#34 The iPad: 15 Years of Wishful Thinking
Ding! A text from my friend Per. The message I’d been waiting for. I killed the lawn mower and checked my phone. There it was: a photo of Per, grinning like he’d just struck gold, holding up a plastic bag with my iPad inside.
Just 24 hours after the iPad launched on April 3, 2010, I had it in my hands. Likely one of the very first in Sweden. Per had grabbed it at the Apple Store beneath the Glass Cube on Fifth Avenue, cabbed straight to JFK, flown home, and there I was—waiting at his door like a kid on Christmas morning.
Including that first one, I’ve owned six iPads: iPad (2010), iPad (2012), iPad mini (2012), iPad Pro 13” (2015), iPad Pro 11” (2018), and now the iPad Pro 11” (2024). Over 15 years, I’ve probably spent more than €10,000 on iPads and peripherals.
Each time, the same thought: This is the one. The device that will finally replace my laptop. Especially since 2015, with the Pro models and the Apple Pencil. I’ll handwrite notes, sketch big ideas, travel light, and look cool doing it. And every time, apart from one six-month stretch without a laptop, I go back to my Mac after a week or two.
So why do I keep abandoning my iPads? And, why do I keep buying them?
First, I’m a writer at heart. Emails, messages, documents, and the occasional newsletter. And writing still feels best on a real keyboard, with a full OS where I can manage windows and workflows without friction.
Second, and this is the part I don’t always say out loud...
I’ve called myself a designer my whole career. And technically, that’s true. I’ve had a hand in shaping more products and services than most. But deep down, I’ve always felt like a bit of an imposter. Because in my mind, however irrational it may be, real designers can sketch. I can’t.
Looking back, every iPad Pro purchase feels less like a tech upgrade and more like a quiet little bet. A hope that this iPad, this one right here, will finally unlock some hidden sketching ability. That it’ll make me into that pencil-wielding creative I’ve always secretly admired.
Instead, here’s how it usually goes:
- Buy iPad Pro.
- Get Apple Pencil.
- Download every drawing app in the App Store.
- Open blank canvas.
- Attempt to sketch.
- Close app. Go back to writing.
Funny how we do that, isn’t it? We don’t just buy products. We buy aspirations. Some buy running shoes to become runners. Others invest in fancy chef’s knives, hoping to release their inner chef.
Me? I buy iPads, hoping to become someone who can draw a straight line with confidence.
Deep down, of course, I know exactly why the sketching magic never happens. Like anything worth doing, it takes practice. Hours of clumsy lines, awkward proportions, and messy failures.
And yet, I’m not putting in those hours. My subconscious may be begging to get that new skill, but my conscious self? He’s sitting comfortably at his keyboard, sipping coffee, writing another newsletter, and finding yet another reason why tomorrow will be the day to start.
And hey. Who knows... Maybe the next iPad will finally do the trick?