The Shortest Path To A Great App

The Shortest Path To A Great App” That is the phrase Apple used in a number of the SwiftUI sessions at WWDC last week. But beyond SwiftUI, there were a number of other announcements at WWDC 2019 that also could lead to a shorter path to a great app.

Taken in total, these announcements have left me feeling incredibly energized.

An Oddball WWDC Week

I have an oddball WWDC week compared to most people attending WWDC, AltConf, or Layers.

For the last eight years, I’ve organized and performed in the annual LIVE near WWDC concert on Wednesday night. The last four events have been benefit shows for App Camp For Girls.

I’ve also had the honor the past few years of closing out AltConf on Thursday afternoon with a lighthearted musical Week In Review session. Of course, I have no idea what I’ll be talking about until after Monday’s announcements.

Preparing for these events keeps me pretty busy until late Thursday afternoon—with a large chunk of Monday set aside for the Keynote and Platforms State of the Union—and then viewing sessions or snippets of sessions as I can.

So Friday is the first day of WWDC week I can dig deeper into everything that has been announced.

An Aha! Moment Before Breakfast

It dawned on me early Friday morning that a set of announcements at WWDC 2019 should make an app I have wanted to build much easier and quicker to create.

The annual LIVE near WWDC show is a complicated undertaking. This past year we had 24 performers playing 18 different instruments on 18 different songs.

In addition, for the past few years, Adam Tow has taken some really fantastic photos of the show.

So, for a long time I’ve wanted to build an app for my band, James Dempsey and the Breakpoints (JDBP). The app would be a place to share photos, lyrics and info with fans, and also be a resource for people performing in the show—the Breakpoints.

Fans would be able to download the free app and without an account, see photos, browse photos of past performances, see lyrics, maybe even play JDBP songs from Apple Music if they are subscribed.

Breakpoints would be able to sign in, see info about the upcoming show they are performing in, view the (ever changing) set list, know which songs they are playing on, and be able to swipe through the chord charts for the songs they are playing on, in order on an iPad (or iPhone in a pinch).

But, until last week, just thinking about building that app was exhausting. It would be just me writing it and would need a lot of infrastructure code to get it right.

Then, Friday morning, the thought occurred to me that these three newly announced technologies could make writing this app significantly faster and easier:

  • SwiftUI
  • Sign in with Apple
  • Core Data / CloudKit interoperability

A Journey of Discovery

Will these three newly announced technologies do the trick? What dead ends, limitations, and blind alleys will I discover?

At the moment I have no idea, and that’s exciting.

I still have videos to watch, documentation to read, and lots of code to write and fiddle around with.

The app I’m building won’t be open source, but I’m hoping to make it an ‘open process’ app. My plan is to write little blog posts as I go.

These posts will be me thinking out loud — expressing what I want this app to do before I’ve even fully investigated how I will implement it. And then reporting what I find as I investigate things and see how they work in practice. The intent is for this to be a public journal or technology travelogue as I go through the process of building an app.

I’m also hoping the posts will help spur discussion and feedback and help us all come to understand these technologies better.

Thanks Brent!

This approach was greatly inspired by Brent Simmons. I’ve always admired Brent’s ability to post in the casual and open manner of “Hey, I’m working on a thing. I’m learning it and I’m not an expert. Here’s what I’m discovering and here’s what is confusing to me.” Brent has been a prolific developer for many years, but he never claims to have all the answers. (Plus he plays a mean keyboard.)

A Last Caveat

This app is a side project. As the glow of WWDC 2019 fades and day to day tasks come back to the fore, there may stretches of time between posts about this app. I appreciate your patience in advance.

Let’s see how short that path really is.

I’m so excited to get started! •

Where I’ll be at WWDC 2019

I’ll be doing a few things next week at WWDC 2019 and wanted to pass along my schedule. Hope to see you at one or more of these happenings!

Tuesday: Micro.blog Meetup

Micro.blog Logo

Tuesday at lunch time, I’ll be at the Micro.blog meetup at the Grace Deli, across from The Hilton.

My good friend—and meetup organizer—Jean MacDonald and I co-host The Weekly Review, a ‘microcast’ podcast about personal productivity hosted on Micro.blog.

Stop by and say hello! We’ll also have The Weekly Review stickers to hand out. You can RSVP here.

Micro.blog Meetup, June 4th, 12 – 2 pm

Wednesday: LIVE near WWDC 2019

James Dempsey and the Breakpoints JDBP Logo
Wednesday night, my band, James Dempsey and the Breakpoints, performs our 8th annual LIVE near WWDC show. The party starts at 7 pm—tickets include an open bar. The band goes on at about 8:30 pm, playing a full concert of original, humorous, programming-oriented, and yes, even chart-topping music.

But the night is more than just music and fun—it’s a benefit concert for App Camp For Girls, with ticket proceeds going to support their mission. Come on out on Wednesday night to a great event for a great cause!

Tickets are still available but going fast. Click through to get all the details and buy tickets.

James Dempsey and the Breakpoints, LIVE near WWDC, presented by Capital One
Wednesday, June 5th, Doors open at 7:00 PM, show starts at 8:30 PM. Party until 11:00 PM

Thursday: AltConf WWDC 2019 Week In Review

AltConf Conference Logo
I’ll be closing out the week at AltConf with my sixth annual WWDC Week In Review, a lighthearted look back at the announcements and events of the week.

After a week front-loaded with announcements and technical talks—this easy-going closing session of AltConf combines humor, music, and perspective.

Join me for what usually proves to be an entertaining and occasionally enlightening session.

And, as usual, there will be a bit involving a ukulele.

AltConf 2019, June 3 – June 6, 2019
Closing Session, Thursday, June 6th, 3:00 PM

A Busy WWDC 2019 Week + Stickers!

As usual, it will be a busy WWDC week with plenty of new announcements and technology to wrap our heads around. If you see me out and about during the week, please say hello!

I’ll also have brand new James Dempsey and the Breakpoints and The Weekly Review stickers to hand out. Just ask for a sticker or two when you say hello!

I hope you can make it out to one or more of these events—see you at WWDC! •


Where I’ll be at WWDC 2018

I’ll be doing a few things next week at WWDC and wanted to pass along my schedule. Hope to see you at one or more of these happenings!

Tuesday: Speaking at the NextDoor Conference

Logo for the Next Door Conference

Tuesday morning, I’m speaking at the Next Door conference, located, remarkably enough, next door to WWDC.

I’ll be talking about two of the more glamorous aspects of app development: build settings and xcconfig files. In the session, we’ll cover the why and how of giving your build settings an out-of-project file experience to make build settings easier to manage.

Registration is open until Monday and a there’s a great lineup of speakers. I encourage you to check the conference out.

NextDoor Conference, June 4th – June 7th
My session about xcconfig files: Tuesday, June 5th, 10:00 AM

Wednesday: LIVE near WWDC 2018

James Dempsey and the Breakpoints JDBP Logo
Wednesday night, my band, James Dempsey and the Breakpoints, performs our 7th annual LIVE near WWDC show. The party starts at 7 pm—tickets include an open bar. The band goes on at about 8:30 pm, playing a full concert of original, humorous, programming-oriented, and yes, even chart-topping music.

But the night is more than just music and fun—it’s a benefit concert for App Camp For Girls, with ticket proceeds going to support their programs. Come on out on Wednesday night to a great event for a great cause!

Tickets are still available but going fast. Click through to get all the details and buy tickets.

James Dempsey and the Breakpoints, LIVE near WWDC, presented by Capital One
Wednesday, June 6th, Doors open at 7:00 PM, show starts at 8:30 PM. Party until 11:00 PM

Thursday: AltConf WWDC 2018 Week In Review

AltConf Conference Logo
I’ll be closing out the week at AltConf with my fifth annual WWDC Week In Review, a lighthearted look back at the announcements and events of the week.

After a week front-loaded with announcements and technical talks—this easy-going closing session of AltConf combines humor, music, and a bit of perspective. I hope you join me to be entertained and maybe occasionally enlightened.

And, as usual, there will be a bit involving a ukulele.

AltConf 2018, June 4 – June 7, 2018
Closing Session, Thursday, June 7th, 3:00 PM, Room 1

A Busy WWDC 2018 Week

As usual, it will be a busy WWDC week with plenty of new announcements and technology to wrap our heads around. If you see me out and about during the week, please say hello!

I hope you can make it out to one or more of these events—see you at WWDC! •


LIVE near WWDC 2017 Info

Click For Full Show Details and Tickets

Wed, June 7th, 7:00 PM – 11:00 PM
City National Civic Theater
135 W San Carlos St, San Jose CA

Join us for the 6th Annual LIVE near WWDC show by James Dempsey and the Breakpoints! It is shaping up to be our biggest show ever!

This year’s show will be about as near to WWDC as you can get. We’re playing at the historic City National Civic Theater — directly across the street from WWDC.

  • For this year’s big event, we’ve teamed up with women@wwdc (formerly WWDCGirls) for a combined cocktail hour and concert—all to benefit App Camp For Girls.
  • Ticket proceeds benefit App Camp For Girls.
  • Amazing new venue — right across the street from WWDC.
  • No WWDC ticket required!
  • All ages welcome!
  • Bar with top-shelf liquors, beer and wine. Your ticket includes a certain number of drinks:
    • ​VIP Ticket: Unlimited drinks
    • General Admission: Three drinks
    • Student / New Grad: One drink

Click For Full Show Details and Tickets

Five Years LIVE near WWDC

As WWDC season rolls around once again, I did the math in my head, on paper, and finally counted on my fingers to convince myself that this year is the Fifth Annual James Dempsey and the Breakpoints LIVE near WWDC show.

This year, we’ve teamed up with WWDCGirls to combine their annual Happy Hour fundraising event with our concert to create an evening of mingling and music, all to benefit App Camp For Girls.

The show is at The Mezzanine again this year, one of the city’s finest venues for live music, plus close to Moscone West.

For full details please visit the event page.

The past five years have really flown by. In the midst of the rehearsals and preparations for this year’s show, I find myself taking a few moments looking back.

LIVE at WWDC
Starting in 2001, I wrote one song a year and performed it on stage during a WWDC session. Each song topic needed to fit in with the theme of the session in some way:

I set out from Apple soon after WWDC 2011. My final song performed at the conference was The Accessibility Song, encouraging developers to ‘share your app with the whole human race’. This song was particularly meaningful to me, since I worked on AppKit accessibility for a half a decade.

LIVE near WWDC
After all that time of playing an annual single-song gig, I wondered if folks might be interested in a longer show. We organized the first LIVE near WWDC show in 2012, put the word out, and hoped people would show up. We were thrilled to see the venue fill up with an enthusiastic audience that first year—we’ve been playing live near WWDC ever since.

James Dempsey and Darren Minifie standing in front of The Liki Song poster, outside of John Colins bar in San Francisco

James and Darren Minifie (guitar, bass) outside the first LIVE near WWDC show in 2012.

Thank You
I wanted to thank everyone that has made these shows possible through the years. A true debt of gratitude to the Breakpoints and Conditional Breakpoints who make the songs come alive with their amazing musicianship. A great appreciation of the amazing sponsors who make these events possible. And of course a thank you that goes beyond words to everyone who has come out and supported us as enthusiastic members of the audience.

Thanks to you all, and I hope to see you at the show on June 15th! •


James Dempsey and The Breakpoints, LIVE near WWDC
A WWDCGirls benefit for App Camp For Girls
presented by Capital One
Wednesday, June 15th, 7:00 – 11:00.
Event information and tickets

Can’t make the show but still want to support App Camp For Girls?
Click the Make A Donation button in the Buy Tickets section of the event page.