photo credit: Carlos Pacheco

Why I keep saying Yes
to YxYY

Alexandra Samuel
6 min readJun 17, 2015

This is a letter I wrote today so that I could read it in February. But why wait?

Dear Alex,

Yes and Yes Yes has just opened its 2016 registration, and you are wondering whether to commit to a fourth year. Since it is now the depths of February you can’t remember what it feels like to be enveloped in heat or watch the sun rise at 5 or even what it means to be surrounded by warm people after a few months of huddling in the anti-social cocoon of winter.

So let me remind you why you want to go back, and how to make the most of your next experience.

Why to go

This is your silent retreat. I know your friends are always trying to convince you to do a Vipassana retreat, but those are people who recharge by being quiet. You recharge by connecting with other engaged, creative, smart, geeky people. This is your Vipassana.

Yes inspires you. You meet and see and hear people who inspire you in so many different ways: in their courage, in their affection, in their playfulness, in their creativity. You see new ways of being here, and it expands your notion of what’s possible and desirable in your own life.

It solves your problems. Last year’s Yes included a conversation that let you figure out how to restructure your work without making you crazy, inspired a new parenting tactic that has been awesome for Peanut, and helped you figure out what you wanted to do with your book project. How many weekends yield *that* kind of insight?

…But not the problems you expect to solve. Part of what’s so amazing about Yes is that you actually can’t predict the kind of aha! moments you’ll experience. So let go of any specific agenda, and let yourself be open to the serendipity of the whole experience.

You get to be a lint roller. Being at the pool at YxYY is like being a lint roller in an ocean of interesting ideas and facts. You find out weird things like who made the art on Chip Wilson’s retaining wall and how long 1 trillion seconds is in years. It’s not the stuff you get from watching Jeopardy: it’s the stuff that actually changes how you see and understand the world.

These are your friends. By year three, the folks you’ve met and seen only through YxYY now feel like your friends. This is your chance to see them!

You get new insights. Each year at Yes you’ve had a few major insights into yourself as a result of your conversations and experiences. Considering that you’d only be able to pay for about five therapy sessions for what it costs you to go to Yes, you’ve pretty much got your ROI right there.

You can offer this experience to someone new. Last year was the first time you brought a friend to YxYY, and it rocked her world. This year, work hard to convince a few more friends to come with you. It is an awesome thing to do for your friends.

Yes lets you practice. Yes lets you practice the most important thing you can possibly practice: being yourself. You know, the self you would actually be if you spent 365 days a year around people who are as open to talking about their most painful breakups as they are to talking about the future of artificial intelligence. And being that you for three days is the absolutely best way to practice being that you for 362 more.

How to go

Book your room right away. As soon as tickets go on sale, buy tickets and book your room at the Ace. Yes, you really do want to stay at the Ace, if only because it makes it easier to change in and out of a wet swimsuit.

Think of a gift. It was nice to bring Coffee Crisp bars and bedazzling rhinestones this year, but you didn’t really have that as well organized as you could. So think about what you want to do for the community in 2016, and get organized in advance so that it works out beautifully. Once you are there you will really want to do something nice for all the lovely people, so think about what that could be.

Pack less. I know you know this, but you keep forgetting: you hardly need any clothes. Lots of swimsuits and a swim coverup, yes. Prom dress: of course. Other than that, you really only need one change of clothes beyond what you fly in/out of — maybe two if you want something a little dressy for the evening. That is enough.

Bring the kids. For the past couple of years you’ve deliberated the idea of bringing the kids, but decided you want to have uninhibited fun. Next year, bring the whole family: this is a great way for the kids to get introduced to a different way of being and enjoying, and you want the Yes community to meet Rob and the kids! Get a room that is fairly central and close to the pool so that you can hang out with friends once the kids are asleep.

Give Sweetie to the Prom committee. Speaking of the kids, be sure to connect Sweetie with the Prom committee. She will pour her heart into the decorating process, and those tiny hands sure are useful!

Eat, or don’t drink. I know the desert makes you feel like you don’t need to eat, but if you’re not going to eat, don’t drink. Conversely, if you want to drink, don’t forget to eat.

Let go of your work brain. You’re always super curious about people’s work and tech lives, because you don’t get enough contact with geek brainiacs in your day-to-day life in Vancouver. But most of the Yes folk spend a lot of time with fellow techies in SF, and they come to Yes to let that go. So if you’re craving a nerd-out, go to one of the focused group discussions — otherwise, skip the work questions and ask people about the best thing they ate in the past week or the most important lesson they’ve learned about recovering from their childhoods.

Be selective about sessions. Last year you went to more sessions than you have in previous years, and even though they were mostly just bird-of-a-feather gatherings for people to talk about a particular topic, you enjoyed your spontaneous conversations even more than these. So don’t feel like you have to go to anything organized — though if you do go, maybe aim for more of the workshop experiences. The “What Should I Do With My Life?” session sounded fab!

Speak up! You’ve been going for three years, and you still haven’t done an Ignite talk or a Moth story or any other kind of sharing/speaking to the group. It’s time, lady! Make this the year.

Don’t ask people if it’s their first year. One of the ways you started conversations this year was by asking people if this was their first Yes. It is an obvious conversation opener — and a way of figuring out if you’ve already met — but it turns out that some newbies felt like there was a little bit of an old kids/new kids divide. So remember that “is this your first Yes?” is a little like peeing in a big circle around the event — better than peeing in the pool, but only by a narrow margin.

Hack Your Kids again. The “hack your kids” conversation has been a terrific way of bringing together parents each year, and learning more about how people handle the intersection between tech and parenting. Be sure to have another one next year, but think about how to bring a little more structure to the conversation, and schedule it for Sunday — that way you can encourage the various parents you meet to come and join in.

Stay on campus. 2015 was the first year you didn’t leave the Ace for a single moment of the event, and you loved it! So don’t feel like you have to go out for dinner or out exploring. Staying on campus the whole time let you relax and enjoy every moment.

Get in the damn photo booth. Three years at prom, and you still haven’t taken a photo in the photo booth? After Sweetie spent all that time on your outfit? What’s up with that??

Say yes. Start saying “yes” the moment you get to the Ace, so you’ll be in the yes frame of mind. Actually, start saying it the moment you book, so you’ll be warmed up to the process. To heck with it: start saying yes right now.

This post originally appeared on



Alexandra Samuel

Speaker on hybrid & remote work. Author, Remote Inc. Contributor to Wall Street Journal & Harvard Business Review.