Last week I watched the iOS development community react to substantial rumors of a major UI redesign slated to be announced at WWDC25. The reactions were complex and I’d say broadly negative, which is a reaction I very much can understand and appreciate.

However, after wandering around in the (literal) wilderness for most of last week testing Pedometer++, my current reaction is now much more optimistic. Not because the fundamentals of the situation have changed, but because I’ve decided that it is essential that I develop a practice of optimism to navigate this complicated season in the Apple developer world.

Optimism isn’t enthusiasm. Enthusiasm is a feeling, optimism is a choice. I have much less of the enthusiastic feelings these days about my relationship to Apple and its technologies (discussed here on Under the Radar 312), but I can still choose to optimistically look for the positives in any situation. Something I’ve learned as I’ve aged is that pessimism feels better in the moment, but then slowly rots you over time. Whereas optimism feels foolish in the moment, but sustains you over time.

I’m not talking about a blind optimism which ignores the realities of a situation, but more the realistic pursuit of the positives of a situation which (at the risk of sounding a bit like Paddington Bear) if you look for, you can nearly always find. Realistically focusing on how things can go well and the positive outcomes will help me sustainably continue to grow and improve my chosen field of expertise which is ultimately my career goal.

So with that in mind…here are six positive reasons for optimism about a possible major redesign coming to iOS 19.

1. It would provide a point of differentiation for my app against other apps who wouldn’t adopt the new design language right away (either large companies which have their own design system or laggards who wouldn’t prioritize it). Any thing I can do which stands me apart from my competitors is helpful and so Apple providing an opportunity where the system rewards those who follow their leadership quickly is a positive.
2. It provides an opportunity to grow my personal design skills. I am by training much more of a developer than a designer, having had to learn most of my design skills on the way. So an opportunity to think through the design of each of my screens is an opportunity for personal growth and improvement. I’d expect to be a better designer after this process than I was would before I started. It is difficult to justify putting in this kind of ground-up work on its own, but if it is encouraged by the platform then I have the benefit from the exercise.
3. It is rumored that the redesign will pull many aspects from visionOS and the way it is visually structured. Having spent a lot of time last year working on visionOS that sounds really promising. visionOS is a fully “SwiftUI-first” UI system which really showed in how it was constructed and how developing for it went. While I have lots of frustrations with visionOS development, the UI system and the related SwiftUI toolset related to it are not one of them.
4. Any holistic design refresh will involve delving into some of the less considered parts of my apps and then allow me to reevaluate and improve them. So often there will be parts of my apps which get neglected over time, which isn’t great for the user. However, if I have an external impetus to get in there and work on them the app overall will benefit.
5. Maybe a bit silly but honestly I just like working on “new” things. I really enjoyed learning how visionOS’s system worked and delighted in the related beautiful apps it resulted with. I would enjoy going through that process again for iOS and have a regular opportunity to do the difficult work of making my apps beautiful in a new way.
6. Something I regularly remind myself as I look at new Apple announcements is that I never have the whole picture of what is to come for the platform, but Apple does. They know if things like foldable iPhones or HomeKit terminals are on the horizon and how a new design would fit in best with them. If you pay attention and try to read between the lines they often will provide the clues necessary to “skate where the puck is going” and be ready when new, exciting things get announced subsequently.

That is the list of things I came up with. The process of coming up with the list was itself a useful exercise. By focusing on the positive outcomes I felt much more balanced in my reaction and think I am now better able to look towards a summer of potentially challenging work with a more hopeful, growth based perspective. I’m not saying in all of this that anyone shouldn’t feel negatively towards Apple or its announcements right now, but this is just a practice/approach I’m cultivating to preserve my mental health and allow me to continue to do my best work in my chosen area of expertise.

The above image represents the sum total of the progress I made yesterday. It sure doesn’t look like much. It is a grid system for an upcoming widget feature I am working on for Widgetsmith. I’m almost embarrassed to post it as the collective effort for an entire day’s professional work, but that is ultimately the point of this post.

I always find coming back from the Christmas break (or any break for that matter) challenging. The regular routines of my working life are joyously disrupted, providing a welcome break and opportunity to re-charge. But when I now sit down at my computer and face the wide-open expanse of possible work endeavors, I rarely have a clear sense of where to start and how to get back into the swing of things.

I’ve faced this struggle hundreds of times over the years of my career and navigated it with varying degrees of success. Over those years, I’ve built up a variety of “tricks” to get me going again. These are little habits or rituals which help steer me towards any degree of productivity again.

The above screenshot is an example of what I call my “Accomplish One Thing” rule. On any day when I’m supposed to be working, I have developed the habit of looking back at my day and looking for at least one thing which I really accomplished that day (ideally something tangible or visible). I tend to think about this as I’m clearing up my desk, ready to return to home life. It really doesn’t matter how big or small that thing is, but there needs to be something which I can point to.

The real magic of this habit is how it helps me earlier in the day. If I know I’ll need to have something tangible to point to later on, I find I am much more inclined to choose meaningful, but manageable tasks on these early days back. Tasks which are useful but also scoped to not overwhelm or daunt me. Obviously, not all jobs which need doing are atomic enough to be accomplished in a day’s work, but usually I find that I can either break larger tasks into smaller pieces or structure the sequence of work to allow for some of these.

The goal here is not to make massive progress; it isn’t about getting back up to full speed again, going from 0 to 100 miles/hour in one swift step. It is about building up my working inertia again. Speed is useful, but inertia is powerful.

Inertia in my working life is the thing which I find most powerfully motivates and animates my progress. It gives you that sense of inevitability about accomplishing the outcome and desire each morning to keep the ball rolling. Inertia is what will get you through the inevitable slumps, disappointments, and mistakes later on in a project. So I want to get it accumulating as soon as I can.

So yesterday I built that grid; today I’ll tackle the next thing I can accomplish in this project, and who knows what will come on Monday. But I know from experience that if I can string together a few days of tangible progress, the future will sort itself out.

This past weekend I was fortunate to be a participant in the “Relay FM 10th Anniversary Extravaganza”, a live show in London celebrating Relay’s decade of podcasting. Relay is the home of Under the Radar. We didn’t quite join at the start but have been part of the network for nearly 9 of those 10 years.

This event got me thinking a lot about longevity, especially as it relates to starting and sustaining a business. While nothing in business is ever certain, I firmly believe that Myke and Stephen didn’t reach this anniversary by accident. They have been careful and deliberate in their approach to building Relay, maximizing the chances of its enduring over time.

I feel like there are two extremes when it comes to starting a business you can build it optimizing for fast growth or you can build it optimizing for sustainability.

In the fast case you are likely rapidly increasing your costs and spending your way to growth. The goal here is to increase your customer base as quickly as possible and use whatever means possible to accomplish that.

In the slower, more sustainable case you are instead being extremely conservative with your costs and growing only as fast as you can without overreaching beyond your stable base.

Having been a close observer of the way Relay has grown and developed over the last decade it was clear they took the sustainable approach. Adding shows and employees at a very measured, deliberate pace. Never getting ahead of themselves and as a result rarely putting themselves in a tenuous position.

It reminds me of the Dry Stone Walls you will often see while wandering in the north English countryside. These walls divide farmers pastures and criss-cross the terrain on hillsides often battered with awful conditions. Yet these walls endure because they were built to endure. The process of building one of these walls is slow and deliberate. Only being able to progress at a rate of maybe 2-3 meters per day, but their lifespans are measured in centuries as a result. Compare that to something like a wooden split rail fence which can be put up at a rate of hundreds of meters per day, but have a useful lifespan measured only in years.

There are no free lunches here. If your goal is to make something which will endure, which can stand up against the storms which will inevitably batter it, you need to start building it with that in mind.

This isn’t to say that the fast, unsustainable approach doesn’t have its place, but moreover it is vital to be deliberate about what you want and be clear eyed about what that will mean for your future prospects. But if you want to make something which will be around to celebrate its 10 year anniversary you’ll probably to build it with stone rather than wood.

In Steve Jobs’s 2005 Stanford Commencement Speech he famously concluded by quoting the back cover of the Whole Earth Catalogue’s final issue.

It was their farewell message as they signed off.

Stay hungry. Stay foolish.

And I’ve always wished that for myself. And now as you graduate to begin anew, I wish that for you.

Stay hungry. Stay foolish.

Early in my career when I heard that quote it hit me as a lovely bit of motivational speaking. Something to encourage you to “get out there and do some good work”. The kind of thing you often hear at commencement speeches. I heard it has a positive affirmation.

Now that I’m further along in my career (and life) it hits me very differently. Now I hear it as a word of warning, a cautionary admonition.

When you are early in your career the best path forward is typically to hungrily strive forward. Embracing every possible opportunity, maybe not with foolish abandon but with consistent, unrelenting determination. You have everything to gain, and nothing to lose.

That works well enough until you achieve some level of success. Success is wonderful and lovely, but it also brings with it obligation. Once you have achieved something worth holding on to, you now need to do the work to maintain it. Once you have had some success now you suddenly have less to gain, and something to lose.

I noticed this in my own mindset after I had my first successes. It became much more difficult to pursue new opportunities with the same determined vigor as I did in the early days. I now would filter my decisions and new pursuits through an analysis of how they could negatively impact my existing accomplishments. It now felt reckless to undertake every opportunity, to jump at every idea.

Rather than being “Hungry and Foolish” it was now the prudent course of action to instead be “Defensive and Skeptical”. To be incredibly circumspect of which opportunities are worth the risk. To take actions which provide stability and preserve what you already have. To become comfortable with slow, measured growth.

I have no idea if this is what Steve Jobs meant in his commencement speech. He could have simply meant it in the positive, motivational sense. But increasingly I wonder if he may have also meant it in the cautionary sense as well. He had certainly overseen tremendous success and undoubtedly had to wrestle with the tension between preserving what you have and gaining something new.

Where I have settled in my own work is to strive to keep some meaningful part of my mindset hungry and foolish. To continue to be open to new opportunities and eager to explore them. I don’t want to end up miserly defending what I have already achieved, I want a professional life still rich with tackling interesting problems. Though admittedly I am more thoughtful in this pursuit.

In doing so one of the weird paradoxes of life also starts to emerge. I start to see that the only way to truly defend what you have is through continuous action. That defensiveness and skepticism are actually more likely to lead to loss. That it is action, and sometimes bold action at that, which allows you to keep hold of whatever success you have. Inactivity is depletion.

I thought it might be interesting to write a series of articles elaborating on the concept of Craftsmanship & Consideration. I feel like I’ve developed a certain perspective about my process which I think could be helpful to others. That said, giving general advice is incredibly fraught.

General advice lacks context. My advice is born out of my unique experience and thus will never neatly apply to someone else’s situation. The best we can hope for is that some small part of my experience is generalizable or universal.

However, when I think about the best advice I’ve received over the years and I found one common pattern. Good advice improves your vocabulary for describing your situation. It helps you to better understand where you are, why you are there, and how you could best change your situation. It can give you a framework to organize your thinking, which is where the power actually derives.

Having the right words to describe something is inherently powerful. It takes the amorphous specters which lurk in the back of our mind and gives them substance; a shape which we can then tackle.

That is the best I can hope for in sharing my thoughts. My situation is unique to me, but by thoughtfully looking back at my own experience I might find some words which are helpful in organizing your thinking about your situation and goals.

I am also fully aware of how self involved this all sounds. That I have something worth sharing, that others should listen to me. I am deeply aware of that.

Confidently writing this kind of thing is difficult for me. Nevertheless whenever I have shared this kind of thing I hear from folks who have found it helpful. So I continue on, regardless of my own lack of confidence and insecurity.