
Mark Twain said, “Never put off till tomorrow what may be done day after tomorrow just as well.” Coming from a long line of procrastinators, that sentiment rings true. It was also my approach to retirement. I put off the decision again and again.
Until now.
After spending much of my career writing about retirement, I finally decided it was time to start living it. I assumed I was prepared. I had spent years researching the topic, interviewing experts and helping others think through one of life’s biggest transitions.
Then I turned in my retirement notice.
What I expected to feel was relief. What I felt seemed more like loss. The experience hit me much harder than I anticipated. In fact, I went through a brief period of sadness that caught me completely off guard.
Retirement looked very different in practice than it did in theory. For the first time, I realized that preparing financially and preparing emotionally for retirement are not the same.
When your identity changes
You can say labels don’t matter, but the truth is they do. For most of my adult life, I’ve been an employee, a writer, a colleague and a contributor. Soon, my title will change to retiree.
Am I old enough? Yes. Have I saved enough? I think so. Am I ready to become the smiling older man walking on a sandy beach? I know too much about retirement marketing to be on the cover of that brochure.
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What surprised me most was how much of my identity was connected to my work.
My office sits on the corner of a busy hallway. I only have to turn toward the door to see who is walking by. Throughout the day, colleagues stop in to share stories, kick around ideas, celebrate successes or talk through challenges. There have been plenty of laughs, more than a few crises averted and countless conversations I’ll miss.
Retirement means stepping away from more than a job. It means stepping away from a community and a daily rhythm that has been part of my life for decades. Recognizing the stages of change can help make sense of the transition.
In his Bridges Transition Model, researcher William Bridges describes three transitions people go through during major life changes:
- It starts with an ending
- Then comes the neutral zone, the period between an old identity and a new one
- Finally, there is a new beginning, ideally bringing with it renewed energy and optimism for the next chapter
Replacing more than a paycheck
I’ll miss getting a paycheck.
I’ve received one every other Friday for decades. Like an old friend, that ritual is comforting and easy to take for granted.
What surprised me is that a paycheck isn’t just income. It’s reassurance. Every other Friday, money quietly appears in my account and confirms that everything is working the way it’s supposed to.
Retirement asks you to replace not only the income but some of that confidence as well. That’s one reason many retirees build strategies around reliable sources of income.
Depending on individual circumstances, annuity products can help create a stream of guaranteed* income that works alongside other retirement assets and withdrawals. A financial professional can help you develop a customized strategy.
Learning Medicare’s lessons
I’ll be on Medicare.
After years of relying on employer-sponsored health insurance, I found researching Medicare to be a maze of parts, enrollment periods, deadlines and rules. A qualified insurance agent helped me navigate the process and reminded me that Medicare is anything but free.
Fidelity estimates the average 65-year-old couple will spend roughly $12,850 on healthcare during their first year of retirement. And that doesn’t include long-term care expenses.
The lesson is simple: Build room in your retirement budget for healthcare costs.
According to the Holmes-Rahe Life Stress Inventory, retirement ranks ninth — tied with marital reconciliation — among the 43 most stressful life events measured by the scale.
In my case, retirement is accompanied by a move, which is also on the list. While I’ll be closer to extended family, I’ll also be leaving behind a network of workplace relationships and social connections.
I’ll be looking for some new friends, and the best remedy is to get busy. Volunteering and community involvement are how many retirees build new relationships. Ken Dychtwald, founder and CEO of Age Wave, recently suggested society could benefit from an Elder Corps — something like the Peace Corps for retirees.
My own plans include joining Toastmasters, participating in a book club, spending time at a health club, reconnecting with my college alumni association and enjoying my son-in-law’s boat.
I should probably let him know about that last one.
The point is to actively seek connection and avoid isolation and loneliness.
I’ll get Monday mornings off
For years, the iconic ticking stopwatch from 60 Minutes triggered my Sunday scaries, shifting my mindset from weekend relaxation to work responsibilities. While I look forward to no longer caring whether it’s Sunday or Monday, maintaining a schedule can provide structure and purpose.
My father, who spent nearly 30 years in retirement, opened an antique shop after a successful engineering career. He didn’t sell much, but he had a place to go every day and a community of regulars and friends.
Turning a passion into a purpose can provide a reason to get up each morning while you’re still finding your footing.
Appreciating the gift
Advances in medicine, healthcare and technology are steadily increasing life expectancy. Longer lives are not simply adding years to the end of life — they are reshaping how people think about retirement and the opportunities it presents.
What I’ve come to realize is that retirement isn’t a single event, it’s a transition.
I’ve spent years focused on the financial side of leaving the workforce. What surprised me was how much emotional preparation was required as well.
From the moment people start saying congratulations to the realization that you’re now on your own path, retirement becomes a new life story.
Retirement marks an important new chapter of my life. The trick is to turn fear into curiosity and anxiety into possibility.
Like most meaningful transitions, it isn’t something you fully understand until you start experiencing it.
* Guarantees are backed by the claims-paying ability of the issuing insurance company.

