As a W2 worker, as soon as I have all the tax documents I need. The longer you wait the more people get in line in front of you in processing, which can mean significant delays on your refund. If I were a business owner and owed taxes I’d wait as long as possible, so as to make the most use of the money I owe them.

I use joplin with joplin server running through a reverse proxy in a docker container. I love it. It also supports encryption, so you could use a more convenient service like Google drive and still be assured of your privacy.

I actually fit it all in my blue jeans! I have a pocket organizer that holds the small stuff and it all works out spacewise. Heavy though, have to wear a belt to keep everything in place.

I have an awesome pocket organizer thing I was gifted that holds all the small stuff. So I’m really only putting like 5 things in my pockets when I’m getting ready to walk out the door.

My kit:

• pocket knife
• flashlight
• wallet
• folding phone stand
• phone
• earbuds
• pen (with a cap, not a clicky)
• sharpie
• breath mints
• 4’ multi-end charging cable
• thumb drive
• lightning > 3.5mm (aux)
• USBC > 3.5mm
• bandaids
• OTC drugs (Advil, Tylenol, Aleve, Benadryl, lactase (I’m lactose intolerant))

Everything on that list was added because I needed it and didn’t have it on multiple occasions. There have been plenty of other things that I would love to carry, but found too bulky to justify.

A note to everyone recommending condoms: they do expire, and can wear through if carried in an environment with friction (wallet, pocket, etc). I prefer to play it safe and make a stop at a drug store should the need arise.