What Am I Going to Do With Deep Dish Swift?
- 8 minsWritten by me, edited with robot assistance.
Deep Dish Swift 2027 is happening April 4–6 in Chicago.
Year five 🍕
And I am so excited about this one.
This year’s theme is retro gaming, and I’ve been having way too much fun with it 😅
Independence.fm is coming out of retirement just for Deep Dish. That still feels a little unreal to type.
Sponsors are coming back. Familiar faces are coming back. And I know there are going to be a bunch of new people around the table too.
It’s going to be a really, really good one.
Which is what makes the rest of this post hard to write.
The other thing I’ve been thinking about
I’ve been thinking a lot about the future of Deep Dish Swift.
And honestly?
I don’t know what it’s going to look like after this one.
So before I decide anything, I want to ask you something.
But first, I want to explain why.
I’m sitting on a blog post
There’s a post on the Deep Dish website right now called The Last Slice.
It’s written. It’s edited. It has pixel art of one last slice of deep dish pizza sitting on a plate in front of the Chicago skyline.
It’s very cute 🍕
It says that 2027, our fifth year, would be the last Deep Dish Swift before I take a real break.
And I haven’t published it.
It’s been sitting there for about a month.
Every once in a while I open it, read it, and close it again.
Part of me thinks it’s right
When I read The Last Slice, there’s a part of me that just… exhales.
It’s very relieving to think about.
For about ten months of the year, there’s a part of my brain that is always working on Deep Dish.
Not the doing part. I’m good at the doing part. I like the doing part.
It’s the tabs.
You know when you have a browser with way too many tabs open? Each one is something you’re not done with yet. You can’t close it, because you still need it. So it just sits there. And even when you’re looking at something else, you know it’s there.
That’s what Deep Dish feels like in my head for most of the year.
Everything I’m waiting on is a tab.
Waiting on an answer from a sponsor. Waiting to see if a speaker can make it. Waiting for ticket sales to pick up.
Everything I can’t finish yet is a tab.
The hotel plans. The food plans. Planning for a room when I won’t know how many people are in it until the end.
Every question I can’t answer yet is a tab.
Will people show up?
Did I follow up with that sponsor?
Is there something I forgot that someone is counting on me to remember?
And I can’t close any of them. Not because I’m not working on them. Because the answer just isn’t there yet. Most of them don’t get answered until the last couple of months before the conference.
So they stay open. All year.
When I’m working on something else. When I’m hanging out with my family. When I’m trying to fall asleep.
None of them are big on their own. But all of them together take up a lot of space.
And I’ve been learning a lot this year about how much having a bunch of things competing for space in my head actually costs me.
It’s not the work that wears me out.
It’s the waiting.
So imagining a year without those tabs?
That feels really, really nice.
Part of me is really sad
And then I keep reading.
The Last Slice talks about people coming to Chicago early and staying late. How the conference is technically three days, but somehow becomes most of a week.
It talks about familiar faces and new people around the table and conversations that pick up exactly where they left off a year ago.
It talks about Kari. We built Deep Dish together, and so much of what people love about it exists because of her.
And it talks about 360iDev.
I was at the final 360iDev. I didn’t even get to stay for the whole thing. Our second kid was about to be born, so I left early. I wouldn’t change that decision.
But I never got to go back.
There’s still a strange feeling knowing that I left a conference I loved and never got another chance to be there.
I wasn’t done with conferences.
That feeling is a big part of why Deep Dish exists.
I wrote all of that because I meant all of it.
And every time I read it, I get sad.
Because I don’t actually want that to stop.
Why I’m telling you this now
I could just figure this out quietly on my own.
Decide. Announce it. Move on.
But conferences end. Sometimes you see it coming, and sometimes you only find out after the fact.
I don’t want that for Deep Dish.
I don’t want anyone to leave Chicago this April saying “see you next year” when I honestly don’t know if there’s going to be a next year.
And if you’ve been thinking “I’ll go next year,” I want you to know that I can’t promise you there will be one.
So I’d rather tell you now, while it’s still a question. Before anything is decided.
If Deep Dish has meant something to you, or if you’ve always meant to come, I want you to have the chance to decide whether this is your year.
So I keep going back and forth
Some days I want to hit publish.
Some days I want to delete it.
Most days I just leave the tab open 😅
Which… is kind of the whole problem.
I want to keep doing Deep Dish Swift.
But I don’t think I can keep doing it the way I’ve been doing it.
The stress of not knowing who’s going to show up is taking a real toll.
And here’s the honest part.
It’s a toll I’m willing to pay.
If the conference is an awesome experience, and a lot of you are there, and the room is full of people who wanted to be there, that is worth it to me.
That is so worth it to me.
What makes it hard is not knowing until the very end.
I kind of want a Kickstarter
This is going to sound a little weird.
What I really want is for Deep Dish to work like a Kickstarter.
You say you’re in. Enough people say they’re in. And then I go build the whole thing.
All of it. The little details that I could never actually plan but somehow end up being everyone’s favorite part.
I know that’s not how conferences work 😅
Most of a conference comes together in the last few months. People decide late. That’s just the shape of it, and I’ve known that since year one.
But that’s also why the tabs stay open all year.
If I knew early on that the people were there, I think a lot of those tabs would just close. And I’d get to spend all of that energy on the fun part.
I’m not actually launching a Kickstarter.
I don’t need a guarantee.
I just need some kind of signal earlier on that people actually want this.
That would change everything for me.
So what happens next?
First, the part that isn’t a question: Deep Dish Swift 2027 is happening. April 4–6. And I’m putting everything I have into it.
After that? Honestly, I don’t know.
There could be more Deep Dishes soon, just like this one.
There could be Deep Dishes that look really different from the ones we’ve had. Smaller. Every other year. A different time of year. A new recipe. A different flavor.
Or I might end up publishing The Last Slice, and there might not be any more after this one.
All of those are on the table.
And I could be excited about any of them.
I could be really excited to keep doing Deep Dish Swift.
I could also be really excited to rest.
Both of those feel true right now. I don’t think either one is the wrong answer.
I just don’t want to make this decision by myself in my head with all the tabs open.
I’d rather make it with the people who make Deep Dish what it is.
So I want to ask you
Is this still what you want?
Do you want a conference this size?
At this time of year?
On this cadence, every single year?
With this level of polish?
And not just want.
Would you come?
Would your company send you? Would you sponsor? Would you bring a friend?
If you want Deep Dish Swift to keep going, I’d love to hear it.
If you’d come, I’d really love to hear it.
If you’d want it to look different, tell me how.
If you think it’s time for the last slice, you can tell me that too. I promise that’s okay.
You can email me, reply to me on Mastodon or X, or find me at the next thing we’re both at.
And if you already know you’re coming to Chicago this April, grabbing a ticket is the closest thing to that Kickstarter, and the loudest way to tell me 🙂
For now, The Last Slice is still sitting there.
Unpublished.
Waiting to see what you all think.
