P4R - Planning for Retirement

Sometime in 2025, I started thinking seriously about retirement.  

I had always known, of course, that I wanted to retire some day.  For many years, when people asked me "when are you going to retire?" I'd say something along the lines of "I don't know.  Maybe in five years?"  And as each year passed, I'd answer the same thing. "Five years."  I think I said that for at least five years.

Early in 2025, I realized the answer had changed.  I realized I was definitely going to retire by the summer of 2028.  Then, as 2025 progressed, it seemed more likely that my retirement would probably be in the middle of 2027.  And so, in mid-2025, realizing I had only two years to plan, I started planning for retirement.  (This has resulted in a series of posts about my thinking, my process, and my experience. P4R = "Planning for Retirement.")

Planning - It's Part of Who I Am

One of my core personality traits is that I am a planner.  I anticipate what the future might look like, and how I can be prepared to meet that future.  I create lists.  I use those lists to guide my actions.  So, as I said, when mid-2025 rolled around, I realized that a Big Change would be happening, and I had better plan for it.

I'm writing this now, more than six months after I started planning, but only six months before my plan will take effect.  (Spoiler Alert! 2026 is the new retirement year.). I hope to use this series of blog posts to record what I did, and why I did it.

P4R - How I Began

As I wrote above, it's been about half a year since my planning began, but what I remember is this. A switch went off in my mind, telling me, really and truly, when I looked ahead at retirement I could count on these facts:

• I'd have 10-11 hours on every weekday that were not going to be taken up by a career or making a living.
• I like time to myself - it's one of the aspects of my job which I appreciated.
• Sherry also likes time to herself.
• I have quite a few activities which I like to do on my own, and I have had very limited time to devote to these activities in recent years.

With those realizations in mind, I first decided I would benefit from planning my Retirement Day. That is, looking ahead to that first day, and then that first week, of being able to go to my Sanctum instead of going into my work office, what would I do with my time?  Or to put it another way?

• When 6:30 AM of the first Monday A.I. (After IBM) came - what would I be doing?
• For how long?
• And then what?

Oh my! My mind started getting excited!  I get to plan!  Not just fuzzy "some day I'd like to do X."  No.  A real plan.  And I'm a planner.  So, how do I make a plan for this?

In some ways, this challenge, this plan, was similar to plans I'd made for years.  

• I had a schedule to work with. 
• I had other people to consider. 
• I had limitations (though not many, when the types of activities I wanted in my schedule began to take shape.)

But in some key ways, this was different from other plans.  And the biggest difference?

• Goals

This is Not Trivial - and Not Big

See, in my life to this point, my plans, and the goals they served, were of two basic types: Trivial or Big. (Yes, there are goals in between. Let's not get bogged down.)

Trivial plans are the kinds we all deal with. Taking a trip? Make a list of what you need, where you need to be, when. That sort of thing.  The "goal" for a plan like that is pretty trivial to identify.  And they become second nature.  You can do them without much thought.

Big plans in my daily life were mostly


work related.  And in those plans, you need to have clearly identified goals.

But as I tried to plan my retirement days, I realized that what I wanted to get out of them -- what my "goals were" -- were neither Trivial, nor Big.  

My retirement days were too important to me to be treated as Trivial.  I knew I needed to put thought into them, or I would feel like I was wasting my time.  If I just said my plan for each day was "do whatever you want," I would spend too much of my time with indecision.  I've spent far too many "days on my own" vacillating back and forth between watching a movie, or reading, or watching an old episode of a TV show. And in recent years, that has meant I spent far, far too much time scrolling through social media, paralyzed by indecision and lured into mindless unactivity. I simply would not allow my retirement days to turn into that.

At the same time, I did not want my retirement to be used in the service of Big Goals. I'm not getting a second career.  While it's possible I might do something unexpected and Big (Maybe write? Maybe design a game? Maybe volunteer for some worthy cause?) I knew what my mind wanted most when I considered retirement was the relaxation and peace that would come from not working towards Big Goals. Other people are certainly wired to want more Big things post-retirement.  I am not.

So I needed Goals of a new kind.  Not Goals which had a schedule.  Goals that mattered. To me.  Goals that would give Personal Fulfillment.

And that seems like a good place to start a new post.  Find it here: Scheduling Goals for Personal Fulfillment

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Side note to you if you're reading this on blogspot: I am moving my blog to substack.  If you want to find it, here's the link: stwill24.substack.com/

Side note to myself: I feel like writing about my journey in this planning phase. I'm not sure who will read it, or who I expect to read it.  But I think I want to be able to go back and remember what this planning time was like. To relive my experience. I suppose that's a sign that I'm hopeful about the future; that I believe I'll look back on this process with satisfaction and some level of fondness.  Separate side note: I know I put "Restart Snippets & Wisps" on my "Goals & More" tab, and I know one of my favorite YouTube Retirement Advisors recommended journaling. Maybe both of those influenced my decision to start writing this account of my planning.