Those questions lie at the heart of a new book called "My What If Year" written by Alisha Fernandez Miranda.
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She's a successful executive who put her career on hold for a year to work for free as an intern.
How did she do it? Miranda credits the support of her husband and two children along with her will to find a way of doing this, but the pandemic lockdowns made it even more difficult.
Now, it's all paying off with book signings and a national TV appearance on "Good Morning America."
Her story is getting such attention because it is as unusual as it is inspiring.
"I was CEO running my own company and just questioning what else is out there?" she said. "What if I tried other things? So I spent a year doing internships at all of the jobs I wanted to do when I was a kid."
The book Miranda wrote about her experiences is the first from podcaster-turned-publisher, Zibby Owens, who explained by saying it is, "a book that can make all of us want to live a better life. I love being a part of it."
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All of this has left the first time author amazed at her good fortune.
"I actually just asked my husband today to pinch me because I could not believe that all of this was happening," Miranda said.
It's just the latest chapter that began during a night out with girlfriends a few years back, "and we were kind of talking about what we would do if one could do anything we wanted."
As a working mom of twins aged 8, she found turning casual talk into a firm plan was very challenging.
"There was a very loud voice outside saying, 'No, no, no, no,' but a really loud voice inside my head saying, 'you have to do this,'" Miranda said.
She grew up loving musical theater so she leapt at the chance to observe rehearsals of "Assassins" off-Broadway. On her way to her first day on the job, she almost knocked out the famous guy who wrote the show.
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"I'm staring into my phone, trying to figure out if I'm going in the right direction, and I bump into this older gentleman, kind of jostle him and I stepped back an got a look at his face which was looking terrified, and it's Stephen Sondheim," Miranda said.
In the end, Miranda found a way to make herself useful -- only to have Broadway shut down due to the pandemic. She pivoted to other internships with an exercise company, an art dealer and an inn that dates from the 1600s on The Isle of Skye in Scotland.
Along the way, she came to the conclusion that she wanted, "the detours to be the main road...and all of a sudden I was taking these detours off the main road, I found they were enriching my life in ways I could not have possibly imagined before."
Today, the Harvard graduate who was on the fast track for so long now makes joy a priority, "because life is so short."
Miranda is fond of asking herself if she is scared while trying something new. And, she is more likely to try something if there is a good chance of failure.