Between Sips

Monument Wealth Management
  • 5.0 (7)
  • Investing
  • Updated Biweekly

Time for a coffee break? Jessica Gibbs, CFP®️ and Emily Harper, CFP®️ answer the most pressing questions successful people ask about using their wealth to create an option-rich life—served one sip at a time. Have a question you want answered? Send it to: betweensips@monumentwm.com

  1. Sep 15

    The 5 Types of Retirement: Which One Is Yours?

    The traditional "work until 65 and stop completely" model is no longer the only way to plan for your future. With Americans increasingly valuing flexibility, career pivots, and experiences during their healthiest years, retirement planning has evolved into a dynamic spectrum of choices: from serial sabbaticals and semi-retirement to coast FIRE and true financial independence. In this episode of Between Sips, Emily M. Harper and Jessica L. Gibbs break down the 5 modern paths to retirement and how to navigate the finances behind them. They explore how to align your wealth strategy with your health span, manage sequence of return risk, navigate pre-Medicare health insurance, and leverage low-income tax planning opportunities like Roth conversions and capital gains harvesting. Whether you want to make work optional, test drive a semi-retirement schedule, or align career timelines with your partner, this episode provides actionable designs for a flexible wealth plan that matches your life. ☕ Today's sip: Grand Ven Rouge 2022 Vintage Chateau La Spitellette Grenache Syrah Mourvèdre blend Emily brought back from Narbonne in southern France. 0:00 - What We're Sippin' on Today 0:47 - Retirement Beyond Walking Away 1:32 - Wine Break And Why Retirement Changed 3:11 - Partial Retirement And Health Span 5:46 - Traditional Retirement And Purpose 7:43 - Financial Independence And Key Risks 11:27 - Sabbaticals As Mini Retirements 12:44 - Coast FIRE And The Psychology 15:21 - Semi Retirement And A Dry Run 17:08 - Flexible Planning With Cash Flow 19:46 - Tax Moves In Low Income Years 22:58 - Health Insurance Before Medicare 26:24 - Couples Choosing Different Timelines 28:30 - Subscribe, Review, Newsletter Signup 29:00 - Closing Disclosures   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/# Listen to Off The Wall, our podcast with market analysis: https://monumentwealthmanagement.com/off-the-wall-podcast/

  2. Sep 2

    Mid-Career Pause or Sabbatical: Weighing the Cost

    When you're navigating your career, pushing harder often feels like the default setting. But as you build real wealth, the question changes: what costs more? Taking an extended mid-career break, or never giving yourself permission to step away? In this episode, Emily and Jessica explore why a sabbatical or gap year shouldn't be dismissed as financially irresponsible. Drawing on Harvard Business School research, they break down why high achievers view extended time off as "regret insurance" and explain why a 6-month pause represents just 1% of a 40-year career. Whether you're looking to explore fears around resume gaps and family obligations, or look at how low-income years actually unlock hidden tax opportunities, or just dive into how to step away without disrupting your retirement timeline, this episode is for you. ☕ Today's sip: Double Trouble Blend from Mammoth Coffee, a boutique roaster in New Orleans, brought back by Emily from a recent trip.   0:00 — What We're Sippin' on Today 1:03 — The Real Question About Cost 3:20 — Sabbaticals As Regret Insurance 6:46 — Responsibilities And Workplace Constraints 11:03 — Perception Fears And Resume Gaps 14:17 — Setting Goals For Your Pause 17:17 — Crisis-Driven Breaks Versus Choice 19:39 — Cash Planning And Benefits Checklist 23:00 — Modeling Tradeoffs And Retirement Timing 25:28 — Tax Wins And Leadership Upside 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/# Listen to Off The Wall, our podcast on investing and markets: https://monumentwealthmanagement.com/off-the-wall-podcast/

  3. Aug 19

    What Parents Miss When Kids Turn 18

    Most parents focus on saving for tuition and managing dorm room move-in logistics. The reality is that the minute your child turns 18, they are legally an adult, and parents lose automatic rights to make medical or financial decisions on their behalf. In this episode, Emily and Jessica break down the crucial legal protections many  miss when sending their child off to college. They explore why simple documents like durable power of attorney, medical directives, and HIPAA authorizations are essential for navigating unexpected emergencies without legal friction. The conversation also provides practical advice on how to talk to your young adult about these documents without making them feel like you are overstepping their independence. Whether your child is moving into a dorm, studying abroad, or taking their first steps into adulthood, this episode covers the essential planning tools that protect them when it matters most. Please see important podcast disclosure information at https://monumentwealthmanagement.com/disclosures 0:00 — What We're Sippin' on Today 0:20 - Important Disclosures And Purpose 0:57 - What Parents Commonly Miss 2:38 - Why Turning 18 Changes Everything 4:52 - Durable Power Of Attorney In Real Life 7:06 - HIPAA And Medical Decision Documents 8:29 - How To Talk About Control 13:09 - Boundaries That Build Trust 15:56 - When Your Child Says No 18:51 - How To Get Documents Done 19:52 - Subscribe, Review, And Newsletter 20:27 - Educational Use Disclaimers   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/# Listen to Off The Wall, our podcast with market analysis: https://monumentwealthmanagement.com/off-the-wall-podcast/

  4. Aug 5

    How to Split Assets Fairly Among Kids

    When children are young, dividing everything equally makes complete sense. But as your family evolves, adult children forge different paths. Some launch successful careers in high-tax states, while others step into caregiving roles, run family businesses, or need long-term support. Defaulting to an even split might seem like the easiest way to avoid conflict, but it often overlooks what is genuinely fair. In this episode, Emily and Jessica explore how to approach estate planning with nuance. They break down the friction points that arise when lifetime financial support, varying income levels, and complex tax rules interact with standard estate documents. The conversation explores why pre-tax retirement money and appreciated brokerage accounts shouldn't be treated equally, and how to offset lifetime gifts like down payments without creating sibling friction. Whether your goal is to minimize your heirs' tax liability or find strategic ways to hand down physical real estate or business interests fairly, this episode is for you. ☕ Today's sip: Si Mi Amour Cuban Coffee Queen Roasters blend brought back from Key West, Florida by one of our listeners :) 0:00 - What We're Sippin' on Today 0:55 - Equal Is Simple But Not Always Fair 6:28 - Lifetime Gifts Change The Math 8:29 - Taxes Can Make Equal Unequal 12:51 - Step Up In Basis Explained 15:13 - How To Monitor Fairness Over Time 18:24 - Business Property And Special Needs 21:16 - Caregiving And Reimbursing A Child 23:33 - Transparency And A Letter Of Instruction 25:24 - Subscribe Newsletter And Closing 25:46 - Important Disclosures 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/# Listen to Off The Wall, our podcast with market analysis: https://monumentwealthmanagement.com/off-the-wall-podcast/

  5. Jul 22

    Am I Financially "Okay"? The Myth of the Magic Number

    Have you ever caught yourself staring at your net worth statement wondering: Am I financially okay? Or, What's the number I need to feel stable? Here's the thing: being okay is a feeling, not a figure. And the idea of a single "magic number" is mostly a myth. In fact, a Nationwide survey found only 38% of investors even believe in having one.  For high earners, that feeling looks completely different from person to person. One person's number is $8M. Another is $30M. What separates them isn't math — it's upbringing, lifestyle, and clarity on the goals and opportunities that lie ahead of them. Fixating on a net worth target amount misses the things that actually move it: rising healthcare costs, inflation, market volatility, and then—the questions of optionality: Can you afford to pivot careers? Retire early? Take a sabbatical? Absorb an accident or disability without it derailing everything else? A number on a page doesn't answer any of that on its own. So if it's not a number, how do you know you're on track? Emily and Jessica walk through their framework including: cash flow-based planning, probability modeling, and adequately protecting yourself against life's uncertainties. The takeaway: there's no magic number — just a probability of success you're comfortable with, protections that actually hold up, and knowing where your money is going.    0:00 — What We're Sippin' on Today 0:54 — Defining What "Okay" Means 4:22 — The Universal Track Signals 9:09 — Protections For Life's Surprises 12:18 — The Myth Of A Magic Number 16:44 — Cash Flow Planning And Probabilities of Success 22:23 — Near Term Cash And Portfolio Risk 24:54 — Subscribe And Get Our Newsletter 25:26 — Final Disclosures Please see important podcast disclosure information at https://monumentwealthmanagement.com/disclosures   Connect with us:  Get our Newsletter: https://www.monumentwealthmanagement.com/subscribe  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/# Listen to Off The Wall, our podcast with market analysis: https://monumentwealthmanagement.com/off-the-wall-podcast/

  6. Jul 8

    Making the Leap to Self-Employment: Know Your Worth

    You've built a great corporate career. You've climbed the ladder, hit your stride, and established real stability. But for high-achieving executives, the next logical evolution may not be another corporate promotion, but taking your expertise into independent consulting, a business ownership portfolio, or an equity partnership. When successful, high-achieving professionals make the leap from a traditional W-2 role into entrepreneurship, it's easy to focus entirely on the opportunity ahead and miss the underlying compensation shifts. Moving between these two compensation systems introduces a unique set of cash flow considerations that should be actively managed to maintain momentum. In this episode, Emily and Jessica walk through what leaving traditional employment actually means for your money—and how to stay in the driver's seat. Because an executive-level move is about more than simply replacing your base salary; it's knowing the value of your total compensation. They look under the hood at how to strategically value every piece of the shift to self-employment—from capturing mid-year bonus cycles and accelerating unvested equity timelines to replacing benefits like insurance plans or 401k contributions you receive beyond your salary. They also cover the structural tax and benefit realities that are easy to miss and expensive to fix—including the out of pocket cost of self-employment taxes, retirement planning, and why you want to explore insurance coverage before you give your notice. If you've been looking at self-employment as just your next exciting career chapter, this episode gives you the insight to support your strategy. ☕ Today's sip: English Garden Herbal Tea Blend from Starbright Farm, a family-owned lavender farm in Whitehall, Maryland.   0:00 - What We're Sippin' on Today 6:02 - How to Calculate Your Total Compensation 8:03 - Self-Employment Taxes And Quarterly Payments 11:34 - Separate Accounts To Stabilize Cash Flow 12:48 - Negotiating Your Exit  13:55 - Health Insurance Costs And COBRA Timing 18:49 - Retirement Match Vesting, PTO And FSAs 20:51 - Noncompetes And Separation Agreement Risks   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/# Listen to Off The Wall, our podcast with market analysis: https://monumentwealthmanagement.com/off-the-wall-podcast/

  7. Jun 24

    No Kids? Here's What Your Estate Plan Actually Needs

    You've built substantial wealth through a high-earning career or business enterprise, carefully navigating your path with dedication. But when you sit down to formalize an estate plan, you quickly run into a frustrating reality: almost every estate planning blueprint assumes a linear default of passing everything down to your children. When you don't have children, the standard playbook completely breaks down. Without a default path, you have to be far more intentional about creating a highly customized framework that outlines who will step into critical decision-making roles during your lifetime and where your hard-earned assets will ultimately go. In this episode, Emily and Jessica break down why over 70% of child-free adults have zero formal legal planning in place and how to overcome the decision paralysis that holds many back. They look past standard templates to discuss how to separate personal trust from operational suitability when choosing executors and powers of attorney, so your autonomy is protected as you age. They also cover structural alternatives to traditional wealth transfers, the tactical advantages of active gifting while you are alive, and how to build custom trust structures to look after aging parents without losing control over the ultimate destination of your remaining wealth. If you want to move away from cookie-cutter legal templates and learn how a qualified estate attorney can build a sophisticated framework for your child-free estate, this conversation is for you. ☕ Today's sip: ONDA Coffee Roasters from Seattle, Washington, featuring an innovative revenue-share model that connects coffee drinkers directly with the growers who cultivate the beans. 0:00 — What We're Sippin' on Today 0:03 — The Big Question For Child-Free Plans 3:56 — Choosing Executors And Powers Of Attorney 7:55 — Long-Term Care Costs And Elder Risk 14:06 — Legacy Choices: Family, Friends, Charity 21:23 — Parents Trust Structures And Hiring A Lawyer 22:24 — Wrap-Up Subscriptions And Newsletter 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/# Listen to Off The Wall, our podcast with market analysis: https://monumentwealthmanagement.com/off-the-wall-podcast/

  8. Jun 10

    Smarter Ways to Share Wealth With Your Kids

    You've spent decades building your wealth, navigating market cycles, and making intentional sacrifices to secure your financial foundation. But a new question arises: At what point does it make sense to start sharing that success with your adult children? Waiting until your children are in their 60s or 70s to inherit wealth often misses the window where that money possesses the highest utility. Today's young adults are navigating a fundamentally compressed economic landscape, facing staggering starter-home prices, several-thousand-dollar childcare line items, and rising healthcare premiums. They are often in their peak expense years long before they hit their peak earning years. In this episode, Emily and Jessica break down why gifting assets while you are alive can be a far more powerful strategy for your family's trajectory. They demystify the gifting rules and limits, and outline strategic alternatives to gifting cash that can help ease your children's financial fatigue without spoiling their work ethic. They also cover strategies like paying tuition or medical bills directly to providers, funding 529 plans for grandchildren, and jumpstarting a child's retirement through targeted IRA contributions.  If you want to experience one of the joys of your success by seeing your wealth put to work when your family needs it most, this conversation is for you. ☕ Today's sip: Mexican Roast from Traeger Brothers, a roaster outside of Charlottesville, Virginia, featuring big citrus, tangerine, and orange notes fused with milk chocolate. 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/# Listen to Off The Wall, our podcast with market analysis: https://monumentwealthmanagement.com/off-the-wall-podcast/

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About

Time for a coffee break? Jessica Gibbs, CFP®️ and Emily Harper, CFP®️ answer the most pressing questions successful people ask about using their wealth to create an option-rich life—served one sip at a time. Have a question you want answered? Send it to: betweensips@monumentwm.com

Information

  • Creator
    Monument Wealth Management
  • Years Active
    2025 - 2026
  • Episodes
    29
  • Rating
    Clean
  • Copyright
    © Monument Capital Management
  • Show Website
    Between Sips