Applying to, prepping for, and speaking at Deep Dish Swift

Hey there! If you're new here, my name is Jacob 👋 I'm a software engineer who loves the Swift language—and I sometimes write about it.

Until recently, I've never presented in front of a group larger than 2 or 3 co-workers, and I've certainly never done any public speaking. Though, I have been on the stage for a live demo where someone else talked while I drove the computer.

At the end of 2024 I began to assess my skills, to see where I needed to grow and plan for 2025. I'm fair at technical diagramming, planning, writing, mentoring and communication. Some of those skills I'm less proficient at than others, but all of them were at a spot that I no longer needed to dedicate a lot of focus on improving them. But there is a glaring gap in my experience: Presenting. So, when Deep Dish Swift released their Call for Papers (CFP) in December of 2024, I applied.

Applying

It was the week of Christmas when I noticed Josh's post on LinkedIn in search for speakers. Mostly out of curiosity, I clicked it. The link brought me to a Google Form that was full of various pizza related questions. I wasn't entirely sure what I would talk about, but I clicked through the form and started reviewing the questions. Around that time I was working on an article—that I still haven't finished—on Phantom Types; I thought it could make a good talk, so I started filling out the form with that article in mind.

Over the next week or so I reviewed that form that Josh put up. Each time I made edits to my answers. Sometimes, I would delete them outright and do it all over again. I wasn't exactly clear on the contents of the talk I was going to write, only that I wanted to talk about the way I use phantom types and how they utilize the compiler to make it harder for us to make mistakes. Eventually—roughly a week later—I was happy with my answers but I couldn't submit them because I had no experience as a speaker. He certainly wouldn't pick me, so what's the point? After I thought about that for a minute, I realized that if he wouldn't pick me, it certainly wouldn't hurt to submit it either. So I clicked submit.

Waiting for the response

As one might imagine, it took a while for Josh to review all of the submissions. He had a full time job, a family, and this major task in front of him. Not only did he have to read every form submission, he needed to consider what talks were unique or different enough to stand out—some talks may have have been too similar to another for example. And if someone has given talks before, he may need to listen to those talks to determine what they would be like on stage. Then he needed to figure out what talks would make a good line up etc.,

I imagine that has to be an insanely difficult process, and especially difficult to allow someone up onto the stage who's never given a talk—even more so if you've never met the speaker.

So after a few weeks went by, I was fairly certain I hadn't made the cut. That's what I expected when I applied. My experience trying to transition into a developer role from banking told me that I wasn't going to get selected. It told me that Josh would have been looking for someone who has already demonstrated their ability, one who was able to perform in this context and had video evidence.

On January 21st 2025, I got an email proving my experience and my expectations wrong. My talk was accepted! Holy crap… My. Talk. Was. Accepted.

Holy crap…

Turns out, "my experience" was some self doubt sneaking in like a familiar voice of someone I trust. At first it was convincing me not to try, but later it was attempting to make me complacent with where I was.

Writing the talk

My talk was accepted January 21st, I started working on it January 22nd. I had never done it before so I wanted to be prepared. I know myself, I have to fail a lot in order to look like I know what I'm doing. I also know that I suck at remembering lyrics to songs, so I can't follow a script. I need to wing it a bit or else I'll start trying to correct myself because I said the wrong words. I chose to use the slides as prompts for the concept and story that I was talking about, that way I didn't need to memorize the exact wording, but I just needed to know what story I was telling and where in the story I was. The slides were both for me and the audience to follow along.

In a couple of weeks, I had what I thought to be a finished talk. As I ran through it, I was taking about 18 minutes… I was supposed to talk for 30. So I started making edits, and before long, I was filling roughly the amount of time I needed to. But something wasn't right. I was bored giving the talk. I found myself rambling, trying to explain reasons why we did things, and providing a ton of context that couldn't be captured by the slides. I also fumbled in the middle. I couldn't seem to connect the beginning to the end.

Eventually, I was interviewed by Malin and Kai for the Slices Podcast and we talked about what I was going to name it and how it was going. At the time I wasn't being completely honest with myself, but after that interview, I gave the talk to a coworker… and nothing was retained. I bored him. I know it 😂

I have to fail a lot in order to look like I know what I'm doing.

I'm glad I did that. Because had I not, the talk would have sucked really bad. So I started rewriting it. I realized the topic was too narrow. What I really wanted to talk about used the topic but it was broader than that. I started writing a new talk that contained many of the slides and concepts from the original one. This time I knew that I didn't want to get into the weeds on the technical decisions. I really wanted to focus on the ergonomics and the feeling of working in the code.

I found new analogies and decided to be more vulnerable and honest about what kind of dumb things we did in the past. I decided to break apart the middle with a video that explained the problem I was attempting to tackle, and it was better. But it still wasn't right… I couldn't get into a good flow.

So I hopped on a call with Josh (who is the guy that set up the conference) and ran it by him. I got so nervous, my 25ish minute talk was 14 minutes long. I flew through it. I stumbled a few times. And I asked him for feedback. This was some of the best feedback I could have gotten. He mentioned a few things:

1. The video interrupted my flow and momentum, don't use the video
2. The end was abrupt, find a way to bookend the talk and make the end more satisfying and less jarring
3. I started with a Game scenario and jumped right into banking. Find a way to transition better
4. More examples
5. Practice pausing, you're moving too fast

There was more, even down to the language I was using, but these really helped shape my talk. So I kept rewriting the talk. I added other examples and began working on better transitions between topics and concepts. I removed the video but replicated it with emojis. I book-ended the talk with the same story from the beginning but without the major mistake that happened the first time. And I practiced at least 10 times a week.

It was April now and the conference was coming up. I needed more practice because I have to fail a lot in order to look like I know what I'm doing. So I presented to a group of about 30 people at the company I consult for; some were at the senior level or greater. I got some good feedback about the slides and the way I was talking about things. But they were surprisingly reserved with sharing feedback. Perhaps they didn't want to offend me because we work together so they held their tongue. But I felt that parts didn't flow well. There were parts I over explained and stumbled on. So I started making some changes.

This is when I decided to use an AI image creator to add some better images to my slides. My video recreation was lame, and one of the examples I had could have used some visual aids. So I started playing with those ideas. I also wasn't satisfied with the ending. It didn't fit. Nor was I satisfied with some of my transitions. So I added another story in between some of the topics, changed some slides, played around with the animations and images… But more than anything else. I kept running through my talk.

The week of the conference, the ending still wasn't right. But I had this new transition that I liked that brought us into the last topic. And I thought that it could make a good transition out if I tinker with it. So I played around and practiced that a bunch. I made my last edit the Friday before the conference started. I spoke in 2 days. I wanted to leave it alone so I knew my slides. I wanted to practice it over and over again so I could drill it into my brain. My last practice was 43 minutes of speaking (my time slot had a max of 45 minutes).

Before the talk

Saturday the 26th came around rather fast. We've got 4 kids, and I was going to be away from the family for several days, so I couldn't bring myself to practice my talk or leave as early as I wanted to. I hung out with them, played with the dog, fed the chickens, and just enjoyed being with my family. Eventually I had to leave. It's a 4 hour drive from my home to O'Hare, so I hopped in the car and finished listening to the Slices episodes on my way down. When I got there I met many people and just sat down and chatted for a few hours. Eventually, we went and had dinner at Fogo De Chao, and then we went back and hung out. I started to get tight and anxious. The talk was tomorrow and I hadn't been practicing. I ended up with a splitting headache and went to bed.

At 5:00 am, I got up. Still had the headache. I drank a gatorade and got ready. It wouldn't go away. So I went to the store and bought some pain relievers and a very large coffee from a coffee shop. I took one on the way back to the hotel and found the crew that was hanging around the lobby and chatted with them. About an hour later the headache was gone, but the nerves were still there a little. There I got to hang out with Stewart Lynch and we shared a similar level of nervousness about getting up there and talking in front of so many people—some of which are literal legends from Apple. Knowing that others were nervous too actually helped a bit.

The conference started. High energy and very good. Stewart went up, powered through his nervousness, and did a stellar job. If he could, so could I. The day moved so fast that I forgot I was nervous. Before I knew it, I was up.

The talk

I was oddly not nervous going up there, plugging in, getting mic'ed up… I was thinking I had that handled until Josh introduced me and I looked out into the crowd. The lights were bright, there were hundreds of eyes on me, and I'd never done it before. I started to introduce myself and get into the flow of the talk when my hands started to shake. I'm glad the remote didn't work for me so I could clench the podium from time to time. By the time I got to the 4th slide I was so tense my headache came back, even worse than the first time. Certain movements and laughing sent a sharp pain around my skull. I knew if I stopped I'd panic, so I kept going. I would get laughs and interactions from the crowd, so I knew I wasn't totally blowing it, but I certainly didn't have the confidence that I was doing well. My mouth began to dry—which never happened when I was practicing. I stumbled a few times, but I kept moving. Before I knew it, I was on the last slide. Josh was up there wrapping up the talk. He mentioned that we'd have shorter break and start the next talk early… so I thought that I powered through the talk much faster than the target 30 minutes.

Immediately after I unplugged, people came up to chat with me. To my surprise, they enjoyed the talk. I wanted to talk with them more, but my head hurt so bad and my heart was pounding—which made my head hurt even worse. I wish I was in better shape so I could have stayed and chatted and watched the next talk. But I needed to go lie down. I made it back to the hotel room, chugged another gatorade, had a pain pill, and lied down.

It took about 45 minutes before I calmed down and my head stopped throbbing. I made it down about half way through the next talk, but I couldn't focus. I ended up sitting outside of the conference center chatting with a few others who needed a break as well. I kept hearing positive feedback about the talk, which was relieving, and it was great to hear that others found the content useful. Eventually we went to the speaker dinner and Stewart was there again offering encouragement and kind words. So were all the speakers. They were an incredible group and I still felt that I didn't belong there sitting in between Stewart Lynch, Antoine van der Lee, and Daniel Steinberg. People I've followed for a very long time.

After dinner, I made my way back up to my hotel room to do what any pro sports team would do, watch the tape. You know, see what I could do to improve. But the self doubting part of me was really checking to see how bad it was.

So I watched my talk and I was shocked that I couldn't tell I was nervous or in pain. People kept saying they couldn't tell, but I thought they were just being kind. They really couldn't. Maybe I did belong there after all.

The Conference

I'm going to write a different article about this conference, but I wanted to take a moment to tell you how great the people are at Deep Dish. It was a truly enjoyable experience. I met many people and made some friends I'm sure I'll have for a very long time. And more than anything, the entire group is encouraging and rooting for you. Not just the speakers. If you're looking for a conference to go to, I can't recommend it enough. By the end, I left thinking I do belong here after all.