In February 2023 I took what my boss at the time called “an extended vacation” which was a 12-day Caribbean cruise that resulted in me taking nine work days off. This trip ended up being a catalyst for my desire to retire early (before age 60) rather than working full-time till at least 62 years of age, which is what I was planning to do up to that point. There were two general issues that lead me determining that early retirement would be right for me, one of which I confronted prior to the cruise and the other which occurred to me during the cruise. The first issue was the fact that taking nine work days off was considered (by my boss at least) as an extended vacation. The second issue had to do with what I witnessed with respect to the other passengers on the cruise.
The issue regarding the length of time I could take off from work definitely frustrated me as I planned to do something during that particular period in February 2023. As with most people, any kind of a real vacation just wasn’t possible in the years 2020-2022. Add to that fact that during those same years the stress level of my job had ratcheted up considerably. Because I was working at home all the time the expectation was that I’d be available for all kinds of hours and that an increased workload might even be a welcome situation to help distract from everything else in the world. I didn’t see it that way but that’s the way the powers that be defined the time. So by January 2023 when I started to plan my time off I really needed a getaway and not just for a few days either. A two-week vacation, something I hadn’t taken during my 11+ years at the is particular company, would afford me sixteen straight days (ten work days and six weekend days) to enjoy my time off. Sixteen days afforded me some nice possibilities for travel. It became clear to me during the early planning for my vacation that, due to my work responsibilities and my company’s lean approach to staffing, a full two-weeks was untenable. So I compromised and decided to start my vacation on a Tuesday and go through the end of the following week.
My experience attempting to try to work out a two-week vacation frustrated me for a couple of reasons. First, I was at the point where I was earning four-weeks of vacation per year in my then position at the company. Even though the leader of our company encouraged people to use all of their vacation time the reality was that people rarely used all of their time because the company hadn’t invested enough in training people to do multiple jobs. I’ve worked at other companies and this is a common approach to staffing. It helps the company’s bottom line but makes suitable breaks from work a difficult thing to work out for employees. Exacerbating the situation was the additional workload of the prior three years that had caused myself (and I’m sure many other people) to experience burn out like they never had before. The second reason was that the reality of vacation time while working is that most people are expected to take the bulk of their vacation when everyone else takes theirs, especially around Christmas, New Years and other holidays at the end of December. There was a time when this was fine with me since I was living with my small children and family travel occurred at times when the kids were off from school. I never preferred to travel during that time because just about everyone else in the world travels during that period and I didn’t enjoy the resulting stress. At this point in my life and career I prefer to take a few days off at the end of December but to save the bulk of my vacation for other periods of time when travel is less hectic and also less expensive.
I was frustrated by my inability to take two full weeks but I accepted the situation and decided to place a positive focus on the time that I could take. It turned out that the Caribbean cruise fit very well into that period as the cruise departed on a Wednesday and returned the second Sunday after departure. Since the cruise was departing from a port about 30 minutes away from me I could just take a rideshare to the port on the day of departure. Once I was on the cruise itself something else became very clear to me. Because of the time of year in between the end of year holidays and the start of school spring breaks the crowd on the cruise was largely older than me. The average age had to be at least 60 with many people aged 70 and older. During the cruise I had a lot of time to think and observe the people on this boat that had thousands of passengers. I made some acquaintances who I’d see at the breakfast buffet, at one of the numerous bars on the ship at karaoke or on excursions in different ports. The whole experience gave me a window on the reality of traveling at an older age, but really not that much older than I was (53) at the time. I saw a lot of people who moved slowly, including a good number who rented electric scooters to get around the ship. I saw people who spent hours per day playing cards in the buffet dining room. I saw people who spent hours every evening sitting at slot machines in the casino. I saw people who, after a week on the boat, coughed repeatedly due to respiratory issues. I found nothing wrong or offensive about any of this. All of those behaviors are a normal consequence of aging. I certainly don’t think that being over age 65 should preclude a person from traveling as they want to either. Being around that for eleven days made me realize how much better it is to travel at a younger age when the body is more resilient and you can be more active.
I thought about my situation at work and how that situation squared with my desire to travel to some very exotic places for hopefully more than just a week at a time. One thing I did envy a bit about the older retired people I met and spent time around on the cruise was the fact that they could choose the best time for them to go on any trip. I knew that as long as I was working a corporate job that I would be limited on my options in terms of timing of vacations. In addition, older retired people could choose longer trips if they so desired. I knew that as long as I continued working any trip I would take would be confined to maybe a week or week and a half. I realize that many people would do just fine in my situation and for years it was just fine for me. But as my age progressed towards my mid-fifties I began to feel as though I wanted to make better use of my time. To use my time as I saw fit. I didn’t want to suffer the stresses of years more working in corporate America only to have the freedom to travel and live as I saw fit another decade into the future. Who knows how stress and advanced age would wear on my ability to enjoy travel by then? As I was thinking about all this I started to write in a notebook that I had brought with me on the cruise and I came up with something I called Plan 55.
Plan 55 was a plan for me to work until the end of 2024, just after my 55th birthday, and then take 18 months off to destress and travel to some far away places. I knew that the cornerstone of such a plan would involve my finances. I’d need to have enough money in savings to support myself without a paycheck for 18 months. I didn’t know for sure while I was on the cruise whether I could make such a plan work but I started to sketch out a broad plan. The point where I started to work on Plan 55 represented a turning point in my vision of the near future. Influenced by the thoughts I was having while on the cruise I began to envision a future where my corporate career would be limited compared to the time I would spend focusing on other activities. There was a part of me that thought it a bit reckless to consider that I might be so near to the end of my working life. After all I wasn’t a multi-millionaire and I always thought that’s what it would take to either consider retiring early or to take an extended career break while still in my 50s. The reality was that I’d gotten used to a lifestyle that could allow me to live without a paycheck on the assets that I’d accumulated. While I wouldn’t be able to support an extravagant lifestyle I still would be about to afford up to $15,000 per year on travel. This was an important consideration since my goal was not to just stop work and sit at home.
Once I realized that a long break from my career would be financially possible that triggered a change in my mindset regarding the possibilities for either an unconventional or early retirement. A change in mindset often leads to new possibilities and that was true in my case too. Having seen how the proverbial other half (in this case older retirees) were living I began to explore my own version of that story, albeit at a younger age. My years of living on a budget, being frugal where it counted and investing for the future seemed to all at once make sense to me. To be honest, I wasn’t sure where all that was headed beyond building larger amounts of wealth. On that cruise I realized that I’d done well and that the best way to honor doing well financially was to live reasonably well. Something that’s hard to do if your life is dedicated to work into your elder years. My eyes were opened to these new possibilities on that cruise in February 2023. Eventually I took a seven month sabbatical in 2024 (which I dubbed a mini-pretirement) which in turn lead me to planning a full early retirement by the beginning of 2027. The pretirement decision is a story in itself that I’ll save for another time. My full early retirement plan is still a work in progress but one that I’m confident I can accomplish. More on that later as well. For now, you know the story of how I came to desire and begin aggressively planning for early retirement.
In The Midst Of A Journey 