How to plan for the transition into retirement

A couple of years ago I spoke to a friend who had just early retirement while he was in his early 50’s.  His pension pot was full, and he had worked incredibly hard throughout his career at Executive level.  He thought ‘why not’?

I met him a year later and he described his life post work through a simple diagram with 3 circles: work, friends and family.  When the work circle was removed, he hadn’t appreciated that many of his friends and social activities were work related, leaving most of his time for family (who he loves dearly).  He has now un-retired and returned to work.

This is not an isolated case.  Too often people think that if their financial situation is in order, everything else will naturally fall into place.

Retirement is one of life’s biggest transitions. For decades, work shapes our routines, our identity, our relationships, and even our sense of purpose. So, when the moment finally arrives, it is natural to feel excitement mixed with a fair amount of uncertainty. Retirement is not simply the end of a career. It is the beginning of a new chapter. And like any new chapter, it is far more rewarding when you approach it with clarity, support, and intention.

Here are five essential things to consider when transitioning into retirement, along with the people you should speak with as you prepare for this next stage of life.

Financial Readiness Beyond the Numbers

Although retirement planning often starts with money, true financial readiness goes deeper than savings and pensions. It is about understanding how your desired lifestyle matches your income sources and what you will need for the years ahead. Thinking about inflation, unexpected costs, and the rhythm of spending once work stops can offer huge peace of mind.

Before retiring, speak with

• a trusted financial adviser
• a mentor who has already retired
• your partner, so you can make shared decisions

These conversations can help bridge the gap between financial facts and your lived experience.

Your Health and Long-Term Wellbeing

Retirement offers more freedom, but it also shines a light on physical and emotional wellbeing. Planning for long term health means thinking about daily habits, movement, nutrition, and how you will maintain independence as you age. Being proactive now makes a meaningful difference later.

Before retiring, speak with

• your GP or health professional
• your partner or family about future care preferences
• friends who prioritise wellbeing, to learn what has worked for them

Health is easier to protect than repair, and retirement is the perfect time to build better habits

Identity, Purpose, and Meaning

Work gives many people a sense of identity. When that structure disappears, the question Who am I now can feel surprisingly unsettling. Thinking ahead about purpose, passions, and the activities that give you energy can turn retirement into a time of growth rather than drift.

You may also want to consider consulting in your industry, joining a Board (voluntary or paid), becoming a NED, volunteering for a charitable organisation, or starting a micro business/’side hustle’.  An Uber driver I had recently was formerly a senior executive who missed meeting new people, plus it meant he could drive people to his city centre Airbnb’s!

Before retiring, speak with

• a retirement or life coach
• a mentor who has transitioned successfully
• your partner or close friends who understand your values

These conversations help you discover what you want to move towards, not just what you are leaving behind.

Daily Life and Lifestyle Planning

Time becomes abundant in retirement. Without structure, this can feel freeing or challenging. Planning for hobbies, social activities, travel, learning, and personal projects can transform your days from empty time into meaningful time.

Before retiring, speak with

• your partner, especially about shared routines
• friends who are already retired
• community groups or organisations you may want to join

These discussions open the door to new routines and minimise any sense of guilt of ‘I should be doing something’.

Relationships and Social Connections

Many people do not realise how much of their social world is tied to work. Once the workplace disappears, so do many casual everyday relationships. Proactively thinking about how to maintain friendships and build new ones can make a major difference to happiness and wellbeing.

Before retiring, speak with

• your partner about expectations and boundaries
• your family about your hopes for connection
• colleagues you want to stay in touch with
• social groups or clubs you may wish to explore

Strong relationships are one of the most reliable predictors of a fulfilling retirement.

Retirement is not the end of your story. It is the beginning of a new and exciting chapter. With the right conversations, support, and preparation, your transition into retirement can become one of the most rewarding phases of your life.

By Ian Weatherup, Managing Director