Funded Contentment: The True Definition of Wealth After Retirement

If you ask ten people what “wealth” means, you’ll get at least twelve answers. Some define it as a net worth number. Some define it as never worrying about money again. Others define it as a beach, a pickleball habit, and adult children who are finally off the payroll.

Here’s the definition that matters most in retirement: funded contentment. All credit goes to Brian Portnoy, who coined this phrase in his “Geometry of Wealth” book.

Funded contentment is the point where your resources can reliably support a life that feels meaningful and intentional to you. It’s not the maximum you can afford. It’s the version of life where you can successfully fund what brings you fulfillment and purpose.

That’s the true definition of wealth after retirement.

Step 1: Start with the life, not the portfolio

Retirement planning often begins with the wrong question: “Do I have enough money?”

A better question is: “What does a good and meaningful life look like for me in retirement?”

Because retirement is not a finish line, it’s a redesign. And redesign starts with clarity.

Try this exercise: imagine it’s a random Tuesday in retirement. Not the dream vacation version. The regular version.

• What time do you wake up?
• Who do you spend time with?
• What do you do that gives the day meaning?
• What do you avoid?
• What do you look forward to?

That “random Tuesday” is the retirement that will shape your happiness, your health, and yes, your spending. If you can describe that day in detail, you’re already closer to funded contentment than most.

Step 2: Define what “enough” means in three categories

Most people lump retirement spending into one big, fuzzy number. Instead, I recommend separating spending into three layers:

1) Essential spending

This is the non-negotiable expense: housing, utilities, groceries, insurance, healthcare, basic transportation, taxes. If the market is doing cartwheels or tantrums, these bills still show up in your mailbox (or email box, as it may be).

Your plan should protect this layer first. In our work, we often think of essential spending as needing the highest reliability.

2) Enjoyment spending

This is the spending that makes retirement feel like retirement: travel, dining out, hobbies, memberships, gifts, experiences, and the budget for being spontaneously generous.

This category is where your values show up. Enjoyment spending is not frivolous. It’s the reason you saved.

3) Legacy and “optional nice-to-haves”

This includes larger gifting goals, charitable giving, helping adult children, second homes, and “someday” purchases. These goals can be deeply meaningful, but they’re usually more flexible in timing and amount.

When people feel anxious about retirement, it’s often because these three layers are fuzzy. The cure is separation and prioritization. Once you know what must be funded, what you want to fund, and what would be great to fund, you can build a plan that actually fits you.

Step 3: Identify your “contentment anchors”

Every retiree I’ve met who feels genuinely wealthy has a few “anchors,” the things that make life feel steady and good. These are usually not the flashy things.

Examples:

• Time with family without rushing
• A weekly routine that includes movement and community
• The ability to say yes to the right opportunities, and no to the wrong ones
• Confidence that healthcare needs won’t derail everything
• A home that fits the season of life you’re in

Your anchors are personal. The goal is to name them explicitly and then fund them intentionally.

If you want a quick shortcut: what are you afraid of losing in retirement? That often points directly to your anchors.

Step 4: Turn your values into an actual spending plan

This is where the rubber meets the road. Values are inspiring. Cash flow is clarifying.

To find funded contentment, we want your spending plan to do three things:

1. Support your best life today
2. Protect your future self
3. Leave room for change (because retirement will change you)

A practical approach is to build a “retirement paycheck” framework:

• Income sources you can count on (Social Security, pensions, annuities, reliable portfolio withdrawals)
• A system for variable spending (travel, hobbies, home projects)
• A plan for irregular big costs (cars, roof, family support, major medical)

People often underestimate the emotional relief of having a clear system. When spending becomes intentional instead of reactive, anxiety goes down and enjoyment goes up.

Step 5: Plan for the part nobody wants to talk about

Healthcare and long-term care. The topics that can clear a dinner party faster than politics.

But they matter because they’re the biggest “unknown unknowns” in retirement. Funded contentment requires confidence that the plan can handle:

• Higher-than-expected medical expenses
• A spouse outliving the other by many years
• A long-term care event, either at home or in a facility
• Cognitive decline, and the need for help managing money

If you build a plan that only works when nothing goes wrong, you don’t have a plan. Because the unexpected will happen.

Step 6: Stress test your definition of “wealth”

Once you’ve identified your anchors and your spending layers, it’s time for the truth serum: testing.

Here are a few questions we run through:

• What happens if markets are down early in retirement?
• What happens if inflation runs hotter than expected for a while?
• What if one spouse lives to 95?
• What if you want to spend more in the first ten years and less later?
• What if you decide retirement isn’t retirement, and you want a “third act” career, business, or passion project?

This is where “funded contentment” becomes real. And it’s also where many people realize something surprising: they don’t need the retirement that society sells. They need the retirement that fits them personally.

Step 7: Give yourself permission to adjust

Funded contentment a continual practice, and your personal definition will change over time. The early years of retirement tend to be more active and travel-heavy. Later years often shift toward family, home, and health. Spending patterns change. Priorities evolve.

So give yourself a framework that expects adjustment:

• Review spending quarterly or annually, depending on how much your expenses fluctuate (not daily, you’re retired, you’re not running a hedge fund)
• Revisit goals after major life events
• Update estate plans and beneficiaries
• Adjust withdrawal strategy and investment risk as your life changes

The retirees who feel most at peace are the ones who stayed engaged enough to course-correct.

The bottom line

Wealth in retirement isn’t about chasing the biggest number. It’s about designing a life you genuinely want, then building the financial structure to support it, through good markets and bad ones.

Funded contentment is the real flex. It’s waking up on a random Tuesday and realizing you’re living your life, on purpose, with confidence that it’s sustainable.

If you’re approaching retirement, already retired, or just quietly wondering whether you’re doing this “wealth” thing right, start here: define your anchors, separate your spending, and build a plan that funds what matters most.

That’s not just retirement planning. That’s a definition of wealth worth aiming for.

This information is meant for educational purposes and not as direct tax or legal advice. Rules and regulations can shift anytime, so it’s always best to consult a qualified tax advisor, CPA, or attorney for guidance tailored to your specific situation.