Notebook with "Your Retirement Checkup" written on the page on a desktop beside a pen, a cup of coffee, and a keyboard.

Unlock your best life with a retirement checkup

Without a solid lifestyle plan, many retirees fall into a default retirement. Then, as the years slip away, they wonder where the time went. A regular retirement checkup can make the difference between surviving and thriving in your later years.

Read on to find out when, why, and how to do a retirement checkup, along with learnings from my own two year reflection. 

It’s true – Time does fly

At the end of June, it had been two years since I left my full-time career behind. It doesn’t seem possible that it has been two years. As the old saying goes, time flies when you’re having fun. 

In What I learned in the first year of retirement, I shared observations from my one-year retirement checkup. At that time, my new normal was starting to take shape. 

Completing my two-year retirement checkup reminded me of why setting aside time on a regular basis for a structured reflection matters. It doesn’t take a lot of time, and helps us to make the most of the gift of freedom and time retirement offers us. 

Let’s look at what’s involved in a retirement checkup. 

Clipboard showing the 10 elements of a Retirement Checkup.

Elements of a retirement checkup

A key component of my retirement coaching and workshops is a retirement readiness assessment. This holistic self-assessment evaluates 10 areas of retirement readiness:

  • Physical health and fitness
  • Mental health
  • Attitude toward aging
  • Family relationships
  • Social connections
  • Community
  • Home
  • Replacing work
  • Sources of meaning and purpose
  • Financial health

The retirement readiness assessment lays the foundation for short- and long-term action planning in the period leading up to retirement. It also forms the baseline for a periodic retirement checkup after the big day. 

When I complete my retirement checkup, I assess my current feelings in each of the 10 areas. As I reflect, I give each element a score out of five, and jot down notes and thoughts for each area. Next, I compare my current assessment to my most recent checkup and look for trends.

Observations from my second annual retirement checkup

My two-year retirement checkup showed improvement in a couple of areas compared to six months earlier. The other areas remained stable. I gleaned a few key learnings from the exercise. 

Setbacks test our resilience

At the time of my 18-month reflection, a leg injury had derailed my fitness activities. That injury reminded me not to take health for granted. It also reinforced that, even if we do all the right things, there are no guarantees. To coin another old saying, we should “make hay while the sun shines” and make the most of each day that we’re in good health. 

Since the beginning of this year, I have worked hard to prioritize healthy behaviours. As a result, I’m feeling much more positive and saw an improvement in my physical health and fitness score this time around.

Dealing with an injury also reminded me of the importance of staying positive when setbacks happen. It’s difficult, but a positive mindset makes a huge difference in our ability to overcome life’s inevitable challenges. 

Purpose is fluid

Although I try to live intentionally and purposefully, there were times over the past year when I felt a little restless. Should I be doing more? Was I doing the right things? 

I’ve come to realize that purpose is fluid. It will change with the seasons and the passing of time. For growth-oriented retirees, a regular Ikigai checkup can help to refresh our sense of purpose in light of current circumstances.  

As I move into year three, I’ll be looking for additional volunteer opportunities that align with my skills, interests and passions. 

Community is essential to connection

Most retirees see a drop in social connections after retirement because one of the key communities that enabled those connections disappears. 

In year two, it really sank in for me that, other than a handful of exceptions, my workplace connections did not follow me into retirement.

When our social networks shrink, our resilience can also decline, so maintaining strong social ties is key to overall wellbeing. 

Community is a prerequisite for building and maintaining friendships and social connections. Unlike individual friendships and relationships, a community is a group of people connected to each other by a common identity, purpose, or set of values. Examples of communities include church groups, charitable organizations, sports clubs, or book clubs. 

One of my goals for year three is to take inventory of the various communities I belong to, and seek new communities.

Regular checkups avoid default retirement

When we retire, we lose the automatic daily structure and routine we get from our jobs. Without a lifestyle plan, many retirees feel lost and drift into a default retirement—doing many of the same things they did while they were working and wondering why something doesn’t feel quite right.

Regular retirement checkups give us the opportunity to identify areas where we’re not feeling fulfilled. We can then create action plans that replace the sense of purpose and accomplishment that we got from our careers. Most importantly, we can reduce the “where-did-the-time-go” regrets that many people feel as they age.

How often should you do a retirement checkup?

The right frequency for a retirement checkup will depend on how you’re feeling about your life in retirement. The cadence will also change over time. 

In the first six months after leaving my job, I did monthly checkups. After that, I switched to quarterly. In year two, I reduced the frequency to semi-annual. I plan to continue with semi-annual in year three, and then eventually progress to annual reviews.

If rigid schedules aren’t your thing, you can simply do adhoc checkups whenever you feel restless or dissatisfied. 


My two-year retirement checkup gave me a couple of areas to focus on. I look forward to seeing what year three brings.

A regular pre- and post-retirement checkup can help you avoid a default retirement and plan for a retirement filled with meaning, purpose, and connection. Contact me to learn how I can help you. 


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