Day 521 of 1000: Experiencing Personal Transformation

I’m undertaking a 1000-day reinvention project, blogging here daily to track my progress. In Friday Flash, I share an epiphany or aha moment from the past week.

In her book Transformative Experience, philosopher L.A. Paul asks: how do you make decisions under uncertainty and ignorance when not only do you not know the probability that different outcomes will occur, but you don’t even know “the structure of the value space of the outcomes for a decision problem”?

Models of decision-making under both uncertainty (which outcome will actually occur) and ignorance (what is the probability with which each outcome will occur) assume that at the very least you know the value (to you) of the relevant outcomes. Paul writes:

A way to put this is that you must be able to describe the state space of your outcomes, and you must have a suitably defined value function for these outcomes. If you cannot know the values of the relevant outcomes or if the values are not yet determined, so that you cannot describe the state space or assign values that will remain constant to outcomes, you do not have the information you need to use these types of models to represent your decision.

Paul focuses on transformative experiences, where the person who is deciding what to do has no idea, or only the vaguest idea, what it will feel like once they have transformed. She uses becoming a vampire as an example: it may be wonderfully exhilarating to live as an immortal, beautiful, blood-consuming being, but as a human you have little to no insight to what that will actually feel like, and how you will value it once transformation has taken place. She says, “in the case of a decision involving a transformative experience, you cannot know what it is like to have that kind of experience until you’ve had it.”

But many real-life transformative experiences are not like becoming a vampire in one important way: they play out over long periods of time.

When someone decides they are done with drinking, and want to be sober, sometimes it will happen with one decision. More often, it will take place over years and various struggles, as the person tries one thing and then another, and then, perhaps, one day quits drinking for good.

When someone becomes a parent, it evolves over time, and it changes over time too, because being a parent of a baby is very different than being one of a middle schooler. And parenting multiple children is challenging and transformative in its own way.

When someone divorces and goes from being married to being single, the divorce decree itself becomes final on one day. But the actual transformation from someone who feels married to someone who feels entirely single can take years.

Becoming a new kind of investor

I’ve been studying investing and trying different things for my whole life, but I only got truly serious about it in 2022 when I sold my house and had a large sum of non-retirement funds to invest.

I rue how long this transformation is taking sometimes, as my portfolio returns lag the broad market. Had I just thrown everything into an S&P 500 fund, or even stuck with an 80/20 U.S. stocks to U.S. government bonds I would have seen far better returns.

I am optimistic, however, and I believe the approach I’m converging towards will give me good results for the rest of my life, not just in terms of returns over time but also when measured by my emotional equanimity and my ability to stick to a plan.

In 2022 I didn’t know what I was going to transform into. I certainly didn’t expect I would become someone who (1) doesn’t believe that you can predict anything in the financial markets (2) manages her portfolio allocation with simple timing rules and (3) also trades options.

This was a little like becoming a vampire. I’ve become someone who was uncontemplatable to me before.

Transformation from married to single

As well I experienced this in my relationship life. When I first divorced, I still felt married. I felt like someone in a life partnership. It was confusing and disorienting.

For a time, probably an entire decade, I tried to get back to who I thought I was: coupled in a long-term relationship, living with my partner.

My life kept unfolding. In each relationship I felt more and more happy when I was alone, rather than with the man I was dating (or living with). I cherished sleeping in my own king-sized bed, by myself. I liked to get up when I wanted and go to bed when I wanted. I disliked that in each relationship, I felt I had to be someone other than who I truly was, to make the relationship work.

And perhaps that’s why I got divorced in the first place. I was already transforming into the single version of me, but I didn’t consciously know it. I didn’t conceptualize it.

I only realized how much I wanted to be single when I moved into my own apartment, as my then-husband and I separated. I felt like myself in that apartment, managing it myself, being either with my kids and dogs (for a week at a time) or being alone (which wasn’t lonely, but rather freeing).

More and more, I have come to believe that our lives unfold largely outside our control. I am beginning to side with the determinists, questioning whether we have free will, and concluding that we only have the appearance of it.

Instead, I think it’s like we are riding a gondola up a mountain, with the movement and destination outside our control.

So this makes the question of “how to decide whether to take on a transformative experience” moot. We will or we won’t, according to the timeline that already exists.

I was always going to be married, and then later find solace, solitude, and happiness in singlehood.

I was always going to make a lot of investing mistakes, on my way to developing my own personal money management practice.

I was always going to give birth to my three beloved children, and see them transform from delightful children to responsible, loving, unique adults. They did that even while suffering through the consequences of my transformations.

Opening to a transformative experience

Nevertheless, I have a sense of my own control over outcomes. And it feels like my thoughts about transformation might help me enjoy this gondola ride more than I could otherwise. Understanding how personal transformation unfolds makes me more accepting of how long it takes, and how uncertain I feel while it’s happening. Even if that was already fated, it feels good to acknowledge it (acknowledgment also fated I suppose).

Some conclusions:

  • Personal transformation of the most important kind takes years to play out, not months.
  • Who you are at the beginning of a transformation cannot understand what it will feel like to be the person you are at the end of a transformation.
  • You don’t actually have any control over who you become through transformation. I found this to be true in both my transformation from a conventional investor to the unconventional investor and trader are I am today as well as in my transformation from married to single.
  • In other words, a transformation chooses you. You don’t choose it.
  • Personal transformation exhilarates, delights, gratifies even as it plays out in half-decade and decade-long and even longer arcs. Personal transformation also terrifies, provokes, wounds.