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Retirement planning for Gen X just isn’t the same as it was for boomers.

So, I’ve been trying to boil it down for a the past few years—asking myself what are the new principles retirement.

And its not a 401k or a waiting until your 65.

It’s five simple pillars. They’re how I plan to stay relevant, keep earning, and actually enjoy the next 20–30 years.

I’ll give you the short version in this newsletter. You’ll want to check out the full video where I go deeper.

Plus I’ll share an AI Prompt on how to be more lucky and we’ll revisit an overplayed Def Leppard song.

Last week I recorded a video that lays out what I call the five pillars of Redefining Retirement.

They’re not theory—I’ve been living them since I left my last day job in 2013. And they’re how I’m building this next chapter out in public.

Here’s the quick version:

1. Entrepreneurship is the new job security. Wages have ceilings. Skills and systems don’t.

2. Experience is your competitive edge. Especially in the AI era. Decades of work give you judgment machines can’t fake.

3. Newsletters are the ultimate asset. Social platforms rise and fall, but email stays. It’s your home base.

4. Play offense with an income portfolio. One stream of income is fragile. Build many.

5. This isn’t about quitting—it’s about reinventing. Retirement doesn’t have to mean fading out. It can mean doing more of what matters.

That’s the high-level view. If you want to see me walk through each one with stories, examples, and mistakes I’ve made, the full video’s here:

Here’s something fun I found on X the other day, an AI “Personal Luck Coach.”

Copy and paste this into your favorite AI chat box:

You are my personal luck coach. Your job is to help me systematically increase the favorable outcomes in my life by developing opportunity recognition skills, expanding my network, and building habits that create more chances for good things to happen.

Your Coaching Approach:
- Give me specific, actionable daily challenges
- Help me reframe setbacks as opportunities
- Train me to notice possibilities I'm currently missing
- Push me gently outside my comfort zone
- Celebrate small wins and progress
- Ask probing questions to help me think differently

Today's Session Format:
- Quick Check-in: Ask me about any opportunities I noticed or created since our last conversation
- Daily Challenge: Give me one specific action to take today that could increase my luck
- Opportunity Training: Present me with a scenario or ask me to analyze a situation for hidden opportunities
- Mindset Work: Help me identify and overcome any limiting beliefs or blind spots
- Tomorrow's Prep: Give me something specific to watch for or be ready for tomorrow

Key Areas to Focus On:
- Network Expansion: Connecting with new people and strengthening existing relationships
- Opportunity Recognition: Training my brain to spot possibilities others miss
- Strategic Risk-Taking: Encouraging calculated risks that could pay off
- Resilience Building: Helping me bounce back from setbacks faster
- Presence & Awareness: Staying alert to what's happening around me

Your Personality:
Be encouraging but not overly cheerful. Be practical and specific rather than abstract. Challenge me when I'm making excuses or limiting myself. Ask follow-up questions to help me dig deeper.

It’s like having a sidekick that nudges you to see more dots—and connect them.

If you missed my longer riff on luck (and how to improve you luck surface area), I wrote about it here:

Def Leppard just played America’s Got Talent.

It got me wondering—are we due for an 80s subculture comeback the way Happy Days and Grease brought back the 50s in the 80s?

Here the video of the performance…

By the way, if I’m being honest, I’ve been sick of this song since about 3 months after it came out. I never intentionally listen to it an more especially when they have SO many other great songs.

But just because I don’t like it anymore, doesn’t mean you wont. Enjoy!

The future isn’t waiting for us to hit 65.

If you want relevance, resilience, and freedom—you build it now.
You stack small moves into big ones.
You reinvent before someone else decides it for you.

That’s what the pillars are really about.

If one of these pillars hits home, do me a favor:
go watch the full video, hit like, and drop a comment with your take.

Not just for me, for the algorithm. Every click helps push this message in front of more Gen Xers who need to hear it.

And if you want to follow along as I keep building this thing out in public, subscribe to the channel. That way you won’t miss the next step.

✅ Ready to Redefine Your Retirement?