The 'Yes, And ...' Rule for a Happy Retirement
Why the most resilient retirees ditch the rigid script and treat their next chapter like an improv scene.
There’s an old joke: "The company gave me an aptitude test, and I found out the work I was best suited for was retirement."
While retirement is no laughing matter, it shares something with comedy, especially improvisation. Go to an improv theater, and it can look as if performers are inventing everything on the spot. An audience suggestion becomes a scene, passed from actor to actor in real time.
When it works, it feels effortless. But behind the humor is a guiding principle that keeps the scene moving: the "Yes, and …" rule.
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This core principle from improvisational comedy was born on stages such as Chicago’s Second City, The Groundlings and Upright Citizens Brigade. Performers accept what’s introduced ("yes"), then build on it ("and"), rather than rejecting ideas or trying to control the outcome. Together, they keep the story alive instead of shutting it down.
"If I start a scene with 'I can't believe it's so hot in here,' and you say ... 'I told you we shouldn't have crawled into this dog's mouth,' now we're getting somewhere." — Tina Fey
Retirement often works the same way. You might see retirees living a rich, fulfilling life and assume it comes naturally. In reality, many apply a similar mindset — one rooted in openness, adaptability and the ability to build on whatever comes next.
That mindset proves valuable in retirement, when life rarely goes exactly as planned. According to research from Age Wave and Edward Jones, 93% of retirees say preparation, flexibility and a willingness to adapt are essential to thriving in retirement. It’s a recognition that surprises, changes and course corrections are almost inevitable.
In that sense, the "Yes, and …" rule offers a practical framework for navigating retirement’s curveballs: Accept what arrives, adjust your plans. But it also helps you make the most of every opportunity to keep building a meaningful next chapter.
How the "Yes, and …" rule works in retirement
Most research and retirement experts agree on two things: you can’t simply wing retirement. But you also can’t expect it to follow a script.
That’s why Kate Feeney, CFP® and wealth adviser at Summit Place Financial Advisors, encourages clients to think in terms of "re-wirement," not retirement.
As she puts it: "Re-wirement works when people expect change, stay connected and remain open to redesigning how they spend their time. That mindset makes it easier to navigate market volatility, health changes and shifting goals while reducing loneliness and regret."
Applied to retirement, the idea is simple: Accept what happens, then adjust intentionally.
That might look like:
- Saying "Yes" to an unexpected market downturn — "And" adjusting withdrawals to stay on track.
- Saying "Yes" to a new interest like tennis — "And" building a fresh social routine around it.
- Saying "Yes" to changing energy levels — "And" reshaping how you spend your time.
Instead of clinging to a rigid plan, retirees who embrace the "Yes, and …" rule might treat retirement as something to refine over time, staying open to opportunity while keeping smart financial and lifestyle guardrails in place.
Timing and purpose in a "Yes, and …" retirement
In comedy, timing is everything. The best performers know when to pause, when to act and when to change direction.
Retirement requires a similar sense of timing. For many people, this phase can last 20 to 30 years. The challenge is figuring out how to replace the time, structure and meaning once provided by work.
Research consistently links a strong sense of meaning in life to successful aging, better mental and physical health, greater life satisfaction and improved coping and adjustment to illness.
Traditional retirement planning tends to focus on the numbers — saving enough, investing wisely, managing taxes and controlling risk. But once the finances are "good enough," a different question takes center stage: What do you want to do with your life?
That’s where the "Yes, and …" rule becomes useful. Instead of treating retirement like a fixed destination, you can view it as an evolving scene shaped by curiosity, experimentation and adjustment over time.
As Feeney notes, work often provides built-in purpose and community. When that disappears, even a well-funded retirement can feel disorienting. "The most resilient retirees," she says, "intentionally replace those anchors — through social networks, volunteering, faith communities, sports or fun activities."
In many cases, it comes down to how people use their time. Ashley Rittershaus, CFP® and founder of Curious Crow Financial Planning, recommends taking a "retirement test run." That might look like extended time off if possible and living as if retired to better understand preferences, values and likely spending.
"How you spend your free time today is often a preview of how you’ll spend it in retirement." — Ashley Rittershaus, CFP
Mitchell Kraus, CFP® and founder of Capital Intelligence Associates, echoes that experimentation matters, but with guardrails. "Total openness without structure can be unsettling," he says. "Most people thrive with a framework for their days: anchor points like regular movement, social connection and purpose-driven activities, balanced with open space for spontaneity. Structure provides stability; openness provides growth."
The need for renewal is real. A recent Transamerica study found that more than a quarter of retirees report feeling exhausted or burned out.
In that sense, retirement follows the same logic as improv:
- "Yes" equals openness. Say yes to curiosity, invitations and new experiences, especially early on.
- "And" equals intention. Pay attention to what gives you energy and meaning and build more of your life around it.
One research team studying what makes a successful retirement concluded: "The acceptance of retirement, mindfulness, a positive view toward retirement, self-efficacy and a healthy lifestyle are important factors that contribute to adaptation to a successful retirement."
In other words, thriving in retirement is as much about mindset and engagement as it is about planning — a truth that humorists have captured long before researchers put language to it.
As Mark Twain famously warned: "Twenty years from now, you will be more disappointed by the things you didn't do than by the ones that you did do."
The "Yes, and …" rule for your finances
Surveys show that retirees' top fear is running out of money, driven by uncertainty around market volatility, inflation and potentially high health care costs later in life. It’s an outcome no one wants to imagine, but some disruption is inevitable.
That’s where the financial aspect of the "Yes, and …" rule comes in. Instead of denying uncertainty, retirees can accept volatility and plan for it.
Experts say this mindset matters most in the early years of retirement. As Rittershaus explains, "Being open to making small adjustments early on in retirement will help avoid having to make larger adjustments down the line. It’s helpful to understand what adjustments you could make if needed, like which expenses you could reduce or eliminate, or other backup plans like downsizing."
That flexibility also applies to investment strategy. Rittershaus recommends stress-testing retirement plans for a range of scenarios — including lower-than-expected returns, early market downturns, higher spending and long-term care needs — so retirees understand when and how they might need to adjust.
Kraus suggests retirees can benefit from "diversified income sources, conservative early withdrawal rates, and a clear distinction between essential spending and discretionary 'joy' spending." He says focusing on liquidity and optionality allows retirees to adapt as markets, health or priorities change, without panic or regret.
Financial success in retirement doesn't require predicting every outcome; it requires preserving your options. Like any great improv scene, a successful retirement isn't about perfectly reciting a script — it's about saying "yes" and keeping the story going.
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