I announced  yesterday that I’m leaving StepOut.

Have you ever spent several years working towards something larger than yourself?  This was my first time doing that.

In college, you have projects that last for a few weeks.  Maybe a semester.   This one lasted me 5 years.  You know the difference between a 5-week project and a 5-year project?

If you’re lucky, if you really care, and if you’re good, you to put your heart into it.

It teaches you to think long term.  To anticipate risks.  To spot opportunity.

I’ve spent the last 5 years optimizing for maximum startup success.  Success is a tricky metric to optimize for because it’s about providing value to others.  After a few months, we discovered that, to be successful, you have to put model in place that allows you to optimize your product for maximal end-user value.  Since StepOut is a dating site, that meant optimizing for maximal quality end-user connections.  Those were my key metrics at StepOut.

I’ve since cleared a lot of headspace that was previously used for such wargames. So what should I use that headspace for?

To an engineer, that kind of sounds like an optimization problem.  What do you optimize for when you’re optimizing your life?  Depending upon your particular professional, politicial, or religious bent, you probably have a different end-game.

A politician optimizes for the most influence.

A priest optimizes for the least suffering.

A doctor optimizes for maximum health.

A teacher optimizes for knowledge.

An artist optimizes for the most beauty.

A marketer optimizes for conversions.

A financier optimizes for the most money.

Of course we all optimize for many other things beyond our purely professional aspirations.  Some are optimizing for the most money.  Others the most health.  The most love.  The length of life.  The least headache and the least heartache.

So what does an engineer optimize for?

Robert Prisig might advocate that an engineer optimizes for quality.  How does one optimize for the most quality in his own life?

There’s a post floating around the ‘net entitled the top 5 regrets of the dying.

1. I wish I’d had the courage to live a life true to myself, not the life others expected of me.
2. I wish I hadn’t worked so hard.
3. I wish I had the courage to express my feelings.
4. I wish I had stayed in touch with my friends.
5. I wish that I had let myself be happier.

Paul Graham, in one if his essays, reverses these regrets into action items he can take daily, and then places them at the top of his to-do list, To remind him every day what’s important.

Don’t ignore your dreams; don’t work too much; say what you think; cultivate friendships; be happy.

Good stuff.  I’m lucky to have these action items as most of my to-do list, not just at the top of it.

TLDR – Optimize for happiness.  Not for comfort.  Life is short.  Live it today.