Gen Y loves to write bucket lists. I keep coming across them.
But bucket lists depress me, because most of the things I’ve done that impacted me the most were things I didn’t plan for– and, in many cases, things that other people suggested I would eventually regret.
Turns out I regret almost nothing. Imagine that. And I keep thinking, heck, why not give ourselves some credit for what we’ve already done?
Let’s call this my Nope, You Didn’t Tell Me So list. Let’s call this my Told YOU So list! Here they are: 6 things I did long before I was old enough to write any bucket lists. Six so-called “mistakes” I’d happily make again, if I could turn back time.
- Missing curfew, skipping classes, and “hanging out.” First of all, I never skipped the good classes, I was always on time for Shakespeare in high school, for example, because I hated to miss a chance to quote Harold Bloom. (Dork!) But I skipped what I could and, you know, went out and – lived. My mother’s not going to like this, but when I rolled in the door at 2 am? Sure, I was probably doing something wrong: smoking cigarettes, freeloading diner coffee, skirting the mosh pit at the concert. But mostly, I was having conversations, falling in and out of love, and in many cases, talking about books. Those late nights and delinquencies shaped me. (And I still graduated with a 4.0 from high school.)
- Writing the high school sports column. I hate sports. I’ve written about skipping gym class before. But making $15.00 per column, writing about sports I’d never even watched, let alone played, taught me the value (and challenge) of writing for pay–and prevented me from going into journalism. (Disaster averted!) It also helped me realize the power of the written word in creating perspective and bringing people together, and for that I’ll be forever grateful.
- Having premarital sex (and love). I’m married now so I’m allowed to say this: I am so glad I didn’t wait for the right moment or the right guy or some mystical romance story. I’m not suggesting teenagers run out and do it, but if you’re safe and ready, no one can put a number on you. I learned about sex and love in fits and starts and I’m a better person (and wife) as a result. Even the bad stuff I don’t especially regret. Without it, I might not understand how amazing it is to really love and be loved.
- Working my butt off, constantly, starting at age 15. When I took my first real job, I had no idea what I was getting into (other than cash). Working all the time was incredibly valuable – and I never let my academics suffer. (In fact, I was running a department at a startup at 21 while going to school full-time. I was exhausted, but very, very happy– and I graduated with a near-perfect GPA.) I learned to work hard, stay humble, and multi-task.
- Sticking to my feminist guns. I put a Simone de Beauvoir quote on my bedroom door when I was 15 or 16. This did not go over well with anyone. Ever. This did not win me friends, admiration, or happy parents. I did get called “bull dyke” fairly often, which, of course, proves my point. But my feminism, coupled with my love of books, helped me persevere as a writer– and as a person. Sometimes, extreme unpopularity is the best teacher of all.
- Living alone in New York City with very little money to spare. The first day in my empty, lonely new apartment in my new neighborhood, I sat by my window, ate a few grapes slick with condensation from the fridge, looked out on the leafy street and sun-dappled brownstones, and thought, “This is the beginning of the rest of my life.” You know what? I was right.
I’m glad I didn’t listen. I’m glad I mucked it up, made mistakes. It made me a better writer, a wiser spender, and a smarter worker. What do you not regret?

Lindsey, I love your blog’s redesign. But, even more so, I love your spin on the typical Life/Bucket list really drives home the point that Life should not be filled with regret, but rather opportunities for lessons that we grow and learn from.
Thanks for the post. It’s a perfect way to start off the week. =)
I’m always impressed, Lindsey. Don’t think I could have pulled all that off, though.
Congrats!
One thing I don’t regret: Dropping out of college to go hitchhiking all over America. Any of my hitchhiking, and my Door-to-Door First National Tour.
I am not a planner and this post feels right. It clicks.
@ Andrea – Thank you, lady. (And credit Luis, third comment down, for design.) I think I wrote it to kick-start my own week, so I’m glad it did the trick for you, too!
@ Jay – You crack me up. Please enlighten us on the Door-to-Door First National Tour. (It also begs the question, was, or will there be, a second?)
@ Luis – Thank you kindly, sir. :-) Planning isn’t right for everyone, even me. And what I didn’t plan for turned out to be the most important. Go figure!
[...] This post was mentioned on Twitter by Lindsey M. Donner. Lindsey M. Donner said: Forget all these Gen Y bucket lists – 6 "bad" things I already did, and don't regret. At all. http://ht.ly/1IW2b #in #brazen [...]
[...] I’m not really in the business of regret. I’ve already talked about it, and how idiotic it is to abstain from things that could be game-changers for [...]
Here is a great place to create, manage and share your bucket list. You can also get some interesting ideas to put on your bucket list from others.
Check it out.
http://www.sharebuckets.com
[...] I know I’ve mentioned that I’m not in the business of regret repeatedly. But what I really mean by that is, I’m trying my damndest to stop manufacturing new [...]