Innovacorp investment manager DAWN UMLAH asks The Great “Lean Out” Question in the latest post on her personal blog, DAWN UNFILTERED. You should check it out regularly for her insights and tales about the VC and technology worlds she lives in.

I was watching Jane McGonigal’s 2012 TEDTalk The game that can give you 10 extra years of life where she referenced The Guardian’s article that outlined the top five 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’d 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

It was mostly men who referenced the top two. One could argue this is due to the generational realities of the time, which would be true. But it did spark a question in me as it relates to the gender gap discussions of today.

What if women are simply choosing to regret less?

After more contemplation, I saw how this could apply to the “lazy, undriven” millennials. Perhaps women and millennials are making a thoughtful, conscious decision to lean out instead of choosing not to lean in. What if some are choosing to heed the advice and wisdom of our elders and are not defining their life by their work ethic and chosen career? How would this change our perception of the gender gap and the utility of millennials?

Is regretting less really a bad thing?