Author Jesse Hurst explains how retirement planning helps reduce the guesswork of retiring through his book “PopEnomics”.

A lot of people approach financial planning with one big fear: that it’s going to feel restrictive. Budgets. Rules. Spreadsheets. Being told what you can’t do with your money.

But in this episode of Retire Today, I sat down with Impel Wealth Management president and author of “PopEnomics”Jesse Hurst to talk about why that assumption gets things exactly backward — and how the right kind of planning actually creates freedom.

As Jesse put it early in our conversation, “A lot of people think financial planning is very constrictive… and I think it’s exactly the opposite. I think it’s very freeing.”

Why Guessing Is the Default (and the Problem)

Most people don’t lack motivation. They lack clarity.

Jesse explained that many retirees have vague hopes rather than defined goals. “Someday I want to retire and live a comfortable life,” sounds nice — but it’s not a plan. Without specifics, people end up guessing on some of the most important decisions of their financial lives.

How much should I save?
Should I prioritize paying off the mortgage?
Is Roth or pre-tax better for me?
Am I saving enough — or too much?

Without a defined target, people default to hearsay. “My coworker did this.” “I read an article that said 8% is enough.” That’s not planning — it’s outsourcing your decisions to someone else’s guess.

Why Stories Stick When Numbers Don’t

Jesse has a way with analogies. By tying retirement planning ideas to pop culture — music, movies, and familiar stories — he finds people actually remember them.

During the COVID period, Jesse began using pop-culture analogies more intentionally. One comparison between Federal Reserve policy and the movie Animal House took off online — and made him realize he’d found a powerful teaching tool.

That insight ultimately led to his book PopEnomics, where retirement planning meets rock anthems, movie classics, and everyday analogies.

Access to Information Isn’t the Same as Wisdom

One of the most important observations Jesse shared came from reflecting on his decades in the profession.

Early in his career, the challenge was simply educating people about what options existed. Today, the challenge is the opposite. “There’s a big difference between access to information and the wisdom to apply it,” Jesse said.

Retirees today are overwhelmed with data — articles, headlines, opinions — but often still unsure what applies to them. That’s where planning shifts from information to interpretation.

The Retirement Puzzle

Jesse described retirement planning as a puzzle — one where each piece matters.

You can’t decide how to invest if you don’t know when you’ll retire.
You can’t know how much risk to take if you don’t know when you’ll need the money.
You can’t spend confidently if you don’t know whether your income supports it.

One story he shared involved a couple who lost track of where they stood financially after COVID, inflation, and market volatility. Using an airport analogy, Jesse explained, “If you don’t know where you are, you can’t figure out how to get to your gate.”

Clarity begins with knowing your starting point.

The Saver’s Mindset — and the Permission Problem

Many people who retire successfully built wealth through discipline — spending less than they earned, avoiding debt, and saving consistently. But those same habits can make it emotionally difficult to switch from accumulation to spending.

As Jesse explained, “They have a hard time giving themselves permission to spend.”

He shared a powerful story of longtime clients who had ample income and assets — but struggled to enjoy them. The breakthrough came when they realized that if they didn’t use their money intentionally, someone else eventually would.

That shift — from fear to permission — is often one of the most important transitions in retirement.

The Bottom Line

Financial planning isn’t about restriction. It’s about clarity.

When you know what you’re saving for, what you’ve already done, and what your money can support, decisions become easier. Spending becomes intentional. And retirement becomes something you can enjoy — not just hope works out.

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About the Author:

Jeremy Keil, CFP^®, CFA is a retirement financial advisor with Keil Financial Partners, author of Retire Today: Create Your Retirement Income Plan in 5 Simple Steps, and host of the Retirement Today blog and podcast, as well as the Mr. Retirement YouTube channel.

Jeremy is a contributor to Kiplinger and is frequently cited in publications like the Wall Street Journal and New York Times.

Additional Links:

Buy Jeremy’s book – Retire Today: Create Your Retirement Master Plan in 5 Simple Steps
Create Your Retirement Master Plan in 5 Simple Steps
Jesse Hurst on LinkedIn
Impel Wealth Management
PopEnomics.com
PopEnomics: 12 Relatable (and Not Boring) Pop Culture Insights for Retirement Success
Jesse Hurst on YouTube
Jesse Hurst on Instagram
Jesse Hurst on X

Connect With Jeremy Keil:

Media Disclosures:

Disclosures

This media is provided for informational and educational purposes only and does not consider the investment objectives, financial situation, or particular needs of any consumer. Nothing in this program should be construed as investment, legal, or tax advice, nor as a recommendation to buy, sell, or hold any security or to adopt any investment strategy.

The views and opinions expressed are those of the host and any guest, current as of the date of recording, and may change without notice as market, political or economic conditions evolve. All investments involve risk, including the possible loss of principal. Past performance is no guarantee of future results.

Legal & Tax Disclosure

Consumers should consult their own qualified attorney, CPA, or other professional advisor regarding their specific legal and tax situations.

Advisor Disclosures

Alongside, LLC, doing business as Keil Financial Partners, is an SEC-registered investment adviser. Registration does not imply a certain level of skill or expertise. Advisory services are delivered through the Alongside, LLC platform. Keil Financial Partners is independent, not owned or operated by Alongside, LLC.

Additional information about Alongside, LLC – including its services, fees and any material conflicts of interest – can be found at https://adviserinfo.sec.gov/firm/summary/333587 or by requesting Form ADV Part 2A.

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Why Retirement Planning Needs More Than Hope (and a Better Soundtrack) with Jesse Hurst