>For any individual of course it all comes down to what allows someone to sleep at night, right?

That, and risk tolerance. You could just as easily call me a coward. Especially when it comes to taxes; There are few mistakes I can make that I can't get out of through bankruptcy. Screwing up my taxes is one of those mistakes. (and I'm in a situation where my revenue, but not my profit, is fairly significant. So obviously, if a substantial portion of my revenues are ruled profits, I'm... in trouble.)

It's also, I'm given to understand, important to maintain a 'good faith effort' to pay the taxes you owe... my understanding is that has a lot to do with what happens after you are audited. If they think you intended to defraud them, that's criminal. If you just made a mistake, well, you've still gotta pay it back plus penalties, but you aren't getting a criminal record.

>You strike me as being really honest by the way simply because (using my own ethics) you do things that I don't do more in the direction of being transparent and to the benefit of your customers at your own expense.

That is the goal I aspire to... I don't always live up to those standards. Usually my failures can be attributed to (or framed as) incompetence rather than dishonesty, but... that can be difficult to determine externally. I personally see dishonesty as way worse than incompetence, even when the effect is the same, though I acknowledge and have a hard time arguing with the argument that the effect is what matters. I actually have some conflicts here because I /know/ I'm overconfident about how quickly I can get something done... but by how much? it varies a lot. Does this mean I shouldn't take jobs? I've chosen to take jobs. I pad my estimates a lot (like 2x) to cover the uncertainty, but sometimes that's still not enough. (and sometimes, it's way too much) I personally see that as a little bit dishonest. But, I don't think it's entirely unreasonable to re-frame it as incompetence, which is easier for me to swallow.

A good way, I think, for me to get around this is to take more 'pay upon completion' type projects. If I make it? great. If I don't? I don't get paid. I'd feel pretty good about that. Unfortunately, most of my good-paying contacts want to go hourly; all the per-job offers I've gotten have been... much less remunerative, for any reasonable estimate of how long the project would take.

I'm not entirely sure that a focus on honesty and transparency is entirely 'at my own expense,' though; It could also be seen as me trying to turn one of my weaknesses into a strength.

I'm sure you can get ahead by pushing that line if you are good at it... but because my line is so, for lack of a better word, conservative, once I step over my line... I have a hard time seeing where other people would set their line. I suspect (partially supported by some tentative exploration when I was younger) that I'd be bad at pushing that line. Worse-off than if I was too conservative.

I don't really see the line between the normal schmoozing and quid pro quo of enterprise sales and the unacceptable kinds of kickbacks. Pushing that line is... difficult; there's a sea of cultural norms that don't make any sense at all to me, and knowing how to give the acceptable gifts and not offer the unacceptable kicbacks is essential to enterprise sales. If you do it improperly, well, everyone sees you as very unethical, and your behavior can easily be seen as criminal. So again, here is both self-knowledge (that where other people draw that line makes no sense to me, so I can't predict where that line would be) and cowardice, in that I don't want to 'guess and check' where the consequences to being wrong are so high.

But yeah, a lot of it is also just what makes me, perhaps irrationally, feel good. I can make a pretty good living as an individual contributor, and my financial needs are small. I

A good example of how it is just irrational good feelings is that I'm mostly okay working for body shops and having someone else do all that shady shit. As long as I do my job, I feel pretty okay. I'd class this as the same variety of hypocrisy as eating meat but being unwilling to kill animals yourself.

Yours is probably a textbook case of someone needing a partner who has a better idea of where that line is seat of the pants wise. I've never needed that it comes naturally. I simply weigh the downside to any decision vs. the upside. It's almost automatic. After a while your brain just works that way.

I'll give you an example (which doesn't relate to business). My state requires front license plates. But I have a nice car that I don't want to mess up. But I also don't care if the cops stop me. So I didn't put the license plate on the car. Worst case is I get pulled over. I get a ticket for $85 or whatever. Maybe in some extreme case something even worse will happen but it shouldn't. So I decide to take that chance. (Nothing has ever happened not that it couldn't etc.).

In the case of the body shops you are probably shielded enough from the down side both legally and also emotionally so you are ok with it. I think that's fine from the way you are describing it.

>Yours is probably a textbook case of someone needing a partner who has a better idea of where that line is seat of the pants wise. I've never needed that it comes naturally.

My life partner, actually, is sort of stepping into the role you describe. It's hard for me letting go, but I'm far more likely to be okay with my partner taking that role than some random sleazebag. I mean, her background is more technical than mine; which is a downside in that role (though an upside for me actually following. Like most technical people, I have a hard time accepting leaders who don't have a technical background.) but eh, hiring for that role is really hard; judging from my past, when it comes to evaluating business people? I'm worse than random.

But it's still ultimately my business, and ultimately mistakes (or unethical decisions) made by that business are still my responsibility. Perhaps I will feel differently if someday I'm no longer the majority shareholder? (my partner is vesting in over time, so I am still the majority shareholder by quite a bit..)

But it's probably good that it's her; we have a lot of shared values and cultural background, and ultimately I see her as a good person, so while she's probably not the best businessperson available, she might be the best at working with me.

>I simply weigh the downside to any decision vs. the upside. It's almost automatic. After a while your brain just works that way.

Yeah, but almost nobody weighs moral concerns as zero. I mean, for an extreme example, you wouldn't murder someone for money even if you were certain you wouldn't get caught, and wouldn't face any negative consequences save those you imposed yourself.

(I'm not claiming that 'sharp' business practices are anything like murder; I'm just pointing out that you have the same line I have, even if yours isn't quite in the same place as mine. Almost nobody does a pure cost benefit analysis with no ethical or moral overlay.)