Reflections on Reaching Retirement Age as I Turn 65

By: Gary Hirsh, CPA, CFP®

My friends often joke that I was looking forward to retirement from when I started working in 1979. With my initial IRA deposit of $1,500 in 1980, I was on my way.

I first seriously considered retiring in 2014 at age 57. I stepped back from a partner role at a CPA firm and had plenty of free time. With three offspring still at home, travel opportunities were limited. At this time, I found out that watching west coast sports on ESPN or other networks and sleeping late the following morning was not all that stimulating. Waking up with no one home was also strangely lonely. My wife was a practicing physician six years my junior and, at that time, had no plans to retire.

Those fortunate few who retire on their terms may regret retiring too soon. Others who felt they could not or chose not to retire until they were ill or physically disabled could not enjoy an active retirement. They missed out on what could have been a wonderful time in life. Some do not retire because they want to avoid other issues or do not think living in an unstructured environment is possible. As someone once joked, “I vowed to be with my spouse in sickness and health, but not every day for lunch.”

The last time I golfed, at age 22, I wrapped my club around a tree on the 11th hole and vowed never to play again. I ski, but a few times a year is sufficient. We love the beach, but October through most of May in the Northeast is not an option, and I’ve never been a massive fan of a full-time warm climate state and need to be near a major city. We travel 6-8 weeks a year, which is terrific, but not full-time. I also found out that travel and other wonderful times are more rewarding as a limited vacation than a full-time vocation.

For me, the biggest issue was being emotionally ready to retire. I was not. Thus, I decided to pursue my goal of using my CFP® designation in the full-time practice of financial planning rather than only practicing it occasionally as a CPA. At HIGHLAND, I can work on my terms to match my wife’s schedule and calendar with a good balance of work and vacations.

As I consider my next phase in life, my advice for anyone financially able to retire is to plan out your ideal lifestyle. Consider recreation, travel, hobbies, or starting another part-time career or volunteer work. Do a trial period as much as you can while still working. Speak with friends and associates and find out what they are doing. It is a delicate balance between regretting that you retired too young or never having lived to enjoy the fruits of 40-plus years of work. 

If you would like to discuss your ideal retirement transition with any of our advisors, as a financial life planning firm, HIGHLAND welcomes those conversations. Schedule a free consultation to come into our office, have a cup of coffee, and chat with a CFP® advisor.