5 Years with an iPhone

Recently on my podcast, How I Built It, I got to speak to Stephen Hackett. During our chat I was reminded of, and subsequently mentioned, the time Phil Schiller (now an Apple Fellow – congrats Phil!) tweeted a link to my blog with the text, “Joe switched!” It was my most popular blog post up until that point, and remains one of the most popular. In honor of that, I wanted to do a new write up: 5 years with an iPhone.

When Phil tweeted that, I was 2 months into my iPhone journey, and made the decision to switch a month prior. Here’s how.

How I was Convinced to Switch

6 weeks earlier, I wrote a blog post called 2 Weeks with an iPhone 6. I talked about how I liked it, but I didn’t like it enough to switch. Then BGR picked it up. I became Twitter friends with someone who wrote there at the time and he covered it.

It got good traffic. I tried to ignore the comments. I just wasn’t all-in to the ecosystem because I know I’d go back to Android.

But then I got an email from someone whose address ended with @apple.com. He wanted to talk. I verified he was who he said he was, and we set up a call.

It’s my goal to get every Android user to switch to iPhone

That’s what he said to me, and I believed it. He walked through some of the points in my blog post, we set up a demo with an engineer. We addressed some of my concerns (like no back button), and at the end of the call he said he wanted to me to send me an iPhone 6 Plus to use for 3 months. BUT…I had to be all in. I agreed. He also included a nice case and an iTunes gift card.

What Helped Me Switch

So I was all in. Turning iMessage on had a lot to do with it. I talk at length on the 2 months post.

After I sent the 6 Plus back, I went out and upgraded to it myself, and I’ve never looked back. Happy Plus/Max user here.

There were a few contributing factors to me switching long-term

  1. Things I loved about Android were more seamless on the iPhone. Things like texting from my computer and paying for stuff…both of which have gotten even more seamless.
  2. I was already using a Mac and had been since 2008.
  3. My tablet was (and still is) an iPad. No matter how you feel about iOS vs. Android, I think it’s fair to admit the iPad is the only real tablet game in town. That put me 2 devices into the ecosystem.
  4. I was gearing up for travel and really wanted good battery life and a good camera. I figured even if I didn’t plan to switch long-term, I’d have a really good phone for my trips.

A Quick Look Back

Before I jump into what I like about the iPhone 5 years on, I thought it would be fun to revisit my 2 Month post and what I thought then.

From 2 Months with an iPhone

Here’s the good:

  1. Incredible Battery Life
  2. Really Nice Photos
  3. Accessories
  4. The iOS and App Ecosystem
  5. Updates as soon as they come out

I’m still super happy with all of these (favorite accessories coming later). I still think the iPhone takes the best photos, but that can be contested. Google and other vendors have made considerable progress in this area. But video…what other mainstream camera has 4K video?

The stuff that impressed me then still impresses me. FaceID, TouchID’s successor, is a revelation. Apple Wallet (Passbook’s successor) is even better.

And here’s the places I thought needed improvement:

Customization: With widgets coming in iOS 14, and several other areas of the OS allowing some personalization, I’m happy with the level of customization I now have on my iPhone. I don’t really want to spend hours tinkering anymore. Now I have just enough. Though I will say, interactive widgets would be nice.

Plus with Shortcuts, I can create my own actions and automations. To my knowledge, Android doesn’t have something like this.

Sharing: This is leaps and bounds better. The share sheet is nice, it works pretty well, and I love that I can add shortcuts to it.

The Back Button: This has been added in the sense that you can go back to the previous app you were in. But honestly with gestures I haven’t missed the back button in a long time.

Clearing Apps: Just read the comments and @replies from the old post/tweet.

How I’m using my iPhone Today

So 5 years on I still love my iPhone. I have the 11 Pro Max and try to do some amount of work on it when I can. My most crucial apps are:

  1. Tot for quick notes
  2. Omnifocus for task/project management
  3. Fantastical because my calendar is everything
  4. CARROT Weather
  5. Overcast for Podcasts
  6. Drafts / Ulysses for writing
  7. Spark for email
  8. Deliveries because I order too much stuff
  9. Shortcuts for custom workflows and automation

I’m also pretty deeply embedded in the Apple ecosystem. All of those apps, except Shortcuts, are accessible from my Mac. I love my Apple Watch, I have an iPad Pro, and an iMac Pro. I concluded the 2 Months blog post with amazement that everything synced over iCloud seamlessly. That’s even more true now.

More apps support it, and universal copy/paste is basically magic.

Areas of Improvement

That said, there are a few places I’d like to see improvement:

  • Siri…obviously. Google Assistant is still so much better, even with the big improvements Siri has seen in iOS 14. I’ve been disappointed in my HomePod for that very reason.
  • More openness in default apps. This is coming incrementally, starting with browser and email. I’d love to see music, maps, and calendar next.
  • Interactive Widgets. I know I said it earlier, and I know widgets aren’t even officially out yet, but I hope Apple can figure out a way to have slightly more live widgets without sacrificing battery life.
  • Replace Lightning with USB-C. Apple. Please. And unlock faster Qi charging while you’re at it.


As far as accessories go, here’s what I’m digging:

  • Caudable Veil (Midnight Green): If I’m going to have a case on my phone, I want it to be insanely thin. I loved Peel for a while, but the quality seemed to go downhill in the last year or so, and I found Caudable. So far, so great.
  • Smart Battery Case: I bought this in preparation for a family vacation that got booted due to the whole pandemic thing. But it has proved useful around the house, especially when the power goes out.
  • SwitchPod: I really love this if I’m recording on the iPhone or need a simple mount for zoom calls on my patio.
  • Qi Chargers: I love me some wireless charging. I currently have 3 I use: The Anker Power Wave II, the Twelve South HiRise Wireless, and a Mophie charger.

While there are more accessories for more devices now, cases is one area that I think Apple is still leading the pack. The variety of size, shape, and style is vast.

What a Different 5 Years Makes

If you had told me 5 years and 3 months ago that I’d be all-in on the Apple ecosystem, including getting the latest iPhone each year, I would have laughed in your face.

But I’ve become a big fan. The quality of the hardware and apps are something I deeply appreciate. My phone is fast, the battery life is great, and I take lots of fantastic photos. I’m excited to see what the next 5 years brings.

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