
Saturday Side Quest will eventually be a subscriber-only post, but I’m opening this week’s edition up to everyone so I can share a PSA — featuring me as a cautionary tale — as widely as possible.
Here we go.
Earlier this week, I asked the question, “What scares you?”
I was going to say that I didn’t mean to put you on the spot, but I absolutely meant to do exactly that.
I know it’s uncomfortable to think about your fears, but it’s also one of the best ways I know to uncover what matters to you most.
I’m not talking about being afraid of spiders. My daughter is afraid of spiders. She has been reduced to tears on multiple occasions by some poor, innocent eight-legged intruder who had no idea she was inciting such panic.
I’m not talking about fear of public speaking, flying, or small spaces. (Although I feel your pain if any of those are on your list of the things that give you instant anxiety.)
I’m talking about the kind of fear that follows you to your death bed.
In her memoir, The Top Five Regrets of the Dying — A Life Transformed by the Dearly Departing, Australian author and songwriter Bronnie Ware writes about what she learned during her time as a palliative caregiver. A review published by the National Library of Medicine includes — spoiler alert — a summary of the biggest regrets people facing their mortality shared with Ware:
“I wish I'd had the courage to live a life true to myself, not the life others expected of me.”
“I wish I hadn't worked so hard.”
“I wish I'd had the courage to express my feelings.”
“I wish I had stayed in touch with my friends.”
“I wish I had let myself be happier”
Are you surprised?
I’m not.
We all know that no one comes to the end of the road and wishes they’d spent more time at the office.
What is surprising is how many of us utterly fail to do the things in our day-to-day life that would save us from arriving on Death’s doorstep stooped beneath the heavy burden of such heartbreaking regrets.
We think we have plenty of time.
We think we will get more chances.
We think we can wait until we feel more ready.
But that’s rarely the case.
And anyway, this isn’t the kind of thing you want to leave to the last minute.
By that point, addressing whatever you’ve left undone, unsaid, or unfulfilled will require a heavy lift to accomplish.
When I was a kid, I wanted to be a writer and an artist. I spent all my free time reading, journaling, and sketching. But I chickened out of art school (even though I was accepted to several), and when I landed at arguably the most conservative college in Boston (Boston College … not really sure how that happened), I didn’t even go for an art- or literature-related major. I chose the catch-all “liberal arts.” In the end, it didn’t matter, because life happened, and I didn’t return after my freshman year.
I also didn’t pursue my creative dreams.
I was recently leafing through a more recent sketchbook, and came across a mind map I made in 2014. It includes a section on “Things That Bring Me to Tears.” The first item: “lost dreams,” followed by the note, “because of fear.” Also making the list: unspoken love, the courage of artists, and admitting you want something.
My list sounded like an echo of Ware’s top five regrets. Ouch.

I’m not sure if I should be encouraged or embarrassed that the things that make me cry are more or less the same today as they were ten years ago. I suppose I could give myself points for consistency, but I’d rather know I’d started putting those fears to rest by living differently.
Which brings us to today’s side quest. It’s a two-parter:
Part 1: Name one thing you’ll regret on your deathbed if you don’t do it.
Part 2: Do one thing TODAY to save yourself from that regret.
Extra Credit: Comment below with as much as you’re comfortable sharing.
Happy Saturday!
P.S. If you need a hopeful little pick-me-up after all that talk about deathbeds, remember that everything you want’s a dream away.
I'm struggling to come up with something I'd regret not doing. I've spent years coming to the realization that all I need is peace in each moment, so I've been focusing on cultivating that.
But some part of me still really wants to help people. I started my blogs for that reason, to pass on wisdom that has helped me.
I do want to feel like I've made a *significant* impact, though.
I guess I just want to be in a place where every day I know that the work I do not only supports myself, but also supports the healing of humanity and our relationship with Earth and Spirit.
It doesn't always feel that way, so I guess I'm not entirely at peace haha 😅
So I suppose this would be my regret: to spend any more of my life working just to survive instead of working for the liberation and wellness of all beings.
I think it is a rare individual who can extract themselves from following a life of shoulds and shoudn'ts. It is a constant and insidious pressure. I find it strange that in my 50s, I still occaisionally have awful dreams about not finishing my highschool or uni degree, such was the pressure of those early days. We are so cluttered with the expectations of others/parents/society it leaves little room for the feeling world to come through and point the way, to follow what the body or instinct knows. But luckily for us this inner wilderness (to borrow from your blog title) will not leave us alone and keeps dropping clues or a bread crumbs to follow. I also like your challenge/quest, and I will ponder on this!