Preparing for Retirement: The Emotional Side No One Tells You About

When people talk about retirement, the conversation usually circles around money, travel, or hobbies. Those things matter, of course — but the most surprising part for many isn’t financial at all. It’s emotional.

“Have you thought about what it will feel like to wake up with no work schedule?”

That single question can stop people in their tracks. For some, it sounds like bliss. For others, it’s oddly unsettling. After decades of structure, waking up to a completely open day is a bigger change than most expect.

We can’t tell you what retirement will feel like, but we can offer ways to observe and manage whatever emotions come your way. Because while retirement brings freedom, it also brings a flood of emotions — some welcome, some less so.

The Emotional Stages of Retirement

Psychologists sometimes describe retirement as following a series of stages: anticipation → honeymoon period → let-down → adjustment → contentment.

Anticipation feels exciting: countdowns, daydreams, and “what will I do first?”

The honeymoon period can feel like an extended holiday. Finally, the alarm clock is banished, and there’s time for long coffees or spontaneous outings.

Then comes the let-down — sometimes called “retirement shock.” The novelty wears off, and a creeping restlessness can set in. Days feel longer, and people quietly wonder, “Is this it?”

With time, most people reach adjustment — a stage of experimenting, finding new rhythms, and gradually settling into a lifestyle that fits.

Eventually, there’s contentment, where life feels balanced and satisfying again. Not everyone follows this path exactly, but recognising the pattern helps normalise what can otherwise feel like an emotional rollercoaster.

When Boredom Creeps In

Boredom rarely arrives overnight. At first, it feels like a holiday. Slowly, though, the days can stretch, and a nagging emptiness appears. The trick is not to panic, but to notice. When you notice boredom has arrived, gently ask yourself:

What might I be missing — some variety, a sense of challenge, or perhaps a bit of company?

This is where “gentle intentions” come in. Instead of forcing yourself into a rigid routine, try shaping your day with small, meaningful acts: write down one thing you’d like to try today; reach out to one friend or family member; get some fresh air even if it’s just for a minute — step outside to water a plant, feel a breeze, or stretch your legs on a quick walk; keep a simple journal of what felt good today. Boredom can then become less of a problem and more of an invitation — a nudge to explore what genuinely gives you energy.

The Identity Jolt

Retirement often brings unexpected realisations about identity. Work isn’t just a paycheck — it’s shorthand for who we are. A vignette many people share is the strangeness of no longer being introduced by a job title: “This is Sarah, she was a teacher,” doesn’t sound the same as “This is Sarah, she’s a teacher.” It’s worth asking yourself:

What parts of your identity do you want to carry into retirement?

Maybe it’s being a mentor, a problem-solver, or a creative thinker. These qualities don’t vanish with your last day at work; they simply need new outlets.

Retirement Isn’t the Same for Everyone

Of course, not all retirees come from a 40-hour working week. Some have been stay-at-home parents and suddenly find a partner underfoot all day. Others have juggled casual or seasonal work and feel a subtler shift. Carers may face both an ending and a new responsibility at once. Each path has its own emotional challenges — whether it’s sharing space differently, missing the quiet, or wondering how to fill long stretches of time. What helps across the board is investing in connections: nurture friendships before you hand in your notice, join clubs, or rekindle hobbies that naturally include others. Emotional wellbeing in retirement is deeply tied to staying socially connected.

Then there are those who don’t get much of a retirement at all — perhaps they are forced to step away from their previous role due to illness, or need to step up to caring for a partner or family member, which brings its own set of emotional adjustments and challenges.

Trials, Tests, and Rehearsals

One idea that might help is a “trial retirement.” No rehearsal can perfectly mimic life after work, but even a short experiment can reveal a lot. If leave is available, consider a week or two off but try not to cram it with chores or outings. Instead, treat it as a gentle glimpse into unstructured days. Notice what you gravitate towards, how the days feel, and what emotions arise. Do you feel relief, restlessness, or pride at how you spend the hours? Some people find the quiet liberating. Others discover the itch of boredom much sooner than expected. Either way, it’s a valuable insight — and a reminder emotional readiness isn’t about avoiding uncomfortable feelings, but understanding and preparing for them.

Retirement is not a single emotion, but a shifting journey. Relief, boredom, joy, and even grief can all co-exist. Rather than tell yourself how you should feel, give yourself space to notice and process what does come up. The question isn’t just whether you can afford to retire — but whether you’re ready to live the life waiting for you.