This past May, I started feeling like I’d been doing Fun Projects for long enough. Since July 2023 I’d been fighting (with love) my urge/anxiety around needing to feel productive, make money, and get back to self-sufficiency, by reconnecting to my sense of Fun and doing Fun Projects.1 But after ~10 months of this, I was feeling a bit hedonistic, and I was suddenly motivated again to work on my career. So the pendulum swings.
I decided to give Coaching another shot, as the most viable candidate for a possible career switch that I could test out immediately. But due to some unlucky timing, I had this burst of motivation right before a series of family + travel plans that kept me away from home for ~3 months, from the end of June to the end of September.
October 2024 was when I was finally back and settled in, and started tackling these new ideas for real–now with Coaching as the primary career thing, and Drawing as the secondary thing I wanted to be more serious about (upping my drawing time from ~30 mins every other day, to 1h/day).2 And then try some stock trading on the side too for fun (this is foreshadowing). I’d dedicate 6 months to really give these ideas a fair shake and see if they had any legs.
It’s now November, 1/6 of the way through, and things are going OK. Building this coaching business has primarily bottlenecked on lead gen and client acquisition work, which I feel lots of resistance toward. But it enables me to do the actual thing I like to do, which is talk to people one-on-one (which I got to do 12 times in Oct!). Coming to this realization in itself means this experiment is working, and that’s heartening–I’ve put in some work, revealed more of the territory, and I’m now processing the new data. Next, it’s seeing “how do you live off of crumbs as you wait for the next hit of magic,”3 and if this is the sh*t sandwich I actually want to be eating for the next while.
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Another recent catalyst for reflection has been Paul Millerd’s new book Good Work, whose premise is essentially captured in the very first line: “Could it be this simple? Just do things you like?” I’m only 1/3 of the way through, but so far it’s been right up my alley as I’m constructing this new life for myself around this exact idea of Good Work.
It’s brought back to mind long-standing questions like:
Funnily enough, literally just last night I went to bed late because I was watching a bunch of videos covering the stock market, and only realized today that it was because I was having Fun4. And maybe I should do more of this and see how that feels 🤔. (I also noticed that I have some internal resistance to the idea of being seen as a “stocks guy”… but if it’s fun it’s fun, what can you do?)
And at a meta level, you could even say that what I’m doing right now with this exploration is itself the Good Work, the thing I’m meant to do. I’ve set aside the time for this 6-month experiment. I’ve got ample runway. All I have is time. Any anxiety is then, in a sense, not real5; I’ve just gotta do what I can do today. Any outcomes are out of my hands.
I’m exactly where I need to be.
i think this realization is directly downstream of starting to read @p_millerd's Good Work but i now strongly believe that my efforts to explore what is Good Work for me is itself part of the Good Work i'm meant to do, and this has been very heartening
— billy (@billyisyoung) November 5, 2024
It’s funny, looking back now, I can see that even my decision to do Fun Projects was still steeped in that same desire to be productive – I couldn’t just Have Fun by wasting time. (And I still can’t, really.) The Fun Projects I chose still had to be producing some tangible result, and had to help me level up skills that I cared about. HOWEVER I still think this was a step in the right direction, toward having more Fun. It’s all baby steps. ↩︎
Some days it feels like this was all a headfake to give me something legible to focus on (coaching), so that I can secretly do the REAL thing I really wanted to do, which is make more art… ↩︎
John Mayer on the songwriting process, from his Tetragrammaton interview with Rick Rubin. Highly recommended, especially if you do creative stuff. (summary thread, source video) ↩︎
My friend asked me what’s fun about it, and I thought it was worth including here:
- Autonomy - my actions are all within my control, as to how much I research, which stocks I pick, relative performance vs SPY
(vs coaching right now what’s in my control is putting stuff out there, but what’s not in my control is how many clients sign up)
- It’s kind of a game, like looking at data and finding gems
- It feels like a more legible and direct path to wealth creation and financial freedom, which I think is an anxiety for me right now ↩︎
The anxieties I’m feeling at this point and time are worries about the future. But also they are just thoughts about some imagined state, and they don’t really change what I need to do today. So I try to let them just pass on by as I focus on what I can do today. ↩︎