There’s a serious question that a lot of people are asking these days after the chit-chat stops.

It is asked by successful people who devoted their entire careers or invested everything to build their companies.

It’s starting to be asked by people in the middle of their careers or early in their entrepreneurial ventures.

The question sounds something like this:

• What do you do after you win “the prize” and have enough money to “retire?”
• It was a great game to build something and be successful and invest wisely, but is that all there is?
• What do you do next after you sell your company?

Some of this comes from the heady bubble we are in with money sloshing around in the tech business and real estate values.

It’s just an amazing time to be growing a tech company and getting your piece of it as a founder, investor, or option-holder.

Some of this questioning is from the new COVID reality that has truly changed our jobs, offices, careers, family lives, travel, and all the stuff “we just showed up and did” for so many years without asking questions.

I don’t have a simple answer to these questions.

But I am talking about it almost every day with successful older people AND younger people chasing their big dreams.

• Is the intense, all-in growth game the real prize itself?
• Do we have to do hard things over and over just to be happy?
• Can someone who is hyper-focused on success and growth ever turn it off and just hang out?