Retirement Series: "Pre-tirement"

More Than an Off-Ramp

✨ New Series

Welcome to a new series on Retirement - posts designed to nudge you towards a more imaginative, forward-tilted mindset about that legendary milestone called retirement.

We’ll cover all the standard parts - financial planning, tax strategy, asset positioning. But we’ll also venture into the not-so-obvious, frequently ignored terrain: how to think about retirement, how to talk about money with people you love, and how to shape the financial legacy your family remembers (and, yes, they always remember).

Finally, this series is intended for ALL ages, life stages and economic status. Starting as soon as possible, makes all the difference. So, please feel free to share! Thanks!

Today’s theme → Pre-tirement.

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📌 The Quick Hit

• Pre-tirement is the art of shifting gears, not slamming the brakes.

• It’s gaining traction as people seek purpose, flexibility, and financial sanity.

• The future isn’t “retired vs. working” - it’s a creative remix of both.

• Done right, pre-tirement becomes the launchpad for your best, most intentional work.

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🚦What Exactly Is Pre-tirement?

I stumbled into this term by accident - an answer I offered when people asked whether I was “retiring.”

“No,” I’d reply. “I’m pre-tiring.”

Yes, I got a lot of quizzical stares and stray chuckles.

But the term stuck because the idea fit. I wasn’t done working; I was simply reshaping work.

As it turns out, pre-tirement wasn’t my invention. It’s been around long enough to earn its own definition: a state between full-time work and full retirement, often involving part-time roles, consulting, creative projects, or a phased step-down in hours.

And it’s gaining momentum for three big reasons:

• Economic realism: Most people aren’t convinced they can glide into retirement on savings alone. A hybrid phase helps the numbers work.

• Purpose with breathing room: Humans don’t thrive in vacuums. Going from “100% productive” to “beige void of nothingness” shocks the system.

• Financial finesse: Phased work stretches savings, postpones benefit withdrawals, and smooths the transition from structured work to self-directed life.

🔎 The View From Inside Pre-tirement

I consider myself pre-tired.

Not idle. Not coasting. Just… redirecting the current.

I left my investment-firm role, but the mission stayed intact: helping people understand their money. Only now the format changed - writing instead of clock-punching, autonomy instead of hierarchy.

Technically, I work for myself. In reality, I work for anyone willing to read the words.

And that shift - toward work that blends competence with passion - has reframed everything. Pre-tirement isn’t a half-exit. It’s the next phase of work, not the end of it.

Where my earlier focus revolved around income, reputation, and professional ascent, pre-tirement has widened the aperture:

• Fewer corporate constraints.

• More intellectual latitude.

• A clearer view of what actually matters.

It’s not a retreat. It’s a reorientation.

🔑 The Real Pivot: From Paycheck Identity to Purpose Identity

Traditional retirement narratives fixate on one thing:

“Can I afford to stop working?”

Fair question. But it’s incomplete.

Retirement is still a young invention - barely a century old - and it rests on the assumption that people stop being economically useful at a certain age.

But we’re more than economic inputs.

We’ve always derived meaning from making, producing, mentoring, crafting, building, analyzing. Work isn’t the villain. Drudgery is. Strip out the drudgery and you get something astonishingly energizing: self-directed contribution.

Pre-tirement lives right there.

In pre-tirement, you’re not done working - you’re just done explaining yourself.

It’s where people try the gig they always wondered about.

Or experiment with a long-shelved skill.

Or remix their expertise into a lighter, more human pace.

Call it “endless work” if you like - not because it never ends, but because you’re no longer eager for it to.

🎯 Why Pre-tirement Might Be Your Real Sweet Spot

In the “gig-economy”, many people:

• Hold multiple small roles

• Run side businesses

• Teach

• Consult

• Freelance

• Tinker with passion projects

Not because they’re hustling to survive, but because the idea of one monolithic job until the curtain falls feels outdated.

Pre-tirement fits the modern rhythm - a blend of security, stimulation, and choice.

And for many, it becomes the most creatively fertile period of life.

✨ Takeaways: Your Pre-tirement Toolkit

In the coming weeks, I’ll describe more about the pre-tirement journey and how to plan for retiring. For now, here are some initial tools to consider:

1. Run a “Retirement Rehearsal.”

Try living for 2–3 months on your anticipated retirement income. It will tell you more than any spreadsheet.

2. Sketch Your “Phase-Down” Timeline.

Ask yourself:

• When could I reduce to 75%?

• What about 50%?

• Could I consult for a few clients instead of one employer?

  Treat work reduction as a dial, not a switch.

3. Inventory Your “Endless Work.”

List the skills, curiosities, and slow-burning passions you’d pursue if time were flexible.

Those become your pre-tirement anchors.

4. Make Healthcare and Benefits a Non-Surprise.

Bridge periods (pre-65, post-employer) can be the costliest. Plan coverage early so your creative freedom isn’t swallowed by premiums.

5. Rebalance Your Financial Strategy.

A phased work period gives you:

• More years of saving

• Fewer years of withdrawals

• More optionality for Roth conversions, Social Security timing, and portfolio risk adjustments

  Use this window intentionally - it’s pure planning gold.

6. Talk to Your Partner Early.

Lifestyle changes ripple through the household. Align expectations now - hours, money, travel, chores, personal space, all of it.

7. Begin Your Legacy on Purpose.

Legacy isn’t just what you leave; it’s what people recount about how you lived.

Your approach to work, money, and transition becomes part of that narrative.

8. Remember: You’re Not Retiring From Work. You’re Retiring From Structure.

And structure is replaceable. Your usefulness isn’t.

👉 Closing Thought

Pre-tirement isn’t simply a “soft landing.”

It’s a threshold - a passageway from prescribed work to chosen work.

And often, that chosen work becomes the most meaningful, most generative, most personally honest chapter yet.

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🚀 Up Next:

Sunday - The Difference in Trading & Investing

Thursday - Retirement Series #2: How to “Pre-tire”

This publication is for brains, not bets. The Other Side of Obvious shares ideas, stories, and general financial information - not personalized investment, tax, or legal advice. Investing comes with risk (including losing money). Talk to a pro before you act. Please take time to read these important disclosures before you get started.