Semi-Retirement

Mike Peluso
9 min readDec 11, 2023

We have a thing here in Chatham County, where I live called “The Chatlist”. It’s an email listserv that’s been around forever. It survived over the years where other listserv’s have disappeared or been replaced by newer tech, I think, because, it’s amassed a good deal of users who depend on it as it’s so specialized. It’s got a narrow focus on the county, and only the county. Any topic that’s not specific to the county isn’t allowed. The Chatlist serves as everything from a platform for political debate, a locals support group, a referral network and once a week it becomes a swap shop where all manner of products are sold. I’ve seen everything from vehicles to farm animals up for sale in the weekly ‘Friday Classified’. In some places people give away things they don’t need anymore but which still have value. This particular week, that’s what I used The Chatlist for. I was giving away some older Amazon Fire tablets that I didn’t really need cluttering up my house, but also didn’t want to throw away. One of the tablets was picked up by a guy for a special needs family member. Of course, being a rural county he stayed around and chatted with me about a great many things. It was when we started talking about semi-retirement that the conversation turned out to be very interesting indeed.

At first we chatted about the tablet and the way the person who it was intended for could use it. We also talked about our careers and current status. We had a lot in common which was a surprise. We both worked in technology in the early part of our careers. We had both gotten sidelined multiple times by the undulation of the greater economy and the machinations of profit-driven tech executives. We both walked away from the high paid tech industries and transitioned to the public sector. Unfortunately that meant we both took a huge pay cut as part of that process. We also both were looking at a semi-retirement period in our life. The big difference was that he was already there.

That meant I could pick his brain as to how he managed everything. In his case he had the benefit of family land which I assume he inherited. He was putting in a ton of sweat equity to get the land to the point where he could live there full-time. He had gone the route of the 401k for retirement savings. I found this fascinating as he had the option of taking part in the state pension plan, but chose not to. My assumption was that he was socking a ton of money away. I say that because when we discussed it, he started talking about how he didn’t like the potential to lose the money in the pension system if he died young. That makes sense because that’s what a pension is, i.e. it’s annuitized retirement. The entire purpose of that sort of retirement plan is to make sure those that survive far into old age don’t run out of money by leveraging the contributions made by those who passed earlier in their life. If you were putting an especially large amount of money away, then I could see where he would want to maintain control over that cash. I, on the other hand, think that the 401K is only one piece of a good retirement program which also includes a pension, and social security.

He was still working at a traditional job, albeit part-time. When we got onto the subject of healthcare, he agreed wholeheartedly that it was one of the bigger issues when it came to semi-retirement. He was just under 60 years old so he doesn’t qualify for Medicare yet . That meant he had to be getting his healthcare from somewhere. He didn’t share if he got it through his time with the state or if he was purchasing his healthcare independently. I guess it also could have been provided by a spouse.

So looking at his situation, he was eliminating the high cost of his current housing situation. He was leveraging some sort of healthcare solution, and he was using his time in his self proclaimed semi-retirement to work on his plan to turn the family homestead into a low cost housing solution and a cash generating small business. Calling what he was doing semi-retirement is almost a misnomer. he was busting his rear end working full time, just not in a traditional job.

In my blog and in my podcast I have spent a good deal of my time talking about traditional retirement. I’ve not spent a lot of time talking about semi-retirement. This conversation got me thinking about it. As it stands now, I have a vague notion that I will leave my current job as soon as lifetime healthcare kicks in. Then I’ll claim retirement, start collecting my minuscule pension from the state, and then go out and get a higher paying job with a for-profit entity until Social Security kicks in. At that point my wife will be close to the time where she can collect lifetime healthcare and start her journey into semi-retirement. That seems like a pretty good plan to me, except that it’s not specific enough.

The points are there, it includes having a guaranteed income (pension) that may not be enough to cover all my bills, but takes a big chunk out of some of them. Semi retirement also includes not having to worry about benefits so as to have great flexibility in what I choose to do. Thank you state retirement health plan. It includes work that closely matches what I need from a work life balance. It’ll last anywhere from 6–11 years or more of my life so this plan has to be pretty specific.

It took me about a decade to move from the private sector to teaching at a community college.

Considering what I know about career transitions, the kind where you don’t hit the great reset switch, that seems about the right amount of time. This means I should be looking at that semi-retirement transition and working on it now with a more concrete plan.

I know I don’t want to continue to work for the state, if only because the way their pension plan is structured, my retirement payments stop if I earn too much money. Naturally continuing with the state is the easiest solution as I’m already in the system. I can just claim retirement, wait six months per the state regs, and then come back and teach as an adjunct. I could also leverage my older workforce background and come back to the state working in that system. I can’t forget that the limitations on my income with this plan also limits growth in my quality of life.

Considering everything that I’d have to deal with sticking with the state for the semi-retirement period of my career, it’s why I came to the conclusion that the better option is to move back into the private sector. There are still many questions with the private sector option. Do I target an education tools provider? That would be very easy as I’m both a technology sales and service guy. At the point of my semi-retirement transition I’ll be heavily experienced with all the current educational tools, which are heavily tech based. This plays right into my strengths. The problem here is the income levels. Educational tech provider incomes are not nearly as high compared to other tech oriented positions. I think it’s because the pay ranges are more aligned to the education industry where these companies pull a large chunk of their workforces from.

I could go full on corporate by targeting one of the big tech firms in my area. These include Lenovo, VMware, CISCO, and SAS among others. Realistically, to do this, I’d have to spend my time over the next ten years developing the skills and knowledge they require. For example, linux is a huge deal in the corporate world and I honestly don’t know much beyond the basics. So is working with one of the major cloud providers. If I do decide to become an expert in these topics, so I could easily move into a position like a sales engineer, I’ve got a decade to do it. Considering where I work, I can learn a lot in that time. Yet, I can’t forget that this option is really more full-time and not semi-retirement. It’s a ton of work and stress and doesn’t give me any sort of flexibility.

I could just buy my way into something completely different. I could go into business with something that’s pretty much a guarantee to work, but maybe not a guarantee to make big bucks. As I’ve written, I love watching Discovery Plus. I watched a video where a couple purchased a small island in Panama that had a little bar area already built out. They turned their island into a refreshment stop for boaters. I liked that idea. It’s a bit like what people here in Chatham do. They buy, or as my new friend did, inherit land, and work it in unique ways, like turning a chicken house into a venue for things like weddings.

Speaking of that specific semi-retirement gig, something like that is exactly what my wife wants. She likes the idea of owning a venue. It’s minimal day to day work relative to owning something like a restaurant, but if you can make the investment, it offers a considerable payout. The challenge there is the investment needs to happen now to make it a reality in ten years. I’m completely open to this idea, even if all I’m buying is desirable dirt I one day hope to develop. For a brief second I thought about buying a franchise as a viable option, but when I do that, especially if it’s retail or food, It’s like I’m working for corporate america as those types of franchise operations come with lots of issues, they require a 24/7 commitment, and no matter what the franchise broker says, there are questionable returns for your investment.

Semi-retirement is as complicated of a transition as any job change. I used to say that the day you get a job you start working on getting your next job. That’s how I feel today, only it’s a bigger change. I need to plan the next phases of my life. I have a template but now I think I need something that is much more concrete. To make matters more complicated it has to fit around my wife’s career, which, unfortunately, has a ten year delta from mine. I’ll continue to work on it and hopefully in a year or two I’ll have started to build a solid foundation for the next phase of my life. As far as moving forward with my next plan, maybe I just need to give away more things on the chatlist. If I do that I’m sure it’ll allow me to meet more semi-retired folks who would be happy to help me along on this journey.

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Mike Peluso

Mike Peluso writes is about the collision between the professional world and life. Read more at www.pelusopresents.com or listen to the Peluso Presents Podcast