Trusting people is hard. I constantly struggle with this. I dentify with people who have had similar backgrounds. This means I’m trusting people that may not deserve it.

When it comes to subjects I’m not familiar with, this trust could be dangerous. I’m also very cynical. I find myself compulsively consulting Wikipedia when I hear new information. Even Wikipedia may not convince me on its own. Usually by the end of this cycle I’ve educated myself as much as one can be educated in the course of a day or two. I spend way too much of my time doing this. Not efficient.

For the most part I think I have good judgement with people. At least as far as who to trust (those who know me would joke, “nobody”). I lean towards the negative, though. I probably cut out plenty of people who are certainly trustworthy because of some small red flag that alarms me. I’m like a deer, spooked by a cracking twig and in flight before even assessing the danger completely. Which is odd, because in the physical realm I’ll fight before flight. The ethereal network of trust just spooks me.

When I evaluate someone to see if I trust them as a provider of information I first consider the scope of their expertise. A good example is a lawyer. If I’m talking to an IP lawyer and they give me advice, I independently verify it. I feel I must do this. By the time I’ve come to terms with the information and understand it, I have increased my knowledge of IP law. I’m surprised how often I get wrong information by experts.

There has to be some balance between knowing enough to trust people and being a subject matter expert. I’m still desperately trying to find this. I spend an inordinate amount of time learning things that are not directly beneficial. I’m always a fan of learning and I love to study but there are countless things to study that are more topical and relevant to my life. I’m giving up time to do something that seems I shouldn’t have to be done.

I think this is why reputation is so important in life. It’s the metric of trust. If people I trust trust someone, I should also trust that person. The less I trust the person referring, obviously the less I trust the stated reputation.

Often people tell me that I should meet someone they know. This requires I trust the person making introductions. Rarely does this work out in everybody’s favor. I know that I generally avoid making introductions except for a very small number of people. I want to make sure my introductions have value.

What drives people to make these introductions? I know plenty of people who seem to have no other purpose in life other than to introduce people. I find myself avoiding these types of people, and I probably shouldn’t. I assume they’re successful in the introductions they make for others or they wouldn’t be able to do it. It is too much of a leap for me to trust blindly. Partially because I don’t think they know enough to trust me or judge me accurately enough. If they don’t know me how can I believe they trust the person on the other side? How is it better than just posting on Craigslist?

It probably doesn’t matter. I think the only time the trust and accurate judging really matters is when people are in a position of extreme power. The people that can change a life drastically with a boolean decision; venture capitalists and angel investors are this type. Even most employers. In spite of all the above, given an opportunity to meet with any person in the position to alter lives, I will meet them.

By their very position in life they are worth trusting in many categories. I may not trust their technical knowledge or other specific knowledge, but sitting down over a cup of coffee with any established business person will yield tremendous amounts of information. Information I’m depriving myself of due to my cynicism.

That information may turn into trust for the source. Or it may turn into skepticism. I know there are people in positions awarded only through deceit and abuse. It’s sad, but true. This is where my golden rule in life comes in.

If someone does something to someone else, expect they will also do it to you.

That’s the core of my trust evaluation. I see how someone works and interacts with other people.