Over the past year, when I began telling team members, investors, LPs and other stakeholders about my transition, their

Given Apple’s reputation for “magical” UX, you’d be forgiven for assuming that I’m the idiot here and I’ve simply locked my screen orientation and forgotten about it, but I really haven’t.

In the decade since Apple released the iPad, there’s one particularly gross “feature” that’s been neglected in update after update. I’m speaking, of course, of the unfortunate way that iPads handle iPhone apps.

The weird thing is, even when you hit the “expand” button to zoom in, it still doesn’t fill the screen completely… Instead of stretching to 100% in one direction and letterboxing the other (like watching a “wide-screen” movie with black bars on 2 sides), Apple opted to letterbox all four sides.

The Messages icon is a classic example, as many have pointed out. But for me, the absolute worst is the bell icon for Notifications in System Preferences. It genuinely looks like a departing employee left it there in an attempt to have one last laugh following unfair dismissal.

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one buys my eBook they get an email from me with the eBook attached and a personal thank you from me. This simple little hack creates some weird and whacky conversations. People feel that like they’re more than a customer when they get a personal email that isn’t automated from the writer they enjoy reading.

I’ve tested it with pro apps such as Logic Pro and Final Cut Pro X, and it works perfectly, so far. The same goes for third-party stuff like Ulysses, Omnifocus, Microsoft Office and Toggl, but I’m under no illusion — that can change pretty quickly with a new operating system.

I upgraded both of my production Macs to Big Sur on the day of release (or, at least tried to because, a) I feel a duty to do so for my audience, and, b) I’m a geek and like new stuff.

That’s why I’m writing this blog. I’m sure I didn’t do everything right in executing my transition, but that isn’t the point. I’m not here to share a playbook — I don’t think one exists. I want to share my experiences and vulnerabilities with full candor in the hope that other founders can have a resource that I lacked; that they can learn from my experience and feel less lonely than I have through this process. I also hope this piece can help build greater empathy and understanding among the investors, teams and families that have backed, supported and lived with founders whose struggles might at first seem opaque or impenetrable but are, in essence, deeply human.

Let’s start from the beginning… Before the Retina Display “made everything blocky” or the iPhone 4’s “AntennaGate” prompted Apple to give out free silicon bumpers, we had the early App Store. At the time, all of the mere 100,000 apps were made for tiny little original-iPhone screens. The iPad, with its larger and more-square display, simply couldn’t render the iPhone apps full-screen without stretching or cropping them.

Now here’s my grievance: With your iPhone app sitting awkwardly in the middle of your screen, you have two options: By default the apps would render at “1X” (appearing exactly as you would see them on an iPhone) or by tapping a little button in the bottom right corner you could switch to “2X” and it would “zoom in” to fill more of the screen.

To spare 1st-gen iPad buyers from having to wait for the developer community to build apps tailored for the iPad, Apple decided to band-aid the problem by simply centering the iPhone apps in the middle of the iPad screen. It’s not the most elegant fix, but it worked well-enough and Apple had faith that the developers would come through.

But if you rely on your Mac for work of any kind, I’d wait. That’s always my advice; it’s simply too big a risk to go ‘all-in’ on a new Mac operating system if you need that machine to make money and put food on the table.

This probably made a lot of sense back in 2010 given the difference between iPhone and iPad’s aspect-ratios and resolutions. 2X was as big as you could scale an app and still come out with an even number of pixels, which was important to keep apps from appearing blurry or distorted.

I’ve tested it with pro apps such as Logic Pro and Final Cut Pro X, and it works perfectly, so far. The same goes for third-party stuff like Ulysses, Omnifocus, Microsoft Office and Toggl, but I’m under no illusion — that can change pretty quickly with a new operating system.

Now it’s been a decade and most apps I use on my iPad these days are built specifically for iPad, but every once in a while I’ll decide to check my bank account or -honestly- do anything outside of my artificially-created bubble of iPad-supporting apps and I’m jolted back to reality.