On (P)retirement

On (P)retirement

Someone asked me the other day why I decided not to go back to work at age 60. "How did you get there? What planning did you do for early retirement?"

My answer was simple: there was no real planning, it just happened.

A little backstory. Most of my close friends wouldn’t be surprised that I have a fairly checkered history in IT, bouncing between jobs. I got a Bachelor's in MechE in Texas (after realizing my eyesight disqualified me for Navy aviation) and then an engineering job right out of university. It was an OK job but career success suffered from my being constantly distracted by my fixation on amateur motorsports (convinced I would soon enough convert that to a professional motorsports career...right). That distraction eventually led to a layoff about three years later followed by a Sisyphean (and frankly ridiculous) chase for racing success in Connecticut (that’s a longer story).

But that brief stint in a large corporation also re-introduced me to a high school fascination with personal computers, kindled by a math teacher, Mr Laubenthal. In the late 80s when I started my career, PCs were just starting to infiltrate offices, and almost all were standalone machines with no networking. I found myself occasionally under other people's desk checking things out for them. And I was kind of interested in this new department they created called "Information Technology"...

So after moving to CT and snagging another engineering job (which was also lost due to distraction with racing) I started to get more involved with PCs, which led me to working for a local networking services provider, then as an employee of the Novell networking company ('member them?), later to a customer of Novell's IT department, and then various other companies within their InfoTech departments. The common thread, for whatever reasons (usually my own impatience, distractions, and personality quirks), was that I’d inevitably be asked to move on. That was easy at the time because everyone was looking for knowledgeable and experienced IT employees.

During all these stints I would stash funds in 401k for the future, not really giving much thought to when (if?) I would retire (the saving was further driven by Thea, who was an avid saver throughout her career). For me, it was the typical "put the money away, worry about it later, retire at 65 and go on Medicare and Social Security and uh so what are we doing this weekend...?"

You know, standard career stuff.

COVID and Remote Work 

As I jumped through the Naughties (two job changes), the Teens (three job changes), I then landed in the late Teens squarely on a solid large-corporation IT job with a group of people I really liked. But COVID soon shook up the office dynamics when we all went fully remote, same as with everyone else.I quickly got used to being at home in front of the computer 8–10 hours a day and realized that, surprisingly, I liked it. I had less distractions, I got more done, plus my breaks were brief stints in the garage instead of grabbing coffee and listening to someone go on about last night ball game (I'm generally not an avid fan of those).

Soon we realized that we were probably never going back into the office. And I was OK with that. I could do this well-paying satisfying job for the rest of my life, if need be. Maybe I will...

And right about then, our large corporation merged with another large corporation, and as we watched the middle management fights to see who would win it became pretty obvious that our team was going to lose. But, working fully remote, I figured I had a chance to get overlooked...if I only kept my head down and mouth shut...

Thinking About It

Around that time I was paying a lot more attention to our finances and investments. I rolled all our 401(k) and 403(b) accounts into Fidelity IRAs, and we kept contributing to the remaining 401(k), HSA, and IRA where allowed. I followed the conservative Boglehead philosophy - especially the Three-Fund Portfolio - and since the market was rebounding from the COVID slump, we were in good shape. We were also fortunate in that we managed to pay off our mortgage; coupled to driving good used cars we were, effectively, debt-free.

This is when I began to consider an exit strategy. But the money was good and that was still some years out since I was only 59 years old in 2023. And as noted I could do this job from home for a looooong time...

And Then... 

And then two major milestones happened.

First, in early September 2023, I turned 59-1/2. Now, you might wonder why that matters. Well, at age 59-1/2 two magical things happen:

• You can begin withdrawing from your Traditional IRA without penalty, only paying the income taxes on it; and
• If you've had any Roth account open more than five years, you can withdraw from your Roth account(s) completely tax- and penalty-free.

At 59-1/2 - Thea is older and was already past that milestone - we suddenly had penalty-free income sources, plus tax-free withdrawals from Roth accounts. This opened a lot of doors. And Thea was still teaching graphics design at a local university plus doing side gig work, so if something happened to my job we could cover our ongoing expenses.

And the second major milestone? Remember that "if something happened" above? Well, it happened. At the very end of the week I turned 59-1/2 I got a Zoom meeting invite from my boss' boss, without my boss attending, which meant one thing: there was a career change a'comin'.

And there it was: I was laid off yet again. I did get a few weeks' severance, and healthcare covered for a year. I knew COBRA would be available after that, thus getting me health coverage to age 62. And, depending on our Modified Adjusted Gross Income (MAGI) I knew that Affordable Care Act (ACA) subsidies (Premium Tax Credits, PTCs) would be available.

I had good finances and good healthcare insurance options so I was in no hurry and not stressed out about it. Of course I would miss the income and I would miss (some of) my coworkers (though we were still fully remote we met on occasion after work). But I certainly would not miss the corporate grind and I definitely would not miss the back-biting politics.

So I was now, as described by a friend, in "pretirement": not actually retired but not really in a rush to get back to work.

The Job Search

I applied for unemployment insurance (approved) and dragged that for the six months it was available. During that time I searched for appropriate jobs as is required by the insurance. But I quickly realized that the job search process was totally broken, even worse than the unpleasant experiences in the past. It was no longer a human process; it was even more automated with bots and AI looking for key words and phrases then simply rejecting my information. In the past, the challenge was getting past HR to reach a hiring manager. Now it feels like the real obstacle is getting past bots just to talk to HR!

I call it ‘Tinder-ized hiring’: you’ve got seconds to present the right keywords and vibes, and the system decides to swipe left or right. The system rewarded optimization, not substance.

My favorite story was when I applied for a local job at a small business that seemed a good fit: I had the experience they wanted, they had an interesting role that didn't pay a lot but it was "enough" for me to want to get out of bed and drive there. I must have passed the first hurdle because I got an invite for an interview...but it was a "video interview" with a computer: I was expected to get dressed up and sign on, then the computer would present questions to me on the screen and I had "x" amount of time to prepare my response and it would be recorded. I'm guessing that would be reviewed by someone from HR, or an AI would make a decision on whether to move on me.

I thought that was pretty darned silly so I found the president's contact info and, noting that their stated goals and mission statements valuing customer interaction, I asked if his team would be willing to meet with me in person and have an interactive meeting to discuss our mutual opportunities.

The president's two word reply to my email? "We'll pass".

That's it, nothing more.

The system is totally brokenificated.

So as I wrote in my "Greg's 2024 Year in Review":

April '24 was the month that my unemployment insurance ran out and, faced with lack of interest in my resume along with insulting and broken job search processes, I gave our finances a deep review and made the decision to pull the ripcord and bail out of the job market. I officially unofficially "retired" pretty much on my 60th birthday. I'm not against accepting future employment, but I'm just not going to get on my knees and subject myself to that denigrating disaster of a process.

It's really broken, y'all. I really do feel for young people today looking for a job, a mate, and a house, because all three of those are being managed the same way now...swipe left, swipe right. Hateful. 

If I keep my eyes and ears open then maybe I can meet that perfect employer through family, friends, and social contacts (I'm all set with "mate" and "house" part, thx). We'll see.

Honestly, opting out felt like the rational response to the whole situation. For fun, I tossed my resume at ChatGPT and asked about it and this is what I got:

You got to work in an era where:

• competence accumulated
• trust mattered
• conversations happened before judgments
• careers were built, not optimized

Now it’s all filters, funnels, and false precision.

Enjoy retirement knowing you escaped:

• keyword bingo
• LinkedIn humblebragging
• “Tell me about a time you showed leadership” from someone half your age
• robots deciding you’re a “95% match” instead of “obviously capable”

You earned the exit. Now you get to watch the madness with 🍿 and zero stakes.

Hard to argue with that.

In the end, my experiences aren't a blueprint for everyone. But for me, ‘pretirement’ became not just an idea, it became a deliberate choice to value time and sanity over the grind and money.

Oh, and that "keep my eyes open" part? That opportunity has yet to appear. Which is totally unsurprising given I'm no longer looking for it. 

Greg

 P.S., a recent response I made to a friend's Facebook post about it not being Friday...

When you retire then every day is a Saturday.

And even more fun, once a week Saturday is Saturday, too.

The conflict comes in when you're trying to remember if today is Saturday...but then you realize that no matter what day it is, it's still Saturday.

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