What Would I Even Do?

October 15, 2025

🎙️ What Would I Even Do? Turning Your Decades of Experience Into Your Next Business

Episode Summary

If you've ever asked yourself "What would I even do?" when thinking about your next chapter, you're not alone—and you're not short on ideas. According to the Kauffman Foundation, entrepreneurs over 55 are nearly twice as likely to launch successful businesses compared to those under 35. The secret? They're not inventing the future—they're recognizing patterns from decades of watching real problems go unsolved. Your hesitation isn't about creativity; it's about confidence in recognizing the goldmine of market intelligence you've already accumulated.

While younger founders are guessing at what problems might exist tomorrow, you've spent 30+ years observing what actually breaks in business. You know why "obvious" solutions fail, where systems bottleneck, and which fixes create more problems than they solve. That's not just experience—it's extraordinary competitive advantage. This episode challenges the myth that starting a business requires innovation, when what it actually requires is observation, pattern recognition, and the courage to trust what you already know. The IDEATE framework breaks down exactly how to systematically identify high-value problems hiding in your professional history.

Through Curt Roese's story of returning to graduate school at 62, you'll discover the 10-Minute Experience Audit that maps your entrepreneurial goldmine, the 50-Idea Sprint that pushes past obvious solutions to breakthrough concepts, and the Five-Conversation Method that validates ideas before you invest a dollar. Learn why fractional consulting lets you get paid to test your business concept, how your network provides better market intelligence than any research report, and why the problems you solve "in your sleep" are worth serious money to others. This isn't theory—it's the exact process experienced professionals are using to build profitable second-act businesses.

This episode transforms "What would I even do?" into "Here's exactly what I'm building, and the market has already validated it." Whether you're contemplating your Pivot 65 moment or actively testing business ideas, you'll leave with concrete next steps and the confidence that your most successful chapter doesn't require reinvention—it requires recognition of what you've been building all along.

Note: This episode is produced using NotebookLM to capture insights and structure powerful storytelling with clarity and depth.

🔗 Links & Resources

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🌟 About Retirepreneur

Retirepreneur® is where retirement meets reinvention. Founded by Curt Roese—former CFO, CPA, and recent graduate of the University of Florida's Master of Science in Entrepreneurship program at age 63—this platform helps adults aged 55 and above create meaningful second acts through business ventures, flexible work, and purposeful living.

We share real stories from people who've successfully navigated career transitions later in life, offering practical advice and a supportive community for your next chapter. Your experience isn't a limitation—it's your unfair advantage.

#RetirementEntrepreneur #SecondActBusiness #EntrepreneurshipAfter55 #Pivot65 #IDEATEFramework

Episode Transcript

Podcast Episode: What Would I Even Do? Turning Experience into Opportunity

Welcome to another episode of the podcast. I’m your host, here with this week’s executive summary for busy entrepreneurs building their second-act business.

Today’s episode is designed for maximum impact in minimum time. We’re diving into one of the biggest hurdles professionals face when they start thinking about their next chapter:

That paralyzing question — “What would I even do?”

It’s such a common feeling, isn’t it? You’ve spent decades managing complex projects, budgets, and teams. Yet, the moment you consider launching something of your own, all that hard-earned wisdom can suddenly curdle into hesitation.

It’s like you start believing you need a groundbreaking, world-changing idea just to begin.

But the truth is — and this is the key mindset shift — it’s usually not a lack of ideas holding you back. It’s a lack of confidence in the value of your existing experience.

You might think, “I did that for 20 years; it must be ordinary. Everyone knows this, right?”

But it’s not ordinary.

Think about it: younger entrepreneurs are often trying to invent solutions for problems they think might exist tomorrow. You, on the other hand, have spent decades observing reality. You’ve seen what actually happens.

That gives you extraordinary market intelligence — you know exactly where systems break down, why obvious solutions fail in practice, and where the real bottlenecks appear.

Now, some might wonder, “Do I really have that kind of insight? Was I just watching the same office mess-ups for years?”

Fair question. It brings us to the story of Retirepreneur founder Curt Roese.

When Curt went back to grad school at age 62, he realized he wasn’t learning brand-new concepts. He was learning to recognize the immense value of the patterns he’d seen repeat across industries for decades.

The difference isn’t just noticing a recurring problem — it’s understanding why the fixes failed. That understanding becomes your built-in filter against bad ideas.

And that deeper insight — the why — is your entrepreneurial goldmine.
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Actionable Insight #1: The 10-Minute Experience Audit

Let’s get practical. Here’s a simple exercise to unlock that value right now.

Grab a pen, set a timer for 10 minutes, and just write. Don’t overthink it.

1. List five recurring problems you solved again and again in your career — the headaches that always landed on your desk.

2. List three things people always came to you for. What did colleagues, clients, or friends consistently ask your help with? Maybe simplifying complex information, calming chaos, or navigating tough politics.

3. List two industries or micro-niches you understand better than most outsiders.

When that timer goes off, you’ll likely see something powerful:

The best business ideas aren’t discovered — they’re remembered.

Your history already maps them out.
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Turning Insight into Action: The I.D.E. Framework

Now that you’ve identified your unique experience base, how do you turn it into action?

That’s where the I.D.E. Framework comes in — built specifically for second-act entrepreneurs like you.

Let’s look at the first three steps.

I — Identify Problems Worth Your Time

Be ruthless. Filter out the “nice-to-have” problems and focus only on those that cause real pain.
Ask yourself: Could someone get through their day — maybe grumbling, but surviving — without this solution?
If yes, it’s probably too weak. Focus on problems that cost real money, time, or missed opportunities. That’s where your best ideas live.

D — Discover in Your Own Backyard

Look for opportunities hiding in plain sight — the things that feel easy or obvious to you.
That ease comes from mastery.
Processes you’ve refined for years or challenges you can now solve in your sleep are incredibly hard for others. To them, your know-how is a shortcut — pure gold.

E — Evaluate Without Overthinking

Analysis paralysis kills more good ideas than failure ever will.
Run these three fast tests before investing time or money:

1. Is someone already charging for something similar?
If yes, great — it proves there’s demand. Competition is validation.

2. Would you have paid for this solution five years ago?
This ensures you’re solving a real, remembered pain — not a theoretical one.

3. Can you explain the value in one sentence?
Example: “I help small marketing agencies cut reporting time by 50%.”

If you can’t express it clearly, you haven’t defined the problem — or the solution — well enough yet.

If you can answer “yes” to all three, stop researching and start testing.
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The 50-Idea Sprint

Here’s your next challenge: Quantity creates quality.
Set another timer — 15 minutes this time — and write down 50 ideas related to your experience. No filtering, no judging. Just write.

Why 50? Because the first 10–15 ideas will be obvious. The magic happens around number 25 or 30, when you push beyond the comfortable surface level. That’s where creativity and experience start to blend — and real innovation appears.
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Quick Win: Use Your Network as Market Intelligence

Before spending a dime or building a website, reach out to three former colleagues this week. Ask one simple question:

“What’s the single biggest operational or strategic headache you’re dealing with right now?”

Don’t pitch anything — just listen.

Their answers are pure gold. If two or three mention similar challenges, you’ve just found a high-pain, real-world problem worth solving.

That kind of firsthand intel beats weeks of online research.
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Low-Commitment Validation: Fractional Consulting

Still not ready to launch? No problem.

Try fractional consulting — also known as the Pivot 65 approach.

These short-term, project-based roles let you get paid to test your future business idea.

Companies want seasoned professionals with 15–25 years of specialized experience — people who can think strategically and make decisions, not just execute tasks.

It’s a low-risk pilot for your next act.

You validate two things at once:

1. Whether you actually enjoy the work in this flexible, second-act format.

2. Whether clients value your expertise enough to pay a premium for it.

You’ll build confidence, testimonials, and maybe even your first few clients — all while getting paid to experiment.
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You’ve now turned that intimidating question — “What would I even do?” — into a confident statement:

“Here’s exactly what I’m building next, because the market has already validated it.”

That’s your executive briefing for this week.

If you found value in these insights, share this episode with a fellow Retirepreneur and subscribe to the Retirepreneur Weekly Newsletter at Retirepreneur.com.

Your most successful chapter is just beginning.

Until next week, keep building.

What Would I Even Do?

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