We at WalkingWomen are many over 60’s women passionate about keeping active, remaining curious and living our best lives for as long as we go on.
We seek out women who write about the topic, can help others challenge their thinking and who gives tips and ideas to support those going through change.
Jessica McGregor Johnson is a specialist coach in this field and has written and spoken on the topic . We were lucky enough to have Jessica help create a WalkingWomen Retirement Retreat in 2025 and she is still beside us to offer more for you.
Check out her work and her retreat if you would like to join ..
Jessica writes…
Retirement can feel like a three-sided coin. For some, it’s a long-awaited freedom after decades of work. For others, even when expected, it can feel daunting – like a looming loss of identity. And then there are those who are “being retired,” a group who often face not only an identity shift but also the sting of feeling pushed out.
Across all three experiences, one thing makes the difference between struggle and satisfaction: planning. Not just financial planning – the internal planning that prepares your identity, purpose, and sense of contribution for a new chapter of life.
A client on a recent retreat reminded me of this. He had more than enough money to retire comfortably, yet his deepest fear was losing his income – not because he needed the money, but because income equalled his value. It was how he measured his worth to himself, his family, and the world.
Beyond Finances: Emotional Planning
Financial planning often starts decades before retirement, but emotional and psychological planning usually happens only in the final year. Retirement feels wonderfully distant until you get close – then the potential losses rise to the surface. This is when it becomes essential to consider what brings meaning to your life, where a new sense of purpose will come from, how you’ll redefine your identity, and how you’ll continue to feel useful.
The Four Stages of Retirement
Dr. Riley Moynes in his TED talk describes these four stages of retirement.
1. Vacation/Holiday – A period of rest and novelty.
2. Loss – When the emotional gaps make themselves known.
3. Panic – The urge to find another job to regain purpose.
4. Reinvent – Creating a new identity, meaning, and way to contribute.
I believe thoughtful planning lets you skip stages two and three entirely – jumping straight from vacation/holiday to reinvention.
But first let’s look at the challenges, do they resonate with you?
The Loss of Identity
Identity can be the biggest stumbling block – especially after a long, successful, demanding career. One of the first questions we ask when meeting someone is, “What do you do?” It’s our shortcut to understanding who someone is. When you’re newly retired, that question can feel uncomfortable because the familiar answer – I’m a CEO, I’m a teacher, I’m an engineer – no longer applies.
For years, your title has shaped not only how the world sees you, but how you see yourself. Even though we are all far more than our jobs, losing the title can feel like losing a part of who you are.
Workplaces also give us context and belonging. They create our daily interactions, our sense of place, our emotional and intellectual structure. Remove that, and your identity can feel suddenly hollow.
The Loss of Purpose
Purpose is tied closely to routine. Many people grumble about their work routines while they’re in them, yet once removed, the absence can feel disorienting. Work gives direction. It gives a “why” for getting up in the morning.
Most careers also offer a built-in sense of community. Colleagues rely on you, and you rely on them. Without that, life can feel aimless. The question “What am I supposed to do now?” is no small one. Purpose is essential to a healthy, meaningful life. Retirement requires shifting from a career-driven purpose to a personally inspired one.
The Loss of Usefulness and Contribution
One of the deepest human needs is feeling useful – contributing to something larger than ourselves. Many roles provide this automatically. You may believe in your company’s mission, your profession, your clients, or your team. You may feel you’re contributing through innovation, care, leadership, or problem-solving.
I once had a client who worried he had no legacy outside of work. Eventually, he realised his true passion was his family. Supporting his children and future generations became the legacy he wanted to nurture.
Recognising that you still have something to offer
and finding new arenas to offer it – is essential for a happy retirement.
The Inner Impact
Much emphasis is placed on financial readiness, but the psychological impact is often overlooked. Without emotional preparation, those retiring can face depression, especially if their transition lacks structure. Loneliness can creep in quickly without planned activities and connections. Humans require interaction, purpose, and a sense of self to thrive.
“Being Retired”
For those retired unexpectedly – often in their late 50s, through mergers, acquisitions, or restructures – the shock can be profound. Even with financial security, the timing can feel wrong. Suddenly, they are without work and without preparation.
A man on one of my Retire Happily retreats arrived certain he needed a new job. I encouraged him instead to explore the question, “What would it look and feel like to live a bloody wonderful life?” At first he was baffled, but slowly he realised he could give himself permission to enjoy the next phase. Once he did, the path ahead opened – rich with possibilities for himself and his wife.
Reinventing Yourself
To ensure that you get the retirement you’ve worked so hard for you need to look at what reinventing yourself looks like. Topics like; Identity, New Purpose, Usefulness and Contribution. Staying Connected and Managing your Emotions are all crucial.
I have run Retirement Retreats for both individuals and couples for years and Walking Women and I have got together to bring you a Retire Happily Week. With a mixture of presentations and individual coaching, whilst staying in a beautiful place and doing some fantastic walks, this week is designed to bring you clarity as to what you want your retirement to look and feel like. Addressing the topics above you’ll go home with a plan so you can step into your retirement with ease and excitement.
A recent participants said:
“…Talking through what retirement might actually look and feel like, and what my sense of purpose could be afterwards, made a real difference. Having something positive to look forward to helped me to finally let go of my old role and start to embrace this next chapter. Jessica also gave me some thought-provoking ideas – not necessarily the answers, but prompts that made me look at myself, and what’s possible, in a new light.…”
Retirement is a profound shift – one of life’s biggest – but it can be one of the most joyful eras if you embrace it. More time for yourself, more time with family, more time for put off dreams, more time simply to enjoy being alive. With planning – both practical and emotional – you can make retirement the cherry on top of your life.
