High-achieving women often wear exhaustion as a badge of honor, pushing through until the warning signs become impossible to ignore. For Molly Rosen, co-founder and co-CEO of Project Next Leadership, that moment came while driving between obligations, fantasizing not about a vacation, but about simply being allowed to stop. That recognition led to a sabbatical that stretched from one year to six, a journey that ultimately gave her the perspective, resilience, and clarity to build the leadership coaching company she runs today.

In this episode, Melissa Joy, CFP®, sits down with Molly to explore the realities of burnout for senior women leaders, the under acknowledged impact of perimenopause on career performance, and what it actually takes to build a life and career that is, as Molly puts it, human-sized. Drawing on more than two decades of coaching executives at companies like Pixar, Airbnb, DocuSign, and Samsung, Molly shares the patterns she sees most often in high-performing women, and the strategies that help them find their way back to themselves.

What You'll Learn

• Why working harder stops working at the executive level, and what actually drives advancement
• How burnout differs from a bad week, and why the body often signals it before the mind does
• The underreported career cost of perimenopause and menopause for high-achieving women
• What it means to ask "What is it that only I can do?" and how that question changes everything
• How to strategically step back from the workforce and return with greater clarity and purpose
• Why women leaders consistently rate themselves lower than others rate them, and how to close that gap
• The role of peer networks and cohorts in sustaining women at the top

Website: https://www.projectnextleadership.com

The previous presentation by PEARL PLANNING was intended for general information purposes only. No portion of the presentation serves as the receipt of, or as a substitute for, personalized investment advice from PEARL PLANNING or any other investment professional of your choosing. Different types of investments involve varying degrees of risk, and it should not be assumed that future performance of any specific investment or investment strategy, or any non-investment related or planning services, discussion or content, will be profitable, be suitable for your portfolio or individual situation, or prove successful. Neither PEARL PLANNING’s investment adviser registration status, nor any amount of prior experience or success, should be construed that a certain level of results or satisfaction will be achieved if PEARL PLANNING is engaged, or continues to be engaged, to provide investment advisory services. PEARL PLANNING is neither a law firm nor accounting firm, and no portion of its services should be construed as legal or accounting advice. No portion of the video content should be construed by a client or prospective client as a guarantee that he/she will experience a certain level of results if PEARL PLANNING is engaged, or continues to be engaged, to provide investment advisory services. A copy of PEARL PLANNING’s current written disclosure Brochure discussing our advisory services and fees is available upon request or at https...

Almost everyone has heard of a prenup, but very few of us have actually sat down and thought one through in practical terms. In this episode, Melissa Joy, CFP®, opens up a candid, surprisingly approachable conversation about what prenuptial agreements really are, who they are for, and why they belong in the financial planning discussion. Whether you are considering one for yourself or thinking about the next generation in your family, this is a topic worth understanding before the question ever comes up.

Melissa is joined by Kaylin Dillon, CFP®, a fee-only financial planner in Lawrence, Kansas, who has built a specialty around couples with separate assets, blended finances, and prenups. Kaylin reframes the prenup as a partnership exercise rather than a defensive move, walking through what can go into an agreement, why each partner needs their own attorney, how inherited and family wealth complicate things, and the single biggest mistake couples make. It is a thoughtful, practical look at planning for marriage with eyes wide open.

What You'll Learn

• What a prenuptial agreement actually is, and why it is not only about divorce
• Why each partner should hire their own family law attorney, and how that protects the validity of the agreement
• What can go into a prenup, from current assets and debts to future businesses, homes, life insurance, and even estate terms
• Why inherited and family wealth is one of the most common reasons couples pursue a prenup, and how to protect both sides
• The legal standard of unconscionability, and why a 30-day runway before the wedding is far too short
• The number one mistake couples make: rushing the process before agreeing on their own goals
• Why a joint financial plan is Plan A and the prenup is usually Plan B
• How a prenup coach can support a couple alongside their attorneys to keep the process focused and less expensive

Connect with Kaylin:

Website: kaylindillonfinancial.com

The Prenup Coach: prenupcoach.com

Instagram: https://www.instagram.com/theprenupcoach/

The previous presentation by PEARL PLANNING was intended for general information purposes only. No portion of the presentation serves as the receipt of, or as a substitute for, personalized investment advice from PEARL PLANNING or any other investment professional of your choosing. Different types of investments involve varying degrees of risk, and it should not be assumed that future performance of any specific investment or investment strategy, or any non-investment related or planning services, discussion or content, will be profitable, be suitable for your portfolio or individual situation, or prove successful. Neither PEARL PLANNING’s investment adviser registration status, nor any amount of prior experience or success, should be construed that a certain level of results or satisfaction will be achieved if PEARL PLANNING is engaged, or continues to be engaged, to provide investment advisory services. PEARL PLANNING is neither a law firm nor accounting firm, and no portion of its services should be construed as legal or accounting advice. No portion of the video content should be construed by a client or prospective client as a guarantee that he/she will experience a certain level of results if PEARL PLANNING is engaged, or continues to be engaged, to provide investment advisory services. A copy of PEARL PLANNING’s current written disclosure Brochure discussing our advisory services and fees is available upon request or at https...

Women are told to lean in, negotiate, and step up. And many do. But new research reveals that doing all the right things still isn’t enough — and may actually work against them. On this episode of Women’s Money Wisdom, Melissa Joy, CFP®, sits down with award-winning journalist and author Stefanie O’Connell to unpack the systemic forces that penalize women for their ambition, and what that means for their careers, their wealth, and their lives

Stefanie’s book, The Ambition Penalty: How Corporate Culture Tells Women to Step Up and Then Pushes Them Down, draws on research across sociology, psychology, economics, and public health to dismantle the persistent myths used to explain away the gender pay gap. This is not a conversation about what women are doing wrong. It is a conversation about what the system is doing to them.

What You’ll Learn:

• Why the most commonly cited explanations for the gender pay gap — job choice, caregiving, and lack of negotiation — are not supported by the data
• How ambition itself is weaponized against women as they advance beyond entry-level roles
• Why elevating a single woman into leadership can actually make gender inequity worse
• How the ambition penalty shows up in personal relationships, not just the workplace
• What pay transparency and collective action can do that individual best practices alone cannot
• The research-backed threshold at which women’s representation in leadership begins to close pay and promotion gaps

About Stefanie O’Connell:

Stefanie O’Connell is an award-winning journalist and the author of The Ambition Penalty: How Corporate Culture Tells Women to Step Up and Then Pushes Them Down. Her work draws on interdisciplinary research to expose the structural forces behind gender inequity in pay, leadership, and power. She also writes the Too Ambitious newsletter.

Website: tooambitious.com

Book: ambitionpenalty.com

Newsletter: Too Ambitious on Substack

Instagram: stefanieoconnell

LinkedIn: Stefanie O’Connell on LinkedIn

The previous presentation by PEARL PLANNING was intended for general information purposes only. No portion of the presentation serves as the receipt of, or as a substitute for, personalized investment advice from PEARL PLANNING or any other investment professional of your choosing. Different types of investments involve varying degrees of risk, and it should not be assumed that future performance of any specific investment or investment strategy, or any non-investment related or planning services, discussion or content, will be profitable, be suitable for your portfolio or individual situation, or prove successful. Neither PEARL PLANNING’s investment adviser registration status, nor any amount of prior experience or success, should be construed that a certain level of results or satisfaction will be achieved if PEARL PLANNING is engaged, or continues to be engaged, to provide investment advisory services. PEARL PLANNING is neither a law firm nor accounting firm, and no portion of its services should be construed as legal or accounting advice. No portion of the video content should be construed by a client or prospective client as a guarantee that he/she will experience a certain level of results if PEARL PLANNING is engaged, or continues to be engaged, to provide investment advisory services. A copy of PEARL PLANNING’s current written disclosure Brochure discussing our advisory services and fees is available upon request or at https...

What does it look like to turn a hobby into a thriving business — with no roadmap, no industry model to follow, and a drafty warehouse as your starting point? Melissa Joy, CFP®, sits down with Christy Howden, CEO and co-founder of Wolverine Pickleball, to trace an extraordinary entrepreneurial journey from stay-at-home mom to leader of one of the country’s first pickleball-centric destination facilities.

Christy shares how a 2017 New Year’s resolution sparked a business she never could have predicted, and how she and her business partner bootstrapped their way from rented school gyms to a 38,000 square foot facility that has become a community hub for connection, play, and purpose. Along the way, Melissa Joy, CFP®, weighs in on what financial planners can and cannot say about investing in private businesses and why having a frank conversation with your advisor matters more than the answer you get.

What You’ll Learn

• How Christy and her business partner built Wolverine Pickleball from the ground up with sweat equity, community volunteers, and a minimum viable product mindset
• Why 80% of their investors were women and what it means to make a lifestyle investment that overrides professional financial advice
• How Melissa Joy, CFP®, approaches conversations about investing in small businesses and passion projects
• The funding realities female entrepreneurs face and why the statistics around fundraising make building community capital even more important
• How a second act business can emerge from a life transition and why community is often the renewable energy source behind entrepreneurial endurance
• Practical ways listeners can support small businesses beyond just showing up

Connect with Christy: wolverinepickleball.com

https://www.instagram.com/wolverinepickleball/

https://www.facebook.com/WolverinePickleball/

Third-party rankings and recognition from rating services or publications are no guarantee of future investment success. Working with a highly rated advisor does not ensure that a client or prospective client will experience a higher level of performance or results. These ratings should not be construed as an endorsement of the advisor or by any client, nor are they representative of any one client’s evaluation. Generally, ratings, rankings, and recognition are based on information prepared and submitted by the advisor. This ranking is based on data as of 12/31/2025. The ranking was released on 02/12/2026. Pearl Planning and Melissa Joy did not pay any compensation to be considered for this rating and does not pay an annual fee for marketing usage of the logo. The methodology used to determine The Michigan 50 Companies to Watch award can be found here: Please visit the ranking methodology page for more info.

The previous presentation by PEARL PLANNING was intended for general information purposes only. No portion of the presentation serves as the receipt of, or as a substitute for, personalized investment advice from PEARL PLANNING or any other investment professional of your choosing. Different types of investments involve varying degrees of risk, and it should not be assumed that future performance of any specific investment or investment strategy, or any non-investment related or planning services, discussion or content, will be profitable, be suitable for your portfolio or individual situation, or prove successful. Neither PEARL PLANNING’s investment adviser registration status, nor any amount of prior experience or success, should be construed that a certain level of results or satisfaction will be achieved if PEARL PLANNING is engaged, or continues to be engaged, to provide investment advisory services. PEARL PLANNING is neither a law firm nor accounting firm, and no portion of its services should be construed as legal or accounting advice. No portion of the video content should be construed by a client or prospective client as a guarantee that he/she will experience a certain level of results if PEARL PLANNING is engaged, or continues to be engaged, to provide investment advisory services. A copy of PEARL PLANNING’s current written disclosure Brochure discussing our advisory services and fees is available upon request or at https...

The financial news cycle moves fast, but the fundamentals of investing have not changed. Melissa Joy, CFP® sits down with Ben Carlson, Director of Institutional Asset Management at Ritholtz Wealth Management and author of five books including his latest, Risk and Reward, to explore what history actually teaches us about markets, human nature, and the psychology behind smart long-term investing. Ben brings equal parts data and storytelling to make the case that understanding the past is one of the most underrated tools an investor can have.

From the inflationary spiral of the 1970s to lost decades and the dot-com aftermath, Ben and Melissa walk through the market cycles that shaped today's investing environment and what those periods reveal about our own tendencies as investors. They also dig into the coming wave of wealth transfer, why women will increasingly control the bulk of financial assets, and why the financial advice industry is not yet ready for it.

What You'll Learn

• Why studying financial history matters and what it reveals about the range of possible outcomes
• How inflation in the 1970s shaped investor psychology in ways that still resonate today
• What the lost decade of 2000 to 2010 teaches about diversification and why that lesson keeps getting forgotten
• Why simplicity in a financial plan beats complexity almost every time
• How to build a portfolio durable enough to survive a wide range of outcomes without requiring you to predict the future
• Why preparation is more valuable than prediction when it comes to investing
• What the great wealth transfer means for women and why the financial advice industry needs to catch up
• How human nature is the one investing variable that never changes across market cycles
• What Ben's list of 20 investing beliefs reveals about discipline, self-awareness, and behavioral finance
• Why the best financial plan is the one you can actually stick with through difficult markets

About Ben Carlson

Ben Carlson is the Director of Institutional Asset Management at Ritholtz Wealth Management and the author of five books on investing and personal finance, including his latest, Risk and Reward. He is the creator of the blog Wealth of Common Sense and co-host of the Animal Spirits podcast.

Book: Risk and Reward

Blog: awealthofcommonsense.com

Podcast: Animal Spirits

The previous presentation by PEARL PLANNING was intended for general information purposes only. No portion of the presentation serves as the receipt of, or as a substitute for, personalized investment advice from PEARL PLANNING or any other investment professional of your choosing. Different types of investments involve varying degrees of risk, and it should not be assumed that future performance of any specific investment or investment strategy, or any non-investment related or planning services, discussion or content, will be profitable, be suitable for your portfolio or individual situation, or prove successful. Neither PEARL PLANNING’s investment adviser registration status, nor any amount of prior experience or success, should be construed that a certain level of results or satisfaction will be achieved if PEARL PLANNING is engaged, or continues to be engaged, to provide investment advisory services. PEARL PLANNING is neither a law firm nor accounting firm, and no portion of its services should be construed as legal or accounting advice. No portion of the video content should be construed by a client or prospective client as a guarantee that he/she will experience a certain level of results if PEARL PLANNING is engaged, or continues to be engaged, to provide investment advisory services. A copy of PEARL PLANNING’s current written disclosure Brochure discussing our advisory services and fees is available upon request or at https...

Nearly a quarter of Americans have no traditional next of kin, yet the financial planning industry has long operated as if everyone will eventually have children. Melissa Joy, CFP® sits down with Maddy Roche, co-host of the Child Free Life by Design Podcast and Chief Growth Officer of Partnerships for Child Free Trust, to talk about what changes and what becomes possible when you are building a financial life without kids.

Maddy brings both personal and professional perspective to the conversation. As someone who is child free by choice, she shares how a financial plan created specifically for her shifted her entire mindset around spending, legacy, and the concept of dying with zero. She and Melissa dig into why estate planning has been so hard for this demographic to complete, why that needs to change, and how Child Free Trust is filling a gap that trust companies and traditional advisors have largely left open.

What You’ll Learn

• Why child free people represent a distinct and underserved financial planning demographic
• How planning assumptions tied to children create blind spots for advisors working with this group
• Why long-term care insurance matters more than life insurance for most child free people
• What the die with zero philosophy means and how it gives child free people a financial permission slip to spend and experience more
• Why upwards of 70 percent of child free people do not have a legally binding estate plan in place
• How to reframe estate planning as contingency planning and why it matters long before death
• What roles are required in a complete estate plan and why they are especially hard to fill without children
• How Child Free Trust serves as a professional fiduciary in the roles of medical and financial power of attorney, executor, and trustee
• Why hourly billing rather than assets under management makes professional fiduciary services more accessible
• How the Child Free Trust care document captures everything from pet care plans to end of life wishes

Estate Planning and Membership: ChildFreeTrust.com

Thought Leadership, Podcast, and Community: ChildFreeInsights.com

The previous presentation by PEARL PLANNING was intended for general information purposes only. No portion of the presentation serves as the receipt of, or as a substitute for, personalized investment advice from PEARL PLANNING or any other investment professional of your choosing. Different types of investments involve varying degrees of risk, and it should not be assumed that future performance of any specific investment or investment strategy, or any non-investment related or planning services, discussion or content, will be profitable, be suitable for your portfolio or individual situation, or prove successful. Neither PEARL PLANNING’s investment adviser registration status, nor any amount of prior experience or success, should be construed that a certain level of results or satisfaction will be achieved if PEARL PLANNING is engaged, or continues to be engaged, to provide investment advisory services. PEARL PLANNING is neither a law firm nor accounting firm, and no portion of its services should be construed as legal or accounting advice. No portion of the video content should be construed by a client or prospective client as a guarantee that he/she will experience a certain level of results if PEARL PLANNING is engaged, or continues to be engaged, to provide investment advisory services. A copy of PEARL PLANNING’s current written disclosure Brochure discussing our advisory services and fees is available upon request or at https...

A new type of savings account has entered the conversation, and if you have young children, you need to know about it. Melissa Joy, CFP® sits down with Ann Garcia, CFP®, returning guest, college funding expert, and author of How to Pay for College, to break down the newly created Trump accounts. Also known as 530A accounts, these IRA-style vehicles are generating a lot of buzz, and Ann helps separate the hype from the reality so families can make smart decisions about whether and how to use them.

The conversation goes beyond the new accounts. Melissa and Ann also respond to a widely shared Wall Street Journal article about a financial planning expert who is skipping 529s for his own kids, and explain why that strategy works for a very small slice of the population but could leave most families short. They close with practical wisdom on how to talk to your kids about money at every age, and why starting simple is always better than waiting until you have the perfect lesson plan.

What You’ll Learn

• What Trump accounts (530A accounts) are and how they work
• How to open an account and claim the free government funding your child may be entitled to
• Why Trump accounts are generally not the best vehicle for college savings, and what to use instead
• How the kiddie tax affects withdrawals and why it matters for your planning
• The difference between how Trump accounts and 529s are treated on the FAFSA
• The Wall Street Journal article making the case to skip 529s, and why Ann and Melissa push back
• Why the 529 remains one of the most flexible and tax-efficient tools for college savings
• When and how to help your young adult children get their first Roth IRA open
• Why automating your financial life is the antidote to always being in triage mode

Connect with Ann Garcia, CFP®

Website: howtopayforcollege.com

Book: How to Pay for College

The Mather Group: themathergroup.com

The previous presentation by PEARL PLANNING was intended for general information purposes only. No portion of the presentation serves as the receipt of, or as a substitute for, personalized investment advice from PEARL PLANNING or any other investment professional of your choosing. Different types of investments involve varying degrees of risk, and it should not be assumed that future performance of any specific investment or investment strategy, or any non-investment related or planning services, discussion or content, will be profitable, be suitable for your portfolio or individual situation, or prove successful. Neither PEARL PLANNING’s investment adviser registration status, nor any amount of prior experience or success, should be construed that a certain level of results or satisfaction will be achieved if PEARL PLANNING is engaged, or continues to be engaged, to provide investment advisory services. PEARL PLANNING is neither a law firm nor accounting firm, and no portion of its services should be construed as legal or accounting advice. No portion of the video content should be construed by a client or prospective client as a guarantee that he/she will experience a certain level of results if PEARL PLANNING is engaged, or continues to be engaged, to provide investment advisory services. A copy of PEARL PLANNING’s current written disclosure Brochure discussing our advisory services and fees is available upon request or at https...

What would it look like to stop working at 50? Or to step away from a high-powered career and spend your time doing something that lights you up instead?

For many women, this is not just a dream. With the right plan, it is a very real option. Melissa Joy, CFP® sits down with Bridget Grimes, founder of Wealth Choice and co-founder of Equita Financial Network, to talk about what retiring in your 50s or 60s actually requires, from knowing your cost of living to healthcare coverage, Roth conversions, and finding purpose on the other side.

Bridget is a financial planner, CFP Board Ambassador, and fierce advocate for women and women-led financial firms. She works with breadwinner women every day who are building toward financial independence, and in this conversation she pulls back the curtain on the planning conversations that make early retirement possible.

What You’ll Learn

• What Coast FIRE is and why it resonates with so many high-achieving women
• Why knowing your actual cost of living is one of the most important retirement planning inputs
• How a stair-step retirement, with part-time or passion work, can meaningfully improve your financial picture
• Why healthcare is the biggest wild card for anyone retiring before Medicare eligibility at 65
• How to think about COBRA, the ACA exchange, and HSAs as part of your early retirement plan
• Why having multiple account types, taxable, pre-tax, and Roth, gives you flexibility and tax options
• How Roth conversions work as a multi-year strategy and why doing them all at once can backfire
• What the Rule of 55 means for 401k access and how it differs from IRA rules
• Why rebalancing your investment allocation matters when you stop earning and start drawing
• How to give yourself permission to think about what you actually want your life to look like
• Why early retirement is as much a social and emotional transition as it is a financial one
• What to look for in a financial advisor if you are planning to retire earlier than traditional ages

Connect with Bridget Grimes

Website: wealthchoice.com

LinkedIn: linkedin.com/in/bridget-venus-grimes-cfp

Facebook: facebook.com/wealthchoice

Instagram: wealthchoice_

The previous presentation by PEARL PLANNING was intended for general information purposes only. No portion of the presentation serves as the receipt of, or as a substitute for, personalized investment advice from PEARL PLANNING or any other investment professional of your choosing. Different types of investments involve varying degrees of risk, and it should not be assumed that future performance of any specific investment or investment strategy, or any non-investment related or planning services, discussion or content, will be profitable, be suitable for your portfolio or individual situation, or prove successful. Neither PEARL PLANNING’s investment adviser registration status, nor any amount of prior experience or success, should be construed that a certain level of results or satisfaction will be achieved if PEARL PLANNING is engaged, or continues to be engaged, to provide investment advisory services. PEARL PLANNING is neither a law firm nor accounting firm, and no portion of its services should be construed as legal or accounting advice. No portion of the video content should be construed by a client or prospective client as a guarantee that he/she will experience a certain level of results if PEARL PLANNING is engaged, or continues to be engaged, to provide investment advisory services. A copy of PEARL PLANNING’s current written disclosure Brochure discussing our advisory services and fees is available upon request or at https...