You've kept watch over a certain area for a while, whether that place be a military camp, a criminal encampment, a noble's stash of money, or something similar. You prefer to be high up in places, looking down on the area with a telescope or something similar.

Skill Proficiencies: Investigation, Perception

Tool Proficiencies: Choose one from Cartographer's Tools, Disguise Kit, or Navigator's Tools

Languages: One of your choice.

Equipment: A spyglass, a dagger, a bell, a payslip about your latest job, a set of common clothes, a set of fine clothes, and a pouch containing 15 gp.

Suggested Characteristics

Wathcmen are quite often just relegated off to the sidelines, although many are still passionate about their jobs. They try to keep their eye on everything, but who says they can all the time?

d8	Personality Trait
1	I tend to keep on watch at all times, but sometimes the urge to sleep overpowers me.
2	I'm known for having slow reaction times to situations happening far away.
3	As I'm working, I often play small card games to keep myself awake.
4	I find it hard to get work, and I can't tell why anyone won't hire me.
5	I spend a lot of time outside of work polishing my spyglass. It is my pride and joy, after all.
6	I've committed myself to every shift I take. Whether I'm good or not depends on whether people are hurt or if something is stolen.
7	I use my spyglass every opportunity that I get. I loved to play with my one as a kid, and getting to use it in my job is amazing.
8	I'll work anywhere. Criminal syndicate, entrance to the Border Ethereal. You name it, I'll work there.

d6	Ideal
1	Helpers. I see something happening, I do something about it. It all depends who's side the person is on. (Good)
2	Protection. I do my best to keep things and people safe. There's a reason they hired me, after all. (Lawful)
3	Finders-Keepers. If I see something small laying around that's unsecure, most of the time I take it. It's not like they're going to notice it's missing. (Chaotic)
4	Awareness. I'm quite often aware of horrendous things happening to other people. I mean, I am the one often doing those things. (Evil)
5	Care-free. I don't care much for anything. Every person and piece of gold could travel down the Styx for all I care. (Neutral)
6	Acceptance. I try my best to take people at face value. Then I dig a little deeper. But I always accept who the are for who they are. (Any)

d6	Bond
1	Someone close to me was killed because I failed to keep watch. I aim to take revenge.
2	I've bound myself to work for a crime syndicate to pay for my debt. I need to get myself a way out of this hole.
3	An old family heirloom was stolen from me while I was sleeping. Maybe it's time that I go looking for it.
4	I need to rest soon after working for so many groups, I'm sure I've made at least a few of them unhappy.
5	One night I got drunk and may have accidentally gotten into a bar fight with a noble. Pray I don't run into him again.
6	Not again will I let one of my family members ruin my life just because they thought I don't know what I'm doing.

d6	Flaw
1	I forget to look out for the people I care about around me.
2	I tend to be impulsively reckless, and need someone else to try and reign me back in.
3	I'm afraid that I'll forget to take care of people that ask for my help.
4	I judge all my skills far more than they should be, so all I do is question myself.
5	I follow orders, even if I think they're wrong.
6	Once I start drinking, I quite often can't stop.