The Conversation We All Keep Dodging: Estate Planning
Between Sips
Estate planning has a reputation for being heavy, uncomfortable, and easy to avoid. Between sips of a Rhode Island coffee, Jessica and Emily talk about why that avoidance is so common, even among thoughtful and successful people, and why it can create more stress down the road. This conversation reframes estate planning as a way to protect your life, your relationships, and the people you love, not a checklist for the end of life. From incapacity planning to outdated documents, they explore how small decisions today can create clarity and peace of mind later, without making it overwhelming....
info_outline
How to Set Goals Without Overhauling Your Life in 2026
Between Sips
A new year has a way of making people feel like they need to figure everything out at once. Goals, priorities, plans, all piled together in January, like our life restarts with the change in the calendar. In this first Between Sips episode of 2026, Emily and Jessica talk through a more realistic way of thinking about goals, one that leaves room for life stage, time constraints, and changing priorities. They share why so many people struggle to articulate what they want, and how narrowing goals too quickly can cause us to miss opportunities that really move the needle. The conversation takes...
info_outline
What People Get Wrong About Roth IRAs and Conversions: A Guide for Busy Professionals
Between Sips
Roth IRAs, backdoor Roths, conversions… most people know these terms, but not why they matter. In this episode, Emily and Jessica break it all down in plain English and focus on the real question: How do you create more flexibility for your future self? With uncertainty around tax policy and retirement rules, the way your money gets taxed can have as much impact as how it’s invested. The good news? You have more control than you may think. Emily and Jessica walk through the key moments when a Roth conversion might be worth considering—career pivots, sabbaticals, business transitions,...
info_outline
How to Plan for Your Child’s Education
Between Sips
College can feel far away when your kids are still young, but the questions around their future tend to show up early. Over a favorite cup of coffee, Emily Harper, CFP® and Jessica Gibbs, CFP®, talk through the mix of hope, uncertainty, and planning that surrounds education today. They share what they’ve learned as financial planners and college graduates, touching on rising costs, changing career paths, and the value of defining your own philosophy before focusing on numbers. The conversation wanders through personal stories, shifts in the education landscape, and the small steps families...
info_outline
Retiring Before 65: What It Really Means
Between Sips
We’ve all heard 65 is the magic retirement age, but who decided that, anyway? In this episode, Jessica Gibbs, CFP®, and Emily Harper, CFP®, share a fresh take on what it means to step away from full-time work before that milestone. The conversation moves between money and mindset, the realities of healthcare and savings, and the freedom of redefining what retirement even looks like. They talk through how to prepare, what “enough” might mean for you, and why the emotional side of this transition matters just as much as the financial one. For anyone wondering when work starts to give way...
info_outline
Should You Retire When the Market is Down?
Between Sips
Markets are down, your retirement date’s circled on the calendar—now what? Emily and Jessica unpack how to protect your peace of mind, why your “sleep-at-night factor” matters, and what it really means to retire on your terms. Tune in to hear how market volatility can impact your retirement portfolio if it happens at the wrong time. Plus, understand the value of stress-testing your portfolio and how to reduce your anxiety around retirement. Please see important podcast disclosure information at 0:14 - Intro 2:39 - Can You Retire in a Down Market? 5:18 - Why Timing of Returns...
info_outline
OBBBA Review: Tax Moves to Make Before 2025 Ends
Between Sips
The “One Big Beautiful Bill” is here—and it’s changing the math on deductions, income timing, and year-end tax strategy. In this episode we cut through the complexity to spotlight the most important moves to make before December 31, 2025. We unpack what high earners need to know about charitable deductions, the new 35% cap, clean-energy credits, and how to make the most of your AGI and MAGI thresholds—without drowning in details. Pour yourself a cup of your favorite brew and tune in for clear, actionable ideas on how to finish the year tax-savvy and confident. Please see important...
info_outline
Unique Ways to Donate to Charity Beyond Writing a Check
Between Sips
“Cash isn’t the only way to make an impact. Complex assets—like private business shares or alternative investments—can sometimes be the most powerful gifts.” Emily M. Harper, CFP® Charitable donations come in many forms: cash, stock, assets. In this episode, we’re talking about charitable donations in the form of complex assets, such as privately held business shares, crypto, oil and gas royalties, and more. Depending on your situation, it may make a lot of sense. It can help maximize the impact of your gift while also increasing your tax efficiency. That being said, there is much...
info_outline
Post-Exit Planning: How to Manage Your Investments & Cash Flow After Selling Your Business
Between Sips
For business owners, the day you sell your business can feel like you’re crossing the finish line. In reality, it’s actually just a new starting point for the beginning of your post-exit life. One of the biggest questions we hear after a successful sale is “What should I do with all this money?” In this episode, Jessica and Emily tackle the financial side of post-exit life: the benefits of a cash strategy, why you should be thinking about your portfolio’s total return (not just income), and why behavior is often the biggest threat to long-term investing success. Tune in to learn more...
info_outline
Life After Ownership: Defining Your Next Chapter After You Sell a Business
Between Sips
“Liquidity can open a lot of doors, but purpose tells you which ones to walk through.” Selling a business is an amazing accomplishment, but it is often followed by an identity crisis that can leave former business owners in a spiral. The purpose you committed yourself to every day is suddenly gone – what’s your purpose now? In this episode, we discuss how to approach life after business-ownership: how to find fulfillment, what to do with the money, and where to look for your next project.Whether that’s joining a board, angel investing, or pursuing philanthropic...
info_outlineA new year has a way of making people feel like they need to figure everything out at once. Goals, priorities, plans, all piled together in January, like our life restarts with the change in the calendar.
In this first Between Sips episode of 2026, Emily and Jessica talk through a more realistic way of thinking about goals, one that leaves room for life stage, time constraints, and changing priorities. They share why so many people struggle to articulate what they want, and how narrowing goals too quickly can cause us to miss opportunities that really move the needle.
The conversation takes into account experiences, health, career, relationships, creativity, and giving, not as a checklist, but as different parts of life that often compete for attention. Along the way, we reflect on how money fits into all of it, not as the point of the plan, but as something that supports the choices successful people make.
This episode is for anyone heading into 2026 feeling thoughtful rather than decisive, and looking for a steadier way to think about the year ahead.
0:00 — Champagne, A New Year, And Fresh Starts
4:40 — Why Goals Need Meaning
9:40 — The Bucket List Framework And Three Goal Buckets
15:20 — Health, Stress, And Spending Without Guilt
23:00 — Career Growth, Creativity, And Cash Flow Confidence
32:10 — Relationships, Time Poverty, And Support
39:20 — Finance As An Enabler, Not The Goal
Please see important podcast disclosure information at https://monumentwealthmanagement.com/disclosures
Connect with us:
Get our Free Private Wealth Advice Newsletter: https://www.monumentwealthmanagement.com/subscribe
LinkedIn: https://www.linkedin.com/company/monument-wealth-management/
Connect with Emily on LinkedIn: https://www.linkedin.com/in/emilyharpercfp/
Connect with Jessica on LinkedIn: https://www.linkedin.com/in/jessicagibbscfp/
Instagram: https://www.instagram.com/monumentwealth/#