Helping You Learn to Enjoy Your Money
One of the most interesting conversations I have with clients isn't about market returns, tax strategies, or whether they'll have enough for retirement. It's often about something much simpler and much more human: giving themselves permission to spend the money they've worked so hard to save.
For decades, retirement planning has focused on a single concern: Will I run out of money? Yet for many successful retirees, the bigger challenge turns out to be the opposite. They've accumulated enough, their financial plan supports their goals, and they're financially secure, but they still struggle to spend.
In a recent episode of Kitces & Carl, financial planning thought leaders Michael Kitces and Carl Richards discussed this phenomenon of underspending in retirement, a challenge that is far more common than many people realize.1
The Habits That Create Wealth Can Become Obstacles in Retirement
Think about what it takes to become financially independent.
Most people who retire comfortably didn't get there by accident. They spent decades making thoughtful decisions, living below their means, delaying gratification, and consistently prioritizing future security over present consumption.
Those habits are incredibly valuable.
The challenge is that retirement requires a different mindset.
As Michael Kitces described, many retirees develop an identity around being careful with money. He shared the example of a client he nicknamed "Frugal Bob," whose sense of pride came from being the frugal member of the family. Even though Bob could comfortably afford to spend more, doing so conflicted with how he saw himself. 1
I've seen similar situations many times. The issue isn't that someone doesn't have enough money. The issue is that saving has been part of their identity for 40 years. Asking them to suddenly spend freely can feel uncomfortable, even when the numbers clearly support it.
What got them successfully to retirement isn't always what helps them make the most of retirement.
When the Math Isn't the Problem
As planners, our natural instinct is to reach for the numbers.
When someone worries about spending, we review cash flow projections and retirement income plans. We show them that their plan remains strong even if they take the trip, replace the car, remodel the kitchen, or help a family member.
Those analyses are important. They provide confidence and context.
But as Kitces noted, showing someone they can afford something doesn't necessarily mean they'll feel comfortable doing it. 1
Many retirees understand intellectually that they have enough money. What they struggle with is the emotional reality of watching account balances decline after spending a lifetime seeing them grow.
Carl Richards put it well when he suggested that once clients understand the facts, continued reluctance to spend often isn't a math problem anymore. It's an identity issue, a habit issue, or sometimes even a fear issue.1
That's an important distinction because additional spreadsheets rarely solve emotional challenges.
Learning to Spend May Be a Retirement Skill
One idea from the discussion particularly resonated with me.
Richards proposed that spending should be viewed as a skill that requires practice, especially for people who have spent their entire lives mastering the skill of saving. 1
"Instead of reasoning clients into spending, it may be more effective to reframe spending as a new skill to be practiced." 1
I think that's a powerful way to look at it.
We wouldn't expect someone who hasn't played tennis in thirty years to walk onto the court and immediately feel comfortable. We'd expect some practice, some experimentation, and a gradual rebuilding of confidence.
Spending can work the same way.
Rather than making dramatic lifestyle changes, retirees may benefit from small steps. Maybe it's taking a weekend trip they've postponed for years. Maybe it's treating grandchildren to an experience they'll always remember. Maybe it's investing in a hobby that's been sitting on the back burner since their working years.
Small, intentional expenditures can help people discover that spending money on meaningful experiences doesn't threaten their security. In fact, it may enhance the life they've spent decades preparing to enjoy.
Spending Isn't the Goal
It's important to emphasize that the objective isn't to convince people to spend more money.
Some retirees genuinely enjoy living simply. They don't dream about luxury vacations or expensive purchases. They're perfectly content with a quiet lifestyle, and there is absolutely nothing wrong with that.
The goal is not increased consumption.
The goal is alignment.
What matters is ensuring that money serves the life someone wants to live.
That is why some of the most valuable retirement conversations have very little to do with investments and everything to do with values:
- What brings you joy today?
- What experiences would you regret not having?
- What relationships matter most?
- What would make this stage of life deeply meaningful?
Richards suggested exploring things clients may have loved in the past but stopped doing because life became busy with careers and family responsibilities.1 Those conversations can uncover passions, interests, and dreams that have been waiting for the right season of life.
Sometimes the result is a new adventure. Other times it confirms that someone is already living exactly the way they want.
Both outcomes represent success.
Purpose Creates Permission
One pattern I've noticed is that people often find it much easier to spend when there's a deeper purpose attached to the expense.
A trip with children and grandchildren.
Helping fund a grandchild's education.
Supporting a charitable cause.
Creating family memories while everyone is healthy enough to enjoy them.
These decisions rarely feel like "spending" in the traditional sense. Instead, they feel like an expression of values.
As Richards emphasized, conversations become much more meaningful when spending is tied to what matters most rather than framed as merely reducing an investment account balance. 1
Money becomes a tool rather than a scoreboard.
Redefining Retirement Success
For most of our working lives, success is measured through accumulation.
The retirement account grows.
The investment portfolio increases.
Net worth climbs higher.
Retirement asks us to change the scorecard.
Success is no longer about accumulating the most money possible. It's about using financial resources in a way that supports the life we want to live.
That could mean travel. It could mean family. It could mean philanthropy. It could mean pursuing passions that were set aside while building a career.
The retirees who seem happiest aren't necessarily the ones with the largest account balances. They're often the people who have found a way to connect their financial resources to what they value most.
As planners, that's where some of our most meaningful work happens.
Not simply helping clients accumulate wealth, but helping them confidently use that wealth in ways that enrich their lives, strengthen their relationships, and create lasting fulfillment.
"Ultimately, the opportunity for advisors is to help clients align their money with what matters most." 1
Because at the end of the day, the goal of financial planning isn't just financial security.
It's helping people use their money to live a life they truly enjoy.
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Source
- Michael Kitces & Carl Richards, "Helping Retired Clients To Actually Start Spending And Enjoying Their Money: Kitces & Carl Ep 178," Kitces.com. Available at: Kitces & Carl Episode 178.