Freedom from Success

How I Take Risks Without Consequential Harm from Uncertainty

How much money should I have? How high up should I be in my career? How good should my reputation be? How well connected should I be?

The default answer to these questions is often “as much as possible.”

I obviously prefer having more of these things rather than less, but what I don’t like is having an obligation to acquire them, or worrying about preserving them once I get them. And if what I’m seeking in life is satisfaction and peace of mind, do I even need any of these things beyond a certain amount?

From the satisfaction aspect, the “as much as possible” target is already a hopeless one. Maybe satisfaction can be found from the pursuit of “as much as possible,” but it definitely can’t be found at the destination, because such a destination doesn’t exist.

And even though more freedom can be had from having greater wealth, connections, status, and reputation, the act of pursuing and preserving these things is paradoxically a burden on freedom because such efforts restrict the range of things that can be done. For instance, protecting my reputation may require me not to say certain things, or protecting my wealth may require me not to spend it.

These things can also be affected by random events in life, and I definitely dislike depending on things outside of my control.

My Combination of Risk and Paranoia

As I was in the process of redesigning my lifestyle around the things that give me the most satisfaction and peace of mind, I knew I had to take some risks. I had to consider quitting my job, giving up my income stream, spending some of my wealth, spending some of my time, losing my career status, and possibly losing some of my reputation (at least within some circles).

Now, I actually consider myself very risk averse. But I choose extremely carefully what things I want to protect, and what things I want to speculate with. I’m paranoid about protecting the things that really matter, but at the same time I’m comfortable taking risks with the other things.

The things that I’ve chosen to fiercely protect are my family’s current standard of living, our health, some marketable skills, and enough savings to cover six months of expenses. In fact, I’ve already written off everything else. If I end up with nothing else apart from the things I’ve chosen to protect, I wouldn’t have lost anything important to me. This exercise removes my downside from uncertainty because I’m already operating with the assumption that I don’t have any of the superfluous things. Fate cannot harm me, but I’m still keeping the upside.


Originally published at danielvassallo.com on February 19, 2019.