Staring Down Retirement

I’m in my mid-50s. I’ve spent more than 30 years in corporate America, and I’m officially staring down the barrel of retirement. More specifically, I’m trying to figure out when I can retire.

For most of my adult life, I’ve dreamed about the day I could walk away for good. I’ve attended countless retirement parties, smiling politely while quietly battling jealousy. I’ve openly judged the people who retired and came back as consultants. I’ve questioned those who kept working well into their late 60s and 70s.

But now that I’m approaching that long-imagined “finish line,” I’m realizing retirement isn’t nearly as simple as it looked from my 30-year-old vantage point.

Lately, I’ve been thinking about the reality of having every day — all day — completely open. Yes, I’ll sleep in. I’ll travel. I’ll work out more. But I can’t always be traveling. Sleeping in only fills an extra hour or two. A workout covers maybe another hour. The math doesn’t lie — that leaves a lot of unstructured time.

And unstructured time, without intention, can quietly become emptiness.

For most of my life, my thoughts about retirement revolved around money. The numbers. The spreadsheet. The “Do we have enough?” But recently, I’ve been learning about the less discussed side of retirement — the psychological and emotional side. The need for purpose. The need for structure. The need for community. The need for a reason to get out of bed.

I’ve never defined myself by my job. In fact, I haven’t even liked parts of it. But I’m beginning to understand that even if you don’t love your career, it still gives you identity, rhythm, relevance, and built-in human connection. And when that suddenly disappears, something shifts.

So alongside running the numbers with my financial advisor, I’m preparing in other ways.

I’m finally starting the business I’ve been thinking about for a decade.

I’m collecting real, old-fashioned puzzles for brain health.

I’m building a rhythm of junk journaling to keep my creativity alive.

I’m intentionally nurturing relationships outside of work — the ones I’ll lean on later.

And maybe most importantly, I’m learning to appreciate what my full-time job gives me right now: steady income, health benefits, a 401(k) match, structure to my days and years, a sense of contribution, and daily interaction with other humans.

I’m also softening.

I no longer judge colleagues who work well into their 70s. I no longer roll my eyes at the retiree who comes back as a consultant.  It may not be the path I choose but I understand it now in a way I never could at 35.

Retirement, I’m learning, is deeply personal. Circumstances vary wildly. Desires evolve. Identity shifts. 

And that understanding feels like growth.

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