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?




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