The Software Games: Endless Grind
What if your career was an RPG?
“Aaaand... merge.”
Finally. Three hours on that stupid memory leak. I stretch and look around. Empty office, again.
A notification pops up:
+20 XP (Debugging)Just twenty damn experience points. I still remember my excitement when fixing my first memory leak gave me 500. I was sure I’d reach staff by 25.
I grab my things and head out.
I turned 30 this year. Nine years already since I graduated college.
The first three were pretty amazing. Everything was new, the XP just flowed in.
And then I hit the wall.
I’ve been stuck at Senior Engineer for six years.
I pull up my stats while waiting for the elevator:
Thanks Linear for supporting today’s article!
Here’s the team version of the XP trap: sticking with a project management tool everyone hates because switching feels hard.
You know the symptoms: Engineers don’t update tickets, PMs chase people on Slack, work is invisible until someone asks about it in standup.
Teams that switch to Linear see the difference immediately:
5x more teammates create issues - Linear makes it easy for anyone to submit feedback or report bugs through Slack, email, or support tools
90% more issues logged - Engineers actually track their work because it takes seconds. The work that was always happening becomes visible
Issues resolved 3.3x faster - From bug identification to feature shipment, teams move at higher velocity
Linear’s switch campaign runs through February. 2-way sync keeps your legacy tool updated while you try it, no big bang migration required:
The way leveling works is simple. Eight skills, four primary and four support. You grind XP, your skills level up, and your general level follows.
Junior to Mid takes about 10,000 points per skill. Mid to Senior is 100,000. Senior to Staff is a million.
Staff is where most people get stuck. You need your primary at a million, six others at Senior, and you’re allowed one stuck at Mid.
That wouldn’t be so bad if not for the fact that XP for doing the same task keeps shrinking, in parallel with the requirements getting harder. That’s so unfair.
Twenty points. Toward a million.
The drive home is quiet. Rush hour ended hours ago.
Somewhere along the way I convinced myself that reaching Staff level would fix everything. It's not rational, but I can't shake it. Better salary, letting me send more to my family. Finally buy a small apartment. Dates would go better. I’d finally be set for life.
917,200 out of 1,000,000.
It feels so close, just 83k points to go. But when I do the math (which I do every day), it’s still 10 years at the current pace.
I’ll be 40.
I scroll my phone in bed, not really looking at anything.
I never wanted to be a job hopper. I watched my friends leave every two years and thought they were doing it wrong - always starting over, never building real depth.
That wasn’t going to be me. I wanted to build deep expertise.
And it worked, sort of. Whenever something breaks in a way nobody understands, it ends up on my desk. The debugging guy. I like that. I’m great at it.
Just took me six years to notice it stopped teaching me anything.
I put the phone down and stare at the ceiling. Sleep doesn’t come for a long time.
The endless grind
Ok, back to (a much happier) reality.
In the last couple of months, I got addicted to reading the LitRPG genre. It’s a fiction genre that blends fantasy/sci-fi with video game mechanics, introducing elements like levels, stats (Strength, Intelligence), quests, and experience points (XP).
It got me thinking:
What if our software engineering careers were like a game? If we could quantify our experience based on something that is not just years on the resume?
In an RPG, the first levels are pretty easy. You kill some low-level monsters and progress quickly.
Slowly, those same monsters are not challenging enough. The XP you get barely moves the needle. You have to push yourself, going to more dangerous areas, fighting monsters closer to your level (or ideally, a bit higher).
It works as the “Zone of Proximal Development”, which is the sweet spot for progression (although that one talks about mentoring as a way to help others progress)
Tackling challenges that are too hard is just a recipe for failure (and for losing confidence in yourself).
But doing the same things all over again leads to stagnation.
It doesn’t mean you need to switch companies - in most cases, you’ll have a lot of internal opportunities. The problem is that those opportunities don’t just arrive out of nowhere.
Games are addictive because of the constant progression and growth.
What if YOU as a manager, spent more effort to adjust the game difficult for your team? One of the biggest challenges of our job is to balance the needs of the company and the needs of our engineers, and finding growth opportunities is at the crux of it.
From what I’ve seen, most engineers will just leave if they keep doing the ‘known’ parts again and again, building feature after feature, with the same tech stack, serving the same scale.
If your engineers were characters in an RPG, what skills would they want to level up? In what areas are they stuck grinding? What can you do to help?
Final words
If you love reading fantasy, I highly recommend trying out the LitRPG genre, it’s pretty addictive.
Here are my recommendations:
Dungeon Crawler Carl - start with this one.
The Completionist Chronicles Series
All the skills - a deck building one!
He who fights with monsters
Chaos Seeds Series
Jake’s magical market
Defiance of the fall - currently reading, great so far!
I’d love any other recommendations! (Didn’t Dungeon Born, The Primal Hunter, and a couple of others).
Loved this article! A great mental model honestly