As a person who is contemplating early retirement from my career, which I define as retiring before the age of 60, I have decided to ensure that I fully understand the why of my decision to retire early. I do this for the reason that I want ensure that my purpose is strong enough to carry me through what will surely be some ups and downs of choosing to walk away from a lucrative corporate job at the age of 57, as I plan to do. I’ve found in life that having a strong why for doing anything complicated or difficult is central to the prospects for succeeding and being happy with whatever life challenge one chooses to take on. I’m also aware that there are many people who have expressed regret about retiring at a certain point in their lives due to it leading to boredom and a loss of the general direction that comes with maintaining an active career. I certainly don’t want that to be me.
I’ve done some research on the demographics of retirement and one thing that I was surprised to find out is that a good percentage (about 25%) of people who consider themselves retired are under the most common retirement age in the US, which is 62 (and driven by the fact that 62 is the first age when a person can claim Social Security retirement benefits). There are a good number of people in government jobs (including the military, teaching and first responders) who are able to claim a full retirement after 30 years of service. Some of these people may choose to take a different job to supplement their pensions but a good number choose to just be retired. There are also people (my mom was an example of this) who have served for many years in corporations and are offered exit “packages” during their 50s that make retirement possible. Still, retirement at age 57 as I’m contemplating is considered by many people to be early. It’s good to know that I’ll be far from alone though.
Why The Heck Not?
My why in terms of early retirement is represented by a series of desires, rather than the simple desire to not work for a living anymore. I think that’s a very good thing because a deep why will instill a deep commitment to my purpose in life post-career. More than anything my desire is driven by the fact that (by the time I’m 57) for 36 years roughly 70 percent of my days (I’ve worked on this calculation) will have been dictated by my career. That’s a very long time and could represent close to half of my life when all is said and done! It’s really more than that actually because I started working when I was 12 years old delivering newspapers seven days a week and steadily held part-time jobs from then till age 21 when I graduated college. So I’d like to have full control of my days as much as that is possible. And I do have plans for those days. I’d like to focus more on cultivating my physical and mental health. I’d like to focus more on improving my relationships, including the relationships with my daughters. I’d like to learn about what I want to learn about. I’d like to create what I want to create. Finally, I’d like to be able to travel, going where I want when I want. Writing it out like that sounds like I want a hell of a lot out of this life. Should I? Why the heck not?!?!
There’s a price to pay for such freedom and it’s one I’ve been paying for years via my hard work, planning and conscientious saving and investing. I have lived in places smaller and less fancy than ones my salary could afford. I’ve driven the same car for 18 years (and counting). I’ve eschewed getting a new smartphone every year like many people do. I’ve certainly enjoyed extravagances here and there (mostly around travel) but I’ve paid my early retirement bill up front so far by living modestly compared to my income. Now there must be a yang for every ying and each coin has two sides. I feel that my sacrifices must be honored by enjoyment of the riches I’ve accumulated. Not massive or great riches mind you. But modest riches that I think a smart person could manage to make last for at least my lifetime. Based on how things are going now I could certainly be tempted come age 57 to keep pushing and growing my riches into the multi-millions. The way I feel now though is that every year retirement is deferred that it will end up being a year that I’ll regret because there are things I can do well in this season of my life that won’t be so easy to do in later seasons. I would also have regret at a later time to have the money to do things but not the energy or desire to do so.
Pretend Life Is No Way To Live
So I feel like that by the end of next year (2026) the timing will be right for me to embark on the next phase of my life journey. I expect that my budget and savings will be in such a place that will allow me to support myself not only on a basic level, but at a level where I’ll be able to do some world travel each year. Of course, plenty of my goals can be achieved right at or close to home but for me the urge to wander is also strong. I’ve always felt good satisfying that urge in my life. A person needs free time to wander well though. In 2024 I embarked on what I called a pretirement (or sabbatical, if you wish) for seven months, receiving partial pay and benefits from my employer at the time. That free time stoked my desire for a full retirement as it showed me the possibilities of having more free time.
I very much enjoyed not having to deal with sitting in front of my computer for hours a day performing (what I consider at least) menial tasks and responding to a myriad of issues and problems related to my job. I enjoyed not having to manage out of the blue urgent requests from my clients and co-workers. The two business trips I’ve been on haven’t done anything to dissuade me from wanting early retirement either. For me the excitement of a trip is so much more satisfying if I’m setting the itinerary on the other end. The business trips I’ve taken so far in 2025 put me back in familiar surroundings that I still find to be quite depressing. For the most part it’s the same people and the same conversations in environments (like massive, frigid hotel ballrooms) that offer nothing in the way of genuine stimulation. So I sit there and pretend to be engaged and pretend to be very interested in the presentations and conversations. But pretend life is no way to live at all.
Why Still Needs A Strong How
One of the most important aspects of my preparation for early retirement has been centered around financial preparedness. I’ve been living on a budget for years, saving and investing, and paid off all debt…including my mortgage. My plan, at a high level, is to have saved $225,000 (or more) outside of retirement accounts to support myself from age 57 to age 60. (After age 60 I can draw from my 401(k) retirement account, which stands now at more than $1.1 million.) $150,000 of that will be to cover my $36,000 per year ($3,000 per month) essentials budget and $14,000 per year for travel and leisure. The remaining amount will be my emergency fund. The one aspect of my early retirement budget that will likely cost the most each month is my health insurance. Leaving my job means that I essentially have two options with regard to health insurance. One is to continue the health insurance from my job, which I’ll be entitled to do for up to 18 months but at my own expense (between $800 and $1,200 per month). Another option is to shop for private health insurance which could lead to me needing to change my doctors right way and could be more expensive. The thing is that, as with just about all working people, my employer covers most of the premium cost of my current insurance. So even though the continuing insurance is a convenient option it’s also expensive. Unfortunately in the realm of health insurance finding inexpensive options can be a bit complicated. There is a possibility of procuring affordable health insurance via HealthCare.gov since my income will surely be less than $60,000 per year for the first few years of retirement.
Other aspects of my life that I have to arrange in order to successfully move into early retirement are in good order. I live in condominium that is 100% paid for but certainly costs money to live in. Association fees are headed towards $600 per month next year most likely, insurance is $100 per month and rising, and taxes are about $250 a month and undoubtedly rising. Just under $1,000 per month to keep the roof over my head is fine for now. Certainly better than any similar rental so I don’t have any moving plans in the near future. Thankfully I’m still in very good health and feeling fit, although age has taught me that there are more aches and pains in addition to occasional ailments that can slow me down. While I’m grateful for health the thought that health fortunes could change continues to drive my desire for early retirement. Certainly as I’ve traveled I’ve encountered people much older than I am traveling extensively. I’ve always thought that it was nice that they had the energy while reminding myself that travel just becomes more difficult with age. For years I’ve been one to delay gratification in order to achieve greater goals but now I recognize that the time must come to take advantage of the fruits of ones labor.
The Property Dilemma
While the situation with my condo is good for now I do wonder about the future. The costs to live here concern me so I’ve gotten involved as a condo board member which has added to my headaches. There are a steady stream of important issues to be addressed and now matter how the board addresses those issues some people will be unhappy. Part of the why of my early retirement involves easing general burdens that add stress to my life. While living in a condo is definitely less stress than having owned a 74 year old home there are stresses, and issues related to being involved with the board are certainly part of that. I could easily resign from being on the board at any time and that’s something I will consider in the future. Likewise, there is the option to sell my condo in the future and go elsewhere. But where? The truth is that the years I’ve lived in apartments have been largely stress free ones. Renting in the right place could be an answer and early retirement would be a wonderful time to have the time to research more affordable and more desirable places to live in the long run.
One pitfall with rentals is the fact that the cost will go up every year and in the long run it’s not a good investment. You’re also subject to the rules of the landlord about how you can decorate your home, etc. Frankly such rules have never bothered me since if I don’t like the environment of an apartment as it is then I just won’t rent there. Rent can’t be recouped but then again neither can HOA fees, insurance costs and real estate taxes, all of which are ever rising as well. At a certain point in life perhaps it’s worth it to cash out of a property and amortize that money over many years with the idea of covering the cost of rent. It’s something worth considering and looking into. So I’ll add to the why of my early retirement the opportunity to take the time I need to research and find a more ideal place to live.
One way or the other I know that I do want a home base that‘s mine. Some people get the big idea to sell their places and live a vagabond lifestyle traveling from place to place. Others fully expatriate and set up shop in foreign countries. I’ve already thought through these possibilities in my mind. While they sound wonderful and carefree they also create problems that are not easily solved. Such as the need to have a street address where you can get mail for banking and tax purposes in particular. You also need a home base near medical providers that accept your health insurance, and that you can use for an extended period if you should require treatment for an injury or illness. There are reasons beyond that but those are the most important ones to me. One thing the “snow birds” that come down from the Northern US and Canada to Florida have shown me is that you can live between two places for months at a time. In my mind that’s preferable to attempting to go with no fixed address or attempting to permanently reside outside the US.
In Conclusion
The one thing that cannot be denied in terms of a reason for early retirement it has to do with time. You cannot make more of it. You can only enjoy the time that you are gifted with in this life as long as you have it. I doubt that years from now I’ll have regrets about early retirement that would include things like wishing I worked for more years. It’s much more likely that I would regret working for more years simply to add to an already healthy fortune. For me the time is now to prepare for the time in just 18 months when it will be time to move to the next phase of my life where I set the agenda and tempo of life.
In The Midst Of A Journey 