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.

This is the time of year when we very often will see Apple commentators posting their “Wishlists” for WWDC. These are enjoyable and helpful to frame our perspectives going into next week. I don’t have one of those but I do have a handful of wishes for tiny details I’d love to see fixed/changed in the OS releases we have next week. These are minor annoyances or little things which have bugged me in the last year.

iOS: Scroll to app in Cellular Data list

When you are trying to do networking in an app for which Cellular Data has been turned off you will receive this helpful dialog saying data is unavailable.

Tapping on “Settings” will open the Settings app to the correct section, but it doesn’t scroll this list to expose the app which initiated the request. So I’m instead endlessly scrolling around trying to find it.

Bonus points if an option to “Enable Cellular” was added to the initial dialog in the first place, though I could understand the intention behind making this a two step confirmation.

watchOS: Fast Charging Indication

The Apple Watch Ultra’s battery life is fantastic. It has transformed the way I use my Apple Watch while out on long wilderness hikes. The small downside to this amazing capacity is that charging the battery up can take a very long time, especially if you aren’t doing a ‘fast charge’.

When fast charging an Ultra it takes on the order of 1.5 hours for a full charge. Fast charging requires the special USB-C Fast Charging cable which comes with the Ultra and a specific power supply. If you don’t have the right power supply then it will fall back to the older slow charge system, which on the Ultra takes forever.

I wish this battery status screen would show the text “Fast Charging to Full.” whenever you are fast charging. This would give me confidence that my power supply was up to the job. At home this is less of an issue, but when traveling or adventuring this gets complicated. I think I have found a portable battery which can fast charge the Ultra, but I have no way to confirm this is actually happening outside of running a stopwatch and waiting. Which can lead to some frustrating moments if I’m topping up my watch during a lunch break on a long day out and have confidence I’m getting as much charge as possible.

visionOS: Less squelchy Optic ID unlock sound

This one may be very specific to me but I find the Optic ID unlock sound on the Vision Pro very unsettling. It sounds like someone stepping on a bunch of grapes, a most unpleasant squelching sound. Really anything here would be better, there are countless other great unlock sounds on iOS/watchOS/macOS. Please use one of those.

WWDC is one month away and while I was out on a walk this morning I got to thinking about how I was feeling about it.

This will be the 16th(!) consecutive WWDC which I have attended¹. My first in 2009 was a few months after the birth of my oldest child. He has never known a world where I didn’t disappear the first week of June to focus on my work. It is a pivotal fixture in my annual rhythm.

This last year has been a complicated one as an indie app developer. I’ve been in this community for long enough to know that there are always ebbs and flows in sentiment, and this year has lots of reasons to be feeling the ebb side of things. From new policies which introduced tremendous uncertainty and undermine our importance to the ecosystem, to challenging platform launches…there’s a lot to feel conflicted about this year.

But as I wandered through the woods somewhat surprisingly my feelings kept coming back to how excited and eager I was to once again head to Cupertino. I’ve learned that whenever I’m surprised by a feeling, it is a good idea to interrogate it because it’s an opportunity to learn something about myself.

What I came to realize was that the reason I was excited about WWDC had very little to do with the actual announcements themselves, but instead it was all about the people I’ll get to spend the week connecting with.

Little did I realize that when I was arriving to my first WWDC I was actually connecting for the first time with a group of people who would change my life. A community which valued and celebrated the things I strove towards in my work. I had found my people. Being a part of that community has been incredibly important to me, both professionally and personally.

It isn’t necessarily that Apple itself is the root of this community, but moreover (especially in those early days) they provided a focal point for like-minded developers and designers to coalesce around, which became this community. Apple aspires toward many of this community’s values, but as they have expanded their reach and scope, they feel more like the multi-trillion dollar company they in fact are. There are still countless folks within Apple who are absolutely my people, but over time, I’ve noticed that there is a growing separation between the corporation and the community, at least in my mind.

So what are the core values of the community which I feel so privileged to be a member of? It wasn’t easy to narrowly boil it down but the more I walked, the more it clicked in my head that I could summarize it as: people who are deeply concerned with the Craftsmanship of their work and build things through a process of deep, intentional Consideration.

Once that definition had entered my mind I was sure I’d finally captured an idea which had been amorphously swimming around in the back of my consciousness. I was finally able to neatly describe what I find so special about the community I have the privilege to gather with each June.

Craftsmanship

Craftsmanship deals with the ‘how’ of our design and development process. It is about meticulously building things in a manner which isn’t slapdash or only partially complete. It is about striving to not cut corners or avoid the tough problems. We are people who want to do our best work and don’t need to justify why building something the right way is the best way. We want to improve our craft and seek continuously to learn and grow in our ability to deliver high quality work. We enjoy the process of iteration until we find the most beautiful solution and seek beauty in even the smallest detail.

Consideration

Consideration is about the ‘why’ and ‘what’ of our design and development process. We are building solutions to problems which enrich the lives of the people who use our creations. Before we build something we take the time to consider its implications. We strive to build things which are inclusive and have far reaching benefits. We focus on the long term. We strive to make things which have lasting, enduring value. We seek to be kind, both to ourselves and our users. We are mindful of the impact we can have.

Inspiration

Every single time I’ve left WWDC I’ve felt inspired, motivated and eager to get started on the next season of development. Sometimes this has been because of the announcements made on Monday morning, but more often it is because of the people I have met and spent time with. There is something joyously affirming about being with folks who value the same things you care about. A reminder that you aren’t alone or silly in wanting to do your job in a certain way. Of course not everyone attending WWDC thinks this way, but enough folks do for it to feel unifying.

Each year at WWDC I am also reminded of why this community was formed around Apple’s platforms. The company is filled with folks who deeply care about the craftsmanship and consideration of their products. The secrecy of the company means they are often hidden away from public view, but at WWDC they are given the opportunity to express this. Seeing their commitment to quality is contagious.

These ideals aren’t always expressed in the final output of the company (though if I’m being totally honest neither am I able to always live up to them myself), but I am convinced that they endure as an integral part of their culture. The pressures of being one of the largest companies in history will naturally hinder the expression of these ideals, but they still appear to be core to Apple’s process…which gives me hope. Hope that while the path won’t always be linear, the trend will continue to be towards craftsmanship and consideration.

I continue to be excited about spending a week learning how I can improve my craft, be more considerate in my designs, and spending time with others who feel the same way. If I can still feel that way after 15 years of doing this, then I’m a part of something truly special.

See you in June.