For me, it’s pretty simple.
If I’m starting a long project that could take hours or even days, I open a fresh session for it. That project gets its own space, and I let the agent work through it without mixing it with everything else.
But for everything around my actual work, research, organizing things, keeping track of projects, checking where previous tasks left off, figuring out what still needs attention, etc., I keep as much of that as possible in one main conversation.
It’s way easier to manage.
I see people with dozens of sessions open at the same time, and at some point you’re not really managing your work anymore.
And I think there’s also this weird illusion of productivity that comes from starting a bunch of sessions. You see 20 agents running and it feels like you’re doing a ton of work.
But you still have a limit.
You can only keep track of so many things at once. You still need to know what stopped, what finished, what needs review, what needs another pass, and what you completely forgot about three hours ago.
That gets exhausting fast.
The more of my work I can keep in one place, the easier it is for me to stay organized and actually know what’s going on.
Some people argue that a long conversation burns more tokens. Maybe it does. Even if it costs me 10% or 20% more, I honestly don’t care.
If that extra usage gives me much better productivity and saves me from constantly jumping between sessions trying to remember what the hell I was doing, that’s an easy trade for me.
Quick tip: Don't use multiple sessions for your daily, ongoing work.
Keep everything in one session as much as possible.