“Open When You Need Encouragement to Take Risk”

“Open When You Need Encouragement to Take Risk”

I received a strange envelope addressed to me in my own handwriting. “What the hell is this?” I thought.

I’d forgotten all about writing that letter nine months earlier at the Women At Woodstock retreat. It was during one of our Evening Salons, when Diane Baranello led a thoughtful discussion about making change in ones’ life; going in a new direction that we haven’t allowed ourselves to go before. She handed out little letter cards, one for each of us. She said, “On the flap of your card, you’ll see I’ve written a prompt or a question. Think about it, then write yourself a letter about it. Then seal it up, address it to yourself, and give it back to me.”

The note on the flap of my card said, “Open when you need encouragement to take risk.”

Here’s what I’d written:

You have taken many risks in your life. Some have turned out well. Some have not. But the only times that things have changed were the times when you took risks.

What have you lost your nerve to risk? Is it something new, or something you’ve wanted, planned, and committed to do, over and over again?

Whichever it is, it is time. Do it now.

Isn’t it true that as you’ve grown older, despite the many mistakes you’ve made – or maybe because of those mistakes – the risks you’ve taken have become better informed, better planned, better supported, and more highly rewarded? Your “risk-taking-skill” has grown and matured just as you have. You are better at it than you were a half-century ago, than ten years ago, even than last year. Use your smarts. Use your seasoning. Use what you know to be true about yourself. Go with what you know is right for you, and go now.

Don’t say, “Later.” Today is yesterday’s later. It’s not that the right time needs to come along, it’s that you need to call today the right time.

Go forth. You have my permission. You have my deepest desire, my fervent hope, that you do.

Do it, whatever it is.

You don’t know how much later is waiting for you. You do know today is right at your hands.



The sudden appearance of that letter in my life, long after I’d forgotten the words that I’d written, gave me the push I needed to move forward on an idea I’d been mulling over for many months but that I’d let fade away. I think my advice to myself was pretty good. Lesson: When you talk to your inner self, sit up and listen.

P.S. What would you do if I sent you my letter of encouragement to take risk?

P.P.S. I just did.

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