Making the leap to leave my secure income behind was much harder than just hitting the number on a spreadsheet and walking away. Here were the major emotional factors I considered when pulling the trigger.
In the years I was pursuing my goal of financial independence, the decision of when to retire seemed pretty cut and dry. Obviously I should retire the moment I hit the number my calculations had shown would support me for life. As I approached that target, however, the decision became more nuanced as I’m sure many a retiree has faced.
Chief among my doubts about pulling the trigger was whether it was worthwhile to work just a little bit longer and build up some more cushion. Sure, I’d built some projections. But what if I were wrong on healthcare costs? What if I decided late into life that I wanted more luxuries than I accounted for? What if the stock market dropped more than I expected? What if…?
I began to ask myself why, specifically I was decided on exactly that year to retire. Why not one year later? Or two? Why exactly now? What made the tradeoff of risk to reward optimal in this particular year?
I had exhausted the data-driven parts of the decision-making process. No one could quantify for me how much the stock market would drop during my retirement, or foretell what healthcare would look like and whether I would need to eventually enter and pay for nursing home care. I had projections already which involved my best guesses for these things. What was left was simply the emotional parts: How would I value the feeling of taking on ‘risk’ by having less buffer against the feelings of joy from gaining my freedom earlier?
Here were the main components in that struggle, and how I feel about them now, a year and a half later.
How Happy Was I With The Status Quo?
One of the most important components to this decision was how happy I currently was in the status quo. Staying longer and generating more buffer money gained me something. Naturally, to make a decision as to whether I should pursue that, the question became: how much was I giving up? How happy or unhappy was I in my current set-up?
The answer was pretty unhappy. The job itself and the people were amazing as jobs go, but it was a mediocre fit for my interests. The role I was in was probably a 50% fit for me. The analytical and research components were up my alley, but the role also celebrated and asked for traits I found exhausting and unrewarding. There was a lot of travel, a lot of negotiation and salesmanship and traits suited to an extroverted, push-push-push type of personality. Towards the end, I often described my job as feeling like I was holding a winning lottery ticket…for another person.
Talk turned towards making a run for the senior-most roles in the organization. At year end, we’d talk about what they had in mind for me and what I would need to do to demonstrate competence. That list was 90% stuff I disliked. More management of other people. More travel. More salesmanship. More politics.
The perks, the pay, and the prestige were fantastic. The people were smart and great to work with. Everything else was kind of a slow-moving horror show for someone like me, at least at that point in my life.
There were other skills and interests I was impatient to pursue. I wanted to go out and discover for myself what life would be like when I had an 80%+ fit with my skills and interests.
Timeline for Other Major Life Changes (Read: Kids)
This was a big one. Here I was, having spent years impatiently thinking about pursuing projects that were more aligned with my overall interests. I knew at some point soon, I’d get the chance to pursue these new projects. But wait, we also wanted kids. At what point would we be having these munchkins? Wouldn’t they impact my ability to wholeheartedly pursue these passions of mine?
Sure, plenty of parents found balance in their lives between raising children and other interests. But did I want my first taste of pursuing these projects to be compromised by the time-intensive work of raising an infant? And if I didn’t want to start the next chapter in my life juggling both kids and these new projects – if I wanted to give myself pure time to focus on these new projects, at least for a little while – how would that timeline fit with having kids?
Mr. Money Habit is a few years older than me. After his 30th birthday, he began making noises about having children soon-ish. As he said to me, he didn’t want to be in his 60’s by the time our kids graduated college. I figured I should probably start having kids by the time I was 30 since we wanted a few. Cool. We still had a few years, so we set that aside for a bit.
But the year before I pulled the trigger on retirement, we were spending Thanksgiving with his side of the family and a particular experience made us reevaluate how much time we had. His sister and her husband had two adorable children, aged 3 and 6 at the time, and his sister was pregnant with a third. These kids were some of the sweetest, engaging, and delightful children I’d ever met, and we spent a whole day playing superheroes, pony show, and running around the house like crazy with them.
In a breath between picking up the kids and pretending they were intergalactic spaceships, his sister was talking about how she was feeling during her pregnancy. “Exhausted,” she said. If she could give us one piece of advice, she continued, it would be to start having kids earlier. In her mid-30’s now, she found it difficult to muster the energy to keep up with all of them.
By the end of the day, we could see what she meant. We had been there for a single day, and we were completely, bone-deep exhausted. For the next two days, my arms were sore from lifting the kids and throwing them around. I said to Mr. Money Habit, “I’m 27 and one day of this was my limit. What’s going to happen if we wait until I’m in my 30’s to start having kids?”
That put a wrench in my retirement plans. I was determined to have at least a year to pursue my projects before we started trying for kids. I had also now decided that even at 27, my energy levels might barely be adequate for the task of raising children.
Part one of the answer to: “why retire now?” had become “because we want kids soon, and I need time to pursue my projects unfettered before that happens.” As it turns out, we now have the first kiddo in the house, and this concern couldn’t have been more well-placed. Newborns are way harder than I expected, and now what I know now I wouldn’t wait past 30 or 31 to start having kids unless that somehow translated to thousands more dollars one could put towards hiring childcare to make it easier.
Aside from the prospect of children upending our lives before I’d had a chance to work on my passion projects, there was also a series of events leading up to the year I retired which caused me to fully appreciate my own mortality.
I have been lucky thus far not to have anyone close to me pass away. Both my grandfathers had died before I was born, so I never had a relationship with them. My two grandmothers are wizened, tiny ladies with tons of spunk and physical health. In the year I was 27 turning 28, though, it felt like the world came crashing down. My mother had unexplained numbness and pain along half of her body – at the time it was getting worse, with no concrete diagnosis. My father had a heart arrhythmia and a host of other issues. A close friend of mine’s mother passed away suddenly, much too young and in circumstances that were less than ideal. A colleague’s father died from cancer at 50 – he didn’t talk much about it, didn’t even take much time off in those final weeks with him even when offered the chance. Then one of my grandmothers was diagnosed with tumors which required surgery to remove. At over 90 years old, there was a very good chance she wouldn’t be getting back up off that operating table.
I found myself running through my usual morning routine and sitting down to work at my desk numb and empty. I might hang up from a conference call and suddenly think, “what am I doing here?” And then I’d look out the glass windows of my office at the colleague whose father was in the midst of dying and ask myself, “what is he doing here?” With these reminders of how little time and health we have left in the world, was this where we really belonged? What kept pulling us back to the office when other, frankly more important things were happening?
I thought to myself that I had probably 50 years left to live. Of those, maybe 20-25 would be years of relatively good health, and maybe 10-15 of those were ones in which I’d have the kind of herculean energy needed to do certain large building-focused projects like starting a non-profit or building a business or re-launching my entire field. Sure, many people did these things well past the age of 45, but could I count on myself being one of those people, especially given the medical issues in my family line?
Given that I had 10-15 years of project-building years ahead of me, how many more did I want to spend being a professional investor? Given that I was going to have kids (wonderful, amazing, life-elevating kids who would nonetheless be a time sink when it came to project-building), how many of my remaining 1-3 kid-unfettered years did I want to spend being a professional investor?
To be fair, very few jobs will hold up when you ask “I’m dying in X years, do I want to spend another 10-50% of my remaining life doing this?” But once seen, I couldn’t unsee it. I began to resent every board meeting, every call with a CEO, every meeting with colleagues where work wasn’t perfectly complete or there was even the slightest hint of BS.
When thinking about when to retire, my brush with mortality made my answer “as soon as possible.”
Pulling The Trigger: A Year and a Half Later
I retired in 2016. At the time, I had vacillated between wanting to quit immediately and seeing myself staying at least another year, but eventually the emotional considerations above tipped the balance in favor of retirement. I’ve had a lot of trouble trusting my gut in the past, and making this decision based on such ambiguous considerations was difficult. With the benefit of a year and a half of retirement under my belt, though, I have more perspective to add to the equation.
In short, I am excessively pleased I made the sort of value and priority decisions I made a year and a half ago that led to my retirement sooner vs. later.
In the time since I’ve retired, I got to make several trips to see my parents and grandmother I would have otherwise been unable to make. All have stabilized medically and I hope have many years of good health ahead of them. I couldn’t have known that was the case, and there were several dark times particularly with my grandmother that I remember feeling incredibly grateful that I had the opportunity to drop everything and fly across the country to be with her. While they are healthy now, I think often about how precious our time is together. There was an excellent article on Wait But Why called The Tail End, and my retired status allows me to feel I’m striking the right balance of time with my parents and other loved ones.
We have also now welcomed our first child into the world. It’s been a huge identity shift, both happy and terrifying. Having had a year to try out many of my interests before we tried for kids has turned out to be invaluable for my mental health and happiness. I did all sorts of things like horseback riding, starting a blog, binge-reading books and staying up until 5 am. I took advantage of a bazillion lunch specials in the city while everyone was indoors working. I got to see more of NYC’s neighborhoods. That was all great. But the benefits of having had that year of freedom weren’t just the experiences I had, but the insurance against regret I have for future doubts.
For example, being pregnant for 9 months put a real cramp in my style. Being active was more challenging. Mustering up energy to work on Project X was harder. Travelling was hard, and by the trimester felt downright impossible (at least for me). Any of this could easily turn to my resenting this kid or our decision to become parents. But because I had that year to myself, these phantom parallel lives are easily dispelled.
I have a good friend who is at a different place in his life. He is financially successful and single. He loves food and loves to travel. So that’s what he does. This year he has sent me photos of charcuterie boards from his trip to Italy and Spain. He’s about to jet off to Paris for a spontaneous solo trip because he found a last-minute great deal. I found myself recently grumping to Mr. Money Habit about how pregnancy sucks. I want to be eating charcuterie in Italy. I want to eat all the bread and cheese in Paris, and sit at cute cafes sipping a cappucino. When we were planning our babymoon, the destination that was at the top of my list was the UK. It would be fantastic to get outside of London and see some quaint towns with history. This gosh darned pregnancy was the only thing standing in my way!
Except that it wasn’t. Because you see, I’d had a whole year (actually year and a half before I actually conceived) to travel internationally. And do you know how many trips I took out of the country? Zero.
All the time and money necessary to make it happen, but I actively chose to loaf about in my pj’s instead. Believe me, the thought had crossed my mind several times to grab a friend and travel or even solo trip. My parents were also going on several international trips to which I was invited, but I declined. When I told people I wasn’t working, the first thing they invariable asked about was travel. And with all these reminders and opportunities, I gave an unequivocal ‘no thanks’ to the idea of exotic travel. I traveled to see family, but sightseeing in new locales was not high on my list. Reminding myself of that made all my potential resentment go away.
Likewise with exercise. I was a healthy weight pre-pregnancy, but I wouldn’t say I was particularly fit. During my working years, I told myself that I would be physically active if only I had the time. With a year or more of nothing but time and no material change in my fitness habits, at least now I can confront the idea that the challenge to physical fitness is something internal to me rather than an external constraint. Not the happiest thought, but the feeling of control over the outcome is quite empowering.
I found the decision of when to retire to be a nuanced, difficult one to pin down. What guided me during the process was a hard look at how I would prioritize different values and messages about my life. While I can’t say for sure how I’ll feel about it until I see the full outcome unfold over the decades to come, I can say at least that a year and a half out, this strategy was an optimal guide to achieving happiness and peace with my decision. For those struggling with this decision or approaching it soon, it’s an exciting opportunity to come to terms with what you value and why. I hope you make the most of it. It’s a once-in-a-lifetime experience of its own.
What emotional considerations go into your timeline for financial independence?