Pearl Planning

Pearl Planning You work hard for your money. We help you make the most out of it.

06/18/2026

The data is clear: women leaders consistently rate themselves lower than others rate them.

Molly Rosen, co-founder and co-CEO of Project Next Leadership, shares what her 360 assessment research reveals about how women leaders see themselves versus how they are actually seen. The gap has real consequences: not raising your hand, not speaking up, running harder instead of smarter, and assuming recognition will come from effort alone when advancement at the executive level requires something different entirely.

Working harder is what got many women to leadership. It is not always what gets them further. Listen to the full episode to hear Molly and Melissa Joy, CFP®, discuss what actually moves the needle.

https://podcasts.apple.com/us/podcast/womens-money-wisdom/id1583888433?i=1000772952101

What does burnout actually feel like in your body before your mind catches up?Molly Rosen, co-founder and co-CEO of Proj...
06/16/2026

What does burnout actually feel like in your body before your mind catches up?

Molly Rosen, co-founder and co-CEO of Project Next Leadership, knows firsthand. After more than two decades coaching senior executives at companies like Pixar, Airbnb, and DocuSign, she hit a wall that a vacation could not fix. What started as a planned one-year sabbatical stretched to six, and what she learned in that time completely reshaped how she coaches women leaders today.

In the latest episode of Women's Money Wisdom, Melissa Joy, CFP®, and Molly explore burnout, perimenopause, strategic rest, and what it means to build a career and life that is genuinely human-sized.

Listen here: https://podcasts.apple.com/us/podcast/womens-money-wisdom/id1583888433

06/15/2026

Your partner's business debt can land on your personal balance sheet.

A prenup might be the tool that protects you both.
On the Women's Money Wisdom podcast, host Melissa Joy, CFP®, and prenup specialist Kaylin Dillon, CFP®, dig into a risk many couples miss. When one partner signs personal guarantees on a business, the other can be exposed without even knowing it. Kaylin offers a refreshing reframe: rather than living with the unknown, a couple can use a prenup or postnup to protect the business and open the door to real financial transparency.

Protection and honesty, working together.

06/11/2026

Getting a prenup? You and your partner each need your own attorney, and the reason matters more than most couples realize

On the Women's Money Wisdom podcast, fee only financial planner and prenup specialist Kaylin Dillon, CFP®, explains why separate counsel is not just a formality. When each person has their own attorney, each person has someone advising them on what is truly in their best interest, and in many states that separate representation is part of what makes the agreement hold up.

But as Kaylin points out, a sound prenup never ends up protecting only one person. That is no way to start a marriage.

Most people have heard of a prenup. Far fewer have ever thought one through in practical terms.On the latest episode of ...
06/09/2026

Most people have heard of a prenup. Far fewer have ever thought one through in practical terms.

On the latest episode of Women's Money Wisdom, host Melissa Joy, CFP®, sits down with Kaylin Dillon, CFP®, fee only financial planner and founder of The Prenup Coach®. Kaylin walks through what goes into a prenup, why each partner needs their own attorney, and the biggest mistake couples make: hiring attorneys before they have agreed on their own goals.

She also makes the case that a prenup or postnup is not just protection. Done right, it is the thing that makes real financial transparency possible in a marriage.

06/08/2026

The ambition penalty does not start at the entry level. It compounds the moment women begin to translate potential into power.

On Women’s Money Wisdom, Melissa Joy, CFP®, and journalist Stefanie O’Connell, author of The Ambition Penalty, examine what the research shows about when and why the backlash intensifies.

Early career ambition is broadly accepted. It is when women seek advancement beyond the entry level that the penalties begin to compound.

Listen to the full episode of Women’s Money Wisdom

06/04/2026

Stefanie O’Connell, award-winning journalist and author of The Ambition Penalty, joins Melissa Joy, CFP®, on Women’s Money Wisdom to share what the research actually shows: women are ambitious, they are confident, and they do ask for more. And they are still penalized for it.

From job offers rescinded to being labeled not a team player, Stefanie breaks down the real consequences women face when they do everything right and still do not receive the same rewards as their male peers.
Listen to the full episode of Women’s Money Wisdom

What does it actually mean when we say women face a gender pay gap? And why hasn't it moved, even as women have become m...
06/02/2026

What does it actually mean when we say women face a gender pay gap?

And why hasn't it moved, even as women have become more educated and more ambitious than ever?

Melissa Joy, CFP®, sits down with journalist and author Stefanie O'Connell to dig into the research behind her new book, The Ambition Penalty. The conversation covers the myths we keep hearing about why women fall behind, what the data actually shows, and what it might take to change things at a systemic level.

Worth a listen if this topic has ever crossed your mind at work or in your own financial life.

New episode of Women's Money Wisdom out now: https://podcasts.apple.com/us/podcast/womens-money-wisdom/id1583888433

06/01/2026

Wolverine Pickleball has local breweries on the tap wall, goat yoga in the schedule, and up-and-coming entrepreneurs launching their businesses inside its walls.

That was not exactly the original plan. But Christy Howden, CEO and co-founder, built something that keeps growing into more than she imagined.

“We’d like to put our marketing might behind them with all of our community to help them get a good launch and get their business going.”

This is what it looks like when small businesses invest in each other. Christy joined Melissa Joy, CFP®, on Women’s Money Wisdom to share how she built it.

05/28/2026

Nobody tells you this part of entrepreneurship.

Christy Howden, CEO and co-founder of Wolverine Pickleball, built one of the first pickleball-centric destination facilities in the country. And she’ll be the first to say the behind-the-scenes is nothing like the highlight reel.

“Entrepreneurs are definitely built different. It’s a roller coaster. You never turn it off.”

What keeps her going? Spreading joy, mentoring the next wave of entrepreneurs, and a community that shows up for her the way she shows up for them.

Her full story is on Women’s Money Wisdom with Melissa Joy, CFP®.

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