Preparing For Retirement: Making your Retirement Transition Easier By Douglas Montgomery – Executive Transition Coach

Five years ago, I took an early retirement package and left the familiar safety and comfort of corporate life to become an independent executive coach. The plan, which has been evolving, was to work 2 to 3 days per week and spend the rest of the time doing things my wife and I wanted to do. It represented a major life style change, and felt scary and exiting at the same time. I’d like to share some of my learning with those of you preparing for retirement or a similar career transition.

Are you moving from or towards?

We come to retirement in different ways; some choose early retirement, others are ‘encouraged’ or told to take early retirement, and some hit a mandated retirement date. Whichever it is, when preparing for retirement, notice whether your attention is on moving towards something new or on moving away from the old career. I am told that at times of change, 40% of people are moving away from something and 40% are moving towards something new. When our attention is on moving away from the old job, we tend to be focussed on what is left behind: what we didn’t like and are glad to be rid of, and things that we will miss and may feel we are being deprived of. We can feel different emotions, e.g. relief, resentment, disappointment. Having our attention focussed on what we are leaving behind means that we may not paying attention to the opportunities that lie ahead.

Having our attention predominantly on looking forward enables us to think ahead to what we want to do. We may realise that we are holding fear about the uncertainty of what lies ahead. We may be excited about changing course and planning ahead. It is important to pay attention to both the past and the future, so notice where your attention is and spend some time looking in the other direction.


Leaving working life, a job or organisation after a significant period of time unavoidably results in loss. That loss can come in many forms: loss of status, loss of certainty and predictability, loss of relationships, loss of belonging, loss of purpose and of identity.

While we may physically have walked through the gates for the last time, mentally we may take a lot longer to leave. This mental retirement is similar to grieving. In preparing for retirement, we may need to go through a process of recognising what is lost, acknowledging its meaning and importance to us and accepting that it has gone. We each create an unspoken expectation of our organisation and how it will treat us and our work.  This unspoken psychological contract is not agreed with the organisation and so it does not know anything about it. When the organisation does not behave the way we have expected it to, our psychological contract is broken and can cause significant resentment, anger or anxiety. I remember expecting some of my work to be valued, used and built on after I left. Instead it was discarded, and a new direction adopted.  As a result, more than a year after leaving, I found myself feeling resentment and deflation; how could they be so stupid? This illustrates that we may not be fully aware of all our loss until we actually experience it.

Create a good ending

How do you normally end relationships, jobs, projects? Making a good ending when leaving for retirement is an important act of closing one chapter in order to enable the opening of the next, and is too often underestimated.

One way to make a good ending is to find ways to acknowledge those who have supported you through your time in an organisation. This has two-fold benefit. Firstly, you are thanking others for their contribution to your achievements, successes, the learnings and the memories you are taking with you. Secondly, you are inviting others to take the opportunity to acknowledge you and your contribution to their lives and work. Without this acknowledgement and invitation, we can leave with a sense of something missing and unspoken; a lack of recognition of having been there. I used to experience this when I left jobs or projects as quickly and as quietly as I could – a “midnight flit” as we say in Scotland. When I left for early retirement, I spent time letting others know how they had supported me and contributed to my being able and ready to leave looking forward to what lay ahead. Starting my new life felt much easier and more fulfilling, I had made a good ending of the old career with my contribution across many years acknowledged.

Reconnecting with purpose

Purpose is what brings meaning to our lives. When we are in the midst of a career, our purpose can be consumed by our work; e.g. to earn enough money, to get promoted, be good at our job, become CEO, etc.  When the day comes to retire, and we are suddenly handed back mastery of our own destiny, there may be a disorientating loss of purpose.

Working out what your purpose (new or renewed) is for this next stage of life is an important part of preparing for retirement. Understanding our purpose in life brings direction, happiness and fulfilment, and helps prioritise how we want to spend our time and energy.

I found that having a clear purpose I could articulate made it much easier for others to know how to support and encourage me.

Who am I?

When we have worked for a long time, we can come to think of ourselves as what we do, rather than who we are. Our true identity (self-image, self-worth and value), gets lost in our job, defined by a business card with a fancy job title, a company credit card, laptop and phone and an office with our name on the door. When we retire, we shed these trappings of office and can lose our sense of personal identity. We miss our ego getting stoked, our expertise recognised and valued. We can start to question ourselves;  “If I am no longer the confident expert who is so valued, or the executive leader who commands respect and others follow, then who am I?”.  This can be at best a confidence vampire, and at worst an existential crisis. A coach can support you as you re-connect with who you are and what you want to be known for.

Change of mindset: Survival to life-style

We have spent a career earning money and climbing that greasy pole, competing and ensuring that we earn enough to pay the mortgage, school the kids, subsidise university and new flat, weddings etc. As retirement approaches, it can feel frightening to lose the paycheque, bonus, commission or whatever regular income we have relied on. To some extent, we have been in “survival mode” all these years. Now we are faced with “survival” on pension and savings. We can get into deep-seated beliefs and habits about earning and saving that are challenging to switch off. A good trusted independent financial advisor (IFA) is a valuable support in working out the reality of your finances. Even despite this advice, we may still need help to shift our thinking from “saving for retirement” to “spending in retirement”.

Time – Our most valuable commodity and how not to waste it

As I’ve got older, I’ve discovered that time is my most valuable commodity. While we are working, our time is often not our own and is structured for us.  Once work stops, the routine disappears, and we can find we have a lot of time on our hands. This can be great to begin with, then become disconcerting as we have to fill it. I found it very difficult just sitting reading the paper on weekday mid-morning without feeling guilty that I should be doing something useful or productive!

It may be that you are going to set up a small business or do some part-time work. How will you prioritise work and non-work? It is easy to stay in the old habits of work taking priority and squeezing out everything else. In preparing for retirement, you must consider the new choices available  – what do you want to take priority from now on?

Have a good think about how you want to organise your time. What are the important activities, hobbies, new classes, experiences that you want? What do you want to stop doing? What do you want to do at a different time of the day/week/month/year?   How will you align with your purpose?

It’s not just about you: preparing for retirement with your spouse or partner

Your retirement is not just about you! When we live together for any length of time we fall into habits and routines and get used to how things are. In effect, a set of assumptions are created about how we live together. These include how much time we will each be in the house, what chores we will each do, what we will each contribute financially, how much time we will spend together, alone, with friends and at work. The family may have their own concerns about your retirement, or may be holding assumptions and expectations of you that may be about to change.

When one of the couple leaves work, the routines and norms can change dramatically. The unspoken contract of agreements gets disrupted and can cause significant tension and challenge in the partnership if not addressed.

Take time before the retirement date to talk about what this coming change will mean for each of you. What do you each assume and expect? Talk about what will change and what you each want when the retirement starts. What are you excited about? What are you worried about? Agree a new spoken contract about this new circumstance. Once the reality happens, expect things to be different from what you’ve imagined and continue the conversation again and again as necessary. Remember it’s not all about you! Listen to your partner and be honest with each other.

The liminal space between leaving and arriving 

All the planning and preparing for retirement is useful up to a point, and may or may not survive contact with reality. Planning can be a means of protection against the basic human fear of uncertainty and unpredictability. It is impossible to know what it will be like to be retired until you are experiencing it.   Trust yourself and the world that you will find your own way to be retired. Give yourself time to relax into the experience of being retired, that space of not knowing between leaving and creating your anticipated new life. Enjoy the here and now.

Community and relationships

It can be lonely once you have retired. We lose the meaningful daily conversations with colleagues. We lose our communities of like-minded others. The water cooler conversations cease. Overnight, our built-in work networks disappear.

Finding new communities to join (clubs, societies, volunteering, professional bodies) or increasing our involvement in existing non-work communities are important ways of maintaining connection, relationship and recognition.

And finally,

In the last few months before I retired, I found myself working really hard to finish projects and pieces of work before I left. I had a sense of needing to leave a legacy and make sure that my mark was on the work I was leaving behind.  A good friend (and coach) asked how these few months could change the 28 years’ worth of contribution and legacy I’d already created? I stopped working so hard. When you are preparing for retirement, trust that your legacy is already in place and that the organisation will pick up the slack when you go – none of us are indispensable.

The earlier you start to think about retirement, the easier it is to prepare mentally and plan practically for your new life. This is a major life change, so it’s OK for it to feel disorientating, scary and exciting – that is normal. Talk with colleagues and friends who have already retired, talk to your partner or spouse, and seek support from a transition coach.

About the company:

Transition Peak Limited™ is an online career coaching and training portal that helps companies and individuals move forward and faster following redundancy, retirement or return. Our online programs provide access to tutorials, documents and checklists. We also connect individuals with some of the best career transition coaches and experts in the UK. The coaches and experts can provide workshops, group or one-to-one coaching. Find out more on

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About the Author

Catherine Oliver - Parental Support Specialist
Douglas MontgomeryExecutive and Transition Coach
Doug is an executive coach; whose passion is the development and growth of individuals to fulfil their full potential. Professionally and personally he has experienced at first-hand the challenges and opportunities created by mergers, reorganisations and career and personal transitions. Visit Our Coaches page to find out more about Douglas.