What is the biggest surprise about getting rich?

I grew up lower middle class and always thought the rich were special. I worked hard, went to university, eventually became a professional and worked my way up. During that time, most of my peers and others in my social strata had the trappings of being rich.

In addition to my day job, I built a business which I eventually sold for low 8 figures. I had much more free time and joined some organizations and clubs, and took up fun hobbies which lead to making deeper social connections with the truly rich – namely people who have $10 million+++ of net worth.

With that perspective of going through that journey, I became better able to sniff out who was truly wealthy, and who was a poseur. What surprised me the most was how many people with fancy cars, who take expensive trips and live luxury lifestyles – who by all appearances we’d call ‘rich’ – are economically hanging on by their nails. They weren’t bad people, just misguided and trying to ‘keep up with the Joneses.’

Looking back at my career when I was a full time professional, more than half my peers were in that category.

The truly rich, namely the self-made ‘millionaires next door’ tend not to flaunt their wealth.

What also surprised me about the truly rich is how much they donate to worthwhile charities, not only publicly but anonymously — far more generously than the poseur class.

Lastly, what surprised me was that the children of the truly wealthy (who grew up their whole life with that wealth), more often than not, tend to have serious sociopathic tendencies.

Something I need to avoid at all costs with my kids (pun intended).


I have 10 M but…

This is a real question by someone:

I sold my company five years ago and have built a net worth of ~$10 million, but compared to my friends I feel like a loser and still keep trying hard at startups that stress me out and make me miserable. What should I do?

And here is a really good answer:

Recap of your situation:
You know from experience that positive feelings do not necessarily follow success in business. At least not at $10M, your one data point. You’re limited on time, and the cost of another data point at $100M may be 10 or 20 years of time that could go into raising your kids, not to mention leisure and adventures of all sorts.

Hence you have an Either/Or decision, which depends crudely on this question: will 10x more money cure your affliction of feeling like a loser, or are you better off enjoying what there is to enjoy around you right now and find the true cause of feeling like a loser?

Many people would tell you that being grateful and giving will satisfy you more. There is some truth to this, but that isn’t guaranteed either. In my opinion, it will depend largely on your understanding of your own emotional life and options: how confident and comfortable you are at a deep level with how you decide to live this one life.

It’s useful to avoid morally loaded words like selfishness and generosity to begin reflecting on this topic. Believing you are worth any less for feeling greedy or other unsanctioned and unreasonable emotions, stops you from thinking about whether and how such feelings may actually cause harm.

There’s no substitute for learning what satisfies us through trial and error. Others can offer hypotheses; but devising the learning experiments is up to us. That’s because it is our innermost selves need to learn about our lives. Moralizing the issue hijacks this process with borrowed beliefs and outside authority.

BN: some positive feelings come with strings attached while others don’t. The fun you have with your kids, for example will likely only lead to other fulfilling experiences for you all.

But prestige comes with side effects:

– Fear of losing reputation, having to defend it;
– Spending years acquiring influence when you could be doing something more enjoyable or personally meaningful;
– Having to keep your own ego in check for fear of alienating those around you;
– Arrogance, a tendency to view others as inferior to yourself, leading to loneliness;
– Most people around you want to use you, leading to mistrust and more loneliness;
– The few who do love you for who you are, you don’t have time for; you’ve got fires to put out
– Difficult to acknowledge weaknesses, as they are incongruent with the projected image and therefore particularly disappointing (e.g. this thread).
– Etc. etc…

Why would anyone sign up for all that when there are so many other things to enjoy?



The only everything

None of this is permanent. Not the things you own. Not the ground you walk on. Not this rock we live on or the space it travels. It will all die. So will you.

You’ve got about a hundred years, give or take. Some have more years than others.

This short period you occupy is driven by events and choices. An event happens and, in that moment, you make a choice. Some choices are easy. Others are hard. Some choices we learn from. Others we don’t. Some we must live with for years. Others are fleeting. Yet all constitutes what we call our life.

Even as children it is choices that teach us and guide us. We know that some choices get us in trouble and others get us rewards. This is how we learn what is right and what is wrong. What is dangerous and what is safe. What makes us sad and what makes up happy.

You might make the same bad choices over and over again. It is your choice to do so or to change it. You might make nothing but smart choices and that is very, very, rare. Most of us fail forward. Learning from the poor choices and the smart ones so that we might make more of the later than the former as we grow.

You choose how to use each second. If you choose to use them doing something you hate or putting up with the shit people lay on you, you are wasting precious time. It is a choice. You are choosing to do so. Plain and simple.

One hundred years is nothing in the grand scheme of things but it is all you’ve got. It is the only everything you will ever know. Make the best choices you can.