Older backend dev, multiple projects, and it sucks that context switching is getting harder. Or maybe it is simply unrealistic to handle more than two-three bigger projects?
Posted by Yablan@reddit | ExperiencedDevs | View on Reddit | 36 comments
53 year old developer, mostly backend-focused, with AI help for frontend work. I’ve got several big projects going at once. I maintain two big systems/projects in my current 50% employment, and I am getting into maintenance of another big application from home, on the remaining 50% of my work time.
And in addition to that, I have several hobby projects at home, of which two that I work on sporadically. But lately I’ve been feeling the cost of context switching more and more, and it sucks.
If I haven’t touched a project for a while, it can take me a full day or even two to really get back into it — rereading docs, rebuilding the architecture in my head, remembering the quirks, and just getting back into the flow.
I also have some reoccurring sleep issues, not too severe, but enough to make focus a bit harder. On top of that, I feel like my attention has gotten worse over time too, due to age, and also probably helped along by the usual modern distractions.
I’m starting to think I may need to accept that I can only realistically juggle two, maybe three, big projects this way.
Beyond that, the switching cost seems to get too high, especially if I’m not working on the projects regularly. and it is a bummer, because I have tons of ideas and smaller projects going on, but not the energy to do them all.
I’ve also been increasingly leaning on AI coding agents as a kind of memory helper, especially when I need to get back into a project or restore context. That helps quite a bit. But also of course weakens the mind over time.
So I’m curious how other people deal with this. Does anyone else here feel the same way? How do you manage multiple big projects without spending so much time just getting back up to speed?
Or have you simply come to some conclusion realizing that it is simply not maintainable to work on more than a couple of bigger projects at the time? I think I am slowly getting there. But again, it sure is a bummer.
kyletraz@reddit
53 here too (jk, 36). I juggle 5+ projects, and that full-day ramp-up cost is real. What helped me: I set up git hooks that automatically capture what I am working on and the next steps - so when I return after weeks, I get a quick briefing instead of re-reading everything. The key was to make it automatic, because I would always forget to write status docs.
donalmacc@reddit
Context switching has always been an absolutely productivity destroyers
Anecdotally. The more I’m trying to ram in the worse my sleep is
ritzkew@reddit
Algorithms to Live By quantifies this pretty well. Every context switch costs \~15 minutes of cognitive reload. Three big projects = you're spending an hour a day just remembering where you were. The book's counterintuitive advice: minimum viable multitasking. Batch your context switches instead of interleaving them. Network card designers figured this out with "interrupt coalescing", batching interrupts beats handling each one the moment it arrives. Same principle, carbon-based hardware. :)
Osmium_tetraoxide@reddit
Get your hearing tested, getting a hearing aid early can help your cognition a lot. Eat creatine. Get more exercise in if you're lacking.
In terms of dealing with context switching, try to reduce it, or at least leave everything in complete chunks so you're able to be interrupted at any time with less impact.
Yablan@reddit (OP)
My hearing is perfectly good. I am not THAT old. And geddoff my lawn! Damned kids..
Osmium_tetraoxide@reddit
I didn't realise how badly I needed them until I had a hearing test and started wearing them. I cried a lot since being able to hear properly was overwhelming.
I'm not trying to throw shade, the hearing loss crept up on me over years, so if you haven't had a test (or others reading this) I highly recommend it.
Yablan@reddit (OP)
Great to hear that, and yes, I can imagine how such a thing might help. In my case I am quite sure hearing loss is not an issue, but I might look into it. Thank you.
donhardman88@reddit
I feel this hard. 37 years old, multiple projects, same problem.
What changed for me: I stopped trying to hold the entire codebase in my head and started using semantic code search to get context back quickly.
The workflow: 1. Come back to a project after weeks 2. Ask "what was I working on?" and "how does this module work?" 3. Get actual relevant code with dependencies mapped, not just grep results
Instead of spending a day re-reading files to rebuild mental context, I can get oriented in 10-15 minutes.
I built Octocode for this exact problem - it's a semantic code search tool that indexes your codebase with tree-sitter + embeddings. You ask questions in natural language and get meaning-based results, not keyword matches.
The AI integration helps too - I use it with Claude so when I ask "where was I?" it actually searches the code and gives me context, not just guesses.
Open source if anyone wants to try: https://github.com/Muvon/octocode
Has anyone else solved the "getting back into a project" problem with tools? Or is it just documentation discipline?
Spare_Entrepreneur61@reddit
Yes
Old_Hedgehog@reddit
About 10 years younger, but I have the same challenges.
The thing that works best for me is breadcrumbs. Before stopping work on a given project, I take a couple minutes to stub out next steps. Pseudo-code, comments, a text file of next steps, whatever works for you.
Instead of actually doing that one-last-thing, write out what it is and stop. Leave yourself an easy place to pick back up. Don't stop when you're at a natural stopping point, stop just before it. Otherwise you're leaving an inertia trap for future you.
This gets your brain back into the flow much easier.
Yablan@reddit (OP)
Yes. I always fall into the trap that I have wrapped up a feature, and will pick up the next last day, or that I stopped mid-feature, and will remember what I was working on next day.
But I seldom do remember, and then life comes in the way and it takes days or in case of my hobby projects, maybe weeks until I get back to it.
So as many people here have suggested, I think the best thing is what you say, that ALWAYS spend a couple of minutes at the end of each sessions generating some CURRENT_STATUS documentation, that I can rely on next time I jump into it.
engineered_academic@reddit
IMO the sleep issues are what is going to kill you, literally. Practicing good sleep hygiene and getting enough sleep and exercise has solved a lot of my mental issues when it comes to this job. If I am not well rested my ability to do anything plummets.
Tiny-Sink-9290@reddit
Yup.. I have many days with 2 or 3 hours sleep.. if I wake up to pee (another pain in the ass aging thing that we all experience).. it is hard for me to fall asleep. Especially if things are on my mind. Going thru divorce and unemployed has compounded the issues for me too.
Yablan@reddit (OP)
I know, I know. Believe me, I try.
Tiny-Sink-9290@reddit
Uhm.. are you me? Holy shit.. a tad older.. same issue. I am using 3 to 6 AI windows at a time now.. using AI completely (unemployed so I gotta go as fast as I can or Im done for in this field and will be at Starbucks if I can even find employment there). I keep sending a prompt for one window in another.. and the "That's a different task..." hits me and I am like OH SHIT.. wrong window!
The problem is NOT that we're getting older.. we all do. The problem is those not as old.. don't want to deal with us getting older.. they expect everyone to move at AI speed now and if you can't they want to replace you. Ideally with AI.
kyletraz@reddit
That "full day to get back in" cost is real, and it compounds fast when you're spread across 5+ projects the way you are. I had the same problem and tried the manual approach u/flyer979 describes - rattling off status to the AI before ending a session - but I'd forget, or switch contexts abruptly, and the doc would go stale. I ended up building KeepGoing.dev to automate that layer: it captures what you were working on from git activity and shows you a re-entry briefing when you open each project, so the ramp-up cost is seconds instead of a day. The Desktop Tray menu bar also shows all your active projects, along with time-since-last-session, at a glance, which alone helps me decide which context to reload first. Are you finding the hardest switches are between your employment work and the hobby projects, or between the two big employment systems themselves?
anarres_shevek@reddit
Same thing here. Backend dev, mid 50s. Loads of projects on the go. Sleep issues. What I think I need to do is to rely less on holding all of that in my brain. So, for now, I'm experimenting with AI tools for documentation, and also for re-familiarisation of the code, for projects / areas that I haven't touched in a long time. I'm also using spec driven AI (eg Allium from JUXT; or Open Spec) to improve the quality and brevity of my docs, so they're better suited for me and for the AI. Would love to hear how others are dealing with this.
hippydipster@reddit
This has been my attitude for many many years, even before I could notice my ability to hold massive amounts of information in my head was degrading. You are saved by discipline and process.
It's the same reason a good testing suite saves you - because you cannot see everything, you cannot reliably be right about all the interactions in a large software system. So, you protect yourself by all the things we know we should do, but convince ourselves we don't really need:
Yablan@reddit (OP)
AI coding agents are awesome for this. I have them updating current docs almost as often as I have them writing code. But I have yet to write current status/what I am working on at the moment as reminders. I really have to start doing that.
halfc00kie@reddit
its not age, its bandwidth. context switching between three large codebases with completely different domain models and conventions is genuinely hard regardless of experience level. the research on this is pretty clear, every context switch costs you 20-30 minutes of ramp up time and if youre switching multiple times a day you never actually reach deep focus on any of them. the realistic ceiling for big complex projects is about two, and even then only if they dont both have active fires at the same time. three is just guaranteed shallow work across all of them
flyer979@reddit
I'm a mid-40s dev / ex-founder and here's one way AI is absolutely magical for exactly this problem: For every project I'm working on (4 at the moment) AI maintains both a CHANGELOG and a PROJECT_STATUS doc in the root of the repo, keeping track of every change since inception as well as the last major updates and upcoming steps, which I rattle off to the AI before I finish my session. It's always the last thing I do before leaving the context window.
The next time I open up that project, I just say "Hey, claude (or whoever), where was I?"
And *boom* - a complete, concise, perfectly articulated summary of exactly what was I working on, where I left off, and what I wanted to do next, as of the last time my brain was fully focused on that project. On my better days, it gets me back into that focused mindset almost instantly.
Before AI, I might spend hours reading my most recent commits and code and trying to deduce what I was trying to do, since I was too lazy to actually write these things down, especially for personal projects. Now it takes minutes.
Of course your mileage may vary but it works great for me.
WWWWWWWWWWWWWWWWWW_W@reddit
How do you set up the AI to maintain those documents?
flyer979@reddit
I created a skill to update project status and changelog which I invoke before the end of the session. As a backup (in case I forget to invoke the skill) I also set up rules in the project instructions (so claude.md or the equivalent for whatever tool you use) to make the updates when I commit code or exit.
Yablan@reddit (OP)
I have my AI coding agents updating documentation all the time, both as AI context initialization but also then as a help for me.
But what I haven't done so far is to generate docs on the current status and what I was working on. I really have to make a habit of it, because half the time I stop on something thinking I will pick it the next day, and then weeks go by, and when I finally pick it up again, I have no idea where I was.
Embarrassed_Cut_7559@reddit
i had something like this juggling multiple freelance gigs at once.
Hopeful-Teaching-922@reddit
why is the text centered like that
considerfi@reddit
Something similar. I've written a drop and pickup skill that writes a progress log per ticket and can pick back up where I am and explain to me where I was. I also keep a got project board or something even for personal projects to know what was upcoming. I like the idea of using a local file for upcoming steps.
vanit@reddit
This is actually really clever, even if you weren't even using AI this would be neat.
flyer979@reddit
Awesome idea!
Advanced_Drawer_3825@reddit
Two or three big projects is the ceiling, full stop. I've watched devs on my teams try to juggle five and the quality tanked across the board. The part people miss about switching costs isn't ramp-up time. It's the weird bugs you ship because you only had half the context loaded when you wrote it. Trimming down to two or three isn't giving up. That's the experienced call.
circalight@reddit
The more I age the more I need to be left alone to actually get work done.
mattgen88@reddit
And yet the more people seem to need my review, triaging skills, feedback, etc...
Blue-Phoenix23@reddit
Me too, and the amount of meetings has NOT gone down. We traded too many emails for too many IMs on top of it, and that's even more attention shattering!
Blue-Phoenix23@reddit
I think that's normal, both because of age but, just as importantly - the complexity of what it is you're trying to do. It's easy to manage a bunch of stuff when you're 30 and the stuff you do is so much simpler than it is with 20 years more experience.
Gunny2862@reddit
As an AI skeptic, I will say it allows you to get back up to speed on things when you're interrupted by some asshole on your team.
Dear_Philosopher_@reddit
Enjoy whats left bro.