A mostly monochrome picture of Sesimbra Beach, Portugal. Lots of birds flying around.
Yes, this was taken with my iPhone 14 Pro

Past, pains, predictions and prayers of my love affair with Smartphones

Bob Durie

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I’ve long had a vision of technology that would accompany me wherever I went, and that tech would do wonders for me; both by augmenting my brain in terms of memory, utility, and information, but also in terms of connection and collaboration.

I feel we’re on the cusp of a big leap forward in this regard. The iPhone has taken us very far, but there is much farther to go. This piece talks about my history with smartphones, why what we have today is failing us, why even the term “smartphone” is dated and dead, why there is some hope for innovation in the coming years, and ultimately what my dream mobile device looks like.

This post is long! Feel free to jump to the sections that sound most interesting to you.

History

My first phone with a camera was a Sanyo SCP-8100, purchased in 2004.

A stock picture of a Sanyo SCP-8100 smart phone, which is a flip phone from around 2004.
Sanyo SCP-8100

The resolution of captured images was 288x352, here is an example pic, taken from an apartment I was living at in 2004:

A photo of an interior living living room with a sofa, coffee table, and red painted walls. The photo is of very poor quality.

It seems prehistoric now, but it opened up a whole new world for me. I started using a service called textamerica that allowed you to post pictures with a blurb of text to your own page which they referred to as moblogs, and view a global feed with everyones posts.

I was hooked — and while the phone did have a basic browser, I don’t think I ever successfully uploaded to textamerica on the go. I had to return home, wire my phone to my PC, pull all of the images (it could store about 50 if I recall), and then upload to textamerica from a browser. It was at this time where my primary internet handle I still use came from, ‘mobob’, short for mobile Bob, and a play on the term moblog. If I thought I’d still be using it today I may have dreamed up something more clever, but all in all I’m happy with its longevity and benignness.

iEvolution

Steve Jobs holding up the original iPhone

In 2007 came the first iPhone, and really the birth of the smartphone. For me, it was love at first sight. The iPhone’s capability was the answer to the desire to be connected and free when mobile that had been brewing within me for a few years. Ever since the iPhone 3G’s launch in 2008, I have been an unapologetic Apple fanboy and have had the luxury of purchasing the new iPhone that has come to market almost every year. I look forward to the annual September keynote, placing an order at a scheduled and often inconvenient time of day, and getting that nice new box a few weeks after the announcement.

We’re now in to major iteration 16 of the software and 14 of the device (or 38 depending how you look at it). The iPhone carries on, and things are starting to feel cumbersome.

Back when the App Store was announced in iPhone OS 2, it was a panacea of functionality and opportunity. As a developer, I was incredibly excited to try my hand at making apps from my little home office, have Apple distribute them on my behalf, make a few bucks, and ultimately create something people all around the world find joy and usefulness in.

In the early days, the walls around what an App could do were massive — little access to anything outside of its own experience. For instance, notifications did not exist, there was no integration with the lock or home screens, and no ability to do things in the background. This limited what the apps could do, and over the years Apple has listened to developers and consumers, and regularly announced big additions to its API to open up the walled garden.

While all this is good, it adds a significant amount of complexity, and can increase the risk that the experience will be jarring for end users. Many of my irks (below) are about what I’ll call “hooks” enabled by Apple, that have proven too tricky to maintain as a cohesive experience. In the beginning, adding a few incredibly well designed APIs worked well to open things up and add functionality, but as time went on the interplay between all the now complex integrations has become too much, and I don’t believe it will ever go back to feeling cohesive and simple. In some ways I feel like the iPhone has arrived where Android started, hyper flexible, and all over the place.

Lets fast forward to 2021 when I decided the iPhone 13 didn’t have “enough” to warrant a purchase, so I skipped buying the shiny new thing for the first time since I started. Now in 2022 after waiting two whole years and shamefully admitting even if they changed literally nothing and doubled the price it was still an instabuy, I got the iPhone 14 Pro.

Overall, it is awesome. However there are more things irking me than usual, and this combined with a few industry trends has me thinking about what I desire in a phone/personal device, and why I don’t think the iPhone is going to be my device of choice a few years from now.

Irks

As I mentioned, the iPhone 14 Pro is an astonishing device. It packs a ridiculous amount of horsepower and engineering, and enables a great deal of functionality to be dreamed of and placed on top of it.

This section isn’t about that, it’s about the ways the device is disappointing me.

The new always-on screen was initially quite nice; I can leave my phone on the table and at a glance see the time and if I have any notifications. I thought this was going to be great at night, I can use it as my always on clock! Well… no. It seems the always-on screen turns off after a few hours. And worse, to get it to kick back in I have to tap the screen multiple times (or wait multiple seconds) or press a button for it to come back on. Annoying.

The new customizable home screen options are a welcome addition, but a few things have bothered me. The “Featured Photos” is great, but I can’t actually navigate to the photos it shows. I have decades of photos to see, many I don’t even remember and I greatly appreciate them being surfaced, but if I can’t dig in to them to learn about where they’re from, it frustrates me. I discovered this on the beta in fact, and submitted a ticket about it… never heard back.

In addition to featured photos, the new home screen allows widgets from apps to show up on the lock screen. This is a good step forward. One minor omission I discovered early on is the stopwatch. Timers still count down on the lock screen, so why not show the stopwatch running too? Feels like they might not have talked to the “Clock” team (if that still exists). And why the timer count down is lumped strangely near the bottom of the screen in a non-familiar pattern, when the widget or dynamic island might make more sense? Probably a good reason, but still seems odd.

A picture of an iPhone home screen, with a timer widget counting down.
iPhone home screen showing timer countdown

Screen time hasn’t seen an update in a few years, and it continues to annoy me that always-on utility apps like Google Maps are included in overall screen time. This makes no sense in terms of measuring and trying to control your active attention, and reeks of poor integration and testing.

Focus modes were added in iOS 15 to help with the attention stealing problems (more on this later). Now you can choose a focus mode for “exercise” when you’re out for a run, or “work” so that only your work apps can flag you. I’ve tried it a few times, in a few contexts, and have unfortunately found there is always something that gets in the way and causes me to disable it. Like missing text messages when you happen to be out at 10:30pm but your sleep focus automatically turned on. Or using sleep mode then opening your phone late at night and seeing no badges and thinking you didn’t get texts, but actually you did but it didn’t show a badge — even if the person you received texts from was in your exclusion list. Or leaving a focus like exercise on long after your run is done. I mean, these are all trainable / fixable, but when you miss one call or text you were expecting and trust is gone. I admire the “enable focus mode” suggestions too, e.g. “turn on do not disturb for the duration of your upcoming meeting” but for all the reasons mentioned, I rarely do this because i simply don’t trust the capability.

And don’t get me started about the Phone’s well intentioned “silence unknown callers” setting. I love the theory, but the first time I missed an important call from a doctor I realized I could never use this again.

Let’s turn our attention to Siri, a first mover in the digital concierge space. It feels like it hasn’t evolved much past its introduction in 2011 in the iPhone 4S (!!). Applying some naive engineering organization structure thinking, let’s say the “Siri development team(s)” at apple work on either new value-add features, platform, or improving quality. I’ve seen new voices get added (platform work), and I’m sure it’s gotten better at recognizing voices and working in noisy places (quality), but it feels like they’re not spending much if any time on value-add features (me getting more value from Siri, it saving me time or augmenting my time). Siri shortcuts is one of those value-add capabilities that has come out in the last 5 years and it feels powerful, but short of minor automations with third party apps I’ve gotten little value from it. In my opinion, Siri and its promise of being a digital concierge has powerfully under delivered. My expectations are such that I want to be periodically trained about the new capabilities and value-adds Siri can now perform to save me time, but its left up to me to think “hey can Siri do xyz?” and usually the answer is no. I should add, I have friends that love Siri and feel it really does deliver and saves them a ton of time… so I’ll admit, I may be the problem.

I applaud Apple’s privacy forward changes in iOS 14.5 (which were very costly for some), but it’s resulted in an annoying experience logging in to almost every single app for the first time (e.g. “Ask App not to track”). You’re asked to decide if you want personalized ads with the given app or on websites. Sometimes you get a sob story prior to the system modal that pops up, educating you on the value of allowing that app to track you, how it’ll pay the bills, keeps the app alive. Just another annoying item thrust on all users, gnawing away at our time and diluting the platform experience.

Notifications, when viewed individually, provide incredibly powerful capability to apps and great freedom to connect with users. When viewed holistically from a user experience perspective, I believe they are broken. My iPhone can easily feel like the enemy when I’m getting slammed with notifications but am trying to accomplish some other task. This is part of the not-intentional war on our attention and is not a problem unique to notification center or the Apple ecosystem. Notification center has seen some evolution in this vein, with things like morning summaries of notifications being an option (but annoyingly, drilling in to see the articles they occasionally recombine after browsing them for 15 or so seconds), and relatively easy navigation in to the notification settings for an app (even though the gesture to find the “Options” option on the notifications screen requires a very precise finger swipe that usually results in me clearing the notification, and frustrates the crap out of me every time). It is a natural direction to give more power to the user to tune things, but these solutions pale in comparison to the notification load apps place on users, and the reality that these devices interrupt us dozens of times a day… for questionable reasons. This leads me to think its never going to improve substantially, and why a paradigm shift is needed.

Other smartphones, non-smartphones, anti-smartphones

For all the issues the iPhone has, there are lots of alternatives.

Most obviously, there is Android. No surprise here, short of checking out friends’ devices for a few moments, I’ve never used an Android phone. My well established assumptions are that doing so would take me further in a direction I don’t want to go — more flexibility, more features, more power to the apps, more apps in general, and a less cohesive feel (dating back when they couldn’t do scroll bounce very well). I may very well be wrong here, but my gut tells me I’ll be less happy with android (please challenge me on this if you think I’d benefit from another look).

Then there is a foray of dumb phones out there (I’ll use the term not-smart phone for the remainder of this piece), phones designed with less to do better.

Top of this list for me is the Light Phone 2. It is radically minimal. And as their teaser video describes “it is a choice”, and “we are humans, who are taking back our lives”. I absolutely love the idea of this, but for me from a practical point of view, it goes too far, and cuts out too much of what I’ve now grown to rely on when mobile (more on this later).

I’ve long had admiration for Palm devices, and only in researching this piece did I find out that they released a new device a few years ago, the Palm Phone — I was immediately stoked, but after reading some reviews my excitement dwindled as again, it appears to lack butteriness and reliability.

Want to know about other not-smart phones? This search tool is amazing, and you can see just how many options exist.

Humane Inc.

Now let's move over to a company called Humane Inc. (hu.ma.ne). They launched in stealth mode 4 years ago headed by some early design and delivery folks from Apple. Recently they opened a public discord for speculation and product updates, and are starting to tease where what they might be doing:

Speculation¹ as of now (which could change tomorrow) is they’re building devices that enable technology to improve real life experiences in profound ways, in form factors that we’ve never envisioned or at least have not become mainstream. Think wearables, with a heavy AI backend to provide options we haven’t had before. This detail from one of their patents hints at one area of possibility;

In an embodiment, the wearable multimedia device includes one or more microphones and a headset. In some embodiments, the headset wire includes the microphone. In an embodiment, a digital assistant is implemented on the wearable multimedia device that responds to user queries, requests and commands. For example, the wearable multimedia device worn by a parent captures moment context data for a child’s soccer game, and in particular a “moment” where the child scores a goal. The user can request (e.g., using a speech command) that the platform create a video clip of the goal and store it in their user account. Without any further actions by the user, the cloud computing platform identifies the correct portion of the moment context data (e.g., using face recognition, visual or audio cues) when the goal is scored, edits the moment context data into a video clip, and stores the video clip in a database associated with the user account.

Similar things have been suggested before, like in the movie Her, or be it Google Clips or Glass (which seems to have found it’s niche in the enterprise btw), or lifelogging++ capabilities. Humane has an all star cast, and if anyone can do it, they can. Everything up to now really is speculation, perhaps they’ll focus mostly on software for the first release and level up the concierge experience Siri has failed to deliver on.

Having said all this, it’s this buzz combined with the cumbersome nature of the current iPhone lineup that makes me feel we’re at “peak smartphone”. It’s only a matter of time before some of the capabilities start getting usurped by incumbents in more conducively human, less invasive ways, and I long for this day. The death of the smartphone surely is many years out, but I’m already looking forward to it (least in part to call the mobile devices I carry with me something more than a phone).

Before all this happens… I wanted to take the time to speculate. With the flaws and ideas above seeding my imagination, what would I want in a personal assistant device ecosystem?

My mobile device dreams

For certain, a new paradigm of mobile tech will come. Assuming I’m alive for it, I’m keen to seek it out and attain its benefits, and no doubt, its unforseen flaws — whether it’s in my pocket, on my wrist, projecting on to my hand, controlled and visualized within my brain, or more than likely some form factor I cannot envision. This section will refer to my (mobile) “dream device” but note that this likely will be multiple physical devices, and most certainly backend / cloud services enabling it.

Given many of my gripes with current iPhone are about complexity reducing capabilities, I accept that in fact my dream device will do less than my current smartphone. I’ve dug through how I use my smartphone today² and realize I’m not ready to part with much of its capabilities. Hence, my minimum bar contains quite a lot, and indicates that a not-smart phone or anti-smartphone just won’t cut it.

Lets go over a few examples, what would my ideal mobile device not have?

Would it have a display? Perhaps obvious, but for many of the basic uses, yes it needs one. But in my dream device, the screen wouldn’t have clutter — it would be clean and take me where I needed to go when I referenced it. For instance, why do I keep the “Phone” app icon on my bottom bar of 4 most used Apps? Only because I want to know if I missed a call / have a message, and I can’t rely on seeing notifications. But the rarity of me pulling my phone out and manually making a call is such that it occupies way too much real estate. A UI tuned more towards my anticipated intentions, probably with some great supervised AI to make suggestions, is what my dream device would have. When I get in the car? Launch Google Maps (the last maps app I used). Finished a run? Show me fitness apps. iPhone has already tiptoed into this with suggestions on the search screen, but some are good and some are not, and it’s not doing enough to inspire confidence and take pointers from me.

4 pictures of the Lightbox Lifelogging camera, attached to different positions on the body; pocket flap, chest of a t-shirt, bag strap, and hat.
Lightbox lifelogging camera

What about a camera? For video calls indeed I need a front facing camera, but what about a rear facing camera? I struggle with this one as I recently bought a decent and small point and shoot camera to satisfy the specific need that I wouldn’t have to carry my iPhone around with me to capture moments. Why? In short, because my phone distracts me from real life. With this in mind, and my dream device obviously not distracting me, then yes, yes I’d like my dream device to have a camera. Ideally, a camera setup like the one on the iPhone 14, because it is amazing. Lets also throw in a camera setup that can be always on, always recording (aka lifelogging) — perhaps the camera portion of the device is detachable, and can affix to your jacket. Then tack on some of the Humane use cases around using that video footage. For instance, after meeting a new person at the park, I could ask my device “please capture that last person I was chatting with as John Smith in my contacts, his wife’s name is Margaret”, and it would add the contact and photo, and attach a note with the details captured for future reference.

Messaging and email is an obvious one that is necessary much of the time for coordination and emergencies. But dammit, my ideal device has one set of contacts, and one app for texts and file/image exchange. There are obvious problems with this (i.e. the desirable segregation of ‘friend’ groups the app boundaries provide), but at least when I start communicating with someone regularly that should be visible in a unified chat interface. I do like the “I’m driving / busy” auto replies, so more of that please.

Do I want social media on my dream device? Sometimes yes, but mostly no. To disambiguate, let me first mention “the feed” that most social media apps present. I do not want nor need “a feed” while I am out in the world, intentionally doing things. I may want to push content, and do a quick share of a moment, but while I’m in the world I do not want to be consuming things unless it is in a period of downtime. Social media is generally designed to hook you in from the moment you pull up the app, and avoiding the alluring feeds when you just want to post requires incredible discipline. Going back to my days on textamerica when it was such a novel window into other folks’ creativity, its sad that I’m willing to forgo it entirely given how subversive it has become. And what about notifications for “likes” on that content I just posted? This is a tricky one but I’ll be happy to pull this bandaid off and ditch them, those dopamine bursts are not serving me! My life would be better off scheduling and using some intentional time to go back and review my posts and respond to comments.

What about news? Scheduled summaries that I pull when I’d typically sit down to read the paper is where I’d like to get back to. So I can skip most of this, reading on a small device is a drag anyways, not nearly as enjoyable as on a larger screen.

And games? The games I play are generally not very intrusive so having them when mobile can be handy, but a big exception here is free to play games which generally try to rope players back in with interruptions and offers.

The theme of my dream device here boils down to having a device that somehow understands if I’m “intentionally doing something”³. Mobile phones have blurred the lines of activities that we used to “have a place for”. Watching TV? You do that at home. Eat dinner? You do that at the dinner table or a restaurant. Listen to the radio? In the car when you’re en route somewhere. Writing or working your desk job? At your desk at home or at work. Playing with your kid? You’ll do that wherever, but when you’re doing it, you don’t want to be doing anything else. I want my dream device to adapt to the thing that I am intentionally doing. This means either get completely out of my way, or enhance the thing I’m doing.

What about the times I’m not intentionally doing something? Well… these times are few and far between, and then and only then should it allow me to do “filler” activities. If it is not capable of knowing if its interrupting an important life moment… then please err on the side of caution and don’t interrupt me, nor allow me to meander into spirals, doom or otherwise.

Besides all those run of the mill capabilities, what would my dream device do better?

My dream device would work for me. A personal assistant. Something that knows where I am and augments my experience — not just with display, but other things.

When I walk in to Home Depot, the website should automatically show up on my device if I pull it out of my pocket (or equivalent, i.e. a projection on to my hand or HUD). It should tell me all the times I’ve previously visited, how much money I spent, how long I spent there, photos I took while I was there, and any relevant notes I may have taken. When I’m en route to a restaurant (because when I’m there, my device should only notify me for an emergency), it should offer to recap any previous visits to the same place, and any recent online reviews. It shouldn’t show me notifications or breaking news alerts when I’m doing something. Help make my time in the present more valuable. Like a guided tour at a museum, but with you everywhere you go, making your experiences richer. And not getting in the way — hence keep the content it does share with me compressed and concise, and don’t let me get carried away.

From a life recording point of view, I want to narrate any aspect of my life that I feel is memorable, and have my device file it for me for later usage. This to me is the power of a mobile network connected device, and short of “add milk to the grocery list” we’ve got a long way to go here.

Then when you sit down on the bus and intentionally choose to do so, only then would social apps or news or whatever feeds come up. But it has to be your intention to do so, and only then should the option be there. Arguably times like those are great to just think, or in many cases engage with others around you, so I feel having some additional friction there could still be beneficial.

With the above two points, my dream device will have tightly integrated health and habit tracking, and it will be insanely good. Data will be stored in searchable formats, and the insights it will derive will initially be just ok, but continue to improve over time. For instance, I should be able to easily ask “when was the last time I worked out at the gym, and how did I feel after?”. It’ll be able to tell me how regularly I’ve been flossing, and if I’m getting worse. The device may or may not have the ability to automatically audit habits (only what it can see or detect will greatly limit what it can do), but the assistant should schedule and perform periodic check ins with you to ensure it’s tracking what is important to you. For instance, in the morning when you have your first downtime (perhaps on the toilet or with your coffee) it can ask and do a questionnaire of previous days items, capturing things it cannot automatically (i.e. did you floss yesterday). Then tracking your data for months and years, it could give you personal summaries spanning those years — akin to Strava’s “year in review”, this could tell you how many times you flossed in a year. Further, you could then share this with your dentist! Maybe that's a bit frightening, but for accountabilities sake, I would embrace it.

A quick note on privacy and trust. For many of these capabilities there is a huge amount of my data that needs to be processed, and with access to all this data, privacy is essential. I’m going to hand wave around this one a bit as enabling the power I described above will be very complex and risk laden. However, my dream device would be powered by a company that I inherently trust. Ideally B-corp or similar, not beholden to shareholders and growth at all costs, with a great revenue stream that is not advertising enabled, and where their goals and values are clearly published and in line with mine. If my data is going to exist even in part on their servers, this would make me feel much better about accessing their rich functionality that has my privacy as a key tenet. And if later they get purchased or have a CEO change that steers their ship in a direction that shakes their trustworthy foundation? Hopefully this will be a ways out, but that might trigger the next paradigm shift.

This dream device I’m referring to is surely a long way off, at least for a single device lineup that is seamless and integrated. Initially, I’d expect a combination of devices and ecosystems to enable some of the above — likely a tuned smartphone / network device, plus additional pieces of wearable tech to enable the additional capabilities and streamlined experiences. For any incumbent to come along and deliver on the above holistically will take quite some time, and at least a handful of iterations. In this time there may be mergers and acquisitions, copy cats, failures, scams. However we get there, I’m going to be along for the ride, keen to try what is novel.

Bob, you’re playing the victim

Part of me feels guilty for not training myself on the newest capabilities and tuning my iPhone to better suit my needs. As mentioned, there is a mountain of features that have been added to counteract some of the more irksome issues and I’m sure if I spent more time with them I could have a better experience.

But, we all deserve better. Historically, I’ve been the one that would head to the Settings screen in a new game/app/service first to understand all the knobs and get the most out of it. For better or worse, the Apple ecosystem and its ridiculous success making convenience a reality may have trained me to demand simplicity and met needs out of the box. And when I go to the park and see everyone starting in to their screens, is that a good thing? Shouldn’t everyone be more disciplined, and not just those that spend that time on the Settings screens?

Conclusion

My wishful hunch is we’re on the cusp of a new paradigm of mobile tech, and I hope it will not be long before new devices that do at least one thing that causes our jaws to drop and have wide reach for consumers. At the current trajectory, I’d be surprised if I’m still carrying an iPhone with me 5 years from now (except perhaps as a companion device). The iPhone alone is turning into a quagmire, and there is too much hope coming from other arenas of something better.

Decisions such as leaving the big tech social platforms, joining smaller new platforms, starting group chats, posting to a subreddit, etc., greatly affect how we connect with others and interpret the world. Even larger in scope, our worldly experiences can be greatly hindered by untimely chirps from our pockets, or our eyes not looking at the world around us. A great human-centric mobile device is critical to ensuring humans move forward together. The more intention and focus we have, the less we’ll concern ourselves with moving away from toxicity, as we’ll be spending time moving towards things that bring more connection and improvement to our lives.

Or perhaps some of these advances will happen, but never make it to mainstream — in fact, perhaps you read some of this and thought this is a future you don’t want to be a part of. I can totally understand that. My personal philosophy if it isn’t brutally obvious by now is that of technological optimism, that we can correct our mistakes and make things that do effectively serve humanity for the better. I’ll be sitting there in the niches tinkering with the next generation of mobile technology whether it makes it to mainstream or not.

I’ve covered a lot of ups and downs here and hope you got something out of it. I’d love if you would let me know if anything resonated. Thanks for reading!

[1]: Some additional excellent analysis and speculation on Humane here: https://xrgoespop.com/home/humane)

[2] Below is a non exhaustive list of capabilities I use my smartphone for today, things I would prefer not live without, and how I would like to see them improved in a next gen mobile device.

  • basic utilities; clock, calculator, timer/stopwatch, currency exchange, lists, notes, habit tracking, voice memos, weather — and ALL of this enabled brilliantly via voice
  • calendar — visual view, vocalized morning summaries, easy ability to schedule and navigate to appointments via voice. This pretty much exists now, nothing major needs to change here.
  • voice calls — but not a phone where I’m always reachable and can always make calls, but something that understands the context I’m in, and whether accepting or even making a phone call is something that should be an option.
  • messaging and chat — same caveats as the previous.
  • video chat — surprisingly, I think i can live without this one. I don’t like the idea of staring at someone on a screen and trying to communicate to them on the go, super happy to keep this just on larger screens at home. There are use cases that I’d lose with this, like when I’m at shoppers drug mart and I’m trying to pick out an item for my partner in a sea of options, or when I’m vacationing somewhere nice and want to show someone back home what it’s like.
  • web browser — I need a web browser when I’m at Canadian Tire so I can visit their website to search for things and find the aisle, or to cross reference for pricing (and in some cases just order from amazon). For this, some kind of visual display that can render web pages will be required (could be a screen, projection, or HUD)
  • navigation — maps (+ street view) / gps / sos / find me / find my / ride hailing. All these are essential on the go capabilities these days
  • podcasts, streaming music, audiobooks, radio
  • fitness — Strava, Coros, Health

[3]: I got a lot of the thinking around this section from a great Ben Thompson interview with Eugene Wei).

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Bob Durie

Sometimes focused, sometimes scattered, my opinions about the world, people, tech, purpose, impact, and nonsense.