Why You Should Embrace Regret

by Brenna Holeman

Silvia Colombia Market 13

I think we can all agree that one never regrets avocados

I’m always a little bit wary of people who say they have no regrets. Really? Not one? There’s not one thing you would change about your past, not one decision you made or sentence you said that you’d like to take back?

I used to be one of those people who said “no regrets!”. I used to write it in my high school journals after asking a boy out and getting rejected, or missing out on a party because I felt uncomfortable with who I was. In my fifteen-year-old mind, these were all the regrets that I could possibly have.

Yesterday was my birthday; I turned thirty-one years old. Last year I wrote an article called 30 Things I’ve Learned in 30 Years. Most of what that article said was pretty standard – basically, be nice to people… oh, and read a lot – but numbers 24 and 25 said the following:

24. Do not criticise yourself for things you did in the past – it will only drive you crazy. I have a habit of doing this. I think about that one comment I said that I shouldn’t have, I think about why I turned left instead of right, I think about the time my throat closed up and I couldn’t sing in front of the audience of 2000 people (that was 14 years ago, by the way). And what has this accomplished, all this thinking and self-criticism? Nothing. Nothing at all.

25. Similarly, do not lie in bed at night and think, “what if?”. I do this all the time, and it never ends well. It is pointless. Nothing can change the past, and dwelling on it will only drive you mad. Reminisce about the good times, yes, but realise that there will be more good times ahead (even better times, in fact).”

I still completely stand by those points. Dwelling on things in the past will indeed drive you mad, and there isn’t much you can do to change what’s already happened. Those two point do not mean “no regrets”, though. I believe that after a certain age there’s no such thing as having no regrets, unless you are ridiculously confident, ridiculously egotistical, or, well, this guy:

I still lie in bed at night and think about things I should have done differently, whether it’s from that same day or from two decades ago. As much as I love my life and feel proud of (most of) what I’ve done, I still have regrets, some big, some tiny. Instead of banging my head against the wall in shame, however, I’m trying to take those regrets and learn from them. If those who ignore the past are doomed to repeat it, I’m going to try to do the opposite. Here are some of my regrets, and why I’ve learned to embrace them.


Regret #1: I don’t see my family enough. This is a regret I will probably have my entire life, and sadly there’s not much I can do to change it. My immediate family is all in Canada, spread across Toronto, Winnipeg, and Vancouver. I live across the pond, which means I’m lucky if I get to see them once a year. This also means that it is very important to maintain an active line of communication, whether through email, text, or Skype. When I’m in daily contact with them, I’m happier. Lesson learned: Stay in constant contact with those you love. The distance sucks, but if you want to maintain a close relationship, you have to put in the work.


Most recent family time in Nicaragua

Regret #2: I don’t speak another language, or play the guitar. Over the years I feel as though I’ve become a jack of all trades, master of none. I’ve studied French, Spanish, Japanese, and Russian, yet am only fluent in English. I’ve learned classic piano, flute, and voice, and fiddle around on the ukulele, but do not feel totally confident with any instrument. I’m tired of feeling this way, but I know that the the only way to change is to go out and learn. Lesson learned: Stop saying, “One day I’ll do _______.” If you truly want to learn how to do something, go and do it.

Regret #3: I’ve wasted a lot of time on things like TV and the internet. I work online and I live alone, so if I’m not travelling, often the only interactions I have on a day-to-day basis are those via the internet. I understand that this is not only necessary to my career and my Master’s degree, but a reflection of our time. However, I have occasionally found myself sitting in front of the TV with my laptop on my lap and my phone in hand. I’ve lived a great and a full life, but there are definitely hundreds if not thousands of hours I have wasted browsing online clothing shops and watching mindless shows. Imagine what I could have done in that time – I could have, um, learned another language or learned how to play the guitar (or probably finished my book by now). I’m actively trying to spend less time online; I’m spending a minimum of two hours outside every day, I’m reading more (outside of the bath or bed), and I’m working from cafés and pubs three or four times a week. I realise that this last one means I’m still online, but at least I’m around, you know, other humans. Lesson learned: Go offline. Well, not this instant… please finish reading this blog post first. But then go run around in a field or take photos of clouds or call a friend to meet for coffee or dust off your guitar.

Regret #4: I didn’t leave relationships when I should have. Over the past ten years, I have had one serious relationship of two and a half years and three semi-serious relationships of six months to a year. In each of them I have known that they were going to end well before they actually ended. I used to stay in relationships purely because I wanted to have a boyfriend or because I clung to the notion that things would work out despite ongoing unhappiness. In the past few years, I haven’t had any relationships that have lasted longer than three months, and I chalk this up to a greater awareness of what I want from a partner. I no longer need a man to make me happy or for me to feel fulfilled, so if things aren’t working out, I would rather end it before dragging a relationship through potentially months or even years of frustration. I’ve been much happier this way, and it also means that I have been able to stay friends with people I’ve dated. Lesson learned: If you feel in your heart that things are never going to work out, or that you’re with the wrong person, it’s probably better to end it sooner than later. It will spare both of you a lot of pain in the long run. It also might make you look at the world differently. This goes for friendships as well; if you feel someone in your life is toxic, it is best to cut them loose.

Regret #5: I didn’t feel happy with myself until I was in my late twenties. Despite being quite extroverted and having lots of friends, I’ve spent a lot of time on my own. Sometimes I’ve retreated too far into myself, becoming way too self-reflective. I’ve felt lost and confused by what I truly want in life, and I went through long bouts of unhappiness in my teens and early-twenties. I just wasn’t happy, and I didn’t really know why. Around age twenty-six (coincidentally when I broke up with a bad boyfriend and decided to go travel the world for a while), I just said, “Fuck it.” I was done with being unhappy. I’ve said it before on this blog, and I believe it: happiness isn’t deserved, it is earned. My life is now much fuller and happier (and more content), and I credit this to working hard to make it full and happy. I obviously still have low times, and times when I question just what the hell I’m doing in life, but for the most part I look at the world with positivity and appreciation. Life is too short to be unhappy. Lesson learned: Life is good. If it’s not good, do something about it. Happiness is yours, but only if you allow it in. (Note: I have never suffered from serious depression or anxiety, so I am aware that this advice may not apply to everyone. If you are struggling with depression, here is an article that may help.)

Regret #6: I treated someone badly. I like to think that I’ve never been mean to anyone who didn’t deserve it. I’ve never been a bully, and never treated someone cruelly unless it was completely warranted. I definitely have a bitchy side, but I keep it under control (if you’ve met me and you think, “No, she’s just a straight-up bitch,” please tell me). I do regret how I treated someone recently, though. He was sweet and kind and he liked me a lot. I knew that he liked me, but I was unsure of my own feelings toward him and so – without reason – was cold and distant toward him, even teasing him when I would see him. It was completely immature. I’ve since talked to him about it and apologised, and we’re friends now, but I regret that I acted the way I did when he had done nothing to deserve it. Lesson learned: Just be nice. Don’t be an asshole.


Regretting something or other on a bus in India

Regret #7: I travelled too much. I know – poor me. I do not regret the years of travelling I have under my belt, but I do regret some of the ways I’ve actually travelled. When I first went abroad on my own nearly a decade ago (oh dear God), I was a very greedy traveller. I wanted to see as much as I possibly could in a limited time. I was backpacking in Europe at the time, and I went through something like twenty countries in four months. I wish I would have slowed down and really taken it in, or at the very least visited places other than just the main cities. Lesson learned: Figure out your travel style. If that means spending a month in each place, great. If that means rushing through countries as fast as possible in order to tick them off, by all means go forth and conquer, er, tick. I personally prefer to spend at least a few days in each place, and visit a variety of places within a country, but to each their own. I am writing a post on travel regrets I have very soon, as that’s a whole other ballgame (and I think there will be some funny stories involved… Exhibits A, B, and C).

Regret #8: I didn’t give my number to that cute Scottish guy. I really do regret this one. He was smart and funny and hinted at us hanging out together a few times. He asked when he could see me again and I said, “Oh, I’m sure we’ll run into each other again,” and walked out of the bar with a flick of my hair. Guess how many times I’ve seen him since then? Zero. Damn it. Lesson learned: Don’t be too cool. If you like someone, ask them out, or give them your number. Fifteen years ago, after an incident like this one, I would have written in my journal, “No regrets!” Now I just write, “Oh, you idiot.”


These are just a few of the regrets I have – I have many more. I’m trying to embrace them and learn from them, not hide from them. Do you have any regrets? What have you learned from them?

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Emma May 7, 2015 - 4:59 am

Wow, I identified with almost all your points here (except number 3, I think time you enjoy wasting is never wasted time) and self reflection is very important. I often ask myself if I like the person I am, those times that I don’t is usually during periods when I’ve been unhappy. I love the honesty in all your posts – it’s so refreshing!

Brenna Holeman May 7, 2015 - 3:36 pm

Thank you so much Emma! I have definitely enjoyed wasting time and I think there’s nothing wrong with that, however there have definitely been days that were COMPLETELY wasted and I felt guilty about them after. Those are the times I’m referring to!

Georgina May 7, 2015 - 9:29 am

Great post! I use to have no regrets as well but with age comes wisdom. I think regrets help you learn who you are and make yourself a better person.
I 100% agree with number 1, 2 & 3. I don’t see my family enough (since I am in London and they are a 26 hour flight away in Brisbane, Australia) but the distance has made me make the effort to always talk to them via Skype once a week and snapchat or Facebook chat. Even though we are not on the same continent or even hemisphere I feel our relationship is even stronger than it was 18 months ago.
Number 2, I wish I stuck with Japanese though high school and didn’t give it up because it wasn’t cool to try hard in first year. Now I would have to pay a substantial amount of money to learn it in London and don’t have anyone to practice with.
Number 3, I am now making a conscious effort not to watch crap tv just because there is nothing else on or the endless scrolling. I am going to use this time to reduce the regret of number 2 🙂

Brenna Holeman May 7, 2015 - 3:40 pm

Thank you so much for your comment, Georgina! I’m so glad you can relate. I agree, I feel that my relationship with family is still as strong or even stronger.

Sally May 7, 2015 - 11:53 am

Such a great post! I was nodding the whole way through! I totally agree with 4,5 and 6. We learn from our mistakes and the regrets make us kick ass people and insure we never do those things again! Damn number 8 haha!
Happy birthday 🙂

Brenna Holeman May 7, 2015 - 3:36 pm

Damn number 8 indeed! Thanks for the comment, Sally. 🙂

Nikita May 7, 2015 - 2:38 pm

Numbers 1 and 2 I feel very deeply. And even though I keep in contact with my family, it will never replace actually spending physical time with them. And I’m not sure what to do about that, because I still want to see the world, and no one in my family travels… Maybe my priorities will change with time. Or, even better, maybe theirs will!

I think I’m kind of one of those “no regrets” people, even if I’ve made a ton of mistakes and am not pleased about the outcome, because I value the lessons that come from those mistakes. Sometimes you have to be miserably displeased with yourself to make a positive change, and you need the reminder of how insufferable you used to be to motivate you to not fall into that routine. But I guess whatever name you give to it- mistakes, regrets- is just semantics. The important part is to keep on learning!

Brenna Holeman May 7, 2015 - 3:39 pm

Very well said, Nikita, I couldn’t agree with you more. Thank you so much for your comment!

Melissa May 7, 2015 - 4:41 pm

Oh man…# 2, 3 and 5 for me, completely. I just turned 29 and I realize there’s a lot of things I had some interest in but never pursued and I do feel like I’ve spent so much time on social media; what would I have done otherwise?

I like this post; I think it shows a lot of maturity to be able to handle being this real with yourself. I do think there’s a flip side to being honest about regrets, in that at least for me it makes me conscious of things I have done in life that I am proud of; i feel like I have enough life history as an adult now to also be able to make that list too, which is an awesome thing to be able to do.

Brenna Holeman May 8, 2015 - 4:59 pm

Thank you very much, Melissa! I try to be really real with myself all the time – of course I’ve made mistakes, so I may as well own up to them. I think making a list of things you’re proud of is a great idea, although I’m not sure I’d want to put it online, ha ha!

gemmajaneadventures May 7, 2015 - 11:32 pm

When I saw your link on facebook I thought to myself ‘I don’t have any regrets, I’ve definitely made mistakes and done things wrong but they’ve made me who I am today so I shouldn’t regret them’

I still do stand by that, but after reading your post it’s made me realise that some regrets are justifiable. I too have similar ‘regrets’ although I haven’t labelled them as such, like seeing more of my family (I really wish my sister could visit me on my travels but she can’t afford it, and wants a baby. I know I’ll regret not being there if/when that happens, but I need to travel for myself) I’ve definitely stayed in relationships for too long, and instead of facing problems in them buried my head in the sand, but I’ve learnt from all of those things and they’ve all made me who I am today, and all helped me to finally follow my dreams and book that 1 way flight a year ago! I’ve never been as happy in myself as I have been in recent months, and it’s my mistakes and regrets which have gotten me here! 🙂

Brenna Holeman May 8, 2015 - 5:00 pm

Thank you Gemma! I agree with you, I think it’s been my mistakes and regrets which have gotten me to where I am today, too. Thanks for your comment!

Katie May 8, 2015 - 2:21 am

I think we have led mirrired lives! I have the same regrets but also try not to dwell on them. 26 was also the age that I had an epiphany and my inner happiness began then although I of course also still have ups and downs. I love this post 🙂

Brenna Holeman May 8, 2015 - 5:00 pm

That’s awesome – thanks for sharing, Katie! Glad you could relate.

Christine | The Traveloguer May 8, 2015 - 1:39 pm

Happy Birthday Brenna!
This is such a great post, and so true. I tend to think I generally don’t regret the things that happen, as they lead me to good experiences, but I do regret some of the same things as you.

It’s really hard to be away from your family for so long. I used to feel so guilty about that. Now that I’m home, I sometimes have to remind myself to not take the fact that my family are so close for granted. 🙂
I really need to read more. I used to be such a bookworm, but lately Netflix is really eating into my reading time, (and my writing time) and it is such a waste of time!

Brenna Holeman May 8, 2015 - 5:01 pm

Thank you, Christine! I agree, I have to remember to never take my family or friends for granted when I’m around them. I also need to read more, although right now I have a good pattern where I’ve been finishing one book a week!

Amy May 11, 2015 - 5:10 am

I often regret losing contact with people from my childhood and teens but oddly, since I’ve been travelling and living abroad over the past two years I’ve made more of an effort to stay in touch with the people I value most. Sure, I regret not seeing those people more than once or twice a year, but I also make sure that when I do spend time with them it’s quality time.

Brenna Holeman May 11, 2015 - 9:51 am

Yeah, I’m not quite sure why that happens! I keep in touch with people a lot better now, too. Thanks for your comment, Amy!

Roma May 11, 2015 - 5:17 pm

Ah yes. The no regret people. I can’t relate to them. I have regrets, in fact I have loads of them. Most of them revolve around toxic friendships and boys. (it’s always about boys isn’t it?!) Sure they shaped me to the person I am today, but if I had my time over, would I let them take me to hell and back? Umm no. No I wouldn’t. I’d learn that lesson another way.

I agree with you in the point that it takes til your late 20s for the epiphany to really occur. The Ah-Ha moment is one I still doubt. Am I making the right, the BEST decision? You’re not alone Brenna, we all doubt ourselves. Some just aren’t brave enough to admit it.

Brenna Holeman May 21, 2015 - 4:19 pm

Thank you so much for your comment, Roma, I’m so glad you can relate! I’m not sure that I would redo some of those experiences either, ha ha…

Zalie May 15, 2015 - 1:37 pm

I really liked how you have learned to embrace (and share) your regrets. I think that it is completely healthy and natural to hold regrets in your life…I always find it odd when people say they don’t have any! I have days when I feel like I think about the past way too much but I have realized that that is all about growing and learning more about yourself.

Brenna Holeman May 21, 2015 - 4:20 pm

Yes, exactly – as you know I also can hold onto the past and think about it a lot, but I think we need to do that sometimes! Thanks for your comment Zalie xoxo

Cindi May 15, 2015 - 6:13 pm

Re: #5 — Feel blessed that you actually attained this as early as you did. Many of us older women have taken much longer to become happy with who we are and I know many women who will never attain this. Great blog. I discovered you from the Flipkey article.

Brenna Holeman May 21, 2015 - 4:19 pm

Thank you so much, Cindi! I do feel blessed.

Alex May 19, 2015 - 4:39 am

I think when we’re really young we justify our actions with no regrets, but as we mature a little we try to learn from our mistakes. It’s unfortunate that we have to learn from our own mistakes instead of learning from the many people who did it before us. At least I do anyway! I really feel your on number 5. I’m 26 and most of my friends dread getting older but I’m actually looking forward to it. There is a lot of pressure to find yourself in your 20s and I personally find it taxing! In fact my RTW trip was somewhat spurred by the fact that I am tired of living up to these norms. It’s time for me to make my own happiness!

Brenna Holeman May 21, 2015 - 4:22 pm

I love this comment Alex, I totally agree with you. I’m so glad that you can relate, too!

Alana - Paper Planes May 26, 2015 - 9:02 am

Anyone who says they don’t have regrets is lying to themselves or avoiding changing something they should.

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