I’m undertaking a 1000-day reinvention project, blogging here daily to track my progress. In Thursday Thinker, I share a smart idea or theory.
My elder daughter is in town, helping me during my post-surgical recovery and attending various birthday events. My family’s birthdays cluster in April. Mine is the last of the month, on the 26th. I always breathe a sigh of relief when I reach it because all the celebrations and gift-buying and giving are complete.
My daughter and I walked my dog together yesterday and talked about our lives and how they’re unfolding. She has a big career change coming up and she’s excited about it. I shared with her how much I’m enjoying my unexpected retirement. I didn’t realize what a drain my technology jobs were, as much as I enjoyed the mental stimulation of it and the camaraderie with many kind and smart people. While I was in the midst of that career I couldn’t really imagine anything else.
It reminded me that you can’t figure out a good future for yourself by analyzing and planning. You just need to try things and see what unfolds. In the process your very values might change (which is one main reason why analyzing and planning can’t possibly work — it uses your current values not future unknown values). As I moved away from technology and tried many other possibilities, very few of which involved paid employment, I found that the values of autonomy, independence, frugality, and intellectual discovery rose above the values that my technology career embodied (high pay, prestige, financial security, conventional success).
In her book Working Identity: Unconventional Strategies for Reinventing Your Career, Herminia Ibarra writes:
[We] are not one self but many selves. Consequently, we cannot simply trade in the old for a new working identity or upgrade to version 2.0; to reinvent ourselves, we must live through a period of transition in which we rethink and reconfigure a multitude of possibilities…. [It] is nearly impossible to think out how to reinvent ourselves, and, therefore, it is equally hard to execute in a planned and orderly way. A successful outcome hinges less on knowing one’s inner, true self at the start than on starting a multistep process of envisioning and testing possible futures. No amount of self-reflection can substitute for the direct experience we need to evaluate alternatives according to criteria that change as we do. [emphasis mine]
That’s the key: the criteria you use to evaluate what suits you change as you are changing.
Current preferences don’t tell us about future preferences
In an article on transformative decisions, Jack Maden writes:
Part of the difficulty arising from big life decisions is they typically involve what contemporary philosopher Laurie Ann Paul calls transformative experiences.
Paul defines transformative experiences as having two key characteristics: firstly, you cannot know what they are like until you undergo them, and secondly, they alter you in profound ways.
They are thus both ‘epistemically’ and ‘personally’ transformative: you gain formerly inaccessible knowledge into what it’s actually like to undergo a certain experience, and – crucially – you are also radically changed by it: it reconfigures the way you think, the way you look at the world.
Paul, Maden shares, suggests we should consider revelatory values:
So, rather than ask ourselves questions like, ‘which path will make me happier?’ or ‘which path is better?’, Paul thinks we should ask things like ‘Do I deem the revelatory value of the path itself worth it? Do I want to gain insight into what this path is like? Do I want to discover who I’ll become down this path? Or does the revelation carry no appeal? Am I satisfied with my current preferences, and uninterested in seeing how this new, undiscovered kind of experience will change them?’
And he quotes Paul on the “game of Revelation”:
A life lived rationally and authentically, then, as each big decision is encountered, involves deciding whether or how to make a discovery about who you will become. If revelation comes from experience, independently of the (first-order) pleasure or pain of the experience, there can be value in discovering how one’s preferences and lived experience develop, simply for what such experience teaches. One of the most important games of life, then, is the game of Revelation, a game played for the sake of play itself.
Lately, I’ve been wondering what my life might be like if I finally gave in to my constant desire to trade in my portfolio. I’ve been making tentative steps towards that, spending my days learning about technical analysis and options trading and then making changes to my portfolio based on that.
I hope that beyond developing a money management practice that brings me more financial security, I also develop the kind of emotional strength that trading demands: equanimity, mental flexibility, risk taking, constant curiosity, less clinging to things I can’t control or aren’t important.
So yes — I want to keep doing what I’m doing, developing my trading and investing practice. But I also seek the revelations that lifestyle may bring. As Maden writes, “life is punctuated by a series of revelations that profoundly change who we are.” Am I on the brink of such a profound change? I hope so.