For decades, "someday" felt like a promise. In retirement, it becomes a question: how many of those somedays are you actually going to keep?

There is a drawer in most people's lives, not a physical one, but a mental one, where the deferred things live. The novel you were going to write. The language you were going to learn. The instrument you set down at twenty-two and kept meaning to pick back up. The business idea you sketched on a napkin in 2009 and filed away for "when things slow down."

For most of your working life, that drawer stayed closed because it had to. There was a career to build, a family to raise, a mortgage to pay, a promotion to earn. The somedays were not forgotten, they were just waiting. And the waiting felt reasonable, even noble. You were being responsible. You were building toward something. Someday was always just around the corner.

And then retirement arrived. And the drawer opened. And for a lot of people, what they found inside was not just possibility, it was a quiet, persistent question: how many of these am I actually going to do?

Why "Someday" Feels Different in Retirement

There is a particular quality to deferred-dream regret that is different from other kinds. It is not the sharp grief of something lost, a relationship that ended, a person who died, a door that closed. It is more like a low hum. A background awareness that time is finite and that the gap between "I always wanted to" and "I actually did" is, at this point, a choice.

Psychologists who study regret across the lifespan have found something striking: the nature of regret shifts as people age. In younger years, people tend to regret their actions, things they did that they wish they hadn't. But as people move into their fifties, sixties, and beyond, the balance tips decisively toward regret of inaction. The things not done. The paths not taken. The somedays that never arrived.

Dr. Tom Gilovich of Cornell University, one of the leading researchers on regret, has documented this pattern extensively. His research found that while action regrets tend to fade over time, we find ways to rationalize what we did — inaction regrets tend to persist and even intensify. The business not started. The trip not taken. The creative pursuit set aside. These don't fade the way action regrets do. They stay.

The reason, Gilovich's research suggests, is that inaction regrets are connected to our sense of identity, to who we believe we are and who we believe we could have been. When you don't do something you genuinely wanted to do, you don't just miss the experience. You miss a version of yourself.

The High-Achiever's Particular Trap

If you spent your career in a demanding professional role, you may be especially vulnerable to the someday trap, and for a reason that is both understandable and worth examining honestly.

High-achievers tend to be excellent at deferral. It is, in many ways, a professional skill. The ability to delay gratification, to prioritize the urgent over the important, to keep your head down and your eye on the long-term goal, these are the habits that built a successful career. The problem is that they don't automatically turn off when the career ends.

Many retirees find themselves applying the same deferral logic to their retirement that they applied to their working lives. They'll travel when the grandchildren are a little older. They'll start painting when they've settled into a routine. They'll write the memoir when they feel more ready. The someday thinking that served them professionally has followed them into retirement — and in retirement, it has a different cost.

The urgency that work once provided, the deadlines, the deliverables, the external accountability, is gone. And without that urgency, the somedays can drift indefinitely. Not because you don't care about them, but because there is always something else that feels more pressing, more comfortable, or more certain.

What the Research Says About Regret and Wellbeing

The research on regret and psychological wellbeing in later life is both sobering and clarifying. A landmark study published in theJournal of Personality and Social Psychologyfound that regret is one of the most frequently experienced negative emotions in adult life, and that regrets related to education, career, and self-development are the most common and the most persistent.

But here is what the research also shows: the people who report the greatest wellbeing in later life are not the ones who have no regrets. They are the ones who have done something with their regrets. They have used them as information — as a signal pointing toward what actually matters to them, rather than as a verdict on their lives.

Psychologist Laura Carstensen's work on what she calls Socioemotional Selectivity Theory offers a useful framework here. As people become more aware of the finite nature of their time, they tend to become more intentional about how they spend it, more focused on meaning, connection, and experiences that align with their deepest values. Retirement, in this framework, is not the end of the someday list. It is the first time in decades that you have the time and the freedom to actually work through it.

As we've explored in our piece on the habits of the happiest retirees, the retirees who thrive most consistently are those who approach this chapter with the same intentionality they once brought to their careers, but directed inward, toward what genuinely matters to them rather than what the world expected of them.

The Difference Between a Dream and a Wish

One of the most useful distinctions in navigating the someday drawer is the difference between a dream and a wish. A wish is something you would like to have happen. A dream is something you are willing to make happen. The someday drawer tends to be full of both, and they require very different responses.

Some of the things in that drawer are genuine dreams: creative pursuits, experiences, relationships, contributions that you have wanted with real depth and consistency. These deserve your serious attention and your deliberate action. They are not too late, and they are not frivolous. They are, in many cases, the most important things you could do with this chapter of your life.

Others are wishes, things that sounded appealing in the abstract but that, when you examine them honestly, don't actually call to you with much force. The language you always said you'd learn but never felt genuinely pulled toward. The hobby you mentioned at dinner parties but never actually started. These are worth releasing without guilt. Not every someday deserves to become a today.

The work of distinguishing between the two is not always comfortable, but it is clarifying. And it is the foundation of what we call Passion Archaeology, the process of excavating what you actually care about, beneath the layers of what you were supposed to care about and what you told people you cared about. If you want a structured way to do that work, our guide Reignite the Fire walks you through it step by step.

The Permission Problem

Here is something that comes up again and again in conversations with retirees who are sitting on a someday list: the problem is not that they don't know what they want to do. The problem is that they don't feel entitled to do it.

There is a particular flavor of guilt that high-achievers carry into retirement, a sense that leisure is something you earn through productivity, and that spending time on creative or personal pursuits feels self-indulgent without the justification of a paycheck or a professional purpose. Writing a novel feels frivolous when you used to run a department. Learning to paint feels trivial when you used to manage multimillion-dollar projects.

This guilt is understandable, and it is also worth challenging directly. The somedays in your drawer are not frivolous. They are, in many cases, the expression of the parts of yourself that your career never had room for. The creative impulse that got channeled into strategy decks. The storytelling instinct that went into presentations. The curiosity that got directed toward business problems. These are not lesser versions of who you are. They are the parts of you that have been waiting the longest.

You don't need to justify them. You don't need to monetize them or make them productive or explain them to anyone. You just need to start.

Your Action Steps This Week

1. Open the drawer.Spend twenty minutes writing down every "someday" you have been carrying. Don't edit, don't evaluate, just list. Include the things that feel embarrassing or small alongside the things that feel significant. The goal is to get them out of your head and onto paper.

2. Sort by signal strength.Go back through the list and mark each item with a number from one to three: three for things that genuinely light something up when you think about them, two for things that feel moderately interesting, one for things that feel more like obligation or habit than genuine desire. Focus your attention on the threes.

3. Choose one and take one concrete step today.Not "I'll start planning." A specific, irreversible action. Buy the materials. Register for the class. Book the first lesson. Make the call. The research on behavior change is clear: the gap between intention and action closes most reliably when the first step is concrete and immediate.

4. Tell one person.Accountability is not just for professional goals. Telling someone you trust what you are starting, and asking them to ask you about it in a month, dramatically increases the likelihood that you will follow through.

A Final Word

The someday drawer is not a record of your failures. It is a record of everything you cared about enough to keep, even when life didn't have room for it yet. The fact that those things are still there, still calling to you, still carrying some charge, is not a source of regret. It is a source of direction.

You are not too late. You are, for the first time in decades, actually on time.

For more on building a retirement that genuinely reflects who you are, explore how to enjoy retirement fully and visit our blog for new articles every week.

References & Further Reading

• Gilovich, T. & Medvec, V.H. (1994). The Temporal Pattern to the Experience of Regret— Journal of Personality and Social Psychology; foundational research on action vs. inaction regret across the lifespan

• Carstensen, L.L. (2006). The Influence of a Sense of Time on Human Development— Science; Socioemotional Selectivity Theory and how time awareness shapes priorities in later life

• Roese, N.J. & Summerville, A. (2005). What We Regret Most... and Why— Personality and Social Psychology Bulletin; the six most common domains of regret in adult life

• AARP Research — Life After 50: Dreams, Goals, and Aspirations— Survey data on deferred goals and aspirations among adults 50+

• Bronnie Ware — The Top Five Regrets of the Dying— Palliative care nurse's documentation of the most common end-of-life regrets

• Harvard Study of Adult Development— 85-year longitudinal study on what makes a good life in later adulthood