The surprising psychology of retirement — and why it feels so hard

We often imagine retirement as the final prize. The holiday that never ends. And for a while, it really can feel that way. Many retirees describe the first few weeks or months as a kind of honeymoon phase—a period of well-earned rest, excitement, and freedom. No alarm clocks, no meetings, no obligations. It can feel like you’re finally on that long-awaited vacation.

But at some point—and the timing is different for everyone—that initial high starts to fade. Sometimes it happens after a few weeks. Sometimes it takes a few months, or even a year. But eventually, many retirees begin to feel a kind of fog settling in. The days start to blend. The novelty wears off. And questions begin to surface: What am I working toward? Who am I outside of my job? What gives my days meaning now?

Psychologists call it a major life transition—a term usually reserved for things like moving house, becoming a parent, or experiencing loss. Why? Because it involves a change in identity, routine, and social environment all at once. According to a study published in the journal Ageing & Society, retirees often experience a temporary drop in wellbeing and self-esteem right after leaving work, even if they were looking forward to it.

It’s not hard to see why. Work, for better or worse, gives us structure. It gives us a sense of usefulness. It provides us with feedback—people rely on us, thank us, challenge us. Take that away, and it’s common to feel disoriented.

But that discomfort isn’t a sign that something is wrong. It’s a sign that something important is changing.

What makes this transition harder is the lack of language and tools to support it. We’re told to stay active, volunteer, keep busy. But the deeper work—reconnecting with who you are now and what you want to explore next—gets overlooked.

At LivOn, we’ve learned through interviews, research, and our own experiences that the most successful retirements begin with self-awareness. That’s why we start with personality.

Our upcoming app includes a psychology-informed assessment that helps you reflect on how you like to spend time, what environments bring you energy, and how you want to grow in this next stage. Because retirement isn’t about becoming someone new—it’s about reconnecting with who you are when you strip away the noise.

For some, that means finally picking up a creative pursuit. For others, it’s joining a group, mentoring, or travelling in a way that feels more purposeful. The path is different for everyone.

The important thing is: there is no "right way" to retire. But there is a right way forward for you. And that starts with understanding what you want this chapter to mean.