what is your biggest regret?

It’s a series of short films. 50 people, 1 question. Yes, ask one question of fifty people.

What is your life’s biggest regret?

Whatever the range of answers, something specific will pop into your head, even if you’re one of those people who doesn’t believe in having regrets. I’m always inclined first to think not of a “something” but a “someone.” Someone I should have kept in my life longer. Spent more time with, made every encounter really count. It’s what I thought of on instinct, a quick association with the word “regret.” Regret is tricky for a lot of reasons, and we can often stand there with our arm at our hip, or pulling an eyebrow, wondering why we reasoned the way we did back then. The important part about regret is allowing it in, to inform our decisions now. Fixing it. Making better choices. After watching this film (the talking begins if you drag the start to 1 minute, 50 seconds), I came up with new ones. Bigger than the knee-jerk coulda, woulda, shoulda loves lost.

What’s on your regrets list?
Not doing a semester abroad
Not traveling more
Not doing karaoke enough
Not doing enough adult musical theater (I need to do this! Nerve-racking!)

So now I am planning, finally, my trip to Burma and Chiang Mai, Thailand for this upcoming January, 2014. Though I suspect there will be no adult theater nor karaoke. Baby steps.



  1. Congratulations on planning the trip! Will you be bringing Lucas & Abigail with you, or just you and Phil? Or just you?

    My biggest regret (so far, life is long and I am sure there will be more) is doing a competitive sport in middle & high school. The older I get the more I realize that pretty much all of my memories from age 5 to 18 revolve around the gym or a holiday with my immediate family. Just last weekend my cousins were talking about some trips and time they spent with our grandparents and I felt a pang, because they are gone now and I missed out on unstructured time with them. Those years have such little responsibility and I don’t think I took advantage of that!

    1. Author

      I *think* just Phil and me. We want to be up before Monks take their first meal, pre-prayers. It would be a very different trip with the kids, a trip I wish I could also take. But to do all that we want to do, it will be just us. I really wanted to make it for the floating lights festival, but that’s in November, and you KNOW I can’t miss a Thanksgiving in the USA!

  2. Not sticking with math in high school.
    Not tsking more challenging courses in college.
    Not sticking with piano.

    1. And now that I have thought about it all day, I regret not picking a more flexible profession. I taught for years, and do not want to return/continue.

  3. Majoring in Art. It caused a domino effect financially that affects every aspect of my life 15 years later: where/ how I live, how many kids I can have, lack of travel, etc.

    Asking my parents for money to fly to take care of my grandmother while she was dying. There would have been tons of strings attached, passive-aggressive emotional blackmail, but it would have been worth it to have the honor of caring for my grandma.

  4. Not having traveled to Europe as a teenager; it would have impacted my life and worldview in a more profound way than it did when I first traveled there at age 25. I’ve since been to Europe 14 times.

    Spending too many years of my music career focused on generating income, which required performing (largely) unsatisfying music, rather than dedicating myself to being creative and feeling musically fulfilled and challenged. I (finally) recently took concrete steps to change that and realized what I’ve been missing all along.

  5. Burma is a lovely country and the thought of you (loud, spoiled american) there makes me sad. There are some lovely, grand hotels in Rangoon, where I suspect you’ll visit. Up before the monks ? Why…are you studying buddhism? Taking photos? Trying to go local. Snort.

    I am really gone now..cannot stand reading about you in Asia. Poor Phil, getting henpecked in another continent. What could possibly go wrong?

  6. Not taking Irish dancing lessons when my grandfather said he’d pay for them- it looks so fun:) I think regrets I have with how relationships went- I regret certain events and things I did but ultimately I am glad they ended the way they did (i.e. crash and burn with 2 big loves) as I have these two beautiful little kids who I cannot imagine life without. Ah yes.

    So you and Phil are staying at a monastery (mentioned monks)? I think that sounds incredible. I imagine I would get so excited and think of the photos you will take. It would be hard to put the camera down and just soak it all in. I’d want to document EVERYTHING!

  7. I’m turning 65 this June & quite frankly, I don’t have any regrets. Not to say I didn’t have some very challenging times/relationships to deal with however i tried to look at every challenge as a divine opportunity to learn more about myself & grow!
    One GREAT accomplishment I DID succeed at after a difficult divorce was to fly to exactly where you are planning to go…..Chaing Mai & then Koi Samaui Thailand…ALONE…to meet a freind there. You will LOVE it…& as a long time Thai mMssage bodyworker, make sure you get LOTS of Thai Massage in Chaing Mai…see if you can visit Mama Lek’s schhool of Thai Massage for a session….primitive but one of the best!
    Enjoy your adventure in Thailand!

  8. Not deferring my first year of college so that I could have been near my grandmother when she had cancer. My mom pushed me to matriculate in the fall after graduation to get me out of her hair while she was taking care of my grandmother, and I regret it to this day. My grandmother was a kindred spirit like no other and my best friend. I wish I could have been with her in those last few months and had known that you don’t HAVE TO go to college right after high school. A bit of a downer eh? I wish my big regret was that I hadn’t traveled enough or done more karaoke… not being snide. I’m serious.

  9. A lot of what comes to mind are “little” things: people that I met but never really made the effort to become friends with, friends I let drift away thinking that was just how it worked sometimes. All those little “opportunities” that can add up to your overall happiness, or not, in a time or place…

  10. I dunno. Regret is a big word, as is guilt. How about losing those negative words and turning them into anticipating and excited to try. I think of life as a finite amount of plays. We can use all our turns going back, doubting, re-playing, regretting, or we can move all of our turns moving forward, learning more, not repeating mistakes. Why spend time feeling bad if you only have a finite amount of time? Spend every minute enjoying that very minute – and if that minute sucks…anticipate the next one.

    I try to never regret my life. I always, always, always, send the peeps I love off with the knowledge that I love them. I try to do good works. I try to be kind. Life is short, sometimes. Long, sometimes. But precious, always.

  11. Regrets? I have them on my bad days but most of the time, I try to look at it as each decision/non-decision has made me who I am today and I like that person so to change those steps would make me someone different. I’m here, I’m now, I’m present. We all do the best we can with what we have at the time. Working towards living life without regrets has been freeing for me though it isn’t easy.

Leave a Reply

This site uses Akismet to reduce spam. Learn how your comment data is processed.