Why The Decision To Retire Is Not Easy?
- Jun 1
- 8 min read
The other day I caught up with two ex-colleagues from my first job. [Let's call them Alex and Simon which are not their real names]. It was only because Alex was visiting Melbourne on a holiday that we decided to catchup over lunch. Our friendship group which included two others goes back almost 45 years with a common bond we shared working for Coles, a major Australian retailer as our first employer. We were all in our 20s. We remained with Coles for some time, working at its head office. Between the five of us we had implemented what was considered in the 80s and 90s a state-of-the-art system in logistics and distribution. Soon each of us moved on to other opportunities, either returning to Singapore or to other jobs, while some stayed at Coles.
During the lunch engagement we talked about what each of us were doing in our current phase of retirement. None of us showed any signs of poor health which was a blessing. Simon, a recent widower was involved in the stock market as he is self-managing his own superannuation fund. He says doing this keeps him busy and up to date with financial and geopolitical current affairs. Simon also travels overseas to see family. Alex on the other hand, who lives in Singapore, is involved with spending time with his grandchildren, regularly traveling overseas with his family, doing exercises and tinkering with his classic two-door Alfa Romeo. As he lives in Singapore the most cost-effective option to keep his Alfa Romeo on the road is to register it under the Classic Vehicle Scheme which only allows him to drive it 45 days in a year. Alex admitted that he looks forward to driving and 'double clutching' his Alfa Romeo and hearing the 'vroom' of the engine.
After returning home from the lunch I was reflecting on how Alex and Simon have kept themselves busy and occupied after retiring from full-time employment. While they loved their jobs, I'm sure they obviously entered their season of retirement with a sense of renewed purpose and excitement. While they are among some of my close friends who have retired, I know of many friends who still continue to work well into their late 60s and 70s.
Unless one is forced to retire due to ill health or retrenchment, I asked myself why are they finding it hard to take the step to retire? While many of my retired friends are enjoying and appreciating their new season of life; still being productive and influencing the world around them, I am sure everyone has their own personal reason to do what they are doing - to retire or continue working.
Before moving forward let me set the context of this essay. I believe the season of retirement is not a season when activity, purpose and self-worth cease. I consider the season of retirement as a "retirement to" something new. With this focus I am suggesting in this essay that the decision to retire is not an easy one. I believe the tendency for many who are still working in their senior years are viewing it more as a "retirement from" perspective. Any change can be daunting, especially if it is a change from something stable and comfortable. It is said that change is never easy, no matter how necessary it may be. In this essay I am not even referring to self-employed business owners who created their businesses years earlier. They would have seeded, nurtured and grown their businesses, made a living from it and likely grown in age as their businesses matured. I believe they face other factors when contemplating retirement. Questions like whether to sell the business or hand over to a family member or partner. Or when should they stop when realizing they cannot run the business anymore, either because of age, their strength or mental acumen? This essay may also remind those in their 50s what challenges they may have to consider before retiring.
Over the last five years I have been speaking to friends about the subject of retirement. Some wished they could retire but can't for financial reasons, some in their 60s see retirement as a distant outpost, while others wish to retire but don't know how to bring themselves to that outcome. Here are some reasons why I believe people find it hard to retire. Some are thoughts I've had before retiring, while other reasons have been shared by people I've met.
Perceived loss of identity.
After I had signalled my intention to retire, while still employed a close colleague of mine shared a story of his golfing partner who lamented the loss of his job title after his retirement. No longer was he known as a Chief Executive Officer to his friends and people he met. At best he was acknowledged as a "former CEO", but most times he was simply a "retiree", who had joined the ranks of many other retirees.
When work stops, some people feel that they have lost part of their self-identity. When asked, "What do you do?", most people will answer with, "I'm a teacher." or "I'm a warehouse manager." or "I'm a lab technician." or "I run a business." Their role gave them meaning, purpose and recognition. When the role is entrenched in one's lifestyle - I’m not suggesting that it should - it can be very hard in letting it go in exchange for a generic description like “retiree”.
Feeling a sense of loss of purpose and usefulness.
If there is nothing that will fill the void of purpose or usefulness once someone leaves work, a person who retires can feel that they have lost their usefulness. When once they felt useful in their work and acknowledged by the peers and management for their efforts, this will all go once retired. In a work environment most people are driven by goals, objectives, and responsibilities to peers and staff. If these are not compensated for in retirement, this sense of loss can be a hard pill to swallow when calling "time out".

This is especially true of people who are highly driven and in leadership or senior positions in business. Such people also have a high degree of ambition and are purpose driven. As high achievers, unless there are avenues to perform or contribute post-employment, then the sense of having to slow-down can feel unnatural, frustrating, resulting in the guilt of not performing.
Loss of routine and structure.
Another reason why the decision to retire is not easy is because most people generally like structure in their lives. The schedule of work inherently forces people to be more disciplined than they would otherwise be. How often during a long relaxing holiday have you struggled to know what day of the week it is? Perhaps you have switched off receiving email messages on your iPhone including switching off the alarm setting. While it may be enjoyable and having a sense of freedom might be tolerable for a short period, imagine living as a retiree, post-employment. Without self-discipline and a routine, days can blur into another. The thought of living as a retiree can feel aimless, dull and boring.

Perceived loss of social connection.
If you do not plan ahead, retirement can unexpectedly bring about loneliness and a longing for social connection. Workplaces by its very nature provide daily social interactions with colleagues either formally or informally. Retirement can cause a vacuum in one's social connectedness, which is particularly true if one's friendship circle is mainly work-based.
Considering your current and future social network adds to the challenge of deciding when to retire. Many who delay their retirement may also have a negative perception of seniors living in a retirement village which can magnify their resistance to retire. I have friends who live in a retirement village with a contrary view. They love the lifestyle it provides.
Fear of financial insecurity.
When I posted on social media that I was retiring, I received many congratulatory messages. There was one message I received which summed up the financial fear this friend had in delaying his retirement. He said he wished he could retire, but because he was extravagant when young he had no choice but to continue working. I am sure he would not be alone. A common challenge for those deciding on retirement is having to answer the question, "How much do I need to afford a particular lifestyle until I’m 80-plus years old?” This question may be too hard to answer which may cause people to delay their retirement decision, and say to themselves, "It's easier to keep on working." That's why seeking financial advice is a prerequisite before considering retirement.
The connotation of retirement to aging.
In our Western-dominated culture of work, the season of retirement is unfortunately associated with aging. There is a perceived signal to the world that the person retiring is now getting older - considered a senior - and has come to the end of their work life with little contribution to society. Perhaps this is why many resist retirement because remaining in the workforce helps them feel needed, mentally engaged and helps them maintain a perceived sense of youthfulness.

It is for this reason I use the adjective "active-in-retirement" in my social media profile to signal that retirement is not a cul-de-sac of life, but a crossroad to a new life adventure.
The fear of changes in family dynamics.
When one person in the household has been working for a long time while the spouse has been a stay-home person there can be a period of trepidation when the retirement date is set. Even in a two-income household when one or both partners approach the decision to retire, this same anxiety can occur. Often the anxiety is about existing routines clashing and new routines having to be established. When once the house was quiet and the kitchen was kept tidy, having another person present seven-days-a-week will require some adjustments to be made by both parties. What’s more, with both partners now being at home, may create a perceived open invitation for young ones in an extended family to spend more time there. While they may be loved unconditionally, the new dynamics will need getting used to. While we may laugh about the one partner being relegated to the garage or the grandchildren to play only in the garden or with their grandfather in the garage (lol), it is true to say that if the household is not filled with love, mutual respect and tolerance, the risk of unresolved disruptions can arise.
Having a negative feeling about retirement.
It becomes a self-fulling prophesy if a person sees retirement as a decline in self-esteem, activity or worse, one-step away from an aged-care home. People with these feelings are the most resistant to retirement. On the other hand, those who see retirement as a positive change will achieve much. A quote from an unknown author, "Retirement is the only time when one can enjoy all the good things life has to offer without the stress of having a job."

Despite the decision to retire is not easy for some, many of my friends who have positively accepted retirement have been able to do so quite seamlessly. Some have been involved in contributing back to society like volunteering at council organised Repair Cafes where they help fix toys and small household machines. Others have volunteered their time mentoring young people, helping in charities, and volunteering in faith-based organisations. Most of them have reapplied their skills in their new environments. Some even have enrolled in community-based learning workshops; picking up a new language, doing pottery or learning web-design, and even orienteering.
Those who are happily retired see the essence of retirement as a time for freedom, exploration, and the pursuit of personal happiness. It is not just a transition but a new chapter in life, filled with opportunities to discover and enjoy.

The author of 'How to Retire Happy, Wild, and Free', Ernie J Zelinski said in his book, "Retirement is the last opportunity for individuals to reinvent themselves, let go of the past, and find peace and happiness within."
In conclusion; for many people, the real challenge of retirement is not financial. It is about answering the question, "What is my new purpose?" Answering that question will determine whether retirement feels freeing or unsettling for the individual.



Spot on Steven. Your article drives home the need to think about retirement early and to know what it has to look like to be fulfilling.
Hello Steve.. thought provoking.. as I am heading towards the retirement stage.. some time sooner or later.. I thoroughly enjoyed your illustrations and quotes.. Congratulations .. ! .. and i wish you continue to share your experience through our active blogging..
Ranga
Ex-Karya technologies..
Hey fellow retirement season enjoyer, thx for sharing a great perspective on the new(ish) season we find ourselves in. As usual we can all relate to many of the perspectives you put forward.
Good job once again.