Regrets in Retirement

By Megan Giles: Retirement Transition Consultant.

For many people the thought of retirement can create a level of anxiety because they don’t know what to expect – what life will look like when work no longer consumes the majority of their waking hours and how they will define themselves when their job is no longer a key part of their identity. There are also the worries of what should retirement look like and how they should  be spending their time. Rather than worry too much about the unknown, I thought it would be beneficial to learn a little more about the reflections of those who have trodden the path before us. In particular I was interested to know what retirees would do differently if they had their chance again.

I’ve spent time this week exploring retiree’s reflections online and so in this blog I am sharing the most common reflections that I have come across. Specifically I am focusing on the non-financial elements of retirement..

Image: Glasses lying on table

There were plenty of people who lamented how they had saved and accessed their investments, however, I’m not a money expert. A well-informed and robust financial plan is critical to greatest flexibility in retirement and if you have concerns in this space, I highly recommend you seek the advice of a financial planner you trust.

What are the most common regrets?

Holding grudges

  • After a significant disagreement you may not want to be the one to offer the olive branch for fear of being seen as weak or wrong. By not forgiving others (particularly those close to us), however, that grudge can become all-consuming when you suddenly have more free time at your disposal. And not only that, but anger detracts from the good things in life– what has time for that?! Furthermore, strong relationships and networks are an asset because like it or not, as we age we become more dependent on others
  • Action: Make the first move and offer to reconnect with that person you have been distancing yourself from

Not planning for the additional leisure time

  • For most of our lives work consumes the majority of our waking hours. Without a plan for this additional free time the risk exists that one becomes directionless and their sense of well-being is reduced.
  • In a relationship there are two common challenges 1) that without a clear plan of what you will do together and independently, the feeling of living out of each other’s pockets can become overwhelming and you’d rather be back at work than spending time with your significant other and 2) you get swept up in the other persons plans and your own goals and desires are sidelined.
  • Action: Put some time aside (ideally with your significant other) and articulate what will be important to you in retirement and how you might fill your days. Download the Reflecting on You Planning Sheet to get started

Not travelling sooner in retirement

  • There is a tendency to postpone travelling when you’re newly retired, both because you believe that your good health will continue and you fear expending your retirement savings too soon. The reality is that you never truly know what is around the corner.
  • Action: Trips don’t have to break the bank so start planning to ensure the holidays you dream of (big or small) become a reality

Not taking better care of themselves

  • Having good health can help to ensure that retirement truly is the best time of your life. It enables you to action those items on your dream list. Unfortunately chronic pain or poor mobility can limit what you are able to do (e.g. hop in and out of a 4X4 or hike between villages in Cinque Terre) and with the average life expectancy for women now in the mid-80s retirement could be a long time to simply manage rather than thrive. The good news, however, is that it’s never too late to start making positive changes to your health.
  • Action: Whether you have retired or are thinking about it, talk with your GP about the things you can do to ensure the best quality of life for you

Not keeping up with technology

  • There are so many ways to communicate online these days – Facebook, Snapchat, LinkedIn and Whatsapp just to name a few. Whilst the online world can seem daunting, not becoming familiar with these new developments can make it harder to connect with younger people, namely grandchildren.
  • Action: Use this as an opportunity to engage with your grandkids and ask them to help navigate the different ‘apps’. Even if you never regularly use Snapchat or only ever follow two people on Twitter, at least you know what all the fuss is about!


Don’t let retirement happen to you or opportunities pass you by – learn from the experiences of others and take action to create a lifestyle that is fulfilling, meaningful to you and lights you up each day!

To read about these regrets and reflections in more detail, follow the links below:

If you enjoyed this article you may also like to read What should retirement look like for women over 60? and 4 people to see to plan for retirement.

Whilst the prospect of retirement should be an exciting time with so much freedom, for many this can actually create a sense of anxiousness.

Work is such an important component of our lives – it’s where we achieve, create bonds, share our wins and our challenges, and it provides a structure to our week. How do we know what we are or who we are without it??

If this is something that is playing on your mind, why not book in for a free 15 min Virtual Cuppa and we can chat through anything that is worrying you as it relates to retirement.