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Journaling for a Life of No Regrets

How to ward off the top five regrets of the dying through writing

The top five regrets of the dying is a contender for one of the most profound pieces of content to spread through the internet over the past few years. Viewed nearly 3 million times in the first year after it was published, giant media outlets like Huffington Post and the UK’s Guardian newspaper re-published the main take-aways from the original post by palliative nurse Bronnie Ware. They went viral.

The article’s simple statements tap into one of our most existential fears: that we will look back on our lives during our last days and feel, among other emotions, regret.


It’s been nearly two years since Bronnie’s article was first shared en masse. Beyond a moment of deep thought, a hint of fleeting anxiety, and a like n’ retweet, however, have her observations really changed the way we approach our limited time?

I know how easy it is to save an article like this, with the best intention to return to it later, only to let it languish, forgotten until the next time I spring clean my bookmarks (i.e. never). I know that I don’t want to look back at the end of my life and regret things that I have the power to change.

Earlier this year, I started scheduling Paul Graham’s to-do items in an attempt to stay conscious of how I’m living. To complement this, I’ve also created a set of journaling prompts to review on a monthly basis. Five reflect on the month gone by, and five create a vision for the month coming up.

The Month Just Gone

1. What moments of meaningful connection have I experienced over the past month?

“I wish I’d stayed in touch with my friends”

2. What was the most boldly authentic thing I did over the past month?

“I wish I’d had the courage to express my feelings”

3. When did I dare greatly* and most behave in a way that was true to myself?

“I wish I’d had the courage to live a life true to myself, not the life others expected of me.”

4. What was the most fun I had during the last month? When was I most relaxed?

“I wish I hadn’t worked so hard.”

5. When was I happiest during the past month?

“I wish that I had let myself be happier.”

The Month Ahead

1. What could I do to truly connect with someone in the month ahead?

“I wish I’d stayed in touch with my friends”

2. Is there anything that I haven’t expressed my feelings about? What could I do to express them?

“I wish I’d had the courage to express my feelings”

3. How can I “dare greatly” during the next month?

“I wish I’d had the courage to live a life true to myself, not the life others expected of me.”

4. What awesome thing can I do in the month ahead that has nothing to do with work?

“I wish I hadn’t worked so hard.”

5. What will make me no-holds-barred happy over the next month? What can I do to make that happen?

“I wish that I had let myself be happier.”

I’ve created these because I think we all have the opportunity to experience happiness, courage, authenticity, vulnerability, fun, and relaxation; the issue is that we don’t make time to appreciate and nurture these things when they occur.

It’s not too late to start fostering fulfilment.

Join me?


  • “Dare Greatly” is a phrase borrowed from Brené Brown’s book Daring Greatly (Gotham, 2012), which is about living an authentic, vulnerable, full, and enriched life.