Are You Overdue for a Do-Over?

A Two Old Bitches activity for reconnecting your voice and power.

Diana Nyad swims from Cuba to Florida on her fifth try! (AP Photo/J Pat Carter)

If you had a chance for a do-over, what would you choose to do? And why? Would you change a conversation, a decision, a choice? Would you speak up? Shut up? Stand up? You know those moments or discussions you re-play in your head? You can do something about them!

The do-over has many cousins but no siblings. Regret is a cousin. We sometimes ask our guests on Two Old Bitches if they have any regrets. We are surprised at the range of responses, from those who can immediately connect with deep regret — we think of our conversation with 92-year old Joy Kane who lamented that she wasn’t present enough for her daughters as they grew up — to those who vehemently champion a life without remorse. “If only…” is also a relative. You think about the choices you made and wonder what might have happened if you’d gone left instead of right. The closest relative, in many ways, is the mulligan. It’s a second chance to do something again, especially if the first chance was bungled because of bad luck or events beyond control. Popular with golfers but rare in life.

The do-over is unique, not a regret or a second chance or an idle thought. It gives you an opportunity to think about actions you can take to achieve change. It asks you to recognize the power you might not have fully claimed and how you can use it in the future. It lets you reflect on the past as a foundation for an improved future. And it’s top of mind for many in 2022. In January, the New York Times asked readers to submit suggestions for ‘word of the year’. Do-over words — like recharge, reclaim, recalibrate, renew, repair — were among the most popular.

And so we have this exercise for you. We’ve done this exercise with hundreds of people across many countries and generations in workshops, with small groups, with one other person or by ourselves. Doing it alone gives you an opportunity to think about stories that are meaningful for you and actions that you want to take. It will transport you to important moments in your life and give you an opportunity to re-think your power. Doing it with someone else or a small group always stimulates heartfelt and honest conversation. We came up with the exercise a couple of years ago, when we went to a one-week writing workshop in upstate New York led by Lynda Barry, the beloved cartoonist. We adapted the idea of the Do-Over from an exercise she taught us.

Maybe you want to curl up on a really comfortable chair or couch with your notebook or a writing pad (pen to paper is important. This doesn’t work as well on devices)? Put on your best writing music, ingest whatever it is that makes you mellow and pensive, and begin.

1. Think of a time when something happened that left you with an unfinished or a slightly uncomfortable feeling. A situation that you’d like to do over. Maybe you were embarrassed or wish you’d said something else or failed to speak up or had a dream within reach that eluded you? Hold that thought.

2. Take a blank page in your notebook and draw (see below) a vertical line in the middle of the page and then a horizontal line across the middle. You now have four quadrants.

3. Now you’re going to do free writing. In each quadrant, write until you fill that box. And for each quadrant, once you start writing, don’t let your pen leave the paper until you fill the box.

4. Now, at the top of the first upper left quadrant, write “The Incident”. Start writing as you think of the following questions: What happened? Where were you? Who else was there? What kind of day was it? What is memorable about it? What did the room or space look like? What smells or sounds do you remember? Keep writing until you fill the box.

5. Now write “What I Did” at the top of the upper right-hand quadrant. Start writing as you think of the following questions: What action did you take? Why? With what result? Who was affected? Why did you choose to do that? What considerations did you apply? Again, fill the box.

6. Now write “How I Felt” in the lower left-hand quadrant. Start writing as you think of the following questions: How did the incident make you feel? Why? How would you describe the feeling? Can you still feel that feeling? What made it memorable? Disturbing? Uncomfortable? Don’t stop writing until you fill the box.

7. Finally, in the bottom right-hand quadrant, write: “The Do-Over.” In this final quadrant, write your responses to questions like: What if you had it to do over? What would you do differently? What would you say differently? Or not say? What action would you take? Why? What would you avoid doing? Why? What changes from the last time? What result are you hoping for?

8. Once you finish the last quadrant, take one minute to re-read what you wrote and digest it. Breathe.

The do-over chart.

If you do this alone, you might end here, give your writing time to settle and come back to it on another day. It might give you an idea of some action, some relationship, some belief that you want to change. If you do it with a friend (highly recommended) or a group of friends, you might want to share the highlights of what each person writes and hear comments, questions and feedback from others. Sometimes lightbulbs flash and emotions get triggered from the writing exercise. That’s why it’s important to do this in a safe space.

We’ve used this as a prompt and stimulant for writing and storytelling exercises. And for living better lives. An example, for Joanne, was writing about an incident that occurred when she walked alongside her husband, Ray, as he was being wheeled to the operating room for open heart surgery. They had been taking a one-year “marriage sabbatical” and he asked her to commit to coming back early if he survived surgery. He did and she returned to their home. Going through the ‘do-over’ writing process years after helped her to re-connect with the emotions of those moments, her questions about the future of their relationship, the path that led her back to her marriage. It helped her understand that she loved her husband more than she hated patriarchy. It is a discovery that helps her center compassion and connectedness in her life. She developed a story about it in a storytelling class she took years later.

Idelisse recalled an incident that falls in her “good-girl-remnants category” of do overs.

She went on a second (and last) date with someone she met online. She was pretty sure they weren’t a match — he liked going to local hootenannies — but she pushed herself to give it a chance. Standing on line at the Berkeley arthouse theater, she found herself looking into the dark eyes of an attractive Latinx man standing in front of them. He smiled and she smiled back. They chatted with her silent date by her side as the line moved into the theater. When the movie was over, he asked what she thought of the movie. They kept talking on the short walk up the aisle. When they parted at the exit to the street, he smiled wryly with a glance at her date saying how lovely it had been to meet. Ide never saw the handsome stranger or her date again. This could have been just a minor though sticky regret. As a do over years later it was more. It gave Idelisse another chance to recognize and release lingering, self-imposed good-girl restraints, along with suspicions that she wasn’t attractive or appealing enough to star in her very own rom-com.

Do-overs don’t just arrive on your doorstep; you need to actively pursue them. A doyen of do-overs, Diana Nyad, first tried to swim from Cuba to the U.S. at age 29. She failed and ultimately, on her fifth do-over, she swam the 110 miles at age 64. What’s the great do-over that you’ve contemplated? Play our game and see what emerges!