A really good discussion about personal trust and honesty developed out of the most recent reader mailbag that I thought was worth discussing on its own. First of all, I made a pretty big mistake in my answer. I made a giant assumption that the readers called me on, and it’s worth discussing further.

On a very regular basis, I give cash gifts to people I trust who need them or could, at the very least, use them. I take this out of money that I have and just give it to people that could use it. I’ll give some cash to a relative to help that person cover their power bill. This is something that’s common and normal to me.

When I do this, I am pretty picky about who I give the cash to, but if they’re someone I trust personally, I don’t hesitate to do it. If I found out my grandmother was having difficulty keeping her house, I’d be right there with a check in hand to help her. If one of my cousins that I trust was trying to start a business and needed some seed money, a check would be in the mail in a heartbeat. I almost always do this without asking, and I don’t expect a dime back from them.

Why do I do this? I don’t need any sort of written agreement to know that if I needed something, these people I trust would be there for me. When those people are in a pinch, I will help them, no questions asked. When those people are trying to reach for a dream, I will try to boost them if I can.

To me, personal trust and personal relationships like these are more valuable than money. I can’t possibly put a cash value on knowing that if I lost my home, my family, my children, my job - everything - there are people who would take me in and care for me. I was able to make the leap to being a full time writer because of the support and trust and help given to me by family and friends. I rely on this - it’s an integral part of who I am.

Here’s another way to think about it, through the eyes of charities. I tend to not donate to charities unless I know them well. I need to either be intimately involved myself or have someone I deeply trust be involved before I’ll donate. When I do build that trust, though, I’ll write checks to those charities without even thinking. I’ll evangelize for those charities. I’ll do what I can to help them, because I trust them. I don’t worry any more about whether my check is really helping - I trust the charity, so I don’t worry about it. I don’t worry about what I’ll get out of it - I just trust that they’re doing the right thing for something I care about.

Quite often, I assume the same kinds of dynamics in other families and friendships - and I did so to my own detriment earlier. My response to a reader question about what to do with extra cash was to give it away to a trusted family member or a trusted friend, which is exactly what I would do. I’d look for someone I trusted and use that money to seed something they wanted to do, and I’d be very liberal about it.

My response, which basically just assumed much of this, said to give the cash to a trusted family member and then that family member would probably help with college. I also suggested that giving this money away - because it would provide the added kicker of helping with one’s financial aid case, might be unethical to some, but I considered it completely fair because it’s within the rules - nowhere does it outlaw giving away your money. I did not advocate sheltering money - that’s against the rules entirely.

This was met with instant derision that I was advocating truly cheating the system, and looking back on it, I can see where the outrage came from. The outrage comes from the sense that you should never trust anyone when it comes to money, and that’s a sensible and safe philosophy to live by. The only drawback is that you limit yourself in how much you can trust others, and that cuts you off from some things. Is that a good thing or a bad thing? It’s a personal call each person has to make.

A reader asked me:

Let’s turn the tables. If you randomly received a check for $10,000 in the mail from a relative with no note, what would you do with it? What do you think they would want you do to with it?

I’d probably call them up and ask them why they sent it. If they said, “It’s help for you getting started with your writing career” or something like that, I’d give a big “thank you” and put it in the bank. I can think of a lot of other reasons why I’d just happily accept the gift, and they’re mostly borne out of trust and long-term trusting relationships with people.

Honestly, I wouldn’t really question the gift very much, and this in itself is a demonstration of what I’m talking about.

Furthermore, I’m planning already to give my nieces and nephews some gifted financial help when they go to college. I have no obligation to do so. But their parents have helped me a lot during my young adult life.

Should that be reported on the FAFSA? I think it’s ridiculous to think so. There was no implication whatsoever that any help my brother or sister-in-law gave me, in the form of gifts or personal help or advice, was to be repaid in the form of some assistance to their children. If they had a windfall and mailed me a check right now without a note, I’d still not think of it as any sort of implication that I should assist their children with college.

This all translates directly to my advice to the earlier family. In essence, giving that money to Uncle Phil is just another kind of investment. It’s an investment in people, in trust, in a bond that can’t be quoted in dollars. If you give that money to Phil when he has a good use for it, you’ve probably cemented a bond with someone who will help you in countless ways throughout your life, in ways you see now and ways you don’t, in ways you can measure in dollars and cents and ways you can’t.

From my perspective, trust is about helping people you care for because you can and because you want to, not because you’re obligated to.

If this kind of trust seems alien to you, then you’re not alone. There are a lot of people out there who are guarded, and it’s usually because they’ve been bitten after trusting someone, or they’ve heard too many stories about trust falling apart. They call such trust “naive” or “foolish” - and maybe it is.

But when I go back to my hometown and spend an evening around people I trust that deeply, I realize I wouldn’t trade that sense of trust for anything in the world. It’s that valuable, if you can find it.

So what did I learn? First, I learned that assuming things about the relationships between others can usually get you into hot water. I assumed far too much about the trust in relationships in this family, and because of that, I gave advice that was probably not the best advice to give. I gave advice from my own heart, based on what I would do in that situation - if I had money that I was trying to get rid of in order to get in a better state for financial aid, the first place I’d look is my family, the people that I trust. In a family without that trust, my advice was horribly bad - it either implies an illegal financial agreement or it suggests just tossing your money into the breeze and watching it fly away. Trust makes all the difference, and I assumed too much of it.

Second, I learned that when you give money to others, the worst-case scenario is usually assumed by others. If I give some money to my uncle or my cousin, it’s reasonable to think that others are assuming I’m doing it for personal gain over the long haul, that I must be expecting to be paid back in some fashion. That’s not how I view the world, and viewing it that way takes a big stretch for me.

I’ve explained how I view trust, and how that view can skew things. How do you view trust? How deep does it go? How much value does it have for you? Have you ever been hurt by trusting too much? Have you ever been helped by relying on a trusting relationship?