Shout out to former colleague Brett who asked me to offer some reflections on preparations for retirement; I helped many prepare for that major event in my years of HR work, and here for your consideration are my insights.
Answer big question number one: this one and the second were quoted to me by my long time financial advisor Janice as we discussed when I might retire over the years. #1. Do you have enough? that means have you accumulated enough savings in the various vehicles you are using to save and invest. It also means you have accounted for and covered all of those life obligations like the care/education of your offspring and that pesky mortgage and those ever more expensive vehicles. Those savings/investment accounts plus social security and any other income sources you may have must cover your desired lifestyle and medical insurance if pre-medicare.
Answer big question number two: Have you had enough? This one is different for everyone. I look at jobs on a spectrum that has the word vocation at one very positive end, and the words “It’s Just a Job” at the other. The closer you are to the word vocation in your work, it is likely that you may want to stay around a long time. Those who love their work and feel as if they are on a mission may indeed decide to work well into the their golden years. Those closer to the “just a job” phrase may decide to leave early and FIND their vocation. This is not the only lens on the question, as health, work stress, dealing with toxic personalities, desired geography, grandchildren, and many more factors may be popping up. Just make sure you have question #1 answered first.
Get Good Advice. Now that we have established that credible advice is a good thing, it is critical that you get reputable financial advice. The basics may be offered through retirement programs provided through your employer. If there are workshops offered, attend them. If there are online learning tools available, use them. As you and/or your significant other advance through life, a more sophisticated approach may be needed with a dedicated long term advisor which as noted, I have been blessed with. Stay away from investments that promise miracles unless you are independently wealthy with high levels of risk tolerance. For most of us, the conventional solutions to saving and investing will work just fine in building that nest egg.
Address that healthcare question: if you want to hit the retirement scene before the official qualifying year for medicare, make sure you understand the costs you will confront and do the research well ahead of time. Married couples who both work may want to consider one spouse retiring first in order to maintain health coverage for a time. Use AI tools and you will find answers to all of the questions you have. Connect with other recent retirees from whatever firm you are leaving and get their advice on any surprises or things they misunderstood before leaving. We had an amazing guru in all things retirement named Scott in my former company. Find the Scott at yours.
Start planning early for what you will do with your time. Very early. I have heard any number of retirees say “There is only so much golf you can play.” Sometimes the aging process itself can make physical hobbies like golf less enjoyable, so having a back up plan is critical. If you have been consumed by your job with few hobbies, finding hobbies and interests might be a great hobby in and of itself starting mid-career. This point is the perfect segway into our next.
Find meaning and purpose. For many our careers did this for us, providing identity and purpose. Some are caught up in their work identity more than others, but understanding your own identity is an important part of a successful retirement. A great CEO I worked for used to say that when he retired he went from “Who’s who” to “Who’s that?” over night. Might be good to have a plan to deal with this. Having met some success and secured a C level job at the age of 39, I started thinking about meaning and purpose soon after, ultimately landing on several non-profit boards aligned with my personal values. Later it occurred to me that this could be part of my retirement plan, keeping my brain active, scratching that “strategic” itch on occasion, and more importantly, helping others. For others, it might mean direct volunteer work in charitable institutions. Do not underestimate the importance of having a place to go and something to do that matters to others in your later years.
Become a coach, mentor or advisor. This one deserves special mention outside of the point on meaning and purpose because it is so necessary for those following us. The amount of advice out there on the various apps and platforms that is absolutely toxic is alarming. Whatever your profession may be, giving some of your time to those seeking coaches and mentors, whether through an organization or personal connections, is a great thing to do for your fellow humans, your community, the country and the planet. Whenever I am asked to have coffee and share advice, I do it. What a compliment to be asked! on a grander scale, its called knowledge transfer. Wisdom transfer. Do it.
Deal with the physical realities. Yes we can age well, but to do so, you must confront reality. We will have health challenges and we should plan on it. I am the youngest of seven siblings and when we are all together we tell stories of our various health related issues to the point of laughter. We often reflect that “our health is now a full time job.” Whatever the tests are, the extra steps to know early about anything, do it. Expect knees, hips, teeth and other highly used parts to need attention. Find a doctor that works well with your age group and ensure you act on their advice. Expect metabolism to slow down and hence, to eat less. If like me, you were working in a “fun” company with lots of options to “socialize” aka booze it up, take the opportunity to cut down on the alcohol intake in your retirement. You’ll feel better and add years to your life.
Start showing up. Remember all those things you had to skip because you were busy with work? Now you can go. Just be sure you have good governance in terms of how many things you say yes to. Many retirees report being “busier than ever!!”. Maybe that’s true for the social butterflies. Isolation among seniors is also a chronic problem so if you are on the more introverted side, make sure you have strong social connections whether its through family, volunteering, church or neighbors. I was never much on talking to neighbors while working, but in retirement I have gotten to know a few of them. They’re surprisingly nice.
Return to, increase time spent in, invest in – the spiritual component of your life. Face it, your time on the planet is finite and by the time you arrive at retirement, you will notice that time spent goes faster. My friend Ken would say “life is like a roll of toilet paper, the more you use the faster it goes!” If you believe in the almighty, start spending more time reaching for, learning about, reading about and imitating – the almighty. If you don’t, find whatever means you can to embrace whatever it means to leave the planet better than you found it.
So, current and future retirees, that’s my take on the subject of retirement. May yours be simply a transition into different, more enjoyable, rewarding and meaningful “stuff’!
Bonus: for those interested in finding meaning and purpose here are a few organizations I love that you can investigate for supporting, volunteering and even board work: Guardian Angel Settlement Association, Starkloff Disability Institute, Joybound People and Pets, Catholic Charities of St Louis, La Salle University

One Response
Steve, as always, thank you for the wisdom transfer. Healthcare is daunting, retiring pre-Medicare, but the value of time feels like a greater reward.
Another awesome article thank you!
/Brett