkups) made patients feel like they were getting a deal, and suddenly, sales skyrocketed.

Actionable Strategy: Don’t just price based on costs, price based on consumer psychology. Test different pricing models and see what resonates.


4. Hiring for Skills Alone is a Mistake

I hired some of the most skilled professionals in the industry, assuming that technical expertise was all that mattered. Wrong. Skill without culture fit? A nightmare. We had one incredibly talented Dental Assistant who was a nightmare to work with; rude to the team, dismissive to patients, and resistant to feedback. It cost us more in patient churning and team morale than I could have imagined.

Actionable Strategy: Hire for attitude and train for skill. A cohesive team will always outperform a group of lone wolves.


5. Pivoting Sooner Saves More Than Just Money

I held onto failing strategies for far too long, convinced they would eventually work. Whether it was sticking with outdated marketing methods or refusing to tweak my pricing model, my stubbornness cost me time, money, and opportunities. Looking back, if I had pivoted sooner, the clinic might have had a very different story and the acquisition could have made me richer.

Actionable Strategy: Don’t wait until you’re drowning to change course. If something isn’t working, adapt fast.


Final Thought: Failure is Expensive, But Ignoring It Costs More

Business failures aren’t fun, but they are necessary. If I hadn’t gone through these struggles, I wouldn’t be here sharing these lessons today. The key isn’t to avoid failure; it’s to make sure every failure teaches you something valuable.

So, if you’re in the middle of your own business storm, take a deep breath. Learn from it.

Adapt. And most importantly, keep going.

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