By: Melissa Hampton, CFP® – Founder & Wealth Advisor at Hampton Wealth Management

Imagine waking up on your first day of retirement with complete confidence.
You’re not wondering if you left work too soon. You’re not worried about whether the market will cooperate. You’re not questioning if you can afford the travel, the home upgrades, the generosity, or the slower-paced mornings you’ve always pictured.

You have clarity.

You know exactly what your lifestyle can look like, what you can comfortably spend, how your income will flow, and how your decisions today impact the next 20–30 years.

That’s the foundation of a confident retirement—one built intentionally, not reactively.

For individuals and couples with $1M+ in investable assets, confidence doesn’t come from guessing. It comes from a thorough evaluation of the key components that determine whether your retirement is truly sustainable.

Below are the core areas that must be evaluated before making one of the most important decisions of your life.

1. Understanding When You Can Actually Retire

Retirement timing is not a simple math problem—it’s a life-altering decision that deserves a comprehensive analysis.

To confidently answer “When can I retire?”, we must evaluate:

• Inflation and Long-Term Purchasing Power

Your retirement could last 25–30 years. That means groceries, travel, utilities, healthcare, and everyday costs will continue to rise. Your plan must account for that reality—not just for the first decade, but for the last.

• Appropriate, Sustainable Growth of Your Assets

You need your portfolio to grow enough to support your lifestyle without taking on more risk than this stage of life calls for. Balancing growth and preservation is essential—and it rarely happens by accident.

• Your Personal Version of “Enough”

Every retirement is unique. What matters is whether the assets you have today support the life you want tomorrow. That requires a deep dive into your current numbers, your goals, and your lifestyle expectations—not a generic rule of thumb.

2. Organizing Your Assets for Tax-Smart Income and Thoughtful Risk Management

This is where most high-income earners approaching retirement feel the most uncertainty:

“How do we actually access our money?”

Once your paycheck stops, your portfolio becomes your new source of income. But not all dollars are created equal, and not all accounts should be accessed the same way.

Using The Hampton Method™, we evaluate:

• Which Accounts to Access First

Taxable, pre-tax, Roth—the order of withdrawals can shape your tax bracket, Medicare premiums, and long-term portfolio sustainability.

• How to Position Your Assets for Timely Withdrawals

Money you’ll need in 1–3 years must be handled differently than money you won’t touch for 10+ years. This is how we minimize the risk of selling assets during market downturns.

• Risk Alignment to Your Retirement Phase

Your investments should reflect your life today, not your accumulation years. Aligning purpose, timeline, and risk is essential to navigating both market cycles and planned withdrawals.

A confident retirement requires accessibility, tax-awareness, and thoughtful sequencing—not guesswork.

3. Evaluating Your True Spending Capacity

One of the biggest misconceptions I hear is, “We’ll probably spend less once we retire.” The reality? Most retirees spend more—not less.

You finally have the time to enjoy the life you postponed for years. That often means:

-More travel

-More time with your grandkids

-A second home or extended seasonal stays

-Home upgrades and hobbies

-Rising medical and long-term care costs

A thorough spending evaluation should answer:

• What can you realistically spend each year?

Not a conservative estimate to “play it safe”—but the true range based on your numbers.

• What lifestyle expenses matter most to you?

Retirement shouldn’t feel restrictive. It should feel aligned.

• What spending flexibility do you have across different market environments?

Your plan should show how you adjust—without sacrificing your lifestyle.

This is where confidence begins: knowing that your spending supports your goals today while preserving your future options.

4. Designing a Clear, Intentional Path for Your Legacy

A confident retirement doesn’t end with your lifestyle—it extends to the people you care most about.

For families with $1M+ in investable assets, legacy planning is more than paperwork. It’s about:

-Protecting your spouse

-Supporting children and grandchildren

-Reducing unnecessary taxes, confusion, or delays

-Ensuring your values are reflected in the way your assets transfer

Your Wealth P.L.A.N.™ should clarify:

• How Your Assets Transfer

By title, trust, TOD, or beneficiary—each approach affects taxes, privacy, timing, and control.

• Who Makes Decisions if You Cannot

Your healthcare directive and financial power of attorney should reflect your current wishes and trusted individuals.

• Whether Your Plan Matches Your Goals

Is it structured for simplicity? Protection? Privacy? Control?
Your estate plan should match your intentions, not generic legal templates.

The legacy you leave begins with the clarity you create today.

A Confident Retirement Comes From Clarity, Not Guessing

Preparing for retirement is not about spreadsheets—it’s about creating a plan that supports the life you want to live and the legacy you want to leave.

A confident retirement is built on four pillars:

✔ Retirement Timeline Clarity
✔ Tax-smart, risk-aligned income structure
✔ A real spending plan based on your lifestyle
✔ A thoughtful estate and legacy strategy

This is exactly what The Wealth P.L.A.N.™ helps you accomplish.

Your Next Step

If you’re within 1–5 years of retirement—or newly retired—and you have $1M+ in investable assets, now is the time to get the answers that shape your future.

Schedule an introductory call at HamptonWM.com to explore whether it’s time to build your Wealth P.L.A.N.™.

Investing involves risk, including the potential loss of principal. No investment strategy can guarantee a profit or protect against loss in periods of declining values.

Asset allocation does not ensure a profit or protect against a loss.