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My 16-year-old self would be proud of me today.

After years (decades?) of toying with the idea of learning to animate and taking zero action, I finally signed up for animation classes. And I'm EXCITED. I can't draw at all. But I've always loved animation. I'm curious to see how it goes. It's once a week for 12 weeks, and it starts in just three weeks. I'll be learning the principles of animation and maybe making some super short videos. I'll share whatever progress I make if I decide to keep writing.

I feel like I have had a second wind in the last month; perhaps because of my think week that felt only mildly successful, but I'm in an inspired season of life.

Hey,

Today’s a short one. I’m still in the midst of recovering from a marathon and it’s taking longer than I expected. My body is punishing me after I punished it on Sunday.

What surprised me most was how effective our training plan was. I managed to finish the run without much of a hitch. My hamstrings were edging to cramp for the last 10-15km but never fully got there, thankfully. No actual cramps, no wall, no nausea, just running for almost 4 hours up and down too many hills. Same with Liz running her FIRST marathon ever. #blessed. #proud.

Hey,

The next time I send this we’ll have run our marathon! It’s in just 5 days. Wild. Liz and I have been training for about 7 months, this is the longest fitness training plan I’ve ever stuck with so I’m excited (and incredibly nervous) for this coming Sunday.

It’s a bit embarrassing to admit but this is the longest I’ve every committed to training for something. As someone who advocates for taking the long view and continuous progress, you would think there’s more in my life that I practice this with. It feels good to have stuck with something for so long and I definitely saw improvement. Just this week I crossed 1,000km in training volume! I ran ~150km in the past 3 years, so this was a huge jump for me.

All of this training has allowed me to crush so many different podcasts. I recently started the series Against The Rules by Michael Lewis, author of The Big Short and Moneyball. Each season he covers a different topic. The first was on Referees (people who keep things fair), the second was about Coaches. I particularly liked S2 given my new role as a coach for students.

Hey,

I have a somewhat embarrassing confession to make: my goal for the next 12 months is to become a “personality”. Arbitrary, yes. Fun challenge? Kind of.

Let me explain.

As a member of the Peloton cult, I’ve become a big fan of some of the instructors. They have personality, are fun to workout with, and are generally engage them. When these fans think Peloton, they don’t think of the brand, they think of their favourite coaches. A lot of the coaches have built a brand (and huge following) outside of Peloton. That’s not really my goal. I’m not trying to become famous.

Hey,

One of the nice things about having a job is you don’t have to think much about your routine. Your daily 9-5 (or whatever) acts as an anchor in your schedule – something large and predictable you can plan your day or life around. Each of your days kind of looks the same. You wake up, maybe do something (exercise, breakfast, walk) and then get to work. After work, it’s the same think – eat, TV or read, get to sleep. You might fit in some hobbies, socializing, or save it all for the weekend. While it might not sound glamorous, it’s predictable. And like it or not, we are creatures of habit who crave predictability.

For the last 8 months I’ve been drifting without an anchor. At first, it was liberating. Free from meetings and a schedule I would sleep in, play video games, go to a coffee shop to read when I felt like it, and ride my Peloton. But then the days flowed into one another with little consistency or repetition and I felt stuck.

I tried throughout the year to create a routine once I started client work, but failed. I couldn’t stick to anything. The only routine and anchor I’ve managed to stick to has been my running training, but it’s hard to plan your life around 2h workouts every other day! I’ve made a list of the things I want to do in a day, sketched a calendar on my whiteboard, and attempted iterations of a plan. I have no idea what I’m doing though and days continue to pass me by where they feel half well-spent.

Hey y'all,

I’m writing this week’s newsletter with my head in the clouds. Literally. I’m flying to Toronto for our TKS team retreat. I had an amazing and clever idea for a new name for this newsletter but it came to me at 2 am and I didn’t write it down. All I remember is the word “and” 😒. So helpful.

Today I have 3 short blurbs to share.

1 - I try too hard

Hey,

I’m writing you at the last minute from our Sonder in Toronto, have you heard of them? It’s kind of like Airbnb meets hotel - I think they just buy up old hotels, modernize them + technology, and then rent them out online. There are no staff here and everything is digital (checking in, booking, etc). It’s kind of cool.

Like I mentioned last week, my mind has been racing a mile a minute. I have been bouncing between far too many different ideas but I love the unfocused nature of it.

Hey,

I’m back from Edmonton and getting settled again at home. But of course, we are going to Toronto this weekend for the final week of my sabbatical. As such, I don’t have a lot to say. I’m preparing myself to go back to work and trying to figure out what that looks like.

While closing things in Edmonton, I voraciously consumed information about all things. Personal finance, startups, happiness, cryptocurrency, creativity, productivity, life. On the one hand, that’s great. I hit a serious lull for many months, not reading much. On the other hand, the reason I was so active, is that I was avoiding the goals I had set for myself regarding writing. 😁

Hey,

Since arriving here on Thursday last week, I’ve swam just over 9km and as of when this email goes out, it will likely be closer to 12km. This is more than I have swam in the last 18 months total. When I was planning my trip to Edmonton, I had one main priority: fitness “training camp”.

Back in 2008 I attended a swim training camp in Venezuela as part of the university varsity team. It was the most intense experience of my life: two workouts a day for about a week. These were most often swims, but we did the occasional run or gym session. I think those 7-10 got me to the fittest point in my life. I was actually so out-of-shape by comparison to my teammates, I spent most of the day after our morning swim sleeping…until our afternoon workout. I only got to the beach once where I earned the worst sunburn of my life. I had to steal yogurt from the buffet to help soothe the pain on my shoulders.

All that to say, if there was one thing I was going to do while I was here, it was swim a lot. I didn’t care if I did anything else so long as I swam. I’m happy to report I’ve done a pretty good job sticking to that! I’ve definitely pushed myself more than expected and am able to go much further than I was even just two weeks ago. Aside from that, I spent two days with my Aunt who lives here, just chatting, and did a lot of reading and introspection. I foolishly only packed shorts and t-shirts when coming here, so I needed to buy yet another hoodie on my trip. I also bought one while in Toronto 👉👈.

Hey,

Did you get Monday off? It was a holiday in most, if not all of Canada. A long weekend meant trying to do a few more things than normal. We went to go see Black Widow in theatres! It was pretty fun to be out in the world again, like normal. There were only 6-8 other people in the theatre (all couples) and spread out among 2-3 rows. As soon as the movie started, I totally forgot about the worsening global pandemic. There was no Delta variant or Lambda threat, only Scarlett Johansson kicking ass.

The heat this summer has been increasingly toxic here in Calgary. Coupled with the forest fire smoke, I’ve had good reasons to stay indoors as much as possible. Despite that, I’ve managed to have a few “new” experiences in this post-glasses world. I went for my first swim post-surgery with non-prescription goggles! It was underwhelming and worse than just having prescription ones. I also got my haircut today and for the first time ever, I was able to see what was happening. This explains a lot about my past haircuts…throw in the movie and it was quite the week for my fresh pair of eyes.

I have also started to try to sort out a morning routine for when I return to work. When I actually wake up on time (10-15% of the time), I’m able to do a lot before 9am. I’ve started incorporating a short full body stretch in the mornings featuring a rotating cast of YouTube videos. It’s one of the few times in my life I’ve been making time to stretch and focus on something other than to get faster/stronger. Hopefully any progress I make stands up to the test of reality!

Hey,

I can’t remember if I already told you, but I’m currently on a short two-month sabbatical. I’m about halfway through it now (!!) and I think I’m finally getting into the groove of things. I’m forgotten what day of the week it is, because that’s become a trivial fact to me. Except of course that the bakery is closed on Sundays and Mondays. That’s something I’ve forgotten too many times, often when I’m already at their door. There is a certain pleasantness that exists in this way of living. It’s obviously hard to sustain (no income, only expenses), but one I’ve come to appreciate. I was afraid I would be bored, but instead I’m slowly getting my inspiration back. I try to spend the mornings at a coffee shop reading or writing. Or, like Monday, buying random shit on Amazon. ⏳ Can’t wait to get my new hourglass.

I’ve moved past any guilt I was feeling with “wasting time” and started just living day-to-day, basking in existential uncertainty. I’ve even learned what demons are and the ones that I’m carrying around. Hello need for validation! 👋🏼

As one is prone to do, I’ve become a bit introspective. Aside from therapy, I’ve turned to two different things that have proven effective: Morning Pages and 80,000 hours. Morning pages is a simple exercise out of The Artists Way, a book I picked up the week before my time off. Each morning for the last 4-5 weeks, I’ve written 2-3 pages long-hand in a notebook. It’s the only writing habit I’ve ever had stick. Even after filling almost a full book, I’m still tweaking my routine to see what will work for me long-term. It’s meant to be a brain-dump. I rarely have that much to say so I often write about the dream I had, the day before, or how I have nothing to say. Sometimes though, I use the time to reflect on some questions that are nagging at me. A big one for me lately has been how I want to be spending my time more broadly and the different types of things I want to be working on. How do you even start to think about that question?

Hey,

Last week when I was visiting my mom, I was tasked with sorting through what old tapes and photos I wanted to keep. She had started to slowly clean out all of our old stuff and there were stacks of Disney VHS among a few home movies, notably my short-lived acting and karate careers. Sadly those two never intersected.

Hey,

I’m writing this from my mom’s kitchen in Oakville where the house is kept at 27º🥵. I’ve spent the last few days here after two nights in Toronto. It has been nice to spend some time with family, though I’m definitely worn out now. I’m looking forward to getting onto a plane tonight and head back to Calgary for the next few weeks. How have you been?

I’ll start with a correction from last week.

Hi friends,

As of when this is going out, I’ll be on a plane (!!!) to Toronto. It’s going to be weird, but I’m excited. It’s been awhile since I last wrote anything, around 6 weeks I think, and what a whirlwind it’s been. I’ll give you the highlights. It feels like I’m getting karmic payback (vindication?) for my views on home ownership.

1. We moved into the house we bought.

Hi friends (and new readers 👋🏼), Steven here. This is Product Matters, a semi-regular newsletter on Products and Strategy. Each issue I try to share something I’ve written – usually on the topics of products, digital strategy, and design.

If that doesn’t interest you or you signed up by accident, you can unsubscribe at the bottom of the email. If you like it, share it with others.

I thought I had more to write this week, but ended up not.

Hi friends (and new readers 👋🏼), Steven here. This is Product Matters, a semi-regular newsletter on Products and Strategy. Each issue I try to share something I’ve written – usually on the topics of products, digital strategy, and design.

If that doesn’t interest you or you signed up by accident, you can unsubscribe at the bottom of the email. If you like it, share it with others.

Hi friends (and new readers 👋🏼), Steven here. This is Product Matters, a semi-regular newsletter on Products and Strategy. Each issue I try to share something I’ve written – usually on the topics of products, digital strategy, and design.

If that doesn’t interest you or you signed up by accident, you can unsubscribe at the bottom of the email. If you like it, share it with others.

Surprise! For the last few weeks we have been in the process of buying a house. This may come as a shock to a few people as I've previously written about my thoughts on renting vs. buying, but I think I've stuck true to my principles in our purchase. We weren’t considering it a financial decision so much as a personal one. We had a very specific set of criteria: inner city, yard (of any size), garage or basement for a squat rack, not an apartment. This made renting a longshot - there weren’t many properties that met the criteria. While we still need to waive conditions this week, we plan to move in 6 weeks.

Hi friends (and new readers 👋🏼), Steven here. This is Product Matters, a semi-regular newsletter on Products and Strategy. Each issue I try to share something I’ve written – usually on the topics of products, digital strategy, and design.

If that doesn’t interest you or you signed up by accident, you can unsubscribe at the bottom of the email. If you like it, share it with others.

For the last few week's I've been reading Mindset by Carol Dweck. If you haven't heard of it, it's the seminal book on the topic of the growth mindset, the belief that our abilities are malleable and can be changed. I had been familiar with the topic previously and was a strong believer in the growth mindset. That said, most of what I've read (~60% through) has been examples of how the fixed mindset—the opposite of the growth mindset—manifests. From education to sport or business she pulls examples left and right. And friends, the evidence is damning. I have a fixed mindset. Dweck writes, "When people with the fixed mindset opt for success over growth, what are they really trying to prove? That they're special. Even superior." 🎯

Hi, Steven here. This is Product Matters, a semi-regular newsletter on Products and Strategy. Each issue I try to share something I’ve written on the topics of products, digital strategy, and design.

If that doesn’t interest you or you signed up by accident, you can unsubscribe by clicking here. If you like it, share it with others.

—

Hi, Steven here. This is Product Matters, a semi-regular (lol) newsletter on Products and Strategy. Each issue I try to share something I’ve written on the topics of products, digital strategy, and design.

If that doesn’t interest you or you signed up accidentally, you can unsubscribe by clicking here. If you like it, share it with others.

—

Hi, Steven here. This is Product Matters, a semi-regular newsletter on Products and Strategy. Each issue I try to share something I’ve written on the topics of products, digital strategy, and design.

If that doesn’t interest you or you signed up by accident, you can unsubscribe by clicking here. If you like it, share it with others.

—

How are you doing? It's been a crazy few weeks. I hope you are coping with the new state of the world. The video calls are getting exhausting, though it's the only way to maintain any sense of connection with the rest of the world. Without it, I would only have my partner, my dog, and Slack.

Hi, Steven here. This is Product Matters, a semi-regular newsletter on Products and Strategy. Each issue I try to share something I’ve written on the topics of products, digital strategy, and design.

If that doesn’t interest you or you signed up by accident, you can unsubscribe by clicking here. If you like it, share it with others.

—

Hi, Steven here. This is Product Matters, a semi-regular newsletter on Products and Strategy. Each issue I try to share something I’ve written on the topics of products, digital strategy, and design.

If that doesn’t interest you or you signed up by accident, you can unsubscribe by clicking here

If you like it, share it with others.

Hi, Steven here. This is Product Matters, a semi-regular newsletter on Products and Strategy. Each issue I try to share something I’ve written on the topics of products, digital strategy, and design.

If that doesn’t interest you or you signed up by accident, you can unsubscribe by clicking here. If you like it, share it with others.

—

I have been sitting on this latest blog post for the better part of a year. I started it back then, but never got around to finishing it. Now that it’s done, I haven’t really wanted to send it either. It’s entirely in the realm of “personal development” instead of Product things. I have this strange reticence to share personal development type writing; it feels pervasive on the internet and rarely unique. I am likely concerned that this piece falls into that, so go easy on me.

Hi, Steven here. This is Product Matters, a semi-regular newsletter on Products and Strategy. Each issue I try to share something I’ve written on the topics of products, digital strategy, and design.

If that doesn’t interest you or you signed up by accident, you can unsubscribe by clicking here. If you like it, share it with others.

You can read today’s post online here.

Hi, Steven here. This is Product Matters, a semi-regular newsletter on Products and Strategy. Each issue I try to share something I’ve written on the topics of products, digital strategy, and design.

If that doesn’t interest you or you signed up by accident, you can unsubscribe at the bottom of this email. If you like it, share it with others.

You can also read today’s post online .

Hi,

Happy New Year!

Without getting too much into a reflection on last year, unsurprisingly I didn’t write as much as I had planned. As such, my 2020 goal is to read less and write more. This shouldn’t be too challenging given the standards I set for last year (82 books and like 4 posts). I won’t be counting my internal memos in my objectives (those sent to the team at Versett).

Khe Hy says 25 issues of writing a newsletter is the hurdle you need to clear, both to gain a rhythm but also to really make the habit stick. @carolynz is trying to write 100 pieces this year. These benchmarks are helpful for me trying to get my footing for a regular routine.

Hi,

Happy holidays! Hopefully you are taking some time this season to relax, reflect, and recover from the year passed. This season is usually when I feel the most ambitious but am the least productive, leading some to level of angst. How do you manage this?

Growing up I was fascinated with fashion, specifically streetwear and hipster culture. While the two are not directly linked, I feel there share some interesting characteristics that will become relevant. Most people are interested in fashion for status signalling. Luxury brands act as symbols of wealth and status. Athleisure is a signal that you value an active, healthy lifestyle and are often trying to accentuate this through clothing. Streetwear is worn as a symbol of “cool”, about knowing what is hip, and recognizing that sooner than others.

Hi,

It’s been quite awhile so hopefully you haven’t forgotten about this newsletter. One of the things I have tried to do for awhile is write more, and I actually think I do. Unfortunately, most of my writing is internal at Versett to either the team or clients, meaning I often have little to show for it. I should have a new post to share next time.

Have you ever come across an insight or perspective on your own, solely by observing and thinking, only to later come across the same insight in a book? It’s happened to me a few times recently. I actually find it very reassuring, probably because of ego, to know that I managed to come across the same thoughts without being exposed to them explicitly. What about you?

I have struggled lately to write anything other than incomplete idea dumps into text files. As a result I am going to try re-committing to this email and expand upon my notes here instead of trying to make full fledged blog posts initially. Today's piece is the result of my observation that we view products as static points in time instead as dynamic, evolving organisms.

If you missed it, I wrote about why bad businesses succeed in my latest essay. I'd love to get your thoughts on it.

I was in New York a couple weeks ago working with a couple of founders to both sketch out their idea and beat it up. It's one of my favourite parts of work, as it feels very much like building your own thing. I do my best to get in the co-founder mindset instead of a third-party. During this process it is common to use other apps as inspiration or reference points to convey ideas.

Hi,

Its been a long time since I wrote or published anything, so hello! Last time I wrote I had been working on a small app with a friend. We have finished it though we haven’t released it publicly. Here’s a brief description of it, let me know if it fits your workflow and if you want to give it a try.

The app is called Pigeon, it’s a friend’s and my take on the simple email yourself app (like Captio). As a person who appreciates design, I was sad that Captio was never updated for the newer devices (and wasn’t the best visually), so I built myself an equivalent app to do the same. For those unfamiliar, Pigeon allows you to email yourself in a single tap. It’s most common use case (for me) would be from the Share Sheet. This won’t be for everyone, but those who use Email as their “Inbox” for task delegation might find it useful or faster.

Other than tinkering with apps I have been working on two main things: a crash-course in SEO/Content Marketing & Growth, and looking into Evernote alternatives. I have been reading a variety of books related to growth and SEO and noticed a few things about my reading/note-taking habits.

Hello!

Last weekend I got to spend some time in a mini product sprint/hackathon with a friend of mine. We have built small apps together in the past and challenged ourselves to build an app in 2 four-hour work sessions. Last Saturday was the first and it felt good to be back in the product building trenches. A lot of my work is on more of the strategic level or on larger projects where you aren't really doing any building yourself. It's refreshing to switch contexts. It reminds me of a passage from Systemantics:

There is a man in our neighborhood who is building a boat in his back yard... He works from plans drawn up by himself. Nevertheless, he is demonstrably building a boat and can be called, in some real sense, a boat-builder.

Now if you go down to Hampton Roads or any other great shipyard and look around for a ship-builder, you will be disappointed. You will find in abundance welders, carpenters, foremen, engineers, and many other specialists, but no ship-builders. True, the company executives may call themselves ship-builders, but if you observe them at their work, you will see that it really consists of writing contracts, planning budgets, and other administrative activities. Clearly, they are not in any concrete sense building ships. In cold fact, a SYSTEM is building ships, and the SYSTEM is the shipbuilder. In brief: PEOPLE IN SYSTEMS DO NOT DO WHAT THE SYSTEM SAYS THEY ARE DOING.

Hello there,

This is my first official letter to this list, quite exciting. I have recently launched a new site called How To Build a Product which will house a series of essays on building products. I believe it’s part art, part science, part magic. I hope to dive deep on a variety of topics ranging from the basics to the esoteric.

My hope is that you learn something, maybe enter the world of product, and hopefully start to see the world in a new way.