Will it ever make sense for me to leave for a startup?

I’m 28 and making $450,000 a year at Google. I love my job and everything I’ve been told indicates I’m on the fast track career wise. Will it ever make sense for me to leave for a startup?

Picture the scene:

You’re 73 years old . You retired at 58 but kept on going with other projects because you had no desire to stop working.

Your 41 year old son comes over with his 14 year old boy . Your impressionable grandson of whom you’re so proud.

You’re living in an 8 bedroom house somewhere in Florida because you took up long distance running at 50 and it’s made your joints a little creaky. Warm weather helps stave off some of the pain. And you like the sun

Richard sits with you by the swimming pool sipping an fresh OJ whilst you have your live-in maid prepare you and your family a late lunch.

He looks to you and asks.

Rich : What are you most proud of grandad in your life?

You : Well son, I was one of the fastest rising stars in this software company called Google - you won’t know it. By 28 I was earning $450k. Then by the time I was 40 I was heading up new business development for Asia Pacific and ran that successfully for 7 years before doing various other bits and pieces.

Rich: So work? Ok sounds good grandad.

Richard runs off to play football with his younger brother Mark.

You sit there. And feel a tinge of regret.

Sometimes you lay awake at night wandering if life had would have been different had you have taken the leap back when you are 28. You didn’t need the $450, 000.

You could have survived on a lot less.

You took the easy way out.

transcribed from if it makes sense to join a startup