Good Friends Ask Great Questions

boat to Martha's Vineyard (2019)

Six years ago — summer of 2019 — we were having dinner with close friends from Houston on Martha’s Vineyard. 

One of those long, lingering evenings where conversation flows easily and someone eventually asks the big question:

“What will you do when you’re empty nesters?”

Our friend, who was semi-retired and in a bit of transition, wasn’t sure.

Without hesitation, I said I would dive into work.

Everyone looked at me like I was crazy.

But I remember thinking — why wait? 

Why wait for some future moment and just get started now? 

So I did. 

And looking back, 

I realize that decision was one of the best investments I ever made 

— an investment in my future self.

Next year, we might be empty nesters. 

Will I be in transition? 

Probably. 

Emotionally, at least. 

But this time, 

I feel more prepared because my history of doing something hard 

- like pivoting has proven to me, I can do it. 

So many of my friends don’t need to work, 

but they’re yearning for their second act. 

It's a journey to discover it. Everyone's path is unique to them. 

According to Tom Morgan, whom I met in NYC a few years ago, we both went through the hero’s journey and now follow this myth to make decisions and embrace discomfort.

This time, I’m avoiding the refusal and crisis stages 

— by taking my right-hemispheric impulses more seriously…

and writing about how you too can transition and enjoy your 2nd Act and empty nesting ;-) 

If you are struggling with empty nesting, please reach out!

Tiffany Kent

Your Friendly Wealth Engagement Guide

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