re: Folks who left their employment to pursue their own company/self employment .....

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Curios on this - do you have a format or keep any kind of journal for ideas, etc. Just trying to see what your goal is by doing this. Very good idea and intriguing to me as I continue aging up the ladder.

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No format per say (and this feels so weird writing out).

But I talk to my 15 year old self and ask him if I am making him proud. At 15, I wanted to be rich, successful, sleep with a lot of girls (remember, 15), travel a lot and just do a bunch of cool shite.

What did I do this week that makes him proud of who I am at 40? He wants me to hit on the cute girl at the cafe, go on a challenging hike, try and make some new friends.

Conversations with my 80 year old self are completely different.

Did I spend enough time with my family this week? What did I do physically to give 80 year old ILB great health? Did I eat with him in mind? Did I conduct myself in a way he would be proud of? Did I treat everyone with respect? Am I putting my family in a position of being successful and being a proper role model?

I could go deeper into this but this is the basics.

These are real conversations with note taking and are often very emotional.


ETA: In context of the OP, my 15 year old self would want me to go for it! Take the risk and start my own business. My 80 year old self would be very proud of what I have built and the level of success achieved.

OP - I would imagine your 15 year old self and 80 year old self want the same for you.