Wisdom to Wealth

Most people spend forty years preparing financially for retirement.

Very few prepare for the emotional transition.

In this episode of Wisdom to Wealth, Drew Stevens discusses why many retirees struggle after leaving the workforce—not because they lack money, but because they lose the structure, purpose, and identity their careers once provided.

Most retirement advice focuses on what to cut.

Cut expenses.

Cut spending.

Cut activities.

Cut enjoyment.

But what if retirement was never meant to be about subtraction?

In this episode of Wisdom to Wealth, Drew Stevens explores 12 powerful things retirees should add to life—from laughter and friendships to purpose, adventure, learning, generosity, and confidence.

Retirement is more than a financial event.

It's a life transit...

Retirement advice often sounds like a long list of sacrifices.

Spend less. Travel less. Buy less. Do less.

But is that really the purpose of retirement?

In this episode, Drew Stevens challenges conventional retirement thinking and shares the 12 things retirees should never automatically eliminate from their lives.

You'll learn why family, travel, friendships, health, purpose, generosity, and meaningful experiences may be the most i...

Retirement is supposed to be one of life's most rewarding chapters.

Yet many retirees quietly struggle with concerns they rarely discuss—even with family members.

In this episode, Dr. Drew Stevens explores the emotional side of retirement and reveals the fears that often keep retirees awake at night, including concerns about running out of money, healthcare costs, market volatility, and maintaining independence.

You'll learn ...

In this episode, Drew Stevens discusses the emotional and financial realities many retirees face when approaching retirement without a coordinated strategy. After more than 40 years in financial services, Drew shares some of the most common retirement mistakes individuals and couples make — and what can still be done to improve retirement confidence and clarity.

In this episod...

After more than 40 years helping retirees navigate financial decisions, Drew Stevens has seen one major problem repeatedly surface: many retirees were sold investment products without ever being taught a retirement strategy.

In this episode, Drew uncovers the five biggest retirement myths that Wall Street promoted for decades — from the dangers of blindly “staying invested” to the flaws in the traditional 4% withd...

Smart people make bad retirement decisions every day — not because they lack intelligence, but because retirement is emotional, psychological, and filled with complexity.

In this episode, Drew Stevens shares over four decades of real-world experience helping retirees avoid costly financial mistakes. From analysis paralysis and emotional investing to tax traps and retirement income confusion, Drew explains why many successful ...

Retirement today is more complicated than ever before.

In this episode, Drew Stevens of Wisdom to Wealth discusses the 7 biggest retirement mistakes retirees continue to make — including poor Social Security timing decisions, entering retirement with debt, ignoring inflation, waiting too long for RMD planning, and failing to create a true retirement strategy.

With over four decades of experience helping retirees prepare for r...

What quietly destroys more retirements than the stock market?

Family decisions.

In this episode, Drew Stevens discusses the hidden retirement risks most retirees never expect: adult children becoming financially dependent, emotional financial choices, long-term care planning mistakes, healthcare costs, legacy concerns, and family pressures that can slowly erode retirement security.

With humor, real-world stories, and over 44 years...

Most people heading into retirement believe they’re prepared.

They’ve saved money. Built accounts. Made smart decisions along the way.

But here’s the truth:

Having money is not the same as having a plan.

In this episode, Dr. Drew Stevens breaks down the difference between having a “pile” of assets and having a true retirement strategy.

You’ll learn:

• Why income—not assets—is the f...

Drew Stevens explores the humorous and heartfelt shift in parenting roles as aging parents become like teenagers. He shares personal stories about shifting discipline styles, new senior behaviors around technology, driving, eating habits, and the changing family dynamics as adult children care for their elders with patience and humor.

From unpredictable driving to early dinners, loud TVs, and ALL CAPS texting, this episode captures...

Everyone is worried about the market crashing…

But the real threat to your retirement may be something far more predictable—and far more dangerous.

Taxes.

In this episode, Drew Stevens, PhD, shares a powerful perspective from over four decades in financial services. He explains why so many retirees unknowingly walk into retirement with a major blind spot: they’ve built wealth, but they haven’t built a tax s...

In this episode Drew Stevens argues that many financial advisors are merely order-takers focused on portfolio maintenance and accumulation, not comprehensive retirement planning. He highlights common gaps—tax strategy, IRMA/S, Medicare, Social Security timing, and income distribution—that can leave retirees exposed.

Stevens explains what a true retirement advisor does: build an income-first strategy, coordinate tax-eff...

Are you relying on hope to get through retirement?

In this episode, Drew Stevens, PhD, dives into a hard truth: most people don’t actually have a retirement plan—they have a statement and a lot of assumptions.

From underperforming portfolios to overwhelming debt, Drew explains why so many people feel uncertain about their future—and what it really takes to fix it.

You’ll learn why clarity, structure, and int...

What if one unexpected health event could erase decades of hard work?

In this episode, Drew Stevens breaks down the single greatest financial threat facing retirees today—long-term care costs. With over 40 years of experience in financial services, Drew explains why most people underestimate this risk and how it can devastate even well-planned retirements.

You’ll learn:

• Why 70% of retirees will need care—and ...

Many people fear running out of money in retirement—but in reality, most don’t. So why does that fear exist?

In this episode, Drew Stevens shares insights from over four decades in financial services and explains the real issue retirees face: not a lack of money, but a lack of structure and income planning.

You’ll discover why having assets isn’t enough, how poor withdrawal strategies can create unnecessary ...

Annuities are one of the most criticized—and misunderstood—financial tools in retirement planning. But are they really as bad as people say?

In this episode, Drew Stevens unpacks the myths, misconceptions, and real-world truths about annuities. With over 40 years of experience, Drew explains how these strategies can be used to create predictable income, protect against market loss, and help retirees avoid running out of...

In this episode of the Wisdom to Wealth Podcast, Drew Stevens discusses the most common—and most costly—statement he hears from retirees: “I wish we had met you five years ago.”

This isn’t about major financial mistakes. Instead, it’s about the accumulation of small decisions made without a comprehensive retirement strategy. From claiming Social Security too early to overlooking tax implications ...

Navigating Medicare can feel overwhelming—especially when you’re faced with unfamiliar terms like deductibles, copays, coinsurance, and the infamous “donut hole.” In this educational webinar, From Deductibles to Donut Holes: Deciphering Medicare Costs for Retirees, we break down the real costs of Medicare in a clear, practical, and easy-to-understand way.

Designed for retirees, pre-retirees, and financial pr...