Democracy Cafe

When should you hold on — and when should you let go — for dear life?

That is the question for our Third Annual Alexander Phillips Arete Award.

We invite you to delve into and share with us, — in a written work (poem, essay, short story, what have you, preferably in English, Spanish or Portuguees, but you make the call), or video, or piece of art (drawing, graphic, painting, you name it) — that explores this question.


My late father, Alexander Phillips, was the most careful planner and financially frugal person I have ever known, and one of the most careful and expert investors — financial savviness personified — I have ever known. Dad invested painstakingly every spare penny, putting in many thousands of hours of loving effort into this, over the course of more than half a century. He left nothing to chance or unexpected contingencies — or so he thought, tragically.

A child of the Great Depression whose family had immigrated dirt-poor through Ellis Island to the U.S. from the tiny volcanic island of Nisyros, Greece, my dad, at the tender age of 7, had to become a breadwinner of his family when his own father, Philip (after whom I’m named) died of a massive heart attack at age 57. Dad more than rose to the occasion, supporting his mother and brother and sister by delivering groceries, hawking newspapers, playing piano at dance halls and taverns after teaching himself to play by hear.

Nothing kept this good man down, his spirit indomitable. Dad lived a life filled with accomplishment (I write much about this in my newest book, which I completed just yesterday morning, on my 22nd wedding anniversary).

Even when this overachiever was at the professional pinnacle, Dad still bought clothes and shoes from Goodwill. That’s how penny-pinching he was. By the end of his life, after weathering the recession of 2008, he had accumulated millions.

Dad thought he was in complete control of his assets. .

Dad’s goals in accumulating such savings were at least twofold: 1) If he was ever frail and infirm in his senior years, he wanted to make sure he had enough socked away so he could afford in-home nursing care; he never ever wanted to have to go to a nursing home. 2) he wanted to leave those he loved and admired the most, and whom he felt were the most deserving, with an ample nest egg.

Dad made a tragic error: He hid his investments from prying eyes. Hid them all too well. He thought he’d set up his estate portfolio in a way that was ironclad and would prevent anyone from tapping into or misusing his millions. He was wrong. There was one contingency he didn’t — wouldn’t, couldn’t — take into account.

Dad died on or around September 17, 2011. I was never so much as informed by those with him at the end that he had died. His home was looted of nearly everything of value before any decent soul could arrive on the scene. Gone were nearly all of his investments, nearly all of his assets accumulated for all those decades. Poof. Just a tiny bit of his emergency funds and play money was discovered.

The ‘reasons’ given by one with Dad at the end for why his genuine loved ones like me weren’t informed about his passing remain as chilling and sickening today as they were at the time.

In some ways, Dad brought this on himself. He was determined to control, in a hidden manner, all of his assets that he had amassed over the course of many decades. In the last days of his life, all those decades — more than 50 years’ worth — of the most meticulous planning imaginable unravelled in the blink of an eye.

In the end, this dear man who thought he was in consummate control, lost control of everything – and not just of his finances, though I will not put down in words here what all else he lost control of; it remains too horrific still.

What lessons are to be learned?

For those of you who like to ‘be in control,’ are there times and circumstances when you nonetheless feel you need to just ‘let go’? If so, why? If not, why not?

Conversely, for those of you who live primarily by the ‘let go’ there, are there still times when you hold on for dear life (or would if you could)? If so, why, if not, why not?

Which fears, resentments, angers should you consider letting go of? Which should you hold onto? If you do hold onto them, are there constructive ways in which you can channel them? Can you ever do a little of both — holding on and letting go at the same time? What about love? When should you hold onto it, and when should you let go? What if someone in your life (as was the case with my dad) betrays every trust and confidence and promise imaginable — should you still hold onto that love, for old time’s sake? Let it go? Or should those who are still living out the nightmare of this betrayal, now that my father is gone, try to fashion out of it a new kind of love , while both holding on and letting go?

Odin Halvorson and I so look forward to your submissions, and we remain tremendously grateful for those who submitted in our Alexander Phillips Arete Award competitions of years past.

All winners will receive a signed copy of whatever books from Christopher Phillips they’d like among his five Socratic-philosophical works for adults and seven for children. First place also receives $100 — not from the nonprofit but from yours truly. And we shall also do a give-and-take on our Socrates Cafe YouTube channel for our program Cafe Aretista. And maybe more than that!

As things stand, winners will be announced (though all who submit truly are winners in our book), in mid-September.

Please submit your submissions in Word, JPG, MP3 or MP4 or PDF format, or whatever works best on your end, to:, and