Episode 87: 5 Years From Retirement? Here’s Your Must-Do Checklist

Are you five years out from retirement? If so, you’re in one of the most critical financial windows of your life. What you do—or don’t do—during this period can have a massive impact on your retirement lifestyle, income security, and peace of mind.

In Episode 87 of the Last Paycheck podcast, CERTIFIED FINANCIAL PLANNER® professionals Rob and Archie Hoxton lay out a step-by-step checklist designed for people entering the final stretch of their working years. Whether you’re feeling confident or overwhelmed, this episode is packed with practical moves that make a difference.

Why Five Years Out Matters

It may seem like there’s still plenty of time—but five years is the perfect moment to tighten your plan, fix any gaps, and start rehearsing your future lifestyle. At this stage, you still have flexibility. But that flexibility will begin to close as you approach your last paycheck.

Here are the must-dos.

1. Understand Critical Ages

You’ll want to be ready for the following key milestones:

  • Age 50: Eligible for catch-up contributions to retirement accounts.
  • Age 59½: You can begin withdrawing from retirement accounts without penalty.
  • Age 62: Earliest possible age to claim Social Security (with reduced benefits).
  • Age 65: Medicare enrollment begins—miss it and you may pay lifelong penalties.
  • Age 73–75: Required Minimum Distributions (RMDs) begin depending on your birth year.

These dates matter for taxes, income, healthcare, and how long your money will last. Make sure your strategy reflects them.

2. Audit Your Spending

This is one of the most overlooked parts of retirement readiness. Most people underestimate their expenses, especially for discretionary items like travel, home improvements, gifts, or hobbies.

Rob and Archie recommend:

  • Reviewing 12 months of spending
  • Categorizing expenses into needs, wants, and obligations
  • Looking for subscription creep or lifestyle inflation
  • Building a realistic retirement budget based on actual behavior—not idealized versions of it

3. Visualize Retirement

Retirement isn’t just about leaving your job—it’s about what you’ll do next. Ask yourself:

  • What will your daily routine look like?
  • Will you travel, volunteer, start a business, or take care of family?
  • Where will you live—and will that change?

Defining these answers now helps you align your financial plan with your lifestyle plan.

4. Business Owners: Begin Succession Planning Now

If you own a business, Rob and Archie stress that exiting takes longer than you think. You’ll need time to:

  • Value your business
  • Groom a successor or explore buyers
  • Create a tax-efficient sale structure
  • Plan your income strategy post-exit

Starting this five years out gives you breathing room and negotiating power.

5. Prepare for the Unexpected

Life happens—even to the best-planned retirements. Rob and Archie urge listeners to prepare for:

  • Long-term care expenses
  • Market corrections just before or after retirement
  • Health challenges that affect timing
  • Family needs like helping aging parents or adult children

Having an emergency buffer and flexible spending strategy can help you adapt without panicking.

Final Thought

Five years may feel like the home stretch—but it’s also your best opportunity to fine-tune your plan and lock in confidence. Think of this checklist as your financial pre-flight routine. You want to know that everything’s working before you take off.

Want to go deeper?

Get the full Pre-Retirement Checklist—free. Or schedule a one-on-one planning session with our team at www.hoxtonpm.com/schedule to make sure you’re ready for what’s next.
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Certified Financial Planner Board of Standards Center for Financial Planning, Inc. owns and licenses the certification marks CFP®, CERTIFIED FINANCIAL PLANNER®, and CFP® (with plaque design) in the United States to Certified Financial Planner Board of Standards, Inc., which authorizes individuals who successfully complete the organization’s initial and ongoing certification requirements to use the certification marks.

Episode 86: Barriers to Wealth – 6 Common Mistakes That Undermine Your Financial Future

You’re working hard, saving consistently, and trying to make smart choices. But if building wealth still feels like an uphill battle, it’s worth asking: What’s getting in your way?

In Episode 86 of the Last Paycheck podcast, CERTIFIED FINANCIAL PLANNER® Archie Hoxton and advisor Jimmy Sutch explore the hidden habits and overlooked decisions that quietly erode financial progress. These barriers don’t always make headlines—but they can have a massive impact on your long-term financial security.

If you want to accelerate your wealth-building path, the first step is identifying what’s holding you back.

1. Bad Debt Decisions

Not all debt is created equal. A low-interest mortgage can be a smart tool. But high-interest consumer debt—especially car loans and credit cards—can drain your savings potential.

Jimmy shares the example of a $740 monthly car payment. Over 15 to 20 years, that expense could translate to hundreds of thousands in lost retirement savings if invested instead.

2. Lifestyle Inflation

Earning more shouldn’t automatically mean spending more. But for many families, income increases are quickly matched—or exceeded—by lifestyle upgrades: a bigger house, fancier cars, private schools, or luxury vacations.

The result? No matter how much you earn, you feel like you’re just getting by.

Archie and Jimmy recommend being intentional about upgrades. Are they supporting your long-term goals—or just feeding short-term gratification?

3. Divorce

Divorce is both emotionally and financially disruptive. It often cuts retirement savings in half, reduces long-term security, and triggers expensive legal fees.

While it’s not always avoidable, couples nearing or in retirement should prioritize proactive planning, open communication, and clear documentation—especially when dealing with blended families or separate assets.

4. Emotional Investing

Fear and greed are the two biggest threats to long-term investment success. Panic selling during downturns or chasing “hot” stocks rarely ends well.

Archie emphasizes that staying invested is often more important than picking the perfect investment. A disciplined strategy—aligned with your goals and risk tolerance—is your best defense against emotional decision-making.

5. Hoarding Cash

Holding too much money in low-interest accounts might feel safe—but it’s a hidden risk. Inflation erodes purchasing power over time, and uninvested cash often misses the compounding opportunity of long-term markets.

Keep enough for emergencies and short-term needs, but make sure your savings are working for you—not just sitting idle.

6. Poor Tax Strategy

Taxes are your single largest lifetime expense—and most people pay more than they need to.

Jimmy and Archie point out that strategic tax planning—from Roth conversions and account withdrawals to donation timing and Social Security strategies—can save six figures over the course of retirement. But you have to plan ahead.

Ask Yourself:

  • Do I know my biggest financial blind spot?
  • Am I tracking lifestyle changes or just letting them happen?
  • Is my investment plan driven by goals—or by headlines?
  • Have I optimized my tax strategy over the next 10 to 20 years?

Final Thought

Wealth isn’t just about what you earn. It’s about how you manage, protect, and grow what you already have. Eliminating these common barriers won’t just increase your net worth—it will boost your confidence in the process.

Which of these barriers are affecting you?

Download our free Barriers to Wealth Self-Audit and start making smarter decisions today. Or schedule a consultation at www.hoxtonpm.com/schedule to talk through your personalized roadmap.
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Certified Financial Planner Board of Standards Center for Financial Planning, Inc. owns and licenses the certification marks CFP®, CERTIFIED FINANCIAL PLANNER®, and CFP® (with plaque design) in the United States to Certified Financial Planner Board of Standards, Inc., which authorizes individuals who successfully complete the organization’s initial and ongoing certification requirements to use the certification marks.

Episode 85: Tired of Tax Season Chaos? Here’s How to Prepare Like a Pro

In Episode 85 of Last Paycheck, Rob and Archie Hoxton lay out a plan to make tax time easier and more strategic.

1. Decide Who’s Doing What

  • Book a CPA early
  • Block time for DIY filing
  • Gather your documents in advance

2. Get Organized

  • Account statements
  • Tax forms (1099s, W-2s)
  • Life event documentation

3. Don’t Skip the Review

You are legally responsible for what’s filed. Review every line.

4. Strategy > Scramble

Tax planning starts in November, not March. Make Roth contributions, harvest losses, and give charitably before year-end.

Make tax time smoother with our Tax Prep Organizer Kit.

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Certified Financial Planner Board of Standards Center for Financial Planning, Inc. owns and licenses the certification marks CFP®, CERTIFIED FINANCIAL PLANNER®, and CFP® (with plaque design) in the United States to Certified Financial Planner Board of Standards, Inc., which authorizes individuals who successfully complete the organization’s initial and ongoing certification requirements to use the certification marks.

Episode 84: What to Do When One Stock Becomes 75% of Your Portfolio

Has one stock taken over your investment portfolio? Maybe it’s a company you’ve believed in for years. Maybe it’s a lucky break from an IPO or an inheritance. But now it’s become your biggest financial asset—and your biggest financial risk.

In Episode 84 of the Last Paycheck podcast, CERTIFIED FINANCIAL PLANNER® professionals Rob and Archie Hoxton break down the very real dangers of concentrated stock positions—and the smart strategies that can help you protect your wealth without rushing into a decision.

Why Concentration = Risk

A concentrated stock position is when a single holding makes up a significant percentage of your overall investment portfolio—often 50% or more. That kind of concentration introduces extreme volatility and risk.

Even great companies stumble. Markets shift. News hits hard. And when your net worth is tied up in one ticker symbol, it doesn’t take much to knock your plan off course.

Step 1: Acknowledge the Risk

This isn’t about doubting the stock—it’s about understanding the math. If your one stock falls 40%, there’s no diversification to cushion the blow. Rob and Archie emphasize that even long-term success stories like Apple or Amazon have had periods of steep decline.

Step 2: Weigh Your Options Thoughtfully

If you’ve been holding a concentrated position for years, unloading it all at once may not be smart—or tax-efficient. Here are more nuanced approaches discussed in the episode:

  • Sell in stages: Spread your gains over several tax years to manage exposure and liabilities.
  • Tax-loss harvesting: Use losses in other parts of your portfolio to offset gains from the concentrated stock.
  • Charitable giving: Donating appreciated stock lets you avoid capital gains taxes while supporting a cause you care about.
  • Hold until death: If legacy planning is the priority, holding the stock may offer a stepped-up cost basis for heirs—but that’s not always the right move.

Step 3: Explore Advanced Strategies

For those with larger positions, there are even more sophisticated solutions:

  • Exchange funds: These allow you to pool your concentrated stock with others in similar situations, achieving diversification without a taxable sale.
  • Options hedging: Advanced traders can use put options to limit downside risk, but this is not DIY territory—professional guidance is essential.
  • Direct indexing: Replacing index funds with individual stocks enables more customized tax-loss harvesting while slowly reducing concentrated exposure.

Step 4: Don’t Ignore the Emotional Side

Concentrated stock decisions are rarely just financial. They’re personal. Especially for couples, the emotional attachment to a stock—or the fear of “missing out”—can create tension.

Rob and Archie stress that the role of a financial advisor isn’t just to suggest numbers. It’s to facilitate honest conversations that lead to clear, confident decisions both partners can live with.

Ask Yourself:

  • If this stock fell 40% tomorrow, how would my retirement plan change?
  • What am I afraid to lose—wealth, opportunity, or identity?
  • Am I holding this stock out of strategy or out of habit?

Final Thought

A concentrated position isn’t always bad—but it is always risky. And risk without a plan isn’t a strategy—it’s a gamble. Whether you sell, hold, donate, or diversify, what matters most is that your decision is intentional, informed, and aligned with your long-term goals.

Worried about a stock that’s taken over your portfolio?

Download our free Concentrated Stock Exit Playbook or schedule a consultation at www.hoxtonpm.com/schedule to explore your best next step.
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Certified Financial Planner Board of Standards Center for Financial Planning, Inc. owns and licenses the certification marks CFP®, CERTIFIED FINANCIAL PLANNER®, and CFP® (with plaque design) in the United States to Certified Financial Planner Board of Standards, Inc., which authorizes individuals who successfully complete the organization’s initial and ongoing certification requirements to use the certification marks.

Episode 83: Fact-Checking the Internet’s Worst (and Best) Financial Advice

“Never pay taxes again.”
“Roth IRAs are a scam.”
“Just buy real estate and retire rich.”

If you’ve spent more than a few minutes on social media lately, you’ve probably seen financial advice that sounds too good to be true—and often is.

In Episode 83 of the Last Paycheck podcast, CERTIFIED FINANCIAL PLANNER® professionals Rob and Archie Hoxton take a sharp, practical look at some of the most viral money claims circulating online. They break down the truth behind the hype and offer reliable guidance for anyone feeling overwhelmed by “finfluencer” noise.

Roth IRAs: Still One of the Smartest Moves in Finance

Some creators claim that Roth IRAs are filled with penalties and restrictions—but that’s simply misinformation.

Here’s what’s true:

  • You can withdraw your contributions at any time, tax- and penalty-free.
  • Earnings grow tax-free and can be withdrawn without penalty after age 59½ and five years of ownership.
  • Additional exceptions (like first-time home purchases or disability) allow for earlier access in certain cases.

Rob and Archie stress that Roth IRAs remain one of the most powerful long-term tools for retirement planning—especially in a rising tax environment.

Real Estate Isn’t Magic (or Tax-Free)

Yes, real estate can be a great investment. But online claims that it’s a tax-free goldmine miss some critical facts.

Here’s what you’re still responsible for:

  • Property taxes and insurance
  • Taxable rental income
  • Capital gains taxes when selling—unless you meet specific criteria or use a 1031 exchange properly

Rob explains that these strategies aren’t wrong—but oversimplifying them can lead to costly surprises. “They sprinkle truth with half-truths, and that’s where people get hurt,” Archie adds.

Saving Alone Isn’t Enough—But It Still Matters

One popular message online is that “saving is a trap” or that you’re wasting time if you’re not investing in high-return assets immediately.

Rob and Archie counter this with nuance:

  • Saving builds discipline.
  • It creates liquidity and opportunity.
  • It’s the bridge to becoming a smart investor.

They agree that investing is essential—but skipping the savings phase is like trying to sprint before you’ve learned to walk.

Net Worth Still Matters

Some online personalities claim that net worth is a “vanity metric.” Rob disagrees. Tracking net worth is one of the simplest ways to measure whether you’re progressing toward financial independence. It also helps you see:

  • Your debt-to-asset ratio
  • Your growth over time
  • Gaps or imbalances in your portfolio

Net worth isn’t everything—but it’s not meaningless.

Ask Yourself:

  • Am I basing my strategy on a headline or a plan?
  • Do I understand both the benefits and the risks of what I’m hearing?
  • When was the last time I verified an online claim with a professional?

Final Thought

Financial advice has never been more accessible—or more confusing. With algorithms rewarding attention over accuracy, it’s more important than ever to question what you hear and clarify what applies to you.

The best plan isn’t the flashiest—it’s the one built on your goals, your timeline, and your reality.

Want help cutting through the noise?

Download our Roth Reality Check Guide or schedule a consultation at www.hoxtonpm.com/schedule to build a strategy based on facts—not hype.
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Certified Financial Planner Board of Standards Center for Financial Planning, Inc. owns and licenses the certification marks CFP®, CERTIFIED FINANCIAL PLANNER®, and CFP® (with plaque design) in the United States to Certified Financial Planner Board of Standards, Inc., which authorizes individuals who successfully complete the organization’s initial and ongoing certification requirements to use the certification marks.

Episode 82: These 5 Retirement Risks Could Derail Your Plan (And Most People Miss Them)

Retirement planning often focuses on savings goals, investment returns, and withdrawal strategies—but what about the threats that could quietly knock your plan off course?

In Episode 82 of the Last Paycheck podcast, CERTIFIED FINANCIAL PLANNER® professionals Archie and Rob Hoxton explore the hidden risks that derail even well-funded retirements. These risks aren’t always obvious, but they can have a profound impact if left unaddressed.

If you’re approaching retirement—or already in it—this is the checklist you didn’t know you needed.

1. Inflation: The Rust of Retirement

Even at 2 to 4%, inflation eats away at purchasing power over time. A modest 1% change in your inflation assumption might not seem like much—but over 30 years, it can be the difference between a comfortable lifestyle and an unexpected shortfall.

Archie describes inflation as “the rust you don’t see—until your plan starts to fall apart.”

2. Rising Healthcare Costs

Healthcare is one of the most underestimated retirement expenses. Rob and Archie cite research showing that the average 65-year-old couple could face $300,000 or more in lifetime healthcare expenses—not including long-term care.

With Medicare premiums, out-of-pocket costs, and supplemental insurance all on the rise, your plan needs to account for both predictable and unpredictable medical costs.

3. Behavioral Investing Mistakes

Markets go up. Markets go down. But how you react during those downs can do more damage than the downturn itself.

Rob explains that “investing is more about managing your emotions than your portfolio.” Common missteps like panic-selling or chasing performance can sabotage decades of good planning.

4. Greed: The Other Side of Emotion

Fear isn’t the only emotional threat. Greed can be just as dangerous. Whether it’s chasing the next big stock, jumping on crypto hype, or overcommitting to a “sure thing,” speculative behavior often stems from good intentions—but poor discipline.

If your plan is built on long-term goals, don’t let short-term noise pull you off course.

5. The Wrong Kind of Risk Management

Ironically, avoiding all risk is one of the riskiest things you can do in retirement. Many retirees shift too conservatively and end up falling behind inflation. The real goal isn’t to eliminate volatility—it’s to manage it in alignment with your needs and time horizon.

Rob and Archie recommend maintaining an appropriate level of market exposure to support long-term growth—even in retirement.

Ask Yourself:

  • Am I stress-testing my plan for inflation and healthcare shocks?
  • Is my portfolio structured to avoid emotional decision-making?
  • Have I built in enough growth potential to outpace rising costs?
  • Am I reacting to fear or greed—or following a disciplined plan?

Final Thought

A successful retirement isn’t just about how much you’ve saved—it’s about protecting what you’ve built. Ignoring these risks won’t make them go away. But addressing them now? That’s how you build confidence for the decades ahead.

Which of these risks are hiding in your retirement plan?

Download our free Retirement Risk Audit Tool or schedule a one-on-one session at www.hoxtonpm.com/schedule to ensure your plan is ready for what’s next.
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Certified Financial Planner Board of Standards Center for Financial Planning, Inc. owns and licenses the certification marks CFP®, CERTIFIED FINANCIAL PLANNER®, and CFP® (with plaque design) in the United States to Certified Financial Planner Board of Standards, Inc., which authorizes individuals who successfully complete the organization’s initial and ongoing certification requirements to use the certification marks.

Episode 81: Down 20%? What Smart Investors Do in a Bear Market

The market’s down, the headlines are loud, and your portfolio might be off by double digits. If you’re wondering what to do during a bear market—you’re not alone.

In Episode 81 of the Last Paycheck podcast, CERTIFIED FINANCIAL PLANNER® Archie Hoxton and advisor Jimmy Sutch explore what bear markets really mean—and how savvy investors respond when the market dips 20% or more.

Their message? Don’t panic. Get perspective. Stick with the plan.

What Exactly Is a Bear Market?

A bear market is defined as a 20% drop in stock prices from recent highs. It’s more than just a blip—it’s a sustained downturn that often triggers fear and uncertainty.

But it’s not rare. Bear markets happen roughly every four to five years. They’re part of the normal cycle of investing.

As Archie puts it, “What’s unusual isn’t the bear market—it’s investors staying calm and following their strategy through one.”

What Should You Do in a Bear Market?

Rob and Jimmy outline the practical, proven steps that long-term investors can take during downturns:

  • Start with your financial plan. If your strategy was built well, it already accounted for market dips. Now is the time to lean on it—not abandon it.
  • Adjust your spending temporarily. Consider postponing large purchases or extra travel. Small lifestyle shifts can preserve liquidity without sacrificing your future.
  • Stick with your allocation. Your investment mix was designed for both bull and bear markets. Let it do its job.
  • Rebalance if needed. A drop in stock prices may mean you’re underweight in equities. Buying low through rebalancing could enhance future returns.

What Should You Avoid?

Bear markets tempt us to act—but often, action makes things worse. Here’s what to resist:

  • Panic-selling: Locking in losses by moving to cash may feel safe—but it prevents recovery.
  • Trying to time the market: You’d need to get three things exactly right—when to get out, when to get back in, and when recovery begins. Even professionals rarely do this consistently.
  • Stopping contributions: Continue funding your 401(k) or IRA. Lower prices mean you’re buying more shares—something you’ll thank yourself for later.

Why Missing the Best Days Can Derail Your Plan

According to JP Morgan, missing just 20 of the best market days over a 20-year period can slash your average annual return from over 9% to under 3%. And here’s the kicker: the best days often occur right after the worst ones.

If you’re out of the market during recovery, you may never catch up.

Ask Yourself:

  • Is my current plan built to handle down markets?
  • Have I let headlines shape my strategy?
  • Am I acting based on fear—or following a long-term process?

Final Thought

Bear markets feel uncomfortable—but they don’t have to destroy your financial future. With a steady hand, a smart strategy, and a bit of patience, they can become a powerful opportunity—not just a threat.

Worried about the market?

Grab our Bear Market Survival Guide to help you navigate downturns without panic—or schedule a conversation with our team at www.hoxtonpm.com/schedule to review your plan.
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Certified Financial Planner Board of Standards Center for Financial Planning, Inc. owns and licenses the certification marks CFP®, CERTIFIED FINANCIAL PLANNER®, and CFP® (with plaque design) in the United States to Certified Financial Planner Board of Standards, Inc., which authorizes individuals who successfully complete the organization’s initial and ongoing certification requirements to use the certification marks.