Check out part 1

The decline of Window Phone was just sad and it showed the difficulty of breaking into the American Smartphone market. As I started seeing the writing on the wall, and the slickness of the newly announced iPhone 5s (and and my wife was an iOS user). I decided to jump ship for the first time.

I’ve always traded in or sold my previous phone to fund the purchase of the newest shiny thing, but the iPhone 5s is unique for me because I still own this one (somewhere). This was the device that introduced Space Gray to the world! It was a cool color, but a touch disappointing coming off the really cool black color that the 5 had. This was also the phone that introduced Touch ID and that was the “wow” feature that really got my attention and helped pull me across from Windows Phone.

Next in the line up for me was the 6s Plus (yes I avoided bendgate on the 6) This one stood out to me for 2 reasons: 1. It felt HUGE for the time. 2. The battery life was amazing. Getting 2 solid days of battery on a smartphone was just incredible. It’s a shame that with all the advancements we’ve made since that phone has come out, getting a day of battery is still the standard. At least it hasn’t gotten worse?

Given that the 6 and 6s series was quite a bit more boring than the preceding models, I decided I would check the temperature over in Android land! Enter the Samsung Galaxy s7! It was a time of firsts, my first glass sandwich (ew), and my first Android phone. I was pleasantly surprised coming off the iPhone how everything was mostly just… the same. In the edge of cloud and cross platform apps, switching was (and largely still is) easier than one might think. It was these lack of differences that ultimately meant my trip down Android highway would only be for one brief exit. It turns out I’m just not that into customization (at least not in the few limited ways Android allows). And so, back to iPhone I go!

It was the year of a redesign! Arguable the most interesting and impactful redesign to the iPhone since the 4! The iPhone 10 X had arrived! And I opted for the 8 for some reason… The much forgotten about iPhone 8. It was basically a reskinned 7, except it added wireless charging (yay!) And traded a high quality plastic case for… glass (boo!). That was really it, this one was pretty boring. And so like the flip flopper that I am, I switched to Android again for the last time…

The Pixel 3 was a super fun refinement year. It lacked some of the really outstanding colors that came before(thinking of the blue of the pixel 1), but otherwise it was a fantastic phone. Even today in 2024 looking back on those pictures and seeing the jump in quality from the iPhone 8 to the Pixel, it was just an incredible leap in quality. Sadly I don’t have a good scientific set of photos to compare against here. The software was also really fun. I really enjoyed the “iPhone” like approach Google took with the Pixel line. It’s stock launcher was fantastic, but I still had all the world of launchers I wanted in the Google Play store if I decided to veer from the course. The only blemish for me with this device was battery life. I almost always had to top up at around 2:00 PM every day… ouch.

The paper cuts of not being on iOS (iMessage and the like) with my wife finally got to me when it was upgrade time again. And so I switched once again to the iPhone 11! This was a great year to swap over as the camera improved a lot over the X and Xs and was basically a step sideways from my beloved Pixel 3. All the other niceities of iPhone were still here. The screen size was a real stand out as well at 5.8 inches. It was a smidge smaller than the Pixel but still big enough for activities. I had no complaints with this device!

Next the penultimate device, the 13 Pro! This is where things get less exciting as we are very much in the modern era now. And the 13 Pro was totally “fine” in every way! Great camera, great screen, I even liked the blue color of the 13 Pro, (though it wasn’t as nice as the blue on the 12 Pro line). My only quibbles with this device was the slight size increase (5.8 to 6.1 inches) and the weight… this thing was a brick! I like the shiny look of the stainless steel but the weight was terrible. It was on this device that I opted to get a cellular Apple Watch so I didn’t have to carry the phone with me on walks.

And finally… the 16 pro! Even with Apple Intelligence MIA, this phone is probably one of my favorite iPhones I’ve purchased! The weight has been cut down slightly from the 13 pro, the Dynamic Island is neat, camera control makes for a nice camera launcher, the always on screen is useful, the 5x zoom is welcome as well. My only quibble is the color options on the 16 pro line are somehow even worse than the 15 line.

It’s been a fun journey! At this point I’m “all in” on the Apple ecosystem, I don’t see myself jumping ship (certainly not back to Windows). It will be interesting to see what the future holds on my next upgrade in 3 years.