I still remember the day I officially retired. There wasn’t a marching band, no confetti cannon, not even a cupcake in sight. It was quiet, oddly anticlimactic—and yet, in a strange way, completely perfect. It felt like taking a deep breath after holding it in for forty years. Retirement didn’t hit me all at once. It came slowly, like a sunrise creeping over the horizon. But let me tell you, getting to that peaceful moment didn’t happen by chance. It took planning, reflection, a fair bit of paperwork, and a whole lot of coffee. Of course, working from home made it quite a bit easier since I wasn’t around others to see my expression of glee while planning my ultimate exit.

If you’re reading this and thinking, “I’m almost there, but I’m not quite sure I’ve covered all my bases,” then you’re exactly who I’m writing this for. I want to walk you through the steps I took before I retired—the real ones, the ones that made a difference. I won’t sugarcoat it or pretend it’s all beach chairs and piña coladas (although those do have their place). Instead, I’ll share what actually helped me prepare for retirement in a way that made it not just financially secure, but personally meaningful too.

Let’s start with the obvious, and most anxiety-inducing step: money. I know, it’s not glamorous. Nobody wakes up excited to make a spreadsheet. But getting a clear picture of my financial situation was the very first thing I had to do. I had to sit down, dig through decades of statements, and ask myself the big question: “Can I afford to stop working?” If I had a dollar for every time I ran the numbers, I’d have… well, a few more dollars in the retirement fund. All of those online retirement calculators really helped, but we still doubt the numbers sometimes.

I looked at everything—Social Security estimates, pensions, 401(k)s, IRAs, and that old dusty savings account I’d forgotten existed until it popped up during a deep dive into my finances. I ran my numbers through retirement calculators until my browser history looked like a financial advisor’s Pinterest board. But that helped me come up with a monthly budget that actually worked, one that accounted for rising healthcare costs, taxes (yes, you still pay those), travel plans, and even the occasional spontaneous splurge, like that fancy coffee maker I totally did not need but bought anyway.

Speaking of budgets, one of the smartest things I did was test-drive my retirement lifestyle. For a full year before I officially retired, I lived as if I were already retired. I followed the budget I’d set, cut back on work-related expenses, and tried to get a feel for how much I’d really need month to month. That little experiment was eye-opening. I discovered that I spent way more on eating out than I thought, and that cutting back didn’t feel like a punishment—it felt like liberation. Cooking at home became a kind of therapy (even if the smoke alarm occasionally begged to differ). Yes, things are much different once you finally pull the trigger though.

After getting my finances in order, the next step was tackling healthcare. If you’ve ever tried to read through Medicare options without falling into a coma, you know how daunting this can be. But trust me, it’s worth it to dig in and learn the difference between Part A, B, C, and D. No, it’s not some alphabet soup conspiracy, it’s actually critical. I spent time comparing plans, considering Medigap insurance, and calculating the out-of-pocket maximums I could handle. I even scheduled appointments with a few professionals who could explain things without using the HR legalese too often.

And let me tell you—getting those appointments on the calendar before retiring was key. I lined up a physical, got all my screenings done, and asked every “what if” question I could think of while I still had employer-provided insurance. It gave me peace of mind and made me feel like I wasn’t walking into retirement blindfolded.

Letting go of work came with another important—though sometimes overlooked—step: telling people. And I don’t mean casually dropping it into conversation like, “By the way, I’m leaving my job and never coming back.” No, this part took more tact than I expected.

I had to tell my boss, of course. That conversation was nerve-wracking, like going in to quit a gym membership but with way more emotion. I remember walking mentioning it during a meeting (one-on-one) and it wasn’t easy, but something that has to be done of course.

We ended up talking for nearly an hour. He thanked me for the years of service, and we discussed the transition plan. What struck me was how relieved I felt afterward. Saying it out loud made it real—and also gave everyone time to adjust, plan, and appreciate the closure.

That same clarity was needed at home, too. My wife had known retirement was coming someday, but not the exact day. So one evening over dinner, I dropped the news between bites of meatloaf. Not a big surprise, of course, the decision was pending for some time and she knew it.

Turns out, telling your spouse in advance gives them time to process what your being home every day might actually look like. Because let me tell you—retirement sounds romantic until someone rearranges the kitchen cabinets “for efficiency” and then forgets where everything went.

I also made sure to loop in my adult kids. I wanted them to know not just that I was retiring, but why, and what my plans were. I didn’t want them to worry, or assume I’d be free to babysit at the drop of a hat every Tuesday and Thursday.

These conversations weren’t just about courtesy—they were about connection. By letting my loved ones in on the change, I gave them space to support me, offer ideas, and also adjust their expectations. Retirement doesn’t happen in a vacuum. It affects the rhythm of everyone around you, especially if you’ve been the steady presence or provider for decades.

And you know what? Once I started sharing the news, something unexpected happened: people got excited with me. I started hearing stories, getting advice, and receiving invitations—“You’ve got to try pickleball now,” my neighbor insisted. “It’s like tennis, but for your joints.” Honestly, it helped me warm up to this new phase of life in a way spreadsheets never could.

Once my social calendar started filling up with well-wishers and friends pitching me hobby ideas, I knew I had to answer a question I hadn’t expected to be so tricky: “Who am I without my job?” I didn’t want to sit in front of the TV for the next thirty years, even if the couch cushions were perfectly molded to my shape. I needed a reason to get up in the morning—besides feeding the dog, though he certainly appreciated the new consistency.

To tackle this, I started experimenting before I officially left work. I joined a local writing group. I tried my hand at woodworking (jury’s still out on whether the shelf I built is straight). I even took a watercolor class where my painting of a mountain was mistaken for a blue potato. But hey, I was exploring, and that mattered. It reminded me that I was still curious, still growing, still capable of creating something from nothing. And that mindset made the transition feel less like an ending and more like a pivot.

Another surprisingly emotional but freeing step I took was downsizing. I didn’t sell everything and move into a yurt (though I briefly considered it after a particularly annoying electric bill). What I did was clean out the attic, purge the closets, and donate the things I hadn’t used in years. Less stuff meant less to manage, and more space—physically and financially—for what actually mattered.

I also made sure to have the awkward conversations—yes, those conversations—with my family. I talked about my will, power of attorney, healthcare directives, and all those other things most people avoid discussing until it’s too late. Was it fun? No. Did anyone cry? Maybe a little. But now my family knows exactly what I want, and that’s a gift in itself. The last thing I’d want is to leave them with tough decisions during an already emotional time.

And finally, I wrote a “Retirement Mission Statement.” I know, it sounds like something from a self-help seminar, but trust me it helped. I wrote down what I wanted my retirement to feel like. Not just “more golf” or “fewer emails,” but things like joy, freedom, curiosity, connection. That little piece of paper became a compass I still use. My memory isn’t what it used to be, writing things down really helps.

Looking back, I realize retirement isn’t just something you enter, it’s something you build. Like a house, it needs a strong foundation. For me, that foundation was financial clarity, healthcare planning, identity exploration, social connection, and a dash of humor when things went sideways. I won’t pretend I got it all right on the first try, but I gave myself permission to figure it out as I went. And that made all the difference.

So if you’re on the edge of retirement and wondering whether you’re ready, take heart. Preparation isn’t about perfection. It’s about intention. It’s about showing up for your future self with the same energy you gave your career for all those years. And trust me, that future self? They’ll thank you probably from a beach chair, piña colada in hand. Or whatever your favorite drink may be!