What if the biggest financial surprise in your life isn’t running out of money—but realizing that “having enough” doesn’t feel anything like you thought it would?

In this episode, I explore the hidden side of wealth: the regrets, letdowns, and quiet disappointments that often surface after you’ve hit your financial goals. From savers who can’t spend, to retirees who waited too long for joy, to high achievers who retired from something but not to something, we unpack why reaching your number doesn’t always equal fulfillment.

You’ll hear stories of real people—clients who built millions but treated their brokerage accounts like haunted attics, retirees who postponed joy until it slipped away, and professionals who reached “the dream” only to ask, “now what?” Along the way, we’ll look at surprising research, like why nearly 60% of retirees withdraw less than their required minimum distribution (not from strategy, but from fear), and why the average healthy retirement window is far shorter than most financial plans assume.

This isn’t about blowing your 401(k) on a yacht or regretting you didn’t buy Apple stock in the 90s. It’s about the emotional hangover of achieving your goals and realizing you never practiced enjoying the wealth you worked so hard to build.

In this episode, we’ll cover:

The Curse of the Responsible Saver: why some people can’t spend even when they can afford to.
Deferred Joy: the arrival fallacy that keeps people waiting for happiness until it’s too late.
Retired From, Not To: how lack of purpose, not lack of money, creates regret.
Emergency Spending Accounts: a counter-intuitive way to practice joy with your money now.
Redefining “Enough”: why true wealth is measured in stories, not spreadsheets.

If you’ve ever wondered what life looks like after hitting your financial goals, or worried that the “someday” you’re saving for may not look the way you hope, this conversation is for you.

Because wealth is more than a balance sheet. It’s about spending money—and time—with intention, before it’s too late.

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Episode 310: Transportation and Law Part 1