The Wrongness Iceberg

I'd say you're doing this the wrong way. You're trying to do a mountain of inference on a mole hill of data. Take more data. This has been of my issues in life, and I've found life gets easier when I just ask. There is the concept of managing up - having to manage your manager, doing what you can to make sure your manager gets what they need from you, even if they don't know how to arrange that themselves. If they're incompetent, their incompetence is your problem.

First, you want to be adequately trained. Too many people focus on getting a list of what to do, instead of a list of the figures of merit. What are we trying to accomplish? What are our goals? What does a good job look like? What does a bad job look like? Stephen Covey distinguishes this as the difference between gopher delegation and stewardship delegation.

Second, instead of worrying about icebergs, ask for feedback, good and bad. People refrain from criticism often because they are uncomfortable giving it, and expect you to be uncomfortable getting it. They only bring it up when their annoyance with your failure overcomes their reticence about criticizing you. That's not going to be a fun talk. Preempt that, and make clear that you want to do a good job, and want feedback to improve. That way they can bring up issues before their annoyance has mounted. When they've done that once or twice and it's not a horrible experience, it gets easier for them to give you feedback in the future.

Interesting model. Another one to be on the lookout for is the "socioeconomic iceberg" where a person's passing comment on some aspect of their life history reveals a large mass of socioeconomic difference from you.

When I've been in situations like this in the past I've been way, way too hesitant to ask for help and advice. The proactive thing to do is to ask for help and advice (especially in situations you expect many people to have been in; this becomes less useful the more unique your situation is). This doesn't just mean asking your boss for help and advice as buybuydandavis suggests (although this is a good idea if your boss is willing to help and advise): it means asking

• your friends who have had similar jobs
• your mom if she has some insight into what the owners will and won't care about
• the internet

It took me way too long to realize that the heuristic "consult domain experts if I am not a domain expert" is a great heuristic. One reason is probably that asking for help and advice felt like admitting incompetence, which was an uncomfortable feeling for me. I am in the process of jettisoning this emotional response from my brain and replacing it with a recontextualization of asking for help and advice as doing research, but by querying people's brains instead of Wikipedia.

• While the "see one, do one, teach one" paradigm of learning by doing is prone to such an error mode, personally I don't find it as much of a problem when taking a more "supervised learning" approach - inferring your function from labelled training data. If you just shadow someone doing your exact job for a few days, chances are you'll avoid most mistakes just by copying the observed behavior. For a restaurant job - or most others - that should cover a majority of situations.

• What about the iceberg iceberg, when noticing your first iceberg you realize there was a metric ton of icebergs under the iceberg.

Isn't anxiety the primary problem? The obvious solution to make less mistakes is to gather data and figure stuff out, but you're not asking about that. You're not afraid of making mistakes. You're afraid of people (including yourself) discovering your alleged incompetence. The obvious solution to that is to fix the anxiety problem. Yes, it might be hard and/or require external help, but you said it yourself :

the anxiety has been catastrophic

Thanks so much, this is exactly what I've been going though at my new job, but hadn't been able to put words to it.

Is it possible though that sometimes the iceberg doesn't exist at all? I got a job as dishwasher at a restaurant when in high school. I fumbled food onto the floor, burned my hands, couldn't understand the head chef and was always working an hour after everyone else left. Feeling the iceberg below the waterline, I worked harder, skipping meals and never taking a break.

I left for a better job, and found out that I had been the best dishwasher they'd ever had in the position.

I wonder if you could use defect seeding in service jobs. Your boss's boss makes a deal with you that you deliberately make certain mistakes (of a severity that your boss should notice but that would not directly bother customers), and they'll keep those mistakes from going on your record. Then you wait to see whether your boss mentions those mistakes in your performance review, to get a better picture of how good of a handle they've got on what you're doing.

The proactive thing to do, naturally, is to try to minimize how many mistakes you make.

I think you came close to saying the proactive thing to do just after this. You talked about correcting mistakes. One step behind that is not repeating mistakes. One step behind that is identifying mistakes. Mistakes unseen will be repeated. Identified mistakes might not be repeated, even if they cannot (at the time) be corrected.

Your model builds up your confidence and skills so keep it up! Part of that process is calving off parts of the mistake iceberg, never to be repeated again.

The proactive thing to do, naturally, is to try to minimize how many mistakes you make.

To me, there seems to be something kind of off about this sentence. Suppose I'm trying to get better at a game like Starcraft. Starcraft is sufficiently complicated that attaining a basic level of still (by which I mean "macromanagement": being able to ensure that all your resources are being used somehow, without worrying about using them well) takes hours and hours of practice. And during that practice, you will inevitably make mistakes; the only way to avoid making mistakes is by not practicing. Indeed, every mistake teaches you something, so I'm tempted to say that what you want to do is to maximize the number of mistakes you make.

In short, it seems to me that minimizing the number of mistakes you make doesn't serve the purpose of making you more skilled. So what purpose does it serve?

Congratulations - this is what it's like to go from the lowest level of knowledge (Knows nothing and knows not that he knows nothing.) to the second lowest level. (Knows nothing, but at least knows that he knows nothing.)

The practical solution to this problem is that, in any decent organisation there are people much more competent than these two levels, and it's been obvious to them that you know nothing for much longer than it's been obvious to you. Their expectations will be set accordingly, and they will probably help you out - if you're willing to take some advice.

While entering a new field, you should be aware that there's at least an iceberg of ignorance you have to deal with. As you correctly noted, it's hard to tell which kind of mistakes this ignorance will lead you to make, but your prior for making mistakes should in general be pretty high. What I'm trying to tell is that you should be able to preemptively deal with the discovery of the tip of the iceberg: you should expect it to pop up at some point. Other people should in general be aware of it too; if they don't, just point it out beforehand. Usually the "I don't know how to do it, but I am willing to learn" position is the best one, and it's normally socially acceptable (except if you have previously sold yourself as an expert on the subject). Even if someone forgot how it was to be a newbie, he should know deep down that the only way to get rid of the iceberg is to slowly liquefy it: start small, get rid of the first tip, and then proceed to get rid of whatever comes to the surface next.