by Joe Casey
When Can I Retire?
It’s a harder question today. And it’s less often triggered by a specific date or age – or even a number. It’s more about your readiness. The essence of retirement is freedom. If you’ve earned the freedom to retire, you can taste what it will be like to have the time to do what you want – when you want to. How to structure your day in retirement becomes an inspiring, creative exercise with tons of possibilities. But when will it be the right time for you to walk away? When you’ve built enough financial security to walk away and live on your own terms. When you graduate from the grind to a different lifestyle. When you want time to focus less on pursuing the outward markers of success and more on the other ways you’d like to invest your time.
Readiness is your personal judgment that you’re ready financially and emotionally. It starts with achieving the financial assets to have the security and freedom to retire, but it’s also about the question How will I use the freedom that retirement offers? It’s also about assessing how ready you are to adjust to retirement, let go of many things from your career-focused days, and re-invent yourself in your next chapter.
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Is Your Retirement Planning Balanced Enough?
There are many resources to help you save and invest for retirement, but there are few good resources to help you focus on how to retire well. The traditional supporting structures for retirement have eroded and there’s no roadmap. You have to chart your own course. So retirement planning concentrates on the financial side – until you’re in it and the other side of retirement emerges. You learn quickly that retirement is about both your money and your time.
How Ready Are You to Adjust?
We see that people are often surprised by aspects of the transition to retirement that they hadn’t fully considered. And they can limit freedom until they’re worked through. Many of these are rooted in things that are easily taken for granted while we’re working – and are sorely missed once we’re not. Here are a few areas to prepare for:
- Professional status and identity. Retirement can lead to a loss of status. Research done by Michelle Pannor Silver at The University of Toronto illustrates how the transition can be especially challenging for people. 
- Purpose and meaning. Work can define purpose – and stepping away can lead to feeling adrift. Kicking back and relaxing sounds great, but people can feel empty when goals have been removed from their life. Freedom from work can be thrilling at first, but 20 to 30 years is too long a stretch for vacation mode, especially with early retirement.
- Loss of structure. Working life provides a framework for how we spend our time. It becomes part of the background and we don’t have to think much about it. Moving to blank slate each day sounds exciting, but some people struggle with defining their own structure and creating a new rhythm for their days, weeks and months. How to structure your day in retirement becomes an important task and affects your engagement and satisfaction.
- Isolation. Retirement changes social relationships. That demanding boss? Those unreasonable clients? Those annoying co-workers? You may not miss all of them, but you may miss the level of interaction. Some people struggle to create new social relationships, especially men, who may not have tended to their social networks outside of work.
Experiment With New Ways to Use Your Freedom
Once you’ve dealt with the core issues in transitioning to retirement, it’s time to optimize your freedom. Contrary to what some may think, this doesn’t happen overnight. Here are a few places to start:
- Pursue a new interest. Retirement provides a great opportunity for learning and mastery. Take up something you’ve always wanted to learn about – or take something to the next level. Start small. Take a course. There are more options available today than ever before.
- Return to an old interest. Over the years of a career, some people put something that was a keen interest earlier in life on the shelf. Is there something you always loved to do that you didn’t have time to pursue during your working years? Now you have the time to pick it up again.
- Set new goals. Goals give us something to strive for. Set a few goals in different areas of your life. Start small, build momentum and track your progress. Then take it up a notch, or two, over time.
- Get involved in something greater than yourself. As we age our sights often shift from attaining more success to significance. Have a cause that interests you? Get involved. It will also help you cultivate a new social circle.
- Cultivate a new purpose. Find places where your talents and experience can contribute to the greater good and perhaps make a real difference to someone. A new purpose can help provide inspiration, motivation, and direction. It can also be good for your health. A recent study at the University of Michigan of over 6,500 older adults in the U.S. highlighted an association between purpose and longevity.
Think twice before deciding if you can retire. Take care to make sure you’re ready financially and emotionally – so you can make the most of your freedom to retire.
Joe Casey is a former senior HR executive at Merrill Lynch, who’s created a second career as a retirement coach. He holds a Masters in Gerontology from the University of Southern California and, as a retirement coach and Designing Your Life coach, he helps people discover What’s Next after their primary career.
Related podcast episodes:
You Can Learn a Lot from the Principles of FIRE
Preparing Well for the Soft Side of Retirement
What Unique Challenges Do People Who Love Their Work Face in Transitioning to Retirement?
Are You Ready to Follow Your Own Path in Retirement?
 Silver, M. P. (2018). Retirement and Its Discontents: Why we won’t stop working, even if we can. Columbia University Press.
 Alimujiang, A., Wiensch, A., Boss, J., Fleischer, N. L., Mondul, A. M., McLean, K., … & Pearce, C. L. (2019). Association Between Life Purpose and Mortality Among US Adults Older Than 50 Years. JAMA network open, 2(5), e194270-e194270.