Retirement Planning Needs More Than a Financial Plan with Toni Petrillo

Retirement coach Toni Petrillo and Jeremy Keil explore how to create a meaningful retirement beyond solving the financial side of retiring.

Most people spend decades preparing financially for retirement.

They contribute to retirement accounts, pay down debt, evaluate Social Security strategies, and work with advisors to make sure their savings can support the next chapter of life. By the time retirement arrives, many have a well-developed financial plan that answers the most important question:

“Can I afford to retire?”

On the Retire Today podcast, I spoke with retirement lifestyle coach Toni Petrillo about a different question—one that often surfaces only after retirement begins:

“Now what?”

Toni spent more than 25 years in financial services before transitioning into retirement coaching. What drew her to this work was a pattern she observed repeatedly: people who were fully prepared financially but were struggling emotionally with retirement. In many cases, the retirement plan was solid. The lifestyle plan was missing.

Retirement Creates More Than Financial Change

When people think about retirement, they often focus on the obvious changes.

The paycheck stops. Work responsibilities disappear. The daily schedule opens up.

But retirement also changes things that are much harder to quantify.

It changes identity. It changes relationships. It changes how time is structured.

For many professionals, work has provided answers to questions they rarely needed to ask:

Who am I? What am I contributing? Who do I spend time with? How do I spend my day?

Retirement removes many of those built-in answers at the same time.

That’s why some retirees are surprised when they experience feelings of uncertainty despite being financially secure.

The “In-Between Chapter”

One concept Toni introduced that resonated with me is what she calls the “in-between chapter.”

This is the period after leaving a career but before fully settling into retirement. It’s the space between who you were and who you’re becoming.

Many people want to move through this phase as quickly as possible.

They stay busy. They start projects. They fill every available hour.

But according to Toni, rushing through this stage can actually delay the clarity people are seeking.

The temptation is understandable. High achievers often spend decades solving problems quickly and moving decisively. Retirement feels like another challenge to conquer.

The problem is that retirement isn’t something to optimize the same way you optimized your career.

Some of the most important retirement questions require reflection rather than action.

Why a Pause Can Be Productive

One of the themes that emerged from our conversation was the value of giving yourself permission to pause.

That doesn’t mean doing nothing.

It means creating space to think.

Questions such as:

• Who am I without my title?
• What do I want my days to look like?
• What am I retiring toward?
• Which relationships matter most to me?

These questions rarely get answered in the middle of a busy workweek.

Yet they become central to a fulfilling retirement.

Many retirees assume they’ll figure these things out after they retire. In reality, the transition tends to go much more smoothly when these questions are explored beforehand.

Practice Retirement Before You Retire

One of Toni’s practical suggestions was something I immediately connected with.

Practice retirement.

Not for a weekend. Not for a vacation. Actually practice it.

Take a couple of weeks and intentionally live as though you’re retired. Pay attention to how you spend your time. Notice what energizes you and what doesn’t. Think about who you’re spending time with and how your days feel without work providing structure.

I often tell clients something similar when they’re considering buying a second home in retirement. Before making a major commitment, spend a month living in that community. Experience what daily life actually feels like.

Retirement deserves the same level of testing.

The goal isn’t to create a perfect plan.

The goal is to discover what your future lifestyle may actually require.

Your Career Has Been Managing Your Calendar

One observation that stood out to me is how much structure work provides without us realizing it.

Most working professionals don’t need to think about filling their calendars.

Work does that automatically.

Meetings. Projects. Conversations. Deadlines. Relationships.

Retirement changes that dynamic completely.

Many retirees discover that maintaining social connections requires far more intentional effort than it did during their careers. Work friendships don’t always transfer naturally into retirement. Former colleagues continue operating at a different pace and under different priorities.

As a result, retirees often need to actively build and maintain their social lives.

That might include:

• Reconnecting with old friends
• Joining community organizations
• Participating in continuing education
• Volunteering
• Starting clubs or groups
• Developing new hobbies

The specific activity matters less than the intentionality behind it.

Retirement Planning Is Becoming More Holistic

As financial advisors, we’ve become much better at helping people prepare financially for retirement.

But financial readiness doesn’t automatically create retirement satisfaction.

A comprehensive retirement plan addresses income, taxes, investments, healthcare, and risk management.

A comprehensive retirement plan also considers purpose, identity, relationships, and lifestyle.

Those aren’t separate conversations.

They’re connected.

After all, what’s the purpose of building financial freedom if you haven’t thought about how you’ll use it?

The Bottom Line

One of the most common misconceptions about retirement is that once the financial plan is complete, everything else naturally falls into place.

For some people, that’s true.

For many others, retirement introduces a new set of questions that spreadsheets alone cannot answer.

Financial planning helps you retire.

Lifestyle planning helps you thrive once you get there.

The retirees who seem happiest aren’t simply the ones with enough money.

They’re the ones who have built a meaningful vision for what comes next.

Don’t forget to leave a rating for the “Retire Today” podcast if you’ve been enjoying these episodes!

Subscribe to Retire Today to get new episodes every Wednesday.

Apple Podcasts: https://podcasts.apple.com/us/podcast/retire-today/id1488769337 

Spotify Podcasts: https://bit.ly/RetireTodaySpotify

---

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
• RetireWithIntention.com 
• Connect with Toni Petrillo: retirewithintention@gmail.com
• Toni Petrillo on LinkedIn

Connect With Jeremy Keil:

• Keil Financial Partners
• LinkedIn: Jeremy Keil
• Facebook: Jeremy Keil
• LinkedIn: Keil Financial Partners
• YouTube: Mr. Retirement
• Book an Intro Call with Jeremy’s Team

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.

The content of this media should not be reproduced or redistributed without the firm’s written consent. Any trademarks or service marks mentioned belong to their respective owners and are used for identification purposes only.

Additional Important Disclosures