Something liberating happens when we share our embarrassing, disappointing, vulnerable or regretful experiences. Other people feel compelled to reflect on their own low points, and we all realize how far we’ve come since those awful moments. Here, six business leaders reflect on the mistakes and scary situations they faced this year, and what they learned.
1. Diversified supply chains are crucial.
“When your sourcing is too concentrated, you’re vulnerable. For us, the moment tariffs spiked, it became crystal clear that relying on a limited set of manufacturers and suppliers created real exposure. We had to react quickly, find alternative partners, and rethink our manufacturing footprint. The experience underscored a lasting lesson: Diversification isn’t just a best practice, it’s a safeguard for business continuity.” — Jill Layfield, CEO, Birdy Grey
2. Putting comfort over conflict is costly.
“Leading up to a major system implementation, every time I asked probing questions, our CTO would react defensively. I wanted to give him space, so I held back from getting deeply involved. In hindsight, I was avoiding necessary conflict. The result? The implementation went poorly. Customers were disappointed. We’re still fixing issues three months later. And the CTO resigned. Outcomes matter more than comfort.” — Chad Stark, CEO, Stark
Related: 5 Lessons for Leaders in the Age of Constant Change
3. No one is immune to cyber fraud.
“Weeks after bringing on a new CFO, he fell for a phishing scam that impersonated our COO. The first invoice was for fraudulent consulting services, and the second was for fake construction services. He didn’t follow our protocols, and $300,000 was wired to a scammer. I can’t describe the gut punch of discovering that. By pure grace — and quick action — Chase was able to reverse one of the wires, and we recovered the other through cybersecurity insurance. Even smart, diligent people make mistakes. Make sure you have cyber insurance and safeguards on your bank accounts.” — Marya Khalil-Otto, CEO, Vitality Institute
4. Delays are opportunities for improvement.
“When I was developing my line of mocktails, I had a clear vision of when I wanted to launch. But supply-chain delays, testing rounds, and packaging changes kept pushing that date. At first, I felt like I was falling behind. Over time, I learned to see those shifts not as failures, but as part of the process. Each delay gave me space to refine — whether improving the recipe, rethinking the branding, or making the product more travel-friendly. Instead of fighting every timeline change, I now ask: ‘What can this delay teach me, and how can I use it to make the product even better?’” — Emily Susman, founder, Navi Mocktails
5. Consumer habits don’t change overnight.
“The hardest lesson was realizing that innovation doesn’t equal immediate adoption. I assumed our product’s uniqueness — a beverage that curbs cravings and boosts focus — would be embraced quickly. Instead, it required relentless education, patience, and persistence. Early on, I was frustrated. But I learned that reshaping consumer habits is a marathon, not a sprint. This lesson humbled me. Success isn’t just about a product, but about walking people through the story, patiently, one sip at a time.” — David Allred, cofounder and CEO, Släcka
Related: The Top 5 Mistakes Smart Entrepreneurs Keep Making
6. What got us here won’t get us there.
“This year, we reached a major inflection point where the tactics, structures, and scrappy mindset that fueled our early growth wouldn’t get us to the next level. We had to pause and reevaluate every part of our go-to-market strategy, from CRM and media to brand storytelling. We reassessed every agency partner and redefined roles on our internal team to make sure everyone’s focus and contributions aligned with a larger vision. Scaling isn’t about doing more of what worked in the past.” — Lauren Berlingeri, cofounder and co-CEO, HigherDOSE
Something liberating happens when we share our embarrassing, disappointing, vulnerable or regretful experiences. Other people feel compelled to reflect on their own low points, and we all realize how far we’ve come since those awful moments. Here, six business leaders reflect on the mistakes and scary situations they faced this year, and what they learned.
1. Diversified supply chains are crucial.
“When your sourcing is too concentrated, you’re vulnerable. For us, the moment tariffs spiked, it became crystal clear that relying on a limited set of manufacturers and suppliers created real exposure. We had to react quickly, find alternative partners, and rethink our manufacturing footprint. The experience underscored a lasting lesson: Diversification isn’t just a best practice, it’s a safeguard for business continuity.” — Jill Layfield, CEO, Birdy Grey
2. Putting comfort over conflict is costly.
“Leading up to a major system implementation, every time I asked probing questions, our CTO would react defensively. I wanted to give him space, so I held back from getting deeply involved. In hindsight, I was avoiding necessary conflict. The result? The implementation went poorly. Customers were disappointed. We’re still fixing issues three months later. And the CTO resigned. Outcomes matter more than comfort.” — Chad Stark, CEO, Stark
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