Growing up, I attended Catholic school and was taught by nuns to finish my lunch because there were children starving halfway across the world. I was taught to complete one book before starting the next. Taught to give equal attention to every station of the cross.

This type of perseverance can be a valuable tool in one’s toolbelt. There are moments in life that call for grit, when it’s crucial to push through discomfort and disinterest. But fetishizing finishing isn’t nearly as helpful as it feels. Just the act of completing something isn’t virtuous by itself—the context matters.

We are living in a time of ceaseless information overload and ever-expanding choice. Thousands of photos are posted to Instagram every second, 500 hours of video are uploaded to YouTube every minute, and millions of books are published every year. You can’t consume all that “content” even if you want to. Your time and attention are limited resources. In this context, a better skill than finishing is knowing when to finish something and when to abandon it.

I’ve gotten better at this over the years. I’ve become more attuned to what my body and brain are telling me about the future value of what I’m currently doing. These are the questions I ask myself when deciding whether to stick with something or bail:

• Am I enjoying it?
• Is it feeding my mind or my heart?
• Will it help me accomplish something or solve a problem?
• Will it matter in a year? Five? Ten?
• Is there something I’d rather be doing?
• Have I had enough?
• Might it be better to set it down now and pick it up again later?
• What’s the worst thing that would happen if I give up?

These questions help pressure-test the idea of continuing to follow my current trajectory. And sometimes their answers reveal that I should have pulled off the highway a few exits ago. But no matter how close to the end I am, it’s never too late to stop.

I want to give you permission to quit the thing you’re trying to finish that’s not working for you anymore. It could be a New Year’s resolution you regret making, a book that all your heroes recommended but you keep bouncing off, or even a side project that doesn’t bring you joy anymore but that you keep maintaining out of a sense of duty. Whatever it is, you’ll know it, because just the psychic weight of it being unfinished is stressing you out.

You don’t have to complete everything. You don’t need to be in it for the long haul. Quitting something doesn’t make you a quitter. Instead, it makes you someone who knows their worth and knows what they want. Letting go of one thing can give you space to start something new that will serve you better. And if you regret your decision, it’ll still be there when you’re ready to pick it up again.

My training for the job involved being clapped at a lot while donning the signature blue T-shirt in a room full of folks learning how to sell iPhones and iPads and create Apple “customers for life”. Our teacher was a blond-haired, blue-eyed surfer-turned-computer salesman named JB who wore white earbuds as a necklace. As he taught from the printed material and screened Apple videos for the class, he kept harping on one point that’s stuck with me in the decades since.

I don’t know, let’s find out

JB taught us that there was no way we could know everything there is to know about every Apple product, let alone every app that runs on them, and every way they can fail. He taught us that rather than making up an answer, guessing, or shrugging our shoulders, we should instead say, “I don’t know, let’s find out”. Admitting that we didn’t know was the first step. Then, we were to find out together with the customer by walking over to a Mac and looking up the answer or pulling in another employee who might know the answer.

This one sentence from a retail training manual contains many insights that I’ve relied on every day since in my personal and professional life:

1. It’s okay not to know because we can’t know everything, and we shouldn’t expect that of ourselves.
2. It’s better to admit our ignorance than get things wrong.
3. Even if we think we might know, it’s okay to double-check because getting it right matters.
4. People trust us more when we admit our shortcomings.
5. Learning is better together.
6. People love to see and share in the process of discovery.
7. People trust information more when we share the way we found it.
8. Memorizing isn’t as important as knowing how and where to look things up.

Fuck around and find out

This is another similar phrase that’s become popular since 2020, especially sarcastically in leftist circles. But it’s legitimately valuable advice because sometimes, no amount of Googling or reading about a topic will get you to the answer. Sometimes, trial and error is the only way to learn. By experimenting or fucking around, we learn together by playing together. We do a little science and discover something new about the world that we can share.

Many of the answers to life’s daily questions can be uncovered using these thought technologies. Are you faced with a tricky question in an interview for a new job? Try being honest with the interviewer that you don’t know the answer and explain how you’d research it in detail. Not sure what your gender is? As Mattie Lubchansky suggested on a recent live episode of the Gender Reveal podcast, “fuck around and find out”. Try on makeup, a new set of pronouns, or a binder, and see how it feels!

Let’s make better mistakes tomorrow

Just because you don’t know something today doesn’t mean you won’t know it tomorrow. If you cultivate an attitude that faces the unknown with curiosity, sharing, and experimentation, rather than blame, fear, and stubbornness, you may get a bit smarter every day. You’ll learn much more by remaining open to new discoveries and sharing that journey with the people around you, at work and in the rest of your life. And that continuous improvement, or kaizen, will accumulate like compound interest. It will, in the words of Mike Monteiro, let us “make better mistakes tomorrow”.

What don’t you know right now? What do you want to find out? Let’s do it together.

There’s a simple answer: it’s useful! The unread state of messages in an email app controls things like the number next to the current folder, the application’s badge, and the status indicator next to a message reminding you to look at it. A simple button to say “Oh yep, I know I clicked into it, but I didn’t actually read it or fully process it yet” is a great affordance for users to manage their communications that has stood the test of time. While some argue that flags should be used instead for this kind of message management, they miss the point that flags cannot and do not convey, to either the user or the software, the same meaning as a message being unread.

“Mark as Unread” has been so successful and well-loved in email that it’s been copied by many messaging apps like Facebook Messenger, WhatsApp, and Instagram. And its utility in a casual messaging context is much the same in the slightly more formal email context.

As Tine Welanly put it on Quora:

Let’s say you’re riding the bus and you open a message from a friend, maybe asking you about your plans for the weekend. You have to respond to that but maybe it’s your stop already or you don’t know yet. But if you don’t say anything now, you might forget to respond and then you’ll look like a bad friend. Not to mention you might miss out on some weekend fun.

But the most popular messaging app on iOS, Messages, has never implemented “Mark as Unread” even though users have been clamoring for it for years and it’s been rumored that they tested it. What’s even wilder is that iMessage doesn’t have any other in-app way for the user to signal that they need to return to a message in order to respond to it. The only gesture toward anything like this is an obscure Siri integration.

Messages routinely get forgotten and go unanswered. The missing “Mark Unread” button has no doubt caused countless accidental ghostings, avoidable arguments, and missed opportunities. And its lack has likely made life more difficult for users with conditions that affect memory or follow-through, like ADHD and depression, who may not be able to respond in the moment and have no easy way to record their intention to do so.

So why hasn’t Apple added this feature? If I put on my Product Manager hat, I can think of only one argument that’s likely been made internally to keep this wildly popular feature out of the app. It goes like this: “If we add a button that says mark as unread, wouldn’t users expect that it would unsend their read receipts?”

This is a compelling argument that I was initially sympathetic to, but looking deeper, this just isn’t a problem in the real world. Outlook, which supports both read receipts and Mark as Unread, seems to cause no significant user confusion in this regard. The read receipt exists for the sender, and the local unread status is for the recipient. Simple as that.

Even if this slight ambiguity is too much for Apple to handle, they could instead incorporate another feature from Mail instead: flagging. Allow users to flag a conversation (or an individual message) and then see all their flags in one place, when they’re ready to respond.

Whether Apple chooses to implement this feature as “Mark as Unread”, flagging, or something else entirely, they should implement it, and soon. As more of our communication, both personal and professional, moves online, it’s never been more important that we keep our commitments to each other, that we respond when we say we will, and that we keep dialogue flowing. We’ve long had a great tool for doing exactly that; now that took just needs to meet users where they are.

This article has also been filed as feedback for Apple at FB9838778.

Update: After posting this article, a friend at Apple reminded me that one of the first things he did when he got to the company was try to file a radar for this missing feature. Except he didn’t have to because he found an open bug from yours truly filed in 2009. I’ve been asking for this feature for 12 years and I don’t plan to stop any time soon! Maybe I should try this approach next.

Architects and engineers may be familiar with this concept as “design patterns”: reusable solutions that can be applied repeatedly in the creation of complex systems like buildings or computer programs. It’s not a coincidence that Merlin has also given a talk at Macworld in 2009 about design patterns, because the two concepts do share a lot of DNA. But thought technologies, as I understand them, are often more broadly applicable than design patterns, and can even cross disciplines and mediums.

Before I even knew the term, I had heard about a deck of cards called Oblique Strategies, created by Brian Eno and Peter Schmidt in 1975. The original deck contained 113 cards, each of which gave a suggestion of how to get unblocked on creative problems by encouraging lateral thinking. For example, “Try faking it!” or “Ask your body”. While at first glance these may seem like nothing more than empty aphorisms or clichés, upon deeper inspection, they’re actually hard-won lessons in creativity, distilled into ink and letter-pressed onto paper. They’re little verbal gadgets for your brain to help you be a better artist or musician or creator.

If you’re a fan or practitioner of improvisational theatre, you have likely heard of the thought technology of “Yes and…”, but improvisers have a huge collection of these that they’ve built over decades to understand and improve their art form. Sometimes they’re referred to as “the rules”. But one of the things I love about the word technology in this context specifically is that it is value-neutral. Just like floppy disks or CD-ROMs, thought technologies can become outdated, outmoded, and be replaced by better, more useful tools. There are no good or bad technologies, only better and worse uses of them.

In fact, in an incredibly meta sense, even having an awareness of the concept of thought technologies is a thought technology in itself. Once you become aware of the various mental patterns and cognitive strategies you regularly employ to interact with the world, it becomes much easier to name, record, and consciously employ them. The branch of psychology interested in Cognitive Behavioral Therapy even uses this to help treat patients with mental illness and other cognitive distortions. Once you have built up this personal library of thought technologies you use, you can then examine, improve, update, and replace them as you learn new things about yourself, your work, and the spaces you operate in.

Some of the smartest people I know have recently become invested in building bespoke systems for exploring their own thought technologies over time. Andy Matushack’s working notes, the rapidly-expanding Roam Research and Obsidian communities, Tiago Forte and Nick Milo’s respective online courses on networked thought, and the larger movement toward personal knowledge management systems all point to the idea that as knowledge workers and creative people, it’s much easier to make breakthroughs in our work when we can look at what’s going on in our brain in a more concrete form and operate on those mental models more directly. I’ve even dipped my own toe in the water by publishing 30 of my own thought technologies on my 30th birthday last year.

Giving someone a new way to think about the world is a gift. As someone who’s always trying to learn and grow, I try to treat these gifts with the same respect I have for the physical technology I carry with me in my pocket. Brian and Peter gave musicians hundreds of these gifts in a deck of cards, improvisers hand them down through books and classes, and Merlin and John broadcast them out weekly in an RSS feed. Thanks to that show, I’ve gained a way to think about thinking, and if you’ve never considered the apps that run on your own mental operating system before today, maybe you have too. Think different, I suppose.