Retirement Revisited

Despite my young age, retirement has long been a fascination of mine. Perhaps this makes sense given my interest in many topics generally associated with older demographics, but even since my elementary school days I’ve been thinking about the myth of retirement. Of course by “myth” in this context I don’t mean that retirement isn’t real, but that it’s a highly motivating story fundamental to humans almost everywhere. Having ample time to research and daydream in school, given how little it engaged me, I questioned many of the assumptions and stories proselytized to us by our friends, family, and society as a whole. As assumptions often tend to when scrutinized, many of the mainstream ideas floating around in my head began to make less and less sense. From the idea that going with the crowd produces extraordinary success, to the idea that eating milk, grains and small amounts of meat constituted a healthy meal for everyone (or perhaps anyone) retirement was simply one of many ideas that fell apart. In saying all of this, I don’t mean to give the impression that the most orthodox inputs never produce successful individuals, but that the inputs may be detracting rather than adding. In any case, what the hell am I here to talk about? What I’d like to do, is attempt to share a different way of thinking about retirement and the surrounding assumptions that seems seldom visited.

Very often the reason we feel stuck or continue to engage with habits that we know aren’t serving us, is because we haven’t taken the time to break down where we are making leaps of logic. If we assume that only special people can be graced with the opportunity to love their work, for instance, we are unlikely to set loving our work as a goal. I’ve definitely talked about this sort of logic a fair amount on FourthEye, but as always the most important step is creating a system to routinely question assumptions. When I feel worried or stuck for longer than I would like, I now turn to performing a handwritten Q and A introspective. I try to ask myself cutting questions that I might be avoiding, and start with the central question of “, what am I afraid to feel?” Once I ask that foundational question, it becomes clear what I need to ask myself. Funnily enough, it’s often the case that we already know the answer to certain questions, but writing can help us drill down on exactly what we feel and figure out next steps. I find that handwriting works well for me, because it establishes a stronger connection, but do what is most comfortable for you. The most important thing is to follow the routine, not necessarily for the routine to be perfect. As an example question I might ask myself “, what assumptions am I making, that might be creating unnecessary anxiety?” and then I dig deep to answer the question as best as I can.

Now that we have the preliminary step out of the way, let’s talk about some common assumptions or stories around retirement. One of the biggest things that broke the spell for me, was the idea that I should delay gratification until I’m 65 or maybe 55 if I’m really special, and simply hunker down and save until the fateful day. I don’t know about you but the idea of making a contract with myself to be unsatisfied until I reach a far off point in the unpredictable future strikes me as a tad crazy. I understand that this picture of retirement comes from an age when things changed much more slowly, but in the current moment such advice seems to almost guarantee disappointment. What if instead we got specific about what sorts of things we’re looking forward to, so to speak, so we can incorporate more of them now? One sample question I came up with is “, what would I do if I were 65 today, with the body of a twenty something, and was financially free?” The reason I ask such an odd question is because it helps me to remove the constraints and potential excuses, and makes me take a second look at my so called “ultimate goals.” This isn’t about reverse engineering by the way, although that is a bonus, what I’m suggesting is identify the things you would do if you weren’t too busy, too out of shape, or too financially constrained to do. Maybe your dream scenario is living in the bahamas, and writing cookbooks for your favorite Thai cuisine, while indulging your family to some white sandy beaches (I don’t know random example). How much does this dream scenario really cost? What would you be willing to do, or sacrifice, what have you, to achieve that goal sooner? While I’m not a proponent of building sacrifice into goals, that part of the question helps identify what things we are most willing to ditch. There is so much value in getting insight in to what things you really care about and that bring you joy, versus what doesn’t make the cut.

The final big idea that I want share in this article is how to build our best futures today, instead of “eventually.” Full disclosure, I’m not saying I’ve reached all my goals yet as those are what keep me going, but I actively work to create a life I love today, while still making smart choices. Essentially, I’ve been thinking that a huge factor in when we really get to retire is mindset. No this is not meant to be woo-woo, or a cop out, I think that retiring early is actually a matter of a mental shift. I’ve been experimenting with essentially pretending that I’m retired, no not to other people but mentally, so that when I encounter certain stressors, for instance, I worry much less. Why would a retired person be worried about running out of hours in the day? Why would a retired person be worried about going to meditate on the beach in the middle of the week? This probably sounds a bit weird, and you may be thinking, “Not everyone can do XYZ dude. I’m too busy, have dependants…” I never want people to neglect important obligations, I want people to question “have to’s” or “can’t do’s” and win back their time, freedom and energy. What I would really like, is for as many people as possible to do what they love and create a life and schedule that works for them, instead of against them. Not only would those individuals be happier, but the increase in productivity and positivity would be distributed to the world around them. If you took on the “retired mentality” today, there might be lots of doors that you would open for yourself, and others you would voluntarily put behind you. In this version of retirement, we aren’t being idle, we are actively seeking out things we love, and doing all the things we planned to put off for a few decades until the “fateful day.” Things like self care, managing investments, regularly visiting your favorite town or place, and spending more quality time with friends and family. As I’ve said before, there is no divine verdict on how happy, rich or free we should be. Those decisions rest in our hands, and have to be created intentionally by having a clear plan, and plotting out our various assumptions.

Anyway, as usual there is plenty more to talk about on a topic like this, but I’ll leave it here for today. I hope you found this useful and I’d love to hear from you what questions you really need to ask yourself, but maybe have been avoiding. Post in the comments below, as I enjoy engaging with people on stuff like this.

Congrats on your retirement,

Orion Aeneas Webster,

FourthEye author