The Last Day of Work Before Retirement
Ah, you’ve almost made it to retirement! It is a time to celebrate. You no longer have to set the alarm, fight traffic, and respond to those emails. Colleagues and family may be arranging a celebration this big event, full of talk about travel, sleeping in, and just doing what you want, when you want.
And then the last day arrives.
As you pack up your desk and say goodbye to colleagues, something shifts. The significance of this departure begins to settle in, bringing with it emotions that may not have surfaced before. Thoughts start coming up: This is it. There may be no going back. What felt like an eagerly anticipated finish line suddenly feels like the edge of something unknown.
Actually, you may notice little things (and not so little things) you have enjoyed about work. You may notice the people around you, and the bonds you have formed with so many of them. Will those continue, or will they fade? Memories of your career, challenges you overcame, and accomplishments bubble up as you pack up your things.
Even seemingly small privileges begin to feel much more significant. You may notice the feeling of sitting at your desk, greeting a colleague as you do every day, or even the access that you have in your work role. One day, you walk right into the office as if you own the place. The next, you need permission. No access to email. Projects you once managed continue without you.
Colleagues ask, with the best of intentions, what you will do with all of your free time, and the question hits you differently than you expected.
Perhaps you have had ideas about fixing up the house, some travel, or time with grandkids. Doubt may start to creep in. What am I going to do with myself? Was this the right choice? Will I really enjoy retirement?
Uncertainty, anxiety, and even grief are a natural part of the retirement transition, not a sign that something has gone wrong.
For some, these feelings surface well before the retirement date. For others, reality hits hard on that last day, or in the first quiet mornings that follow. Some people have described waking up drenched in sweat, wondering whether they have made the right decision. Others spend the first weeks feeling as though they are simply on leave, as if work is still there, waiting. Whatever form it takes, the emotional weight of this transition is real, and it deserves to be taken seriously.
One thing is clear from our research on retirement:
You are not somehow failing at retirement if you find it difficult. The struggle is real, and it’s more common than most people think. It’s also not inevitable, and more and more qualified support is available for the personal and emotional side of retirement.
When we stop to consider what retirement actually involves, it makes complete sense that big emotions would arise. Whether retirement is planned or unplanned, it means leaving behind something that has consumed the majority of our waking hours, our professional identity, our daily social world, our sense of structure and contribution.
Research on retirement adjustment confirms that the transition is one of the most significant life changes an adult will navigate, and that psychological preparation matters just as much as financial preparation. Research from the UK's Financial Services Compensation Scheme found that nearly a quarter of retirees ranked retirement among the most emotionally significant events of their lives, third only to having children and getting married.
What Work Has Really Been Providing
Part of what makes the last day so emotionally charged is that work has been quietly providing things we rarely stop to name. The benefits of work for wellbeing vary from person-to-person, and job-to-job. But beyond income, work often provides structure for our days, giving us a reason to get up, a place to be, and a rhythm that organizes our time. It often forms a part of our identity, a sense of purpose, and a community of people who know us in a particular way.
Work also tends to offer regular opportunities for challenge, skill development, and a sense of contribution. These are not small things. And when retirement arrives, all of them change, sometimes overnight. But here’s the important point for us to keep in mind in navigating retirement:
Work is not the only way source of these benefits: of structure, purpose, identity, and positive social connection.
Let’s not get trapped into thinking we need work in order to thrive. This is where work on more holistic planning, such as with a retirement coach, fits in. Preparing for life and personal adjustments in retirement deserves the same care we give to the financial side of the transition, or that we give to preparing for our careers. After all, most people will spend upward of 20 years in retirement. The more clearly we understand our personal journey with retirement, the better placed we are to build something meaningful in place of full-time work.
Three Things You Can Do Now to Prepare
The following are not steps toward a perfect retirement plan. They are invitations to reflect and begin the inner work of preparing for this transition in a way that supports your long-term wellbeing.
1. Reflect on the story of your career. Before you close the door on your working life, it is worth pausing to look back at what it has contained. Not just the job titles and accomplishments, but the experiences that shaped you, the challenges you navigated, the relationships that mattered, and the moments you felt most alive and engaged.
This kind of reflection does several things. It honors the chapter that is ending, which is important in its own right. It also helps surface what has been most meaningful about your working life, which becomes useful information for designing what comes next. And it helps you arrive at retirement with a sense of completion rather than abrupt disconnection.
Journaling is one way to do this. Conversations with a trusted colleague, friend, or coach are another. There is no right format. What matters is giving the story of your career the attention it deserves before you turn the page.
2. Acknowledge what you are leaving behind. For many people, retirement is an opportunity to get away from the aspects of work they no longer enjoy, and this becomes the focus for retirement. Noting those things you look forward to leaving behind is absolutely important as you look toward retirement.
But a focus only on what you look forward to leaving behind can also create blind spots. Alongside the things you are relieved to leave behind, there are almost certainly aspects of work that still bring genuine satisfaction: relationships, responsibilities, a sense of being needed or valued. These are the things that tend to go unnoticed until they are gone.
Taking time to honestly acknowledge both sides, what you are happy to release and what you will genuinely miss, gives you a fuller picture of the transition ahead. It also helps you think more clearly about what you might want to seek out or rebuild in retirement, rather than discovering the gap after the fact.
3. Get realistic about retirement life. Retirement offers something genuinely precious: time. But time without structure or meaning can become surprisingly heavy. The freedom that retirement promises is most fulfilling when it is filled with pursuits that feel genuinely worthwhile to you personally. Not pursuits that simply keep you active or busy.
What have you always wanted to explore but never had time for? What kinds of activities leave you feeling energized rather than drained? Where do you feel a sense of contribution, to your family, your community, or something that feels larger than yourself? What relationships do you want to invest more deeply in?
These are not questions with obvious or immediate answers. They often take time and experimentation to work through. But beginning to sit with them makes a meaningful difference to how retirement unfolds.
What kind of support is available for the non-financial side of retirement?
The retirement transition is significant enough to deserve real support. It is not just about a financial plan, but a thoughtful, personalized process of reflection and preparation for what this next chapter will actually look and feel like for you.
Retirement coaches represent a growing specialty aimed at supporting pre-retirees and retirees with exactly these issues. A Certified Retirement Life Coach is trained specifically in the psychological and social dimensions of the retirement transition. They come from various coaching specializations, which means they are not providing advice based on their own personal experience. Using Retirement Life Plan research-based frameworks, Certified Retirement Life Coaches work with you to explore what this transition means for you as an individual. They help you move from uncertainty to clarity, and from a vague sense of what retirement might be to a genuine vision of what you want it to become.
This is not about creating a bucket list, or being told to volunteer, or being pointed toward generic advice about staying busy. It is about understanding who you are, what has mattered most in your working life, and how to carry that forward into a retirement that feels genuinely yours.
Looking for support with your own retirement transition?
Find a Certified Retirement Life Coach who can help you prepare for this next chapter.
Are you a coach or financial planner working with pre-retirees?
Retirement Life Plan programs equip professionals with research-based tools to support the full retirement transition.
References
Wang, M. (2007). Profiling retirees in the retirement transition and adjustment process: Examining the longitudinal change patterns of retirees' psychological well-being. Journal of Applied Psychology, 92(2), 455–474. DOI: https://doi.org/10.1037/0021-9010.92.2.455
Pinquart, M., & Schindler, I. (2007). Changes of life satisfaction in the transition to retirement: A latent-class approach. Psychology and Aging, 22(3), 442–455.
James, B., Besen, E., Matz-Costa, C., & Pitt-Catsouphes, M. (2012). Just do it?...maybe not! Insights on activity in later life from the Life & Times in an Aging Society Study. Sloan Center on Aging & Work, Boston College.
Financial Services Compensation Scheme (FSCS). (2021, March). Retirement: one of our most emotionally challenging milestones [Press release]. https://www.fscs.org.uk/media/press/2021/mar/retirement-milestones/
