Feel like I don't deserve my job

For the sake of brevity, I'll summarize some of the backstory by saying that I switched career fields not too long ago, took a job working for a long time friend (who owns the business), and have been waiting to get fired for the last few months. I get paid more than twice what I used to make in my last career, have a large office that feels all wrong for someone like me, and feel anxious about my performance all too often.

I'm good at solving problems, and when I'm given a problem within what I feel are my abilities, I'm usually confident about working on it. But being new to my field, I feel like I'm being hit with an information fire hose. That part is somewhat manageable, but it's the days when I come into work and just don't know what to work on that really grind on me. My boss is the entrepreneur type, very self-motivated, not always good at providing a lot of information on things. And sometimes I feel like he just expects me to figure out what I should be working on. I don't feel like I have a good grasp of the business yet, or what to prioritize, so I'm constantly having to ask what to work on. I think he partly understands and is also partly annoyed.

We have a ticket tracker for our work, and he'll sometimes just say, "grab a ticket and work on it." Except the tickets he creates are often short and lacking any real description. So again, I find myself asking what this or that means or what is wanted. I loathe having to ask. I just want problems in front of me with clear objectives so I know where I'm supposed to end up. Then I can figure out how to get there. But that's kind of rare.

My boss stays extremely busy, because in truth, he's the only person qualified to do a lot of the work. I know it wears on him and I wish sometimes that he had just hired another person like him. I can learn things on my own, but it's often highly inefficient. And while I'm fumbling around in the dark trying to learn some vast topic in a few days, I feel completely useless and worthless, like I can't contribute what I should. But I can't ask him to train me either, because in the past when I have, he get's anxious about how busy he is and blasts through the training with quips like "this is really easy", as if everything should be obvious.

Ever since the guy who had my office before me was fired, I've come into work wondering if it would be the day I'd get fired, too. I know part of me would feel a big relief. But I don't really want that...I don't want to fail. I just struggle with self-worth and self-esteem issues, and this job is the biggest challenge I've ever had in my life. I've thought of telling my boss, "Look, I don't belong here. You need to find someone else who can do this right." And if he were just my boss, I might have already. But he's also a friend and I don't want to let him down.

When I'm clear about the work, I do enjoy it. It's not like I hate the subject matter. But I've essentially been put into what is almost a C-level position, and I do not have the confidence for some of the things required. My boss seems to have a delusionally high opinion of me, except when he's annoyed that I did something to challenge that delusion. I just wish the communication was better...a lot better. I wish I had clear objectives every day. I wish I had more of an entrepreneur's mindset (I don't and never will).

But you know what they say...if wishes were horses, or something to that effect.

What is the business and what is your role/position in the business? Some more info might help. chi

Rather not post more specific details about those things.

Rather not post more specific details about those things.

I'm in a similar situation. When the boss is your friend makes things highly unlikely to get done right

Not sure about your field, but are there some kinds of trainings or courses you can take that will get you up to speed? I regularly attend workshops and other things to learn certain things for my work. Sometimes they're held in another city and I go away for a few days.

I'm studying some self paced training. There's just so much information. I realistically need about 3-5 years to absorb it all.

I don't know if it makes sense for you to go on a weekend workshop trip. I guess it depends on what you do. For my field, there are certain software programs I need to understand, so going to those helps me. Also, we have some manufacturers in my field, so I go to some of their events that they host. Lots of helpful people there. I also am a part of several google groups and online communities having to do with those topics.

You just ask questions even if you vex him. There is no other way. Even if he loathes to be asked questions, he will appreciate you more in some months when you will begin to get part of the job done.