There’s this feature in some video games (usually single-player action/adventure RPGs) that allows the player to start a new playthrough of a game after beating it once, but with some added twists the second time through.

When you begin a New Game+ you venture back out into the game world, but you get to keep some of your progress, items, abilities, or upgrades you acquired during your first playthrough. Coupled with this, the game also becomes more challenging: enemies are stronger, dungeons are harder, and there might be hidden bonus content that becomes available to you.

And now in my career, I feel like I’ve “beat my first playthrough”, and I’m staring at the New Game+ screen, deciding if I want to PRESS START, or find a different game to play.

As of next month, it’ll be 7 years (!!) since I joined Wish. I’ve been fortunate to, in many ways, grow up alongside the company and land opportunities that aligned with my interests and my desired career trajectory. I’ve lived multiple lifetimes here (see Appendix for a breakdown). And until recently, those lifetimes built on each other and built toward something desirable.

I started out as a young punk entry-level engineer and I’m now an L6 / Staff Software Engineer, which is something I really wanted and worked hard for. And I, and many of my peers, consider this to be one of the Big Bosses or milestones for an individual in the industry.

Tied up in this, however, I feel like I’ve climbed as high as I care to climb. Or it’s more like: I’ve been climbing, and as I grew to understand the act of climbing, the system, the ‘game’, formed mental models of what to expect 6 months from now, 2 years from now, and as climbing became old hat I lost interest in climbing further (s/o my fellow Type 5s).^2,3

In work terms: I’ve mapped out the general software engineering career ladder in my head, as I see it. I’ve looked at what I like, and what the software career has to offer, and I’ve inhabited most of the overlaps.

And what overlaps in interest remain, keep shrinking. The “cost of doing business” has gone up dramatically, even for me as an individual contributor. The meetings, coordination, consensus, and processes necessary for the machine to grind forward have ground me down. (Going to another startup solves the overhead problem, but is too much of a time and emotional commitment for me nowadays.) I don’t have much left in the tank. I burnt out.

(Of course there’s still new skills I could acquire in software engineering, new responsibilities I could take on, or pivots I could make. Especially with the recent hype around blockchains, ML, LLMs, etc. But the fire is gone. There are no more Bosses I’m looking to defeat. And the quest rewards have had diminishing returns for a while now.)

And at the same time, connected to all of this, I’m pulled and pulled toward my other interests. To other fields that I’m excited about, and make me feel alive, and can help people.^3,4 To the desire to evoke Feeling, which I suspect will never become old hat.

So no, I think I’ll pass on a New Game+ for now. I’m moving in the direction of something else entirely.⁵

trying to brainstorm / invent a job where I can:
- be autonomous
- craft things
- help people via providing a service or providing value (e.g. mercenary, or educator)
- play a (near-)infinite game

open to suggestions too :)

— billy (@billyisyoung) May 2, 2023

Appendix: a breakdown of lifetimes

A more intimate counterpart to my LinkedIn experience list.

1. New grad eng - 3 years

   • The grind years - high-intensity, hard work, near-all-consuming, but at the time I mostly loved it (I will write about this in depth one day…)
   • You did everything - you were your own PM, designer, eng, QA, DS
   • I got whipped into shape, forged from a blunt instrument into an independent, resourceful, and effective engineer (if I do say so myself)

2. Senior eng - 1 year

   • Earned some experience and seniority by this point; I’d seen some sh*t
   • Became a reliable member of the org and domain expert, mentored newer folks
   • Worked on larger-scale projects

3. Engineering Manager - 2 years

   • I was interested in management, and got the opportunity to try it, at a time when the company wanted to scale up
   • Built a team of 5 and trained them up as the “next generation”, expanded our team’s scope and impact and how much we could get done
   • Then got team-wiped (almost everyone left) 🙁

4. Senior/Staff eng again - 1 year

   • Concluded management was not for me, and switched back to IC, but “returned” to a company that was now much larger
   • Got promoted to Staff Eng, which felt like a huge milestone for me in terms of “proof”, validation, credentialism, and probably imposter syndrome (this could probably be an entire post on its own)
   • Came to the realization that the “game” at this level, as I saw it, would take O(2y) to become proficient at, and also I wasn’t really interested in continuing to play:
     • One project can take O(months): take a project idea, build it, launch it, retrospect on what worked and what didn’t (could be anywhere between a complete dud to a complete success)
     • And I found it takes a few projects like this under your belt to gain actual, tangible insight into what works and what doesn’t work at this level, how to improve your shot selection, etc. in order to become what I viewed as a Seasoned, Reliable Staff Eng
   • Everything is a coordination problem, and I don’t really enjoy working at scale, where I’m just 1 cog in a big machine. I enjoy being a big cog, if not an entire machine / subcomponent

Further reading / footnotes

¹ I’ve been thinking a lot about the line from Jim Carrey’s commencement address (timestamp linked but I recommend the entire thing!) where he says: “I wish people could realize all their dreams of wealth and fame, so that they can see that it’s not where you’re going to find your sense of completion. Like many of you, I was concerned about going out into the world and doing something bigger than myself. Until someone smarter than myself made me realize that there is nothing bigger than myself. … No matter what you gain, Ego will not. let. you. rest. It will tell you that you cannot stop until you’ve left an indelible mark on the Earth, until you’ve achieved immortality. How tricky is this Ego, that it would tempt us with something we already possess.”

² Apparently my general mindset and tendencies are textbook Vata-Pitta or Pitta-Vata behaviour (from the doshas in Ayurveda). So as part of my sabbatical, I’ll be experimenting with structuring my life in a more Vata-friendly way, where I cycle through my projects every day, spending 1-2 hours on them each (Vatas are flighty like the wind). Tentative schedule is like: wake up - write - lunch - coaching business stuff - empty space, maybe fiction writing or art or music - dinner - misc time - sleep. Turns out Ursula Le Guin did something similar, so that’s encouraging.

³ I’ve also been stewing on this What is passion? video by Dr. K. on breaking down attributes of passion like the spiritual, neurological, physiological, environmental, and relational (and providing a useful lens to introspect with). I.e. identifying what you want, and then figuring out how to find it.

⁴ This post touches on big, deep questions like: what are my values, what is success (to me), what is fulfilling (to me), what is interesting (to me). And in the past few years I’ve found great benefit in examining these questions through the lens of my own past and my emotional development. Like, what makes me feel this way, why did I put so much weight in getting that promotion, what in me is drawn by the lure of Imposter Syndrome, etc.

⁵ Something else I’m trying to be aware of is to not chase the high of just finding another mountain to climb and climbing it, since I think I’ll just end up back in a similar place of “OK I climbed another mountain and I’m still not satisfied. Now what?” Rather, is there a way to ‘pierce the veil’ and find satisfaction orthogonal to the rat race?