The Time-Optimized Newsletter
Helping move time from finite to infinite (issue 207)
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If you only read one sentence:
Retirement isn’t disorienting because people stop working — it’s disorienting because they haven’t defined who they are without their work.
This Week's Feature
Why Retirees Feel Lost: The Identity Gap No One Prepares You For
🔥 There is an obsession with the money side of retirement.
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When the day comes, the hardest may not be financial. It’s identity.
For 30+ years, work gives you purpose, structure, and community. Then overnight — it’s gone.
No meetings. No deadlines. No “what do you do?” that makes you feel important.
That’s the identity gap — and if you don’t close it, retirement feels less like freedom and more like drift.
💡 Here’s how you close the gap:
1️⃣ Define your purpose beyond the paycheck.
2️⃣ Rebuild structure intentionally (blank calendars = wasted time).
3️⃣ Curate a community that actually fills your life with energy.
If you’re an advisor or HR leader, stop thinking your job ends with the numbers.
Help people with the bigger question: Who am I becoming?
Retirement isn’t just leaving something behind. It’s becoming someone new.
👉 Read the full piece
This Week’s Action Step (2 minutes)
Answer this question in writing, without overthinking it:
“If my job disappeared tomorrow, what would still give my days purpose?”
If the answer feels vague or uncomfortable, that’s not a failure — it’s a signal that your identity is still anchored too tightly to your career.
Featured Free Resource
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Retirement Worry Analysis (RWA)
Determine the impact of worry will and could have on your retirement life.
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Recent Articles
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Time Multipliers: Small Choices That Give Hours Back
“I don’t have time.”
That’s the most common objection I hear when introducing systems like CRMs.
And it’s always ironic—because not having time is exactly the problem they solve.
Most people experience time linearly:
- Do the task.
- Spend the time.
- Repeat.
Time multipliers work differently.
- They cost time once—then give it back again and again.
- Templates. Automation. Delegation.
Not working harder. Working with leverage.
If you feel constantly busy, there’s a good chance time isn’t being lost dramatically—it’s leaking through repetition.
👉 Want to see where your time is actually going—and where it could start compounding instead?
Check out the article.
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The Time Portfolio: Managing Hours Like Assets
⏳ Your calendar is your portfolio. Not your 401k. Not your stock picks. Your TIME.
You’ve only got 24 a day — and most people are spending them like junk bonds. Endless emails. Meetings with no outcomes. Mindless scrolling.
The week we talk about changing that:
✅ Diversifying your time across purpose, health, relationships, growth, and enjoyment.
✅ Understanding the compounding power of small daily investments.
✅ Owning the opportunity costs of how you allocate every hour.
🔥 Stop “spending” time. Start INVESTING it.
This piece will flip how you look at your calendar.
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Mapping Out the First 90 Days of Retirement
🕰️ The First 90 Days of Retirement Can Define the Next 9,000
Yet when people retire — stepping into the most significant transition of their adult life — almost no one builds a 90-day plan.
The first three months after leaving full-time work are formative. They set patterns that influence health, happiness, and purpose for years to come.
In my article that first appeared in Rethinking65, I explore:
✅ The “retirement time vacuum” and why structure matters
✅ Four dimensions advisors can use to guide clients (time, purpose, social health, lifestyle)
✅ A 3-phase, 90-day framework to create early wins in retirement
The first 90 days aren’t a vacation — they’re an orientation to a new life.
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Time Insight of the Week
Work provides three hidden anchors — purpose, structure, and community. When retirement removes all three at once, time doesn’t feel freeing; it feels empty. The solution isn’t filling the calendar — it’s intentionally rebuilding those anchors before the calendar goes blank.
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