on plunges

If you repeated today, over and over, where would you be in 10 years?

Life has no signposts.
There's nobody to tell you to speed up or slow down.
There's nothing preventing you from smelling roses or falling in brambles.

I think we feel lost because there's no absolute destination.
Most people agree that maximizing the happiness of yourself and others is a decent way to live. But even this is a tricky endeavor - exercising and eating ice cream make me happy in very different ways!

Lately, instead of maximizing happiness, I've been minimizing regret.
Which will haunt me more: spending my evenings with friends, or spending my evenings with Friends?

They say that hindsight is 20/20. Regret-minimization asks you to anticipate what your life's rear-view mirror will look like down the road.
It encourages you to look past your immediate desires - to act in your best long-term interest.

Most regrets aren't things that we did. They're things that we didn't do.
Our greatest ghosts are unspoken words, wasted time, missed opportunities. These are the scariest spectres that dance in our dreams.

So what if you had actually taken the time to travel? If you had actually pursued your tap-dancing career?
Well, it probably would've failed.

There's a reason most people aren't following their dreams.
It's because lofty goals demand a lot of risk and a lot of work.

So what does regret minimization look like then?
Sometimes it means exercising, eating well, and saving money.
It also means clearing your schedule to tap-dance, or whatever your plunge is.

I recently realized that I would regret spending my 20s in an office. I was doing things I didn't care about to live in a place I didn't have the time or money to experience!
I want to spend as much of my time making things as possible - it's what I love to do!
Fortunately, I've been spending the past few years honing skills that allow me to work more flexibly. So my next plunge is applying to Toptal, where I'll be able to work flexible hours on interesting projects. Sites like Upwork and Craigslist seem a bit overcrowded, with too much risk of landing bad clients. Toptal has a very selective screening process, which will be great if I get accepted! It'll mean better-pay and higher-quality clients, which ultimately means more time to write essays, bake bread, build robots, make music, and play with lasers.

What I'm trying to say is that successful plunges don't look like plunges at all.
Change your plunge from cliff-diving into community-pool-low-board. Because you'll probably fail a few times, and unsuccessful cliff-dives don't afford you another chance.

Minimize regret and mitigate risk.

In other words, successful plunges require you to remove dirty obstacles coming down the pipe.



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