Why Your Seasoned Perspective Might Be Your Greatest Advantage

I remember the moment clearly: standing at the crossroads of comfort and possibility.

At 42, with a decade at Forrester under my belt and my first book freshly published, I faced a pivotal choice: stay in my safe analyst position or venture into entrepreneurship during a financial crisis.

The year was 2008, and conventional wisdom screamed "STAY PUT!" The economy was in free fall. Security seemed priceless. But something inside me knew it was time to leap.

Starting From Scratch During a Financial Crisis

I founded Altimeter Group completely bootstrapped—no outside funding, just determination and a vision. Those early days were exhilarating. I operated solo for about a year before bringing on founding partners in 2009.

One of my  first milestones was landing three clients before the market crashed. That early validation was crucial, though it wouldn't shield us from the rollercoaster ahead.

The experience was simultaneously wonderful and stomach-churning. Despite business school lessons that "cash is king," nothing prepares you for the weight of being responsible for everyone's paycheck. Cash management became my obsession—constantly asking "How much cash do we have?", paying our team before paying ourselves as partners, watching every dollar as the economy continued to struggle.

At one particular low point, we came within two weeks of missing payroll. We nearly went bankrupt. It's one thing to risk your own financial security; it's another to risk your team's livelihoods. This is the side of entrepreneurship rarely discussed on social media—the sleepless nights, the constant pressure, the tough decisions. But there were benefits I hadn’t anticipated either, and one of them was that, while I was new to entrepreneurship, this wasn’t my first rodeo. 

The Mid-Career Advantage

The entrepreneurial hero’s journey we typically hear about often centers on young founders building empires from dorm rooms. But starting a company later in your professional life offers advantages you don’t often hear about, either: 

1️⃣Your network is established. After a decade at Forrester, I had made invaluable connections who became Altimeter’s first clients and champions.

2️⃣Your expertise is proven. I wasn't selling my potential; I was selling insights and expertise demonstrated through years in the trenches.

3️⃣Your confidence in navigating uncertainty is battle-tested. Having weathered corporate changes, recessions, and industry shifts, I had developed resilience that served me well as the economic landscape shifted under our feet.

4️⃣You know what you don't know. Unlike my younger self, I recognized my limitations—and I didn’t feel the same pressure to do it all. When I realized my weakness in managing analysts, I hired a COO who excelled where I didn't (learn how to identify your team's strengths with my 9s and 4s Framework for leadership excellence here).

The Boon of Business Partners

What surprised me most was how much more fulfilling entrepreneurship felt with partners. While I had complete control over my organization during my solo year, bringing on founding partners transformed the experience.

I'll never forget the four of us hauling IKEA furniture to our San Mateo office, building it together, and creating our "zen nap room"—a place with no desks, just comfortable sofas for brainstorming and the occasional much-needed mid-day nap.

Though reconciling multiple perspectives comes with its own challenges, the camaraderie, shared purpose, and collaborative creativity made the journey infinitely richer.

My Advice for Mid-Career Entrepreneurs

The most common objection I hear from anyone considering entrepreneurship, regardless of age, is "I'm not ready. I need more [experience/education/connections]." 

My response is always the same: You will never be ready. And if you feel ready, that opportunity is probably already gone. But if you’ve got some experience under your belt, you’re likely in a better position than you think. You may not have built something from scratch before, but you probably have the wisdom, expertise, and confidence to tackle the big challenges inherent in entrepreneurship. 

You may have learned, too, that there can be strength in numbers. If you're considering entrepreneurship with partners, establish two things upfront:

1️⃣How you'll make decisions when you don't agree 

2️⃣How you'll dissolve the partnership if needed

And, as I often say, "Don't begin a relationship that you can't end." This isn't pessimism—it's pragmatism that preserves both your business and relationships.

If you’re ready to embark on the next phase of your journey—whether you’re going it alone or not—my Six-Quarter Walk methodology will help you create an 18-month roadmap to success

💭Your Turn 

Are you considering entrepreneurship mid-career? What's holding you back or propelling you forward? I'd love to hear your thoughts.

What I Can’t Stop Talking About 

• New book trailer alert! I'm thrilled to share the official trailer for "Winning with AI," co-written with the brilliant Katia Walsh, Ph.D.! The trailer unpacks why we wrote the book, what you'll feel when first picking it up (not just FOMO, but FOGI—Fear of Getting In), and why it's essential to dive in anyway. Watch it here!
  

• Transform tech fears into wonder. When learning about AI capabilities, I often find myself exclaiming, "It can do WHAT?!" That sense of wonder isn't just entertaining—it's powerful. In a world where rapid technological change triggers fear, curiosity acts as our emotional circuit-breaker. Here’s an experiment to try next time uncertainty strikes. 

• How to build an AI movement. If a tree falls in the forest with no one to hear it, does it make a sound? GenAI follows a similar principle: If no one knows value is being created, it effectively doesn't exist. I talk about how to change that here.  

My Upcoming Appearances

• May 16: Private Executive Retreat, Portland, OR

• Jun 10: Betterworks Webinar, Virtual

• Aug 29: Indy SHRM, Indianapolis, IN
  

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Whenever you're ready, here are three ways I can help you thrive with disruption:

1. Get early access to my upcoming book, co-authored with Katia Walsh, about creating a winning AI strategy: https://charleneli.com/winning-with-ai/ 

2. Take my LinkedIn courses on managing AI transformation:

• "The Manager's Guide to Integrating and Managing AI Agents": https://www.linkedin.com/learning/the-manager-s-guide-to-integrating-and-managing-ai-agents 

• "Transforming Business with AI Agents": https://www.linkedin.com/learning/transforming-business-with-ai-agents-autonomous-efficiency-and-decision-making/introducing-agentic-ai 

3.  Get weekly insights on leadership, transformation, and AI—subscribe to my newsletter on your preferred platform: LinkedIn, Email, or Medium.

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