Billy's Thoughts

Sabbatical Notes #4: October

Posted on Oct 30, 2023 — 6 mins read

I’ve been chipping away at a big post to map out how my thinking has changed since the start of my sabbatical in July (edit: out now!). But I’ve also been getting antsy about not having published anything in over a month. So here’s an update for October!

Do The Thing

“Do The Thing”

“Do 100 Reps”

“Just Do It”

This idea has been like a scalpel for me, continuing to cut through my bullshit. By which I mean: I keep uncovering ways my subconscious tries to avoid Doing The Thing, but once I actually Do It, I’m always like “Oh yeah this is what I wanted.”

The most recent instance of this is with career coaching. I’ll write about this in more detail, but in short: my 1st attempt at establishing a coaching service ended up with me veering off on what I thought was a mandatory subproblem of marketing and getting my name out there. And it turns out I really didn’t enjoy working on this subproblem, so much so that I gave up and then avoided the idea of doing anything related to coaching for a couple months, as other projects seemed much more appealing.

Fast forward to the end of September, and I realized (in the shower, where most of my best ideas come from) that the marketing subproblem might have been completely optional after all, and I should just try to Do The Thing with the least overhead possible. Which could just be me posting to LinkedIn saying, “Hi I’m Billy, I worked at X,Y,Z. If you’re interested in chatting about tech career stuff, here’s a booking link,” and letting people book free 30-minute calls with me.

Because the actual thing I wanted to do was: talk to people and work through their questions with them.

And it worked! I posted to LinkedIn, got 13k impressions, filled up my 20 available calendar slots within the first 4 hours, and then had 24 people sign up on a waitlist. And I’ve since met with 19 people, with more scheduled for November.

Where this ends up going, I have no idea. I’m trying to let go of the desire to white-knuckle and try to force something to happen and just be open and ready for any opportunities that might come up. At minimum, I get to Do The Thing and iterate and learn. AND I get to reflect at the meta layer like, “Do I enjoy this? What about this do I enjoy? Do I actually want to do more of this, or not?”

Big Magic, and new perspectives

Big Magic by Elizabeth Gilbert is a book about creativity, the creative process, and living a creative life (my review). She also wrote Eat Pray Love, and that actually makes her thinking all the more interesting here, e.g.: how do you continue to create, knowing that your greatest success might be behind you? (You can check out her TED talk on this topic, and it’s also a good representation of what the book is like.)

One of the sections in her book is dedicated to Persistence, and it unlocked some things for me:

1. Your work won’t, and can’t, save you

For a long time, a part of me hoped and prayed that by doing creative work, somehow my work would save me. I would achieve great things, transcend my insecurities, become peers with amazing people, be content… something along those lines.

But I recognize now that this hope of mine was an illusion. A mirage. What it actually is, is an internal rift seeking anything external and legible in its vicinity to try to sate itself. Except I’m learning that internal holes don’t truly get filled by external things, and the source of these holes are emotional wounds, which require emotional healing.

Gilbert, who takes inspiration from the Ancient Greeks and personifies Creativity as its own independent entity, frames it this way: pinning all of your hopes on Creativity to save you is far too much pressure and responsibility to put on anyone, stiflingly so. Reconsider your definition of success. Could Doing The Work be enough, could the process be enough, regardless of the fruit and if it attains any worldly success?

(And related questions that I’ve been mulling over: Do you want to be content, or do you want to have your desires fulfilled?1 What does a life well-lived look like to you?)

Somehow, through a combination of all of this (and a lot of introspection and emotional processing), I’ve been able to take my proverbial foot off the gas a little and chill out with respect to my creative process. I’m no longer tensed, gripping tightly, hoping one of my posts blows up and I discover that I actually have this secret talent in writing and I gain people’s praise or something. I’m becoming more content with just doing creative work because it’s beautiful and I enjoy it.

2. The affair

Stay with me here: what if you thought of your creative projects like they were an extramarital affair? In that: someone having an affair always seems to find time for a clandestine meeting, no matter how brief. Even if it’s just 15 minutes. You dress up. Your heart races, and you want to maximize every single precious minute you have together. Your attitude and affection adds to the fire you share with your lover (in this case: Creativity), and good things flow out of this.

Of course, in reality, affairs are no joke and they can absolutely obliterate people. But I can’t help but find this fantastical metaphor and its underlying sentiment alluring. I love doing creative work, and I want to be pursuing it with this level of fervor. And it turns out it is absolutely within my power to adopt this mindset, attitude, and imagery (vs, say, viewing the work like it’s a grind).

3. Why

This one isn’t directly from the Big Magic but a synthesis of (1) + (2) + other insights from my 3 months on sabbatical, including this quote from Nietzsche: “He who has a why to live can bear almost any how.”

At the beginning of my break, I was burnt out to the point of wanting to swear off software engineering for good and never return. I couldn’t stomach even the “most chill case” of just coasting at a 9-5 role at a big company. That cost on my time and energy and soul was still more than I was willing to pay. And I think that’s because, like with creative work, I wanted my job to be the thing that solved all of my dissatisfaction. This was essentially my ‘why’ in my 20s – “work hard, build stability, level up,” says society. (Aside: until what, you have kids? Retire? Die?)

But now, there’s a compelling new ‘why’ that’s taken up residence in my thoughts, and it says:

Keep doing the creative work that you enjoy, and do whatever it is you need to do to keep at it and stay in the game.

And for the first time since ~June, the idea of going back to a tech job doesn’t sound revolting to me. Now, working a 9-5 isn’t about me spending my time and energy doing work that I don’t really care about to who knows what end. Now, it’s about doing what I can to manage my time/energy/resources, in order to keep being able to do creative work in the long term. And I’m kinda OK with that.

  1. “Do you want your desires fulfilled? Or do you want to be happy? Say I can give you a meditation practice that can have you be content with what you have. Would you actually do it? I’m guessing some of y’all would not. Because to be content means to give up your desires. You might say, ‘Screw that, I don’t want to be content with this. I don’t want to give up my goals, I want to achieve my goals. You’re telling me to settle? F*ck that.’” - excerpt from ‘Your Goals Are Incompatible With Modern Life’ ↩︎