Are you uncertain about facts, or just what you want?

I’ve recently been doing some daily career reflection, or, perhaps more precisely, career typing-into-a-Google-doc-at-the-problem. Inspired by this helpful post and similar career planning lore within my social circles, I’ve been brainstorming options, researching them, and trying to rank and filter them. As part of this, for each option I’m answering questions: how would this career be for work-life balance? What’s the pro-social or altruistic impact, if any? Does this feel Amber-shaped, authentic?

And I noticed that writing answers to these questions started to feel stale and frustrating: I’ve considered many of these options before. I’ve looked them up on Prospects.com, badgered acquaintances into informational interviews, diligently written down salary ranges and how many personal boxes they tick.

Realizing this, I was disheartened; it feels like I keep retreading the same ground and rediscovering — or re-typing-into-my-google-doc — the same answers that I really know deep down¹. Generally, the more psychologically integrated I become, I get diminishing returns from talking to myself through journalling; more of my parts are already looped in.

And it occurred to me: my main problem isn’t that I have strong factual uncertainties about what it would be like to be a therapist, or how good a fit I’d be for technical authorship, or how impactful I could be as a nonprofit communications specialist or an entrepreneur. I mean, I do have uncertainties about these career paths. But basically, I can imagine that being a technical author might gratify the part of me that loves writing clear explanatory text, but not the part of me that wants to help people with their personal blocks; and vice versa for being a therapist. And I can imagine that starting some sort of entrepreneurial project/hare-brained scheme would give me lots of freedom and excitement, but little stability or structure; whereas working for a non-profit, or another 9-to-5 type job, would give me that structure and stability, but at the expense of some authenticity and agency.

Instead, my biggest uncertainty is which tradeoffs I want to take; or fundamentally, what future version of myself I want to grow into. It feels about more than just my career. I have many values, each of which implies some archetype I could lean into. Do I want to be an Altruist? A Helper? A Creative? An Epicurean? A Scholar? That’s why this whole project feels so scary and high-stakes.

An optimistic part of me responds: maybe these trade-offs are not so stark. Or they needn’t be, if you just research deep enough, use your ingenuity hard enough. (Call this ‘unfair optimism’²). What if I could get freedom and security, could do analytical solo work and relational work, could have a huge social impact and a pleasant, relaxed life? This (unfairly?) optimistic part is bolstered, I think, by many intellectual traditions I’m immersed in: Internal Family Systems, which insists you can always broker a compromise between the most aggressively polarized parts of you; non-violent communication, which claims the same for conflicting individuals; rationalist goal-factoring; and even polyamory culture, which insists you can have the cake of stability alongside the eating of it of adventure, and that love is infinite (and therefore no hard choices need ever be made).

And yes, I should certainly look for places where I’ve constructed a false tradeoff where it needn’t exist. But like… sometimes there really are tradeoffs! Sometimes you can’t always get all the things that you want, to the extent that you want them! Any hour I spend on one activity simply cannot be spent on another; the economy works such that I must make money to live, and the things that will pay me money don’t exactly correspond to the things that I would most enjoy to spend my time on, or the things that I think would be most beneficial for the world. I wonder if I’ve been blocked on this ‘career’ question for ages because of an unwillingness to commit to one future self… and thus kill, or at least sideline, all my other potential selves.

This week I keep feeling nebulous physical anxiety. I was wondering if it was something I was eating, or hormones. But now I have another candidate: existential angst. The dread related to our fundamental, inescapable, joyful, terrifying freedom.

This is a good realization, I think; at least it makes me feel like less of a fuck-up for not having Just Done the Thing by now. But it also raises the question: how do I make progress on this? I suspect that busy work — googling, typing notes, talking to people — might not be the answer. Maybe I don’t need to glean more knowledge but to shore up my courage and endurance; to find the boldness to step into (one of) the abyss(es).

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1. Incidentally, I sometimes fantasize about solving/mitigating this through better note-taking and/or digesting strategies. I’m a prolific producer of notes and journals of all kinds, and I do have some organizational systems, but they’re not optimal. So if you have a note-taking or distillation app or system you swear by, do recommend it!

2. The term that sprung to mind was ‘cruel optimism’, but that is already a term and I can’t be bothered to wade through the postmodern jargon enough to work out if this is the same thing, so a different term it is.