Margaret spent thirty-one years as a hospital administrator in Bristol, and during her last eighteen months before retirement she kept a running list on her phone titled “Things I Won’t Miss.” The fluorescent lighting in the third-floor corridor. The 6:14 train that was never actually on time at 6:14. Performance reviews where she had to pretend someone’s mediocre quarter was a growth opportunity. By the time her farewell party came around, she had forty-seven items on that list. When I asked her what was on her “Things I’m Walking Toward” list, she stared at me for a long moment and said, “I don’t have one of those.”
Margaret’s situation was not unusual. It was nearly universal.
The conventional wisdom around retirement planning says: figure out your finances, calculate your number, set a date, and count down. The emotional version of this same advice says: think about what you’re tired of, what drains you, what you’ll be relieved to leave behind. Both versions share an identical blind spot. They frame the entire transition as an escape — from stress, from obligation, from structure — and almost never as an arrival somewhere specific.
That distinction matters enormously, and psychology explains exactly why.
The escape trap
Psychologists have long distinguished between two fundamentally different orientations people bring to goals. Approach goals focus on reaching desired outcomes, while avoidance goals center on eliminating undesired ones. Both are real goals. Both motivate behavior. But the research is clear that they produce different psychological results.
Research suggests that avoidance goals generate relief when achieved, while approach goals generate satisfaction.
Relief is temporary. You feel it the morning after your last day of work. You feel it when the alarm doesn’t go off. You feel it at 8:47 a.m. on a Monday when you realize you’re still in your kitchen, drinking coffee that’s actually hot. That relief is real and earned. But it fades — usually within weeks, sometimes within days — because you’ve arrived at the absence of something rather than the presence of something.
Satisfaction operates differently. It builds. It compounds. It comes from moving toward a thing that has weight and meaning for you, and then discovering that the movement itself feels right.
When retirement is planned entirely around avoidance — escaping the commute, the stress, the early mornings — the destination is a void. A pleasant void at first, maybe. But a void.
Why the financial plan isn’t enough
Here’s where the retirement industry has done people a disservice. The entire infrastructure of retirement planning — the advisors, the calculators, the seminars — is built around one question: do you have enough money? Research indicates that a majority of Americans don’t even have a retirement plan, and when researchers investigate what “plan” means, it almost exclusively refers to financial readiness.
The assumption is that once the money question is answered, everything else falls into place. Freedom plus resources equals a good life. But that equation leaves out the variable that actually determines whether someone thrives or slowly fades: purpose.
Research on retirement transitions shows that a significant portion of retirees find the change highly stressful, and the stress doesn’t correlate neatly with financial preparedness. People with comfortable savings struggle. People with modest means sometimes flourish. The differentiating factor, over and over, is whether someone has something specific and meaningful pulling them forward.
I created my course “Your Retirement Your Way” precisely because I watched too many executives — smart, accomplished, financially prepared people — crumble the moment their title disappeared. They had planned meticulously for the departure. They hadn’t planned at all for the arrival.
Identity is the real architecture
Work gives people more than a paycheck. It gives them a daily answer to the question: who am I, and why does today matter?
That sounds abstract until you lose it. Then it becomes the most concrete problem in your life. You wake up and the day stretches ahead with no inherent structure, no one expecting anything from you, and the freedom that sounded so appealing three months ago now feels like standing in an empty room.
Studies on identity development during major life transitions demonstrate how deeply our self-concept gets woven into our professional roles. When the role disappears, the self-concept doesn’t automatically reconfigure. It fractures.
The people who navigate this well tend to have something in common. They started building an identity beyond their job title before retirement, not after. They had a hobby that was more than a hobby — it was a commitment. They had relationships that existed outside the office. They had a question they were curious about, a community they were serving, a skill they were developing for its own sake.
They were walking toward something. And so when the career ended, they didn’t fall into a gap. They stepped onto ground they’d already been cultivating.
The neuroscience of forward motion
The brain responds differently to approach and avoidance states at a fundamental level. Neuroscience suggests that when you’re moving toward a desired goal, the prefrontal cortex — the brain’s planning and future-modeling center — engages in a way that supports creativity, problem-solving, and cognitive flexibility. You can imagine possibilities. You can adapt.
When you’re in avoidance mode, threat-detection systems drive more of the processing. The brain narrows. It becomes excellent at detecting threats and escaping them, but poor at imagining new futures. This is exactly the wrong neural state for designing a life transition.
And yet the way most people plan retirement activates exactly this avoidance circuitry. The internal monologue runs something like: I need to get out of this job before it breaks me. I need to stop commuting. I need to escape this manager. All legitimate impulses. All avoidance-oriented. All engaging the threat-detection system rather than the possibility-generation system.
Flipping that orientation — even partially — changes everything. Instead of “I want to stop commuting,” the question becomes “What do I want my mornings to look like?” Instead of “I want to leave this stressful job,” it becomes “What kind of challenge would feel energizing rather than depleting?”
Small linguistic shifts. Enormous neurological consequences.
Richard Leider’s question
Richard Leider, a researcher who has explored purpose across the lifespan, frames the central question of later life simply: What is my life for?
I’ve always been fascinated by the psychology of the “useful life” — this deeply embedded belief many of us carry that we need permission to keep contributing after a certain age. Retirement, as a cultural concept, subtly communicates that your contributing years are finished. You’ve done your part. Now rest.
But rest as a permanent state isn’t what most people actually want. What they want is autonomy — the ability to choose what they contribute to, when, and how. The escape from work was never really about escaping contribution. It was about escaping compulsion.
That distinction gets lost in standard retirement planning. The entire framework treats retirement as an ending rather than a redesign. I’ve come to believe retirement is actually a PR problem — everyone assumes you’re disappearing, when you could be becoming something you never had the latitude to be during your career.
Leider’s question cuts through all of it. What is my life for? Not what was it for. Not what should it have been for. What is it for, right now, going forward?
Building what you’re walking toward
If you’re approaching retirement — or already in it and feeling the void — studies on meaning-making and psychological well-being suggest a few concrete places to start.
First, separate the relief from the vision. Acknowledge what you’re glad to leave behind. Write it down if you want. Honor it. Then set it aside and ask a different question: if the escape items weren’t part of the equation at all — if they simply didn’t exist — what would you be choosing?
Second, look for what I call approach anchors. These are commitments, relationships, or projects that create positive forward momentum. They might be small. A weekly watercolor class. A standing coffee with someone who challenges your thinking. Volunteering at a literacy program. The scale doesn’t matter. The directionality does. You’re moving toward something, not just away from something else.
I recorded a video about rethinking happiness and purpose in retirement that explores this exact tension—the one between leaving something behind and actually having something meaningful to move toward. It’s something I keep coming back to because I’ve seen too many people wake up on day one of retirement and realize they’ve planned the exit but not the arrival.
Third, protect your cognitive engagement. Brains that stop being challenged don’t stay sharp out of loyalty to their owners. The quiet of retirement can feel peaceful, and it can also quietly erode the very capacities you’ll need to build a meaningful next chapter.
Fourth — and this is the one people resist most — answer the question your career used to answer for you every morning. Why does today matter? Your job provided a default answer. Without it, you need to generate your own. That’s harder. It’s also more honest.
The people who arrive somewhere
Margaret — the hospital administrator with her forty-seven-item escape list — called me about eight months after retiring. She’d had a wonderful first few weeks. Then a disorienting few months. Then what she described as “a fog that smelled like boredom but felt like grief.”
She’d done everything the standard advice told her to do. Traveled. Rested. Read. Saw friends. And still felt like something fundamental was missing.
What was missing was direction. Forward motion toward a thing she’d chosen, not just away from things she’d endured.
Over several conversations, Margaret identified something she’d suppressed for years: she wanted to teach. She’d spent three decades in hospital administration and had accumulated a vast practical knowledge of healthcare systems that junior administrators desperately needed. She started mentoring two early-career professionals through a local NHS training program. Three mornings a week.
“It’s funny,” she told me. “I’m doing something that looks a lot like work. But it feels completely different because I picked it.”
That’s the whole thing, really. The people who flourish in this chapter aren’t the ones who engineered the perfect escape. They’re the ones who found something worth arriving at.
The commute is gone. The stress is gone. The early alarms are gone. Good. Those were worth leaving.
Now the real question: what fills the space they left behind? If you haven’t answered that, you haven’t planned your retirement. You’ve only planned your departure.
I built Your Retirement Your Way specifically for people who want to design this next chapter with intention rather than just hoping it works out—it walks you through creating a vision that’s genuinely yours, not borrowed from someone else’s idea of what retirement should look like.
And a departure without a destination is just drift.
