A Clearer Way to Think About What’s Next

There’s a moment many experienced professionals reach that’s hard to explain out loud.

You’re not burned out.
You’re not done.
But the old answers don’t quite fit anymore.

The question of “what’s next” keeps tapping you on the shoulder. Quietly. Persistently.

And if you’re honest, you might be circling that question instead of really engaging it. Not because you don’t care, but because most of the advice out there feels either vague or wildly disconnected from the reality of decades of experience.

That’s exactly why I’m hosting a free live webinar on Wednesday, January 14 at 11:00 AM CST | 12:00 PM EST.

Why Most People Drift Into Their Next Chapter

Here’s the uncomfortable truth.
Most people don’t design their next chapter. They drift into it.

Not because they lack motivation or ambition, but because no one ever showed them a different way to think about transition. Retirement becomes the default. Consulting becomes the fallback. “I’ll figure it out later” becomes the plan.

But an Encore Life deserves more intention than that.

Designing an Encore, Not Stumbling Into One

This live webinar introduces the core ideas behind The Encore Architects Program, a framework built specifically for experienced professionals who want to use their experience as an advantage, not something to downplay or apologize for.

We’ll talk about what it actually means to design your next chapter, instead of reacting to it.

In the session, we’ll cover:

• Why drifting is the default, and how to avoid it

• How to think about an Encore Life as something you actively design

• The mindset and structure behind the Encore Architects approach

• What the Encore Architects Founding Cohort includes, and who it’s best suited for

This is not a motivational talk. There are no platitudes here.

It’s a working session designed to help you find clearer language for where you’re headed and decide, with more confidence, what deserves your energy next.

Is This Webinar for You?

This session is for you if:

• You’ve built a meaningful career and don’t want to simply “wind it down”

• You know you still have value to offer, but want to be more intentional about how

• You’re tired of vague advice and ready for a clearer framework

If that sounds familiar, I’d love to have you join us live.

👉 Register here to save your spot 👈
The webinar is free, live, and space is limited.

I’d love to see you there!

Your Encore Career Needs More Than Inspiration. It Needs Implementation.

After 40 years leading teams at John Deere, I learned that good ideas die in the gap between knowing and doing. You can attend every workshop, read every book, and map out your perfect encore career, but without systematic implementation, you’re just planning.

That’s why I built LynnAI Pro.

The Free Version Got You Thinking. Now It’s Time to Build.

The free LynnAI tool helps professionals explore the “what” and “why” of encore careers. Thousands have used it to clarify their thinking, identify their strengths, and understand what’s possible after corporate life. It’s designed for discovery.

LynnAI Pro is designed for execution.

It’s the difference between exploring career transition and actually completing one. Between contemplating your value proposition and having one ready to present. Between thinking about your portfolio career and building it, week by week.

What LynnAI Pro Actually Does

LynnAI Pro combines my decade of coaching methodology—distilled from my own 10-year reinvention plus hundreds of client conversations—with AI-powered implementation support. Here’s what that means in practice:

Weekly Action Plans, Not Generic Advice. You don’t need another pep talk about “finding your purpose.” You need a specific action for this week: who to contact, what to write, where to test your offer. LynnAI Pro delivers timed exercises with clear deliverables.

Framework-Driven Transformation. The tool is built on proven frameworks: G.L.E.A.N. for skill translation, S.T.O.R.Y. for narrative development, and the Offer Ladder methodology for revenue generation. These aren’t theoretical models. They’re structures that produced results for executives transitioning from Fortune 500 roles into portfolio careers.

Progress Tracking That Measures What Matters. LynnAI Pro tracks specific transformation markers: network conversations completed, value propositions tested, revenue streams activated. No vague “journey” language—just quantifiable forward momentum.

On-Demand Coaching Without Calendar Coordination. Access strategic guidance at 11 PM on Tuesday or 6 AM on Sunday. LynnAI Pro doesn’t replace human coaching, but it extends it, giving you implementation support between sessions or when you need immediate clarity on next steps.

Who Gets Results With LynnAI Pro

This tool works for professionals who:

• Have proven executive or leadership experience but need systematic approaches to career reinvention

• Want methodology over motivation—you’re past needing inspiration

• Value evidence-based frameworks that show clear cause-and-effect

• Need accountability structures that track actual progress, not feelings

• Prefer strategic guidance they can implement immediately

One client built a portfolio combining board work, mentoring, and part-time teaching—all generating income while maintaining schedule flexibility.

The Implementation Advantage

Here’s what differentiates professionals who successfully design encore careers from those who stay stuck in transition paralysis:

Successful transitioners follow systematic processes. They translate experience into modern contexts. They test offers quickly. They build networks strategically. They track progress quantitatively. They make decisions based on evidence, not emotion.

LynnAI Pro is built specifically to support that implementation mindset.

At 75, I’m still experimenting, still launching, still refining my own portfolio. LynnAI Pro represents my current answer to the question I’ve been working on for a decade: how do experienced professionals systematically design encore careers that generate impact and income?

The answer isn’t more thinking. It’s structured action.

Beyond the Free Tool

If you’ve used the free LynnAI and found value in the exploration, LynnAI Pro is your next step. It takes the clarity you’ve developed and converts it into concrete actions with specific timelines.

This isn’t about finding yourself. You already know who you are. This is about building what comes next—with the same strategic thinking and execution discipline that made you successful in your primary career.

Your decades of accumulated wisdom deserve better than a default retirement. They deserve intentional design. LynnAI Pro provides the systematic framework to build that design.

Ready to move from exploration to execution? LynnAI Pro launches in December alongside structured coaching programs designed to complement the AI tool with human expertise.

Because your encore career shouldn’t just be possible. It should be inevitable.

Sign up for the LynnAI Pro Waitlist

or try the free version here!

How My Team of 19 AI Assistants Helps You Get a Clearer, Faster Encore Plan

If you’re a high-achieving professional in your 50s or 60s, you may be asking a question that’s both exciting and unsettling:

What’s next for me and how do I make it meaningful and financially smart?

I coach executives and professionals who are stepping into an encore chapter, often after decades of success. And here’s something I’ve learned: reinvention isn’t just about choosing a new job or starting a business. It’s about rebuilding identity, designing a life that fits now, and creating income you can feel good about.

To support you at a high level, I don’t rely on willpower and late nights. I use a team of 19 AI assistants (including Claude, ChatGPT, CoachVox, Sintra, Whisper Flow, and Descript) to handle the behind-the-scenes work so our time together stays focused on what matters most: you.

This is not about replacing human coaching. It’s about giving you a coaching experience that’s more organized, more personalized, and more actionable.

What this means for you (the client)

When I use AI well, you get a better outcome, because I can spend less time on admin and more time helping you think clearly and move forward.

Here’s what you can expect.

1) More clarity, faster

You don’t need more information. You need the right structure.

My AI tools help me:

• Capture your goals, constraints, and preferences clearly

• Organize patterns I’m hearing across our conversations

• Turn big, emotional questions into practical next steps

So instead of circling the same doubts for months, you build momentum.

2) A plan that feels personal, not generic

You’ve spent decades building expertise. Your encore path should reflect that.

I use tools like Claude and ChatGPT to help me explore multiple options quickly—then I apply my human judgment and coaching experience to shape what fits you.

That means:

• More tailored ideas

• Better language for your story and positioning

• Clearer decisions about what to pursue (and what to ignore)

3) Your ideas captured, even when you’re busy

Many of my clients have their best insights while walking, traveling, or in the space between meetings.

With Whisper Flow, I can quickly capture and convert spoken insights into usable notes and next steps. The benefit for you: you don’t lose the good stuff.

4) Stronger follow-through between sessions

Reinvention doesn’t happen in a single conversation. It happens in the week after.

My systems help me:

• Send clearer summaries and action steps

• Provide templates and prompts so you’re not starting from scratch

• Keep your progress organized so you can see what’s working

You stay focused, and you don’t have to hold everything in your head.

5) More value without inflating the price

Here’s the part most people don’t see.

To deliver this level of support, many coaches would need a bigger human team—and that cost gets passed on to clients.

Instead, I use a lean, modern setup: my AI team of 19 costs under $1,000/month. That helps me keep my business efficient and invest in the tools and systems that improve your experience—without turning coaching into a luxury reserved for a few.

A quick look at the tools (and what they do for you)

I’ll keep this simple. These tools are not the point—your results are.

• Claude: helps me create clear frameworks and long-form guidance tailored to your situation

• ChatGPT: helps me generate options, language, and fast drafts we can refine together

• CoachVox: helps me keep my coaching approach consistent and aligned with my philosophy

• Sintra: supports my workflow so your experience feels organized and responsive

• Whisper Flow: turns voice notes into usable insights and action steps

• Descript: helps me produce and repurpose audio/video content so you can learn in the format you prefer

What AI can’t do, and why that matters

AI can’t replace the most important parts of this work:

• The ability to hold space for uncertainty

• The discernment to challenge you at the right moment

• The wisdom to help you separate fear from truth

• The human connection that makes change sustainable

That’s my job.

AI simply makes it easier for me to show up prepared, present, and focused on you.

If you’re considering an encore chapter, START HERE!

If you’re feeling the pull toward something new, here’s a simple place to begin:

1. Identify what you’re no longer willing to do

2. Name what you want more of (impact, freedom, income, meaning)

3. Choose one small experiment you can run in the next 14 days

If you’d like a sounding board, I’m happy to help.

A Next Step

If you want, reply with:

• What you’re leaving (or considering leaving)

• What you want your encore chapter to feel like

• The biggest decision you’re stuck on right now

I’ll share a few thoughtful next steps and a simple way to move forward.