Diane Milo

Age: 60


"Life is all about connection. Value the people around you who choose to be connected to you, and do the work necessary to keep those connections alive."

age: 60  


profession: I’ve had many. Although I retired four years ago from a lengthy career in local government, I have been a teacher in one form or another all of my life. And I have also considered performing arts as a profession – both as a performer and a director. Currently, I am in the process of creating my own non-profit organization that will provide opportunities for youth ages 10-20 to tell their stories through various art forms while engaging in community service projects. The goal of the organization is to spark and foster creativity and build empathy in young people and, hopefully, help them to become engaged and compassionate citizens of the world and future leaders in their communities.


What is the best thing about being your age?

I don’t like the word, “retirement.” It makes it sound like everything’s over, which it most certainly is not! Having reached this age, though, when I was fortunate to be in a position to “retire” from a job that has provided me with financial stability, affords me the opportunity and freedom to engage in projects and activities that I am passionate about and that feed my soul without having to worry about making money.

What's your favorite thing you have checked off your bucket list?  

Oh, boy – that bucket list is quite long! I have been fortunate in my life to have done many wonderful things, but there are still so many things left to do and experience! Honestly, one of my favorite bucket list items was accomplished about five years ago, when a group of friends and I went to New York to attend the Tony Awards! That was a thrilling night for all of us! Currently, my most pressing bucket list items are visiting all of the Presidential libraries and completing the 500-mile Camino de Santiago pilgrimage walk in northern Spain. 

What do you consider your greatest achievement?

I have always been one to keep looking forward to the next project or challenge, so I don’t think I have experienced my greatest achievement yet. As I look to the future, I hope that the non-profit that I am starting will represent a significant achievement – not so much in my life, but in the lives of the kids that will be part of it.  If we can make a positive impact in the life of even one child, that will surely be the greatest thing anyone can hope to achieve.

What is your most treasured possession?

The time that I have spent with my theatre family over the past 25 years has great meaning to me.  My most treasured possession has to be my theatre memorabilia – all the programs, photos, mementos, and treasures that I have collected over the years. I spend time with those material things to revel in the countless memories that they represent, and the special friendships that have resulted from those projects.

What is a trait you are most proud of?

I think it is my lifelong commitment to learning. I think it is important to never stop learning – to actively and intentionally be a sponge that takes in the world around you and creates new possibilities. I believe that that is the secret to happiness in one’s life – staying engaged in the world and keeping your heart and mind in the game until the very end!

What advice would you give your younger self?

Don’t waste time! Make sure that the people and activities that fill up your life are worthy of your time and energy. And don’t be afraid to take risks in order to fully pursue your passions. Most importantly, know that you will unexpectedly lose some people who are very important to you. Make the most of your time with them; cherish every moment that you spend with them – and find ways to spend more of those moments together. And take more pictures with them!

What is your motto or favorite quote?

“I am simple, complex, generous, selfish, unattractive, beautiful, lazy, driven.  I am a work in progress.” – Barbra Streisand

Words of wisdom for younger women

Life is all about connection. Value the people around you who choose to be connected to you, and do the work necessary to keep those connections alive. Recognize the opportunities to make new connections with people who will enrich your life. Bring the lifeforce of passion to everything you do – a thing is not worth doing if you’re not “all in!” Learn as much as you can about anything that you can!  And remember that the goal is never perfection. What matters is that you always strive to be the best that you can be, because that is what is within your control. It is through that effort that you will believe in yourself and your worth, and you will have the confidence to pursue the dreams that matter most to you.


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