Richard Sheffield – Medium

Richard Sheffield

Featured Book

Spend Your Damn Retirement Money!: Beat the Spending Fear to Find Your Dream Retirement

Spend Your Damn Retirement Money!: Beat the Spending Fear to Find Your Dream Retirement

Money Was the Tool. Life Is the Goal. Let’s Flip the Switch from Cautious Saver to Responsible Spender.

2025

Richard Sheffield

Richard Sheffield

Stories

Pinned

Published in

The Big Retirement Problem No One Wants to Admit Having — Why Can’t We Spend Our Damn Money?

If you are retired with decent savings and your spending doesn’t make your kids and retirement planner a little nervous, you’re probably…

Apr 6

The Big Retirement Problem No One Wants to Admit Having — Why Can’t We Spend Our Damn Money?

Apr 6

Published in

We Can’t Rage Against the Dying of the Light if We’re the Ones Dimming It

Retirement reveals the truth: the light doesn't die before you do, it just waits for permission.

2d ago

We Can’t Rage Against the Dying of the Light if We’re the Ones Dimming It

2d ago

Published in

My Gratitude Reboot

Why We Need to Remember the Grind to Love Retirement

3d ago

My Gratitude Reboot

3d ago

Published in

Your Retirement Isn’t Broken. It Just Needs Assembly

You’ve spent decades following rules. Now it’s time to ignore the menu and start assembling a life that actually fits.

4d ago

Your Retirement Isn’t Broken. It Just Needs Assembly

4d ago

Why Can’t We Spend Our Damn Retirement Money, Part 12: Post-Traumatic Broke Syndrome

Growing Up with Scarcity, Real or Imagined

Oct 31

Why Can’t We Spend Our Damn Retirement Money, Part 12: Post-Traumatic Broke Syndrome

Oct 31

Published in

Why You Probably Won’t Go Broke in Retirement, Part 3: Let’s Talk About Healthcare

The Boring Reality

Oct 27

Why You Probably Won’t Go Broke in Retirement, Part 3: Let’s Talk About Healthcare

Oct 27

Why We Can’t Spend Our Damn Retirement Money, Part 11: Our Imagination Deficit

How Decades of Discipline Dismantles Desire

Oct 23

Why We Can’t Spend Our Damn Retirement Money, Part 11: Our Imagination Deficit

Oct 23

Published in

The War of Art… and Retirement

The same invisible enemy that stops writers from writing stops retirees from spending.

Oct 18

The War of Art… and Retirement

Oct 18

Published in

Retirement Isn’t a Second Act: It’s a More Authentic Director’s Cut

If you’re ever going to be the real you, the time is now or never.

Oct 16

Retirement Isn’t a Second Act: It’s a More Authentic Director’s Cut

Oct 16

Published in

Let the Tech Bros Give Your Retirement Day a Little Structure

Make Before You Manage (And Still Sleep In)

Oct 14

Let the Tech Bros Give Your Retirement Day a Little Structure

Oct 14

Richard Sheffield

Richard Sheffield

Book Author

Friend of Medium

Atlanta and Miami based freelance writer/author. For reprint and media use, or to collaborate or contract original work, contact rsheff@gmail.com for terms.

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