Curious about your retirement savings? Our How Much Do I Need To Retire? quiz gives you an idea of where you stand and a starting point to think about your long-term planning.

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Your plan might be able to handle market volatility, but it might not handle your income disappearing.

In this episode, Scott breaks down the uncomfortable blind spot facing many high earners—what happens if your paycheck stops sooner than expected. Using a real-world scenario of someone with nearly $3M saved and a large amount of unvested RSUs, he walks through the question most people avoid: “If the job goes away in 3–5 years instead of 7-10, are we actually okay?”

It’s actually a timeline problem, not just a market risk problem. Scott explains how to pressure-test an early exit scenario, separate RSU strategy from income dependency, and ask the bigger question most plans ignore: what is your career capital actually worth if your role changes?

If a large portion of your wealth and income is tied to one company, this episode is for you. It’s about understanding the assumptions your plan is making—and making sure they hold up when it matters most.

Ready to learn more? 

• Scott Frank on LinkedIn 
• Stone Steps Financial 

Leave us a question! 

Money can be confusing, but it doesn’t have to be. When you’re able to understand the complexities, you can make better decisions to improve your daily life. Connect with us at Stone Steps Financial.

Curious about your retirement savings? Our How Much Do I Need To Retire? quiz gives you an idea of where you stand and a starting point to think about your long-term planning.

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You did everything right. You maxed your 401(k) for decades, watched the balance grow, and felt good about where you were headed. Then someone showed you a tax projection for retirement and it was a lot bigger than you expected.

In this episode, Scott walks through why a large, traditional 401(k) balance can quietly become a future tax trap. He breaks down a real world example of how required minimum distributions (RMDs), Social Security, and Medicare premiums can stack up in ways most people never saw coming and what a surviving spouse could face alone.

But this isn't a story about regret. It's about having a window of time to act before the IRS starts making decisions for you.

If 70 to 80% of your investable wealth sits in pre-tax accounts, this episode is for you. Scott walks through four practical levers: savings direction, Roth conversions, taxable bridge accounts, and asset location and closes with three concrete steps you can take right now to get clarity on where you actually stand.

Your401(k) isn't the issue, having one that is overly concentrated without a plan is.

Ready to learn more? 

• Scott Frank on LinkedIn 
• Stone Steps Financial 

Leave us a question! 

Money can be confusing, but it doesn’t have to be. When you’re able to understand the complexities, you can make better decisions to improve your daily life. Connect with us at Stone Steps Financial.

Curious about your retirement savings? Our How Much Do I Need To Retire? quiz gives you an idea of where you stand and a starting point to think about your long-term planning.

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Most people don’t actually want retirement, but they do want relief.

Relief from the schedule. Relief from the pressure. Relief from feeling like they can’t step off the treadmill.

But what if the question isn’t “When can I retire?” and it’s “What would I do if I knew I wasn’t trapped?”

In this conversation, Scott and Nick explore the tensions so many professionals feel but almost never say out loud: the golden handcuffs, the benefits package, the identity wrapped up in a title. And underneath all of it, another question: do I actually need this job… or am I just afraid to look?

Retirement doesn’t always have to mean stopping work. Sometimes it means choosing work, some others it’s testing something new, and every once in a while it means building enough cushion that you walk into Monday differently.

If you’ve ever felt stuck in a role you’ve outgrown, this episode of Real Personal Finance might open a door you didn’t realize was already unlocked.

Ready to learn more? 

• Scott Frank on LinkedIn 
• Stone Steps Financial 
• Nick Covyeau on LinkedIn
• Swell Financial

Leave us a question! 

Money can be confusing, but it doesn’t have to be. When you’re able to understand the complexities, you can make better decisions to improve your daily life. Connect with us at Stone Steps Financial.

There’s a common belief people have about money: you build it, you protect it, and whatever’s left gets passed on at the end.

But what if the timing matters more than the total?

As lifespans stretch into the 90s and portfolios grow beyond what many families will realistically spend, the question starts to change. Would a gift mean more when your kids are buying their first home, raising young children, or launching something meaningful? Would you rather see the impact while you’re here to experience it? And how do taxes, fairness, and family dynamics shape that decision?

This conversation invites you to switch your thinking into a more intentional approach. The big takeaway? Giving isn’t just about numbers, but about when the help lands, how it changes someone’s life, and whether you want to be part of that moment.

If you’ve ever wondered whether to give now or later, this episode of Real Personal Finance will stretch how you think about your legacy.

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Mentioned in this episode:

Die With Zero by Bill Perkins on Amazon: https://www.amazon.com/Die-Zero-Getting-Your-Money/dp/0358567092

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Curious about your retirement savings? Our How Much Do I Need To Retire? quiz gives you an idea of where you stand and a starting point to think about your long-term planning.

Ready to learn more? 

• Scott Frank on LinkedIn 
• Stone Steps Financial 
• Nick Covyeau on LinkedIn
• Swell Financial

Leave us a question! 

Money can be confusing, but it doesn’t have to be. When you’re able to understand the complexities, you can make better decisions to improve your daily life. Connect with us at Stone Steps Financial.

Curious about your retirement savings? Our How Much Do I Need To Retire? quiz gives you an idea of where you stand and a starting point to think about your long-term planning.

— 

Deferred compensation tends to enter the picture when work is going well and income has outgrown the basics. Cash flow feels stable, taxes start to sting, and suddenly there’s a new option on the table that promises flexibility later.

Scott and Nick explore what sits underneath that promise. Deferred comp changes the timing of income, but it also ties future choices to today’s assumptions. Employer stability matters. Payment schedules matter. So does the simple reality that once income is deferred, access and control look very different than they do inside a traditional retirement account.

This episode of Real Personal Finance is an opportunity to slow down before checking the box. To think about how much certainty you actually have about your career path, your tax brackets, and the version of retirement you’re planning toward. Deferred compensation can play a useful role in the right situation, but only when it fits the rest of the picture you’re building.

Ready to learn more? 

• Scott Frank on LinkedIn 
• Stone Steps Financial 
• Nick Covyeau on LinkedIn
• Swell Financial

Leave us a question! 

Money can be confusing, but it doesn’t have to be. When you’re able to understand the complexities, you can make better decisions to improve your daily life. Connect with us at Stone Steps Financial.

Curious about your retirement savings? Our How Much Do I Need To Retire? quiz gives you an idea of where you stand and a starting point to think about your long-term planning.

— 

Taxes tend to fade into the background until something feels off, like a larger bill than expected, a penalty you didn’t see coming or a moment where you wonder whether you handled the year correctly or just got lucky.

In this episode of Real Personal Finance, Scott and Nick talk about how the tax system actually works and why the idea of making one payment on April 15 simply won’t cut it. For example, did you know there’s a pay-as-you-go structure? Or that different types of income can change your tax reality? Scott and Nick go through salaried employees, executives with bonuses or stock compensation, small business owners, and retirees whose income has started to shift.

When you understand what the IRS is looking for and how to build a simple system around it, taxes can stop being a surprise and become something you can manage with less stress throughout the year.

Ready to learn more? 

• Scott Frank on LinkedIn 
• Stone Steps Financial 
• Nick Covyeau on LinkedIn
• Swell Financial

Leave us a question! 

Money can be confusing, but it doesn’t have to be. When you’re able to understand the complexities, you can make better decisions to improve your daily life. Connect with us at Stone Steps Financial.

Curious about your retirement savings? Our How Much Do I Need To Retire? quiz gives you an idea of where you stand and a starting point to think about your long-term planning.

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There’s a moment many people reach at the start of a new year where the question shifts. It’s no longer just about saving more, earning more, or optimizing the plan, but it becomes something deeper. Is the life you’re building actually working for you?

In this episode of Real Personal Finance, Scott and Nick step back from tactics and spreadsheets to explore how money fits into a much bigger picture. They talk about time, energy, talent, and purpose, and how financial decisions tend to fall into place more naturally when you start with the life you want to live instead of the rules you’ve been handed.

You’ll hear a framework that helps clarify what matters most, especially during seasons of change, and why alignment often leads to better financial outcomes anyway. This conversation is about permission, intentionality, and designing a plan that supports the person you want to be, not just the balance you’re chasing.

Ready to learn more? 

• Scott Frank on LinkedIn 
• Stone Steps Financial 
• Nick Covyeau on LinkedIn
• Swell Financial

Leave us a question! 

Money can be confusing, but it doesn’t have to be. When you’re able to understand the complexities, you can make better decisions to improve your daily life. Connect with us at Stone Steps Financial.

Curious about your retirement savings? Our How Much Do I Need To Retire? quiz gives you an idea of where you stand and a starting point to think about your long-term planning.

— 

Retiring early sounds simple when you only look at the balance sheet… until it doesn’t. In this episode of Real Personal Finance, Scott and Nick walk through why the real question isn’t “Is two million enough?” but “What does your life actually cost?”

They use a clear and approachable framework to cover the spending patterns, healthcare realities, tax traps, Social Security timing, and withdrawal strategies that can shape whether your plan holds up over decades or falls apart a few years into the future.

They also explore the levers you can pull if the math is close, like part-time work, test-driving lower spending, or optimizing which accounts to pull from. The goal? Invite you to think intentionally about what you're retiring to rather than just what you're retiring from.

Ready to learn more? 

• Scott Frank on LinkedIn 
• Stone Steps Financial 
• Nick Covyeau on LinkedIn
• Swell Financial

Leave us a question! 

Money can be confusing, but it doesn’t have to be. When you’re able to understand the complexities, you can make better decisions to improve your daily life. Connect with us at Stone Steps Financial.

It’s wild how fast a year goes by, and when you finally look back, the gap between what you meant to do and what actually happened is bigger than anticipated. The trick is that most financial progress relies less on skill and more on removing willpower from the equation.

In this episode of Real Personal Finance, Scott and Nick sit down to talk through the small systems that can move your money in the right direction, even on the busiest weeks.

They walk through the everyday automations that meaningfully change how much you save, how smoothly cash flows through your accounts, and how confidently you can stick to your plan. 

Key topics:

• How setting contributions as a percentage keeps your 401(k) aligned with future raises
• Why automated brokerage transfers turn good intentions into actual investments
• A simple bank-flow setup that keeps spending predictable and stress-free
• How automation supports higher earners with RSUs, taxes, and rebalancing
• Why “what gets automated gets done” becomes your biggest financial advantage

Curious about your retirement savings? Our How Much Do I Need To Retire? quiz gives you an idea of where you stand and a starting point to think about your long-term planning.

— 

Ready to learn more? 

• Scott Frank on LinkedIn 
• Stone Steps Financial 
• Nick Covyeau
• Swell Financial

Leave us a question! 

Money can be confusing, but it doesn’t have to be. When you’re able to understand the complexities, you can make better decisions to improve your daily life. Connect with us at Stone Steps Financial.

The holidays have a way of bringing money and meaning into the same conversation. In this episode of Real Personal Finance, Scott and Nick lean right into that. Between family gifting, charitable giving, donor-advised funds, and changes to deduction rules, this episode walks you through the most practical ways to support the people and causes you care about. It’s a great moment to pause, think about what matters, and check in on how generosity fits into your financial life.

Key Takeaways

 • How gift tax exclusion limits really work when supporting family and loved ones
 • The benefits of donating appreciated stock instead of cash
 • Why donor-advised funds and QCDs can make year-end giving more impactful

Ready to learn more? 

• Scott Frank on LinkedIn 
• Stone Steps Financial 
• Nick Covyeau on LinkedIn
• Swell Financial 

Curious about your retirement savings? Our How Much Do I Need To Retire? quiz gives you an idea of where you stand and a starting point to think about your long-term planning.

https://www.stonestepsfinancial.com/howmuch 

Leave us a question! 

Money can be confusing, but it doesn’t have to be. When you’re able to understand the complexities, you can make better decisions to improve your daily life. Connect with us at Stone Steps Financial.