Using Google Calendar to Prompt the Big Questions

Did you know, if you put a numerical list in a blog title, you’ll get more hits?

  • “7 tips to…”
  • “30 lessons from my 30th year…”
  • “100 affirmations for…”

Some of these lists can be very hard to process in one sitting. How do you work your way through 100 affirmations for a full life? Or 40 questions to ask yourself to find out if the entrepreneurial life is for you?

I’ve tried to sit down with a few lists before and journal my way through the answers, but my interest fades shortly after question #7, like a drawn-out homework assignment.

I needed a way to take these valuable lists a bit more slowly and intentionally.

I finally decided to plug them into my Google Calendar as events with reminders. It’s been a great experiment, so I want to share the details with you.

The Lists

Do this with any list you find intriguing; that’s really the only way this experiment will hold any meaning for you.

I started with Scott Dinsmore’s Live Your Legend 27 Questions to Find Your Passion.  His How to Live Off Your Passion course is also highly recommended. A few examples of his questions:

  • When was the last time you couldn’t sleep because you were so excited about what you had to work on? What was it?
  • If you trusted that your art (your creativity) would support your life, how would you live?
  • Out of all your current work roles, what would you gladly do for free?

I also used 50 Questions That Will Free Your Mind from Marc and Angel Hack Life.

Some of my favorites on their list include:

  • If happiness was the national currency, what kind of work would make you rich?
  • If the average human life span was 40 years, how would you live your life differently?  (This one is startling, because I’d only have nine years left!)
  • What one thing have you not done that you really want to do?  What’s holding you back?
  • Would you rather be a worried genius or a joyful simpleton?

The Sandbox Network is a global community of “achievers” under 30 years old. Even for us old folks (31!), it’s a cool website. They also have a Playbook that I pulled some good questions from, including:

  • Over the next three months, if you were to prototype a microcosm of the future in which you could explore by doing, what would it look like?
  • Where in your current life do you experience the seeds and early beginnings of the future that you want to create?

Then there’s the big list: Farnoosh Brock’s The Only 100 Positive Affirmations You’ll Ever Need at Prolific Living. This is definitely a list you’ll want to take a day at a time.  Here are some of the affirmations:

  • I know that I have a choice in the work that I do in this world.
  • I believe in my ability to change the world on a small scale with the work that I do.
  • I bet today will be a day to remember. Let us go and greet it.
  • The day will come and go, whether I participate or not. Let us participate.


It took me about an hour to plug a few of these lists into Google Calendar. I just put them in, one a day, for the next few months. I set an e-mail and pop-up reminder for my iPhone and then they started coming in fast and furious.

I barely had a chance to process one before a reminder for the next came in, so I found the right pace by scheduling a “prompt” (one of the questions, lessons or affirmations) every other day. This has worked well for me.

Throughout the day, the prompt sits in my inbox, reminding me of a certain level of depth available in life or nagging me with a curious question. After work, I have a full 30 minute drive home in which the prompt weaves in and out of my thoughts.

I’ve really loved this experiment and plan to continue it with new lists as they find me.

Please feel free to tap into the lists I detailed above. Or, here are a few of my other favorites:


Photo credit: Dafne Cholet


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