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Apple vs Google and My Pursuit of Technological Perfection


I am a self-professed techno junky. It is my vice of choice. I used to be a die hard Apple fanboy, but have grown tired of their antics over the years, especially since Steve Jobs, who I had the pleasure of working with on the launch of the video iPod in 2005, passed away. It seems as if they have stopped innovating and have decided to polish instead of chisel.

Over the past 5 years or so I have been platform agnostic. On the computer front, I’ve had a couple of different iMacs and MacBooks, a couple of different varieties of Microsoft Surfaces, and a Lenovo All-In-One Touchscreen PC. In the tablet department I’ve dabbled with every type of iPad available, one or two Android variants and also a Google Pixelbook.  For phones, I’ve had iPhones, Samsungs, Microsoft Phones and most recently a Google Pixel 2 XL.


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My current technology setup consists of a MacBook 12” laptop, which I am using to type this article. We also have a 27” iMac and my phone is as I mentioned above, a Pixel 2 XL. For a while I had tried to use an iPad as my main computer. I had an iPad mini with LTE. Then I traded up and got the initial 9.7” iPad Pro LTE and then traded up again and got the 10.5” iPad Pro LTE. I liked the portability of the iPad but it just wasn’t ideal for typing for all of my writing projects. It was also problematic for Microsoft Excel, the app version wasn’t that good. And, there were times when I wished I had access to Photoshop and Illustrator.

I tried to split the difference by ditching the iPad Pro for the Google Pixelbook. The great thing about it was that it had a full function Chrome browser not a limited function mobile Safari browser like the iPads. The other thing that I appreciate about Google products is the ability to manipulate the GPS functionality to be able to utilize streaming services abroad. This is hit or miss and mostly miss on Apple products.

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The Pixelbook is a nice piece of machinery. It is a nice hybrid between a laptop and a tablet. It folds over to become a tablet and has a touchscreen. It has a very nice built in keyboard for typing and it can run many Android programs. Most of my work, I’d say about 60%, is done in a browser and the Pixelbook fit the bill for those tasks – browsing, email, etc. It was also great for watching YouTube TV in Chrome (especially abroad by tricking the GPS) which I absolutely love. I’ve been a cord cutter for nearly 5 years. I’ve tried all of the streaming TV services as well, but that’s another story for another day.

Where it fell short was the lack of online or Android based apps for my writing.

Besides Microsoft Word, the three apps that I eventually ended up gravitating to for my daily writing tasks are Scrivener (for fiction and long-form writing), Day One (daily journaling) and Bear/Agenda/Ulysses. I haven’t quite settled on which of the latter three I will use in the end for note taking. Only one of the apps is available on Android – Day One. As a result I bit the bullet in July. I gave the Pixelbook to my wife and business partner and purchased the 12” MacBook.

I must say it was money well spent because I have been faithfully writing every day and a big part of that is the adoption of the aforementioned apps and the availability of a laptop inside the house when my wife is using the iMac and more importantly when I am on the road. The MacBook is actually smaller  (11.04 x 7.74 x .052) than the 12.9” iPad Pro (12 × 8.68 × 0.27)  when closed and is much more powerful and useful for my workload which includes occasional Photoshop and Illustrator use.

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As I mentioned above, my phone is a Pixel 2 XL. It’s a really nice device. One of the reasons that I got it was so that I could sign up for Project Fi. Google’s wireless service has a $20 flat fee for calls and texts in the US and a rate of $10 per GB for LTE data anywhere in the world. After 6GB data is free up to 15GB at which point you are throttled back to 2G and 3G speeds. This is important to me because I travel abroad on average of a 4 – 6 weeks a year.

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My usual T-Mobile data plan offers unlimited 2G speeds abroad which is good for emails and light web surfing but is no good for streaming of any kind. Since I am such an NBA junkie I needed to have access to my NBA League Pass while abroad with a fast data plan. Project Fi came to my rescue.

The other thing that is really neat about Project Fi is that there is a Google app called Hangouts that allows you to send and receive SMS and limited MMS messages from any device. Hangouts is available on Android and iOS  as well as web functionality which means that you can text to any phone from anywhere without your phone being on. iMessages requires for your iPhone to be on in order to send SMS and MMS to non-iPhones. You can also make VOIP phone calls from the Hangout app. It acts just like the phone app and the quality is usually pretty good.

Now because I have a T-Mobile family plan I don’t want to have to use and pay for Project Fi data while in the US, so I use the dual SIM Pixel 2 XL to accommodate my needs, or shall I say my wants.

The Pixel 2 XL has an eSIM that only works with Project Fi and it also has a physical nano SIM. They both can not be active at the same time which is not ideal, but I am able to accomplish what I want by forwarding my Project Fi number to my T-Mobile number. My incoming calls ring on my T-Mobile SIM and if I want to make a call from my Project Fi number then I just use the Hangouts app. The problem with this is that I can’t use Google Assistant to make handsfree calls because you can’t choose Hangouts as the default phone app.

Ideally I would like to have a Dual SIM Dual Standby setup on the Pixel 2 XL that would allow me to make and receive calls on the Project Fi number to the main phone app and use data from the T-Mobile physical SIM.

When the new iPhone XS was announced with this capability it became a potential game changer for me. iPhones don’t natively work with Project Fi. In the US, Project Fi actively switches between T-Mobile and Sprint towers to get the most optimal signal. There is a way to activate a Project Fi nano SIM on a Pixel 2 XL and then place it in an iPhone to get basic phone and SMS service, although MMS functionality is limited in iMessages. After being activated on a Project Fi compatible phone, nano SIM can work on the T-Mobile networks on an iPhone.

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This limited functionality is actually perfect for me because I just want to be able to use the main phone app and handsfree calling with Siri. I don’t want or need iMessages for my Project Fi number. I will continue to use Hangouts for messaging so I can have consistency across platforms. This also allows me to not need for my phone to be on in order to communicate via text.

I could then use the eSIM (when the functionality becomes available with iOS 12.1 later this Fall) in the iPhone XS to connect to my T-Mobile account for data in the US and when I travel abroad I can switch to the Project Fi physical SIM for fast data.

I ordered an iPhone XS Max 256GM today on the iPhone Upgrade Program. The entry level 64GB of storage is absolutely ridiculous and is only there to force you to upgrade to 256GB. This little trick accounts for the biggest profit margin for the phone. Why didn’t they make the entry level 128GB? Because they knew that most people wouldn’t upgrade because 128GB is plenty of space, but 64GB isn’t. My Pixel 2 XL is 128GB.

The straw that broke the camel’s back and sent me running back to Cupertino was the productivity apps that I am now using religiously on my MacBook and iMac.

Aside from the writing apps mentioned above I’m also using Flexbit’s Fantasitcal 2 and Cardhop. These are great apps and the former is available as an iOS app and given that I just switched the calendars for the artists that I manage over to Outlook on Office 365 from a proprietary database system that I was using on Knack it makes our lives so much easier.

I also discovered a service called Syncgene which syncs all of my calendars – Outlook, iCal and Google Calendar and my contacts seamlessly and automatically in the background. This means that I can now ask Siri to setup an appointment on my MacBook, iMac or iPhone, accept e-vites inside of Outlook and tell Google Assistant on Google Home, Pixelbook or Pixel 2 XL to setup an appointment and all three calendars will be completely in sync. The service automatically syncs in the background every 30 minutes.

I spent the day paring down my contact list from 3,000 + to less than 1,000. I deleted the contacts from Apple and Outlook and then synced the Google contacts to all three.

So far so good. Believe it or not that was a big problem for me. I had appointments in Outlook that may not have showed up on my Google Calendar on my phone and my contacts were just all over the place. I ended up having to search in two places sometimes to find a phone number or email address. Now that I may be going back to the iPhone I can use my native calendar and contacts on all of my devices, programs and apps and not miss a beat.

So I am patiently waiting for the delivery of my new iPhone XS Max in a couple of weeks. In the meantime Google will unveil their Pixel 3 phone line of Oct 9th. There have been massive leaks of this device on the internet over the past few weeks and to be honest the phone doesn’t look all that remarkable. There is a conspiracy theory out there that posits that Google is “punking” us and that they are going to announce a true game changer of a phone on the 9th. We’ll see.

One thing is clear regarding the comparison of the iPhone XS to event the Pixel 2 – the Pixel 2 has a better camera, so it will be interesting to see what the Pixel 3 will offer in this department. I can always cancel my order and get the Pixel 3 if Google ends up shocking the world.

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However, if the Pixel 3 doesn’t have Dual SIM Dual Standby, unfortunately that’s gonna be a deal breaker for me.

That’s what I love and hate about technology. There is no one perfect solution. There is only a perfect pursuit of technological nirvana. I’ve gotten close to perfect a couple of times and if I’m honest with myself I don’t really want the perfect solution, because then the pursuit will end.

I have the perfect wife, which gives me the license and motivation I need to be a technological polygamist.

So who will I be shacking up with after Oct 9th?

I don’t know, but I’m gonna have fun no matter what.

About the author

Andre Kimo Stone Guess
Andre Kimo Stone Guess

Andre Kimo Stone Guess is a writer and cultural critic from the Smoketown neighborhood in Louisville, Kentucky. He was VP and Producer for Jazz at Lincoln Center in New York and CEO of the August Wilson Center for African American Culture in Pittsburgh. He now runs GuessWorks, Inc. with his wife Cheryl.

Educated Guesses A Blog Full of Guesses