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🎙 The Three Questions
Your Second-Act Success Blueprint
Nearly 1 in 3 U.S. entrepreneurs are 55 or older, yet most experienced professionals struggle to gain traction when they launch their second-act businesses.
Why? They skip the foundation and jump straight to tactics, spending weeks on LegalZoom, logo design, and platform comparisons before answering three critical questions.
This episode breaks down the exact framework successful second-act entrepreneurs use to clarify their path, package their expertise, and monetize their experience without burning out.
The tactical trap is real: you're used to execution, so you jump into doing. But here's the reality check most business advice ignores. Your motivation (income gap vs. legacy vs. staying active) determines your timeline, business model, and risk tolerance.
Trying to build a 12-month course when you need $4,000/month in 60 days is the #1 cause of second-act burnout. The professionals who succeed answer three questions in order:
Why am I doing this?
What expertise am I packaging?
How will I monetize it?
We walk through the 50-plus times rule (what problem have you solved 50+ times?), the efficiency ratio (what can you explain in 10 minutes that saves someone 10 months?), and the three delivery vehicles: consulting for speed (30-60 days to revenue), coaching for recurring income (60-90 days), and courses for leverage (90-180+ days).
Plus, we break down the CFO evolution strategy: how to start with consulting, add coaching once stable, and build courses 18 months in, funding each new step with profit from the one before.
Your age is a massive trust asset. Clients don't want a kid guessing with their money. They want someone who has seen a recession before. You're not competing on who makes the flashiest TikTok video.
You're competing on, I've seen this movie 50 times and I know exactly how it ends. You're selling certainty in uncertain times. The only thing stopping you is the belief that you need permission to sell it. You don't. You just need to package it.
Note: This episode is produced using NotebookLM to capture insights and structure powerful storytelling with clarity and depth.
🔗 Links & Resources
🚀 Join the FREE Retirepreneur Hub - Access business templates, pricing guides, and startup checklists designed for 55+ entrepreneurs. No credit card required.
https://www.retirepreneur.com/retirepreneur-hub
📰 Subscribe to Retirepreneur Weekly - Get real-world second-act business tips every Tuesday.
https://www.retirepreneur.com/subscribe
📖 Complete Field Notes Series: Four comprehensive guides with audio, video, and slide formats
→ Explore at https://www.retirepreneur.com/field-notes
#RetirementEntrepreneurship #SecondActBusiness #ConsultingAfterRetirement #55PlusEntrepreneurs #EncoreCareer
View all episodes
By Curt RoeseYour Second-Act Success Blueprint
Nearly 1 in 3 U.S. entrepreneurs are 55 or older, yet most experienced professionals struggle to gain traction when they launch their second-act businesses.
Why? They skip the foundation and jump straight to tactics, spending weeks on LegalZoom, logo design, and platform comparisons before answering three critical questions.
This episode breaks down the exact framework successful second-act entrepreneurs use to clarify their path, package their expertise, and monetize their experience without burning out.
The tactical trap is real: you're used to execution, so you jump into doing. But here's the reality check most business advice ignores. Your motivation (income gap vs. legacy vs. staying active) determines your timeline, business model, and risk tolerance.
Trying to build a 12-month course when you need $4,000/month in 60 days is the #1 cause of second-act burnout. The professionals who succeed answer three questions in order:
Why am I doing this?
What expertise am I packaging?
How will I monetize it?
We walk through the 50-plus times rule (what problem have you solved 50+ times?), the efficiency ratio (what can you explain in 10 minutes that saves someone 10 months?), and the three delivery vehicles: consulting for speed (30-60 days to revenue), coaching for recurring income (60-90 days), and courses for leverage (90-180+ days).
Plus, we break down the CFO evolution strategy: how to start with consulting, add coaching once stable, and build courses 18 months in, funding each new step with profit from the one before.
Your age is a massive trust asset. Clients don't want a kid guessing with their money. They want someone who has seen a recession before. You're not competing on who makes the flashiest TikTok video.
You're competing on, I've seen this movie 50 times and I know exactly how it ends. You're selling certainty in uncertain times. The only thing stopping you is the belief that you need permission to sell it. You don't. You just need to package it.
Note: This episode is produced using NotebookLM to capture insights and structure powerful storytelling with clarity and depth.
🔗 Links & Resources
🚀 Join the FREE Retirepreneur Hub - Access business templates, pricing guides, and startup checklists designed for 55+ entrepreneurs. No credit card required.
https://www.retirepreneur.com/retirepreneur-hub
📰 Subscribe to Retirepreneur Weekly - Get real-world second-act business tips every Tuesday.
https://www.retirepreneur.com/subscribe
📖 Complete Field Notes Series: Four comprehensive guides with audio, video, and slide formats
→ Explore at https://www.retirepreneur.com/field-notes
#RetirementEntrepreneurship #SecondActBusiness #ConsultingAfterRetirement #55PlusEntrepreneurs #EncoreCareer