I first got into technology in the 1990s. I started out by writing Windows games in BASIC and C++, which helped me start building a sense for what goes into making software.

Then, everything changed. The web overturned the software world. Many of the most important companies and apps of the era were washed away in the sea change. Excited by the huge new opportunities, I dove into designing and developing web apps.

Then, everything changed. Mobile overturned the software world. Again much was washed away, and entire new categories of software business became possible. Excited by the huge new opportunities, I dove into designing and developing mobile apps.

The more I saw the progress of technology, the clearer it became that this is a fundamental process in the software industry. As long as there have been computers, there has been a generational pattern, where waves of new companies sweep in to build the newly possible. Periods of creative destruction, with new paradigms blowing away the old, have created awesome opportunities every decade or so since the 1960s. It seems everything old will soon be new again.

As I’ve built a career in software – and Steamclock’s business – I’ve taken pride in expecting the unexpected. I’ve tried not to get too comfortable in the now, avoided bets that things will stay the same, and tried not to depend too much to the platforms of today, since prophecy tells us all will soon be destroyed by the next Great Reset.

It would seem, today, that a reset is nigh. Mobile platforms have aged and become remarkably stable, and the big tech companies have slowed and matured. It feels like the next big thing is due on set imminently. Honestly, it’s felt like that for years now. Is it chatbots? No. Blockchain? No. AR? I don’t know, but it has to be something. Right?

Ben Thompson, prolific writer of thought-provoking perspectives on the technology industry, recently wrote a thought-provoking perspective on the technology industry titled The End of the Beginning. In it, he argues that no, it doesn’t have to be something:

There may not be a significant paradigm shift on the horizon, nor the associated generational change that goes with it. And, to the extent there are evolutions, it really does seem like the incumbents have insurmountable advantages: the hyperscalers in the cloud are best placed to handle the torrent of data from the Internet of Things, while new I/O devices like augmented reality, wearables, or voice are natural extensions of the phone.

In other words, today’s cloud and mobile companies — Amazon, Microsoft, Apple, and Google — may very well be the GM, Ford, and Chrysler of the 21st century. The beginning era of technology, where new challengers were started every year, has come to an end…

My initial instinct is that this has to be wrong. There has to be something fundamental about technology and software that will continue to drive change, and sustain the “continual beginning” that makes our industry so interesting. Right?

Although there’s always reason to be skeptical of any argument of the form “this time is different,” Ben’s theory is unsettlingly plausible. Over the last decade, more and more of the product ideas and problems we see in technology are problems that would be 100x easier for Apple, Google, or Amazon to fix in their existing products than for a new business to try and address. Maybe today’s giants are the GM and Ford of our industry – the final survivors of an early period of chaos.

While there is something sad about this, if true, I must admit there is some appeal to the idea that I might not wake up one day to find that mobile apps have become irrelevant. I don’t relish the idea that our expertise building on Apple’s and Google’s ecosystems may soon be unceremoniously demoted to “experience with legacy platforms”.

And it has been helpful to consider such a world. When the beginning does end in technology – when what we build today is liable to still matter in 25 or 50 years – how would we think differently about our work? What does it mean if you can no longer count on generational change eventually sweeping away your technical debt or other weaknesses in your company and product?

It seems then that longer term thinking might become more established, driving more full-hearted investment in teams and teaching and documenting and various nice things companies know are important in theory, but can feel quaint in an environment where everything is blown up every sixteen minutes. It wouldn’t be all bad.

It also seems that in a tech industry where the beginning ends – where waves of technical change no longer drive renewal – the onus would fall on us to make the new beginnings we want to see, both in our teams, our companies, and our work.

All that said though, it would be nice if Ben is wrong. It would be cool if there was still at least one more revolution left, something that would completely reshape how we think about technology and how we write software forever.

You know, for old times’ sake.

Two Spies, the turn-based spy strategy game I’ve been iterating on and off for ages, is now live! So far, the initial reception has kind of blown us away: almost a million rounds played, featured by Apple in 100 countries, hit top 25 board and strategy games, more than a thousand five star reviews already.

Admittedly, I try not to put too much stock in app reviews. Once in a blue moon though, when the stars align, they can be a source of positivity. For example, I did enjoy this recent one:

Simply put, well done, good for you, here’s my support, like this, wow, amazing, mind blown, I’m crazy about this, and finally: HECK YA!

Thanks, MrKatFace. I’m glad you like it.

It’s cold season. Yes, that time of year where, despite your best efforts, you have recently contracted one of the over 200 viruses that cause the annoying but survivable group of immune responses we call the cold.

Naturally, you are familiar with the baseline approaches to managing cold symptoms. You drink copious amounts of water, and you get enough sleep. You wash your hands religiously – both to avoid passing the cold on to family and coworkers, and to avoid contracting the dreaded and lengthy compound cold.

In the likely event that you drink multiple coffees a day, you may also want to avoid giving yourself the double-whammy of head cold and accidental caffeine withdrawal.

You know, super simple stuff.

But while self-care is a great start, unfortunately it won’t do much to actually shorten the duration of cold symptoms. Chances are high that, depending on the exact miscreant of a virus that has you in its grasp, you will be mildly suffering for 5-10 days. After a couple days of honest rest, you’re probably going to want to get some stuff done. Thus, you’ll likely find yourself thinking, “Hey, maybe one of the 73 cough & cold medications available for sale at my local pharmacy might make me less of a useless snot-sponge?”

A pharmaceutical black hole

Warily facing 73 different cold remedies in my local Shoppers Drug Mart, I found myself thinking exactly that. I know anecdotally that some of them are ineffective, and some make you feel like a zombie. Unfortunately, none of the packages were willing to admit their ineffectiveness or proclivity for zombification.

So, I started looking for symptoms. This one says it’s good for sore throat, this one mentions a dry cough. Quickly, I got bogged down in noise.

Things came to a head as I was trying to work out which was better: Tylenol Cold, or Tylenol Flu. Exasperated, I pored over the boxes, looking back and forth. As impossible as it seemed, there it was, printed in the legally required black and white: Tylenol Cold and Flu are… identical? The same three active ingredients in the same quantities.

The more boxes I looked at, the more I saw combinations of the same few ingredients, in the same dosages. I saw identical products with different branding. I saw “Day” capsules with the same ingredients as the corresponding “Night” capsules. I saw, for the first time, the deep conspiracy that is the Cold-Industrial Complex.

Now to be clear, I am not a doctor. Nor am I a pharmacist. I’m just a guy that makes apps. A guy that makes apps who, in frustration and congestion, created a sprawling spreadsheet containing the active ingredients of Tylenols and Advils, Sudafeds and ‘Quils, name brands and store brands, hoping to find an answer.

Fortunately, I did find an answer.

It’s the ingredients, stupid

We know in theory that brand names mean little in medicine. There are only a handful of medicines approved for relieving cold symptoms in the US and Canada, and store brand medications pull from the same ingredients and dosages as the household names. In general, cold meds contain 2 to 4 of the following components:

1. Decongestant
2. Analgesic
3. Antihistamine
4. Cough medicine

What is maybe more surprising is that even within a name brand, the ingredients are not consistent. Sudafed, for example, has no consistent ingredient across all its variations. I reviewed a half-dozen cold medicine brands and found that each varied in which components it would use, even between similarly named formulations. Worse, some brands used ingredients that can cause substantial drowsiness in what were ostensibly “daytime” formulas, leading to the regrettable zombie effect.

So your mission, if you choose to accept it, is to understand not the brands, but the drugs. Given your symptoms, recruit one drug each from the following four categories. If you do, you may actually have a chance.

1. Decongestant – Congestion, stuffiness

This may be the ingredient you care the most about. If you’re not congested, you’re probably not looking at cold medicine anyhow. For better or worse, are basically two decongestants worth knowing about:

• Phenylephrine. In theory, phenylephrine causes blood vessels to constrict, relieving stuffy nose and sinus pressure. In practice, it’s unclear how effective it actually is at treating cold symptoms. Multiple studies have questioned its efficacy compared to the fairly large placebo effect of cold meds. While this makes it effectively the backup decongestant, it is increasingly common in cold meds.
• Pseudoephedrine. Yeah that’s right, the hallowed stuff Walt and Jesse first used to cook their first batch. Pseudoephedrine is a vasoconstrictor, reducing tissue swelling in the nose and face, which helps drain out congestion. Given the fact that the evidence generally indicates that it’s more effective at treating congestion than the alternative, why do so many cold medicines have phenylephrine instead? For one, pseudoephedrine can exacerbate certain conditions like blood pressure and insomnia, making it a no go for some people. The bigger problem, though, is meth. In many jurisdictions, pseudoephedrine is a controlled substance as a precursor. In the US especially, you’ll likely need to ask a pharmacist for it, who probably needs to log your personal information to track how much you’ve purchased over time. This is a nuisance, and makes it harder to compare and consider cold formulas that contain pseudoephedrine. Consequently, the majority of cold formulas, even many from pseudoephedrine’s namesake Sudafed, have switched to phenylephrine. Still, if you don’t have a health reason not to take it, it’s probably worth looking into the good stuff – especially during daytime.

2. Analgesic – Pain, headache, fever

This is the component of cold meds that you are probably most familiar with. Most cold meds contain one of the two most common pain killers.

• Ibuprofen. Famously sold as Advil. As an anti-inflammatory, the current literature seems to slightly prefer ibuprofen as the painkiller for cold medication, especially if you have muscle aches. That said, chronic ibuprofen use has been linked to heart and especially stomach issues, so read up and be aware.
• Acetaminophen (Paracetemol). Popularly sold as Tylenol, acetaminophen has an unusual property for such a common drug: it is surprisingly easy to accidentally overdose on. The primary concern is liver damage, which can be compounded when combined with alcohol. For example, you may take a cold medicine which contains acetaminophen and some Robax for a back spasm which also contains it, plus you have a couple beers. Three things that seem innocent could result in liver damage. That said, acetaminophen is generally considered safe when dosed correctly, and ibuprofen isn’t great when taken for long periods of time, so read up and pick your poison.

3. Antihistamine – Sleep aid

Ostensibly, antihistamines might help with congestion. This is certainly true if you’re ill-fated enough to have cold and allergies simultaneously. However, it seems that cold medicines incorporate antihistamines less for their theoretical decongestive properties, and more for the fact that they cause drowsiness.

As it happens, the only drugs approved by the FDA for over the counter sleep aids are so-called first-generation antihistamines. These are also the antihistamines used in cold medicines, as they tend to help people sleep – which is surely something worth doing when you have a cold.

However, unless your cold is so bad that you’re just lazing in bed for the day – for example, if you actually have the flu – you probably don’t want to be drowsy during the day. As such, most cold medicines have a “Day” variant that has no antihistamine, and a “Night” formula that causes drowsiness.

Unfortunately, it is not always that clear from the branding which medications cause drowsiness. For example, I’ve found Advil-brand cold medications to be particularly egregious for having antihistamines in packages that are not branded as “Night” formulations. In my opinion this is reckless. At least one study found a standard dose of first-generation antihistamine to be equivalent to a blood-alcohol level of 0.10 in terms of driving. Watch out for antihistamines if you’re hoping to do things during the day, especially for Advil-branded cold meds or anything without “non-drowsy” on the label.

Of course, if your cold is keeping you from sleeping, an antihistamine can be a welcome companion. “Night” or “PM” formulations of cold meds almost always have an antihistamine in them. In my research, I couldn’t find any compelling evidence that any of the approved antihistamines in cold medicines caused more or less drowsiness than one another, nor that any was especially effective at relieving cold symptoms on its own.

• Diphenhydramine. Sold popularly as Benadryl.
• Doxylamine. Sold, interestingly, under the brand Unisom as a sleep aid. Also interestingly, doxylamine is generally considered safe during pregnancy, and is often used together with vitamin B6 to treat morning sickness.
• Chlorpheniramine. Sold in many store-brand allergy medicines, chlorpheniramine is included in a number of Advil cold formulations that are ostensibly for “Day” usage. ಠ_ಠ

4. Cough – Stimulate or suppress

A cough can be one of the most frustrating parts of a cold, and is liable to spread the virus to those around you. Luckily, the story on cough medicine is simpler than the other components of cold meds – there is basically one popular ingredient that helps you cough, and one that helps you not cough.

• Guaifenesin. Sold popularly as Mucinex. Guaifenesin is an expectorant, meaning it helps thin your mucous so you can cough it up. If you have a productive but stubborn cough, you probably want this to help clear your lungs. Generally it’s only included in the daytime formulations of cold meds, since coughing more at night isn’t exactly desirable.
• Dextromethorphan. This is the key ingredient in Robitussin, and any medicine branded as Somethingorother “DM”. The idea with Dextromethorphan is that it’s an anti-tussive, meaning it reduces the urge to cough. It’s not entirely clear how effective it is, but in theory it’s particularly helpful if you have a dry, nagging cough. Interestingly, in large doses it can be psychoactive. As a result, in some jurisdictions it’s a somewhat controlled substance. Some daytime cough formulations include both Guaifenesin and Dextromethorphan, with the idea that you’ll cough less, but if you do cough it’ll be easier. 🤷‍♀️

Choose Your Fighter

Of course, you don’t have to take my word for it – especially if you have any conditions that may interact with medications. Use this as a starting point for research, and consult a doctor before choosing pharmaceuticals based on a glib rundown from a tech blog.

The key takeaway is that while cold medicines’ brands may provide a helpful placebo boost, the underlying medicines are very much worth knowing and understanding.

There are only a few moving parts here, so consider your symptoms and make an informed choice about which meds you want during the day and at night. With a little research, you too can have cold medicine that may actually help – and avoid becoming a snot zombie.

Although this article is hardly meant to be formal medical advice, if you spot any errors or key omissions, please let me know.

An annoying thing about the future is that, at first, it sucks.

The original iPhone was, to many people, obviously great. Although even the most optimistic iPhone users of 2008 mostly underestimated the impact smartphones would eventually have on work, play, and society, the iPhone was still clearly a product that mattered. A product from the future.

But that was in 2008. If you were to go back in time a bit further, say to 2002, you might encounter the Handspring Treo. The Treo was not obviously great. To optimists, early smartphones were exciting and promising. But optimists get excited by dumb shit all the time. To most people, reasonable people, early smartphones seemed like a sci-fi novelty. And who can blame them? Statistically, it was a sci-fi novelty.

It is brutally difficult to distinguish the next big thing from the last big fad. For every smartphone, we have 100 netbooks. For every electric car, we have 100 jetpacks. Product ideas often seem like they could change everything, but once they become possible, they often turn out to just not be very compelling. So we learn to be skeptical.

At this point, it’s well known that Apple has big plans to develop an augmented reality headset. What’s got people talking recently is not that Apple is working on it, but that they’re reportedly so committed to the project that they’ve disclosed 1000 people on it. According to The Information, Apple leadership believes AR glasses could replace smartphones within 10 years.

Replace the smartphone? Who would want to replace their iPhone with a screen strapped to their face? John Gruber summed up the common sentiment crisply:

Why would people who don’t need glasses want to wear thick glasses all day? And they think it will replace phones in a decade? Do we really want our phone display in front of our eyes all day? I just don’t get it.

No matter how well they pitch it, the Apple AR headset is going to get this kind of reaction from most people. Just like current VR headsets, it is going to be kind of like a phone display in front of your eyes all day, with a bunch of compromises most people don’t really want to make, and it will kind of suck.

Based on Bloomberg’s claim that the initial headset will “focus on gaming, watching video and virtual meetings”, and talk of a dimming function to provide enough contrast for the display, it seems like the initial AR capabilities aren’t even going to be dramatically different than current-gen VR headsets: a 360 degree display on your face, integrated onto your view of the real world in a way that may only be marginally useful.

But Apple’s projection, it seems, is that their integration between virtual and reality will become useful. Incredibly useful. Apple may be optimistic in thinking that the timeline will be only 10 years long, but it seems clear to me that if physics really do make a good AR headset possible – glasses that can usefully and practically render information interleaved with our natural vision – it will change everything. A good AR headset would naturally displace the smartphone as the most useful device in our lives.

Truly good AR

Replacing the smartphone will require going way past strapping an iPhone display to your face. It involves moving far beyond showing video and pretending to be in meetings, and requires delivering on the promise that’s right in the name of the product: augmented reality. Enhancing what you see in the real world.

Now, if you’re cynical about technology – which after the last 5 years I would not blame you for being – you may imagine a future augmented by smart eyewear to look something like this.

Advertising, gamification, constant distractions and chaos, interruptions – basically a Black Mirror hellscape. And to be clear, in the event that high fidelity AR becomes possible, some company will attempt to make such a hellscape, filled with crapware and covering your gaze with nonsense for the lowest possible price.

I challenge you, though, to imagine not the worst that a future AR experience could be, but the best. Imagine instead an AR experience not designed by advertisers, but by Apple – or even better, Apple’s successors. A team obsessively focused on people, taking a distinctly human approach to designing how your glasses could augment what you see.

An augmented thought experiment

Consider what would be possible if your AR glasses could subtly, non-invasively, and pleasantly add any extra information to your field of vision in a tasteful way. If instead of showing messages and popups, they could augment your world in a way that made you happier or more effective. What would you ask them to show you?

A lot of peoples’ minds first go to wayfinding. For example, if you were getting around town, you might ask your glasses to:

• Indicate the ideal route on the road while I drive
• Highlight all parking spots that are currently available
• Show the Lyft that’s coming to pick me up, through buildings
• Ask, “Dude, where’s my car?”

That’s a start, but not a very creative leap from what smartphones do today. AR’s ability to enhance, coupled with the ability to work hands-free, could be really useful for getting things done. You might ask them to:

• Highlight all the wooden studs in this wall
• Show me how to disassemble this bike
• Open my computer display here, at 34” wide
• Highlight the location of this kind of screw, the one I’m looking at right now, when I get to Home Depot

Task-related instructions could certainly be helpful, but things get really interesting when you consider standing orders. Rather than just being a platform for notification popups, AR has the potential to provide calm, context-relevant reminders:

• Whenever I’m at the grocery store, highlight any items that are on my grocery list
• Whenever I open the fridge and something is expired, highlight it
• If I haven’t picked up the mail in the last week, make the mailbox glow
• Rather than popping up an interruption to take out the recycling at 8pm on Thursdays, just highlight the bin until I take it out

With gentle nudges, AR could help make you a more competent human being. Drawing your attention to things that need to be done is a start, but it could also draw your attention to things you want to improve, or things that are potentially unsafe:

• Indicate whenever I pick up a packaged food item with more than 15% of my daily salt intake per serving
• When I’m at a crosswalk, highlight any cars where the driver doesn’t seem to be paying attention
• Show a little orange reminder light whenever I say “you guys”
• If there’s a bear on this trail, in any direction, flag it with a giant red arrow and a flashing label that says “HOLY CRAP A BEAR”

Going beyond adding information, AR glasses could also transform information into a more useful or pleasant form:

• Translate all Japanese into English
• Mute all Avengers spoilers
• Block any ads that animate, anywhere
• Replace that awful painting Grandma loves with a photo of a cute sloth

Finally, just like our smartphones, AR glasses will get additional abilities over time that could slowly make us superhuman in ways that will feel perfectly natural:

• Turn on heat vision, so I can find where the cold is leaking into my living room
• Turn on night sight, so I can find my way down this path without turning on my flashlight
• Put a rear view down in the corner of my vision, so I can live up to my reputation as a parent for having eyes in the back in my head
• Zoom in on the sweet bald eagle up in that tree, so I can behold its majesty

It’s easy to think of AR as just adding a display in front of your face. That’s probably how it will start, and that may have some value in its own right. But if AR is going to replace the smartphone, displaying information in any way similar to a smartphone or smart watch of today would only be an evolutionary link in the chain. A stepping stone.

Where AR has the potential to change everything is the ability not to be “in your face”, but to blend into the world around you. The capability to seamlessly augment your vision is so powerful that if Apple – or anybody else – ever pulls it off, it will upend how we interact with technology as much or more as the smartphone ever did.

Many of the use cases I’ve outlined above may not be feasible for decades, but if seamless AR becomes practical, it will create entirely new uses, behaviours, and capabilities that my dumbass pre-AR mind can’t conceive of yet.

It’s almost enough to get a cynical technologist excited.

To be clear, I don’t know if AR really will replace the smartphone in 10 years. The future will get here on its own time. But it is, I’m pretty sure, just that: a matter of time.

Over on the Steamclock blog, I recently wrote an article about letting users review iOS apps:

There are enough subtle pitfalls around the relevant APIs and App Store Guidelines that it can be easy to get this wrong. Conversations about app ratings often devolve into debates about what Apple will or won’t allow, and it’s hard to remember the exact details and limitations.

As with most product decisions, there’s a naïve way that will get you started but could cause problems, and a series of more-thoughtful ways of doing it for those that want to do it well.

Updated to reflect latest polling, and to add a Vancouver Granville section, through Oct 19.

On Monday, Canada votes.

Last election, Justin Trudeau’s Liberals swept into power. A wave of optimism and enthusiasm won the Liberals the largest gain in seats ever in a Federal election. Trudeau was seen as a champion of the center and the left, and drove the highest voter turnout in over 20 years. The result: a total rout. The leaders of all three other major parties left or were pushed out.

Four years later, things have changed. By most measures Canada is doing fine, but the Prime Minister’s shine has worn off. On one hand, Trudeau kept many of his promises – he appointed Canada’s first gender-balanced cabinet, cancelled the Northern Gateway pipeline, and legalized cannabis.

On the other hand, people distinctly remember the promises he did not keep – cough, electoral reform – and the ones they feel like he made, but hasn’t lived up to. Like, he didn’t say he wouldn’t nationalize an oil pipeline, or eject a prominent indigenous woman trying to uphold the rule of law from his party. He didn’t explicitly say he had no history of repeatedly dressing up in racist face paint. Voters just kind of assumed.

And even if those controversies haven’t changed the party allegiance of many traditional Liberal voters, they’ve certainly dampened enthusiasm for Trudeau among progressives generally.

Of course, thanks to our parliamentary system, voters have a variety of alternative parties to consider. Unfortunately, none of the alternatives seem to be inspiring a ton of enthusiasm either. Despite rigorous campaigning by some fresh faces, the CBC poll tracker changed little for most of the campaign, mostly projecting a minority government by the Liberals or the Conservatives.

While predicting election odds is hard enough in the best of times, we may see particularly inaccurate polling this year since higher apathy and uncertainty about what party to vote for will likely drive down turnout.

Hopefully, this guide will motivate you to use your vote on Monday. It’s in you to give.

• The Issues, or Lack Thereof
• The NDP
• Strategic Voting
• The Green Party
• The Bloc Québécois
• The Liberal Party
• The Conservative Party
• The People’s Party
• Addendum: Vancouver Granville
• Actually Voting

The Issues, or Lack Thereof

Unlike many elections, and certainly unlike those south of the border, there are not a lot of big, emotional issues driving this Canadian election. Still, in an election year where none of the leaders are inspiring a ton of enthusiasm, the issues are going to drive the vote for many people.

As a quick refresher for what the federal issues are, it’s worth checking in on what the federal government actually does in Canada. You may be losing sleep over the sorry state of our road signage, but those aren’t the kind of signs Ottawa is looking at.

At a high level, the question is: who do you want making decisions about the environment, federal taxes, seniors’ benefits, immigration, personal rights, foreign affairs and trade, national defense, large infrastructure funding like public transit or social housing, and some aspects of indigenous affairs and healthcare? You know, the big stuff?

When it comes to platform details, the CBC has a reasonable platforms breakdown of what the parties have to say on some of these key items. For many issues, though, often the question isn’t “who promises to reduce greenhouse gases by what I’ve personally determined is the correct amount”, but rather “who do I expect will in practice make the biggest impact on climate?” And for many issues, the party platforms haven’t laid out a lot of concrete action.

Perhaps that’s unsurprising. In this political moment, there isn’t one critical social debate or national referendum driving parties’ platforms. While that’s maybe for the best, it makes for a bit of a boring election.

To some degree, the boringness is exaggerated because Canada’s political parties currently break down on fairly traditional left-right axes. There is no distinctly libertarian party with a socially progressive but fiscally conservative agenda, for example. Given that, it’s pretty tough for 5 or 6 parties to carve out distinct compelling takes on the issues. As a result, we mostly have different leaders arguing not about what to do, but how much to do it – plus one drunk guy in the corner claiming that climate change is not caused by humans and that rapidly increasing carbon dioxide just means more “food for plants”.

Given that, rather than digging into any issue in detail, I’m going to recap the national parties in rough progressive to conservative order, and consider where they’re at and why you may want to vote for them.

Please don’t hate me.

The NDP

Bringing up the left side of the House, we have longtime social-democrats, the New Democratic Party. As with many left-wing organizations, over the years the party has struggled to find balance between its more radically progressive elements and the more electable ones, and has spent most of its history in 3rd place or worse. That said, if your politics are progressive, and wealth inequality in Canada is a serious concern for you, then the NDP should be on your radar already.

As is their style, the NDP promises to spend more money on social programs than the more moderate parties, and have predictably progressive perspectives on social and climate issues. For example, the NDP is pledging to build 50,000 new affordable homes per year, whereas the Greens promise to build 25,000 and the Liberals are pledging 10,000. Of course it’s easy for the 3rd place party to make pledges, and the bigger question is about which party might actually achieve their targets, and how they’ll pay for it all – a tale as old as time.

When he was elected leader of the NDP in 2017, Jagmeet Singh didn’t exactly light a fire under the party’s base. Most press coverage of Singh has focused on either his early struggles to build a national campaign, or commentary on his deft and moving responses to questions about race. That said, Singh has more recently received positive press for his debate performances, and in the final days of the campaign has seen his polling numbers pick up – both in terms of leader favourability and in party support.

You should consider voting NDP if you’re firmly on the progressive end of the spectrum, especially if they’re likely the strongest progressive party in your riding. For many voters on the left, though, the question of whether to vote NDP in a given election or riding comes down to strategic voting.

Strategic voting

A big question for supporters of 3rd and 4th place parties is always strategic voting. For example, a number of voters who leaned NDP last year voted instead for Justin Trudeau. For those who voted for Trudeau as a “this will be the last federal election using first-past-the-post” candidate, that bridge is now likely burned. On the other hand, those who voted Liberal as a “Stop Harper” vote might consider doing so again, depending on their riding.

Since strategic voting is so riding-dependent, if you’re an “Not Conservative” voter, you’ll need to look up your riding. Although you can just reference Wikipedia, or Justin McElroy’s excellent countdown of every BC riding from least to most interesting, the change in fortunes and polls across parties can make it really hard to project who actually has a chance in a given riding. That’s why I was pleased to find 338Canada, a low-budget but surprisingly in-depth data source for every riding in this year’s election. Don’t miss their projections plotted on the electoral history chart for your riding, which should be helpful in any attempt at voting strategically.

Once you have a sense of what candidates might win in your riding, “anything but Conservative” voters can take an approach like this:

1. If a Liberal, NDP, Bloc, or Green candidate seems to clearly have the best chance of defeating the Conservative one in your riding, then vote for that candidate.
2. If it seems unclear what left-leaning candidate has the best chance, or it’s within the (large) margin of polling error, then vote for the candidate you like best.

The core goal of strategic voting on the left is to not hand a left-leaning riding to the Conservatives due to vote-splitting. While the Liberals are the only progressive party with a real shot at winning the election overall, successfully electing an NDP or Green MP is still a success for progressives in the parliamentary system. This is especially true now, given that a minority government seems likely and parties may need to form alliances.

If only we could get a prime minister who pledged to stop first past the post, we wouldn’t have to worry about strategic voting anymore. One can dream.

The Green Party

Traditionally a protest vote, early this election cycle the Green Party got substantially more attention than usual. This was due in part to the ever-increasing priority of climate as a critical election issue, but also because Greens have had electoral successes at the municipal and provincial levels in recent years.

With more attention has come more scrutiny, and for the first time that I’m aware, the Green Party has gotten press for campaign-trail gaffes – insufficiently vetting candidates, for example. Running a truly national campaign is tough.

An interesting facet of Green Party policy is that unlike other parties in Canada, they pledge to let elected Green Party MPs vote freely instead of being beholden to the party line. That sounds great in theory, but it does have the consequence that in order to confidently vote Green, you need to understand the particular candidate you’re voting for – who may or may not fully agree with the party platform.

While the Green Party is further left than the NDP on some issues, they are surprisingly centrist or neutral on other issues. They don’t consider themselves left-wing, and at most levels of government Greens seem less interested in taxing the rich to help the poor than the NDP do. From a strategic perspective, the Greens position themselves as a plausible alternative both for NDP and especially Liberal voters who want to send a clear message on climate.

Elizabeth May has long been party leader and lone MP, and is the longest-standing leader of Canada’s parties. While this may be the year the Greens pick up a couple additional seats – for example, on Vancouver Island – their support continues to be spread so thinly across the country that they pose a serious challenge in very few ridings. That said, the fact climate is a huge pillar of their platform could make this a landmark year for them.

You should consider voting Green if your riding is one of the few that has a strong Green candidate with a chance of winning, or if you want to lodge a protest vote on behalf of climate. If you’re a Green supporter looking to vote strategically, the rules I describe above all apply.

Bloc Québécois

Given that the Bloc is a separatist party that only runs candidates in Quebec, the personal blog of a tech guy from Vancouver is probably not the go-to source of information on them. On the other hand, they don’t seem to even have an English website, so maybe you are looking for information on them? If so, I apologize.

From what I’ve gathered, support for the Bloc has risen in the polls since last election’s lows, and in a minority government situation they could hold the balance of power. So they’re important to Canada, but not an option on most Canadians’ ballots.

You should consider voting Bloc if you’re a left-leaning voter who is interested in Quebec separatism and have actually read about their platform in French. Or, perhaps, if you’re an “Anything but Conservative” voter who is in a riding where Bloc is the best defensive vote.

The Liberal Party

The Liberals are Canada’s winningest political party, longtime experts at finding a balanced position in the center of Canadian politics – in the middle, but a bit to the left.

In 2015, Trudeau’s positivity, charisma, enthusiasm, and vocal support of progressive social values earned the Liberals a lot of new votes. He got “Stop Harper” votes from the left, open-minded votes from the right, previously non-existent votes from the young, and a non-trivial number of votes from fringe-party voters eager to do away with First Past the Post.

Over the last four years, the Liberals haven’t exactly screwed Canada up – by most measures the economy is doing well, and he fulfilled most of his promises – but he’s managed to alienate various voting constituencies that lent him their votes in 2015, especially on the left. Perhaps worse for the Liberal party, he’s annoyed enough of his base that Liberal turnout will almost certainly be lower this time around.

That said, there is an enduring appeal to centrism, and the Liberals continue to be the party whose views are closest to the median Canadian. Since the demise of Canada’s Progressive Conservative party in 2003, the Liberals have also been the closest we have to a libertarian party – the most fiscally conservative party you can elect that is still progressive in a social sense.

Perhaps most importantly for the Liberals, they are the stereotypical “not Conservative” strategic vote. As in most modern Canadian elections, the Conservatives and Liberals are the only two parties with a shot at actually forming government. In ridings that the Conservatives have a good chance of winning, the Liberals are often the next most likely party to win. You can read my overview of strategic voting above.

An amusing wrinkle for the center-left Federal Liberals every election is that the de facto right-wing political party in British Columbia is called the BC Liberals. I find this funny in two ways: both that the two parties share a name but have quite different positions in politics, and that BC is a liberal enough place that the most conservative major party we have is titled the “liberals”.

You should consider consider voting Liberal if you’re a moderate or centre-left voter who thinks Trudeau really does mean well and is learning from his various foibles, or if you’re a progressive voter who falls in the “anything but Conservative” camp and the Liberals have the best shot at defeating the Conservatives in your riding.

And please, if you voted for Trudeau last time and are annoyed at him for one of many valid reasons, please still take the effort to vote this year – even if it’s just to formally record your displeasure.

Conservative Party of Canada

In 2003, the center-right Progressive Conservatives and the right-wing Canadian Alliance merged. While this annoyed the most moderate and most radical factions of those parties, it vastly improved conservatives’ electoral chances in this country, and led to almost 10 years of Conservative government.

With this merger, voting became simple for many Canadians: they knew their views were conservative, and no longer had to weigh just how much social conservatism they wanted along with their tax cuts: the conservative base just ticks the box for Conservative. If that’s you, then you’re probably just hate-reading this article in order to send me angry email. Which is fine. Hi! Sorry! 😅

Voting is perhaps more interesting, though, for the libertarian-minded voter. Nowadays, we have Liberal/Conservative swing voters – people who are neither enthusiastic about the Liberals’ economic approach nor the Conservatives’ social or environmental policies. Each election, these voters must take a side, or perhaps lodge a protest vote for the Greens. Fun Fact: Elizabeth May was a policy advisor for the Progressive Conservatives in the 1980s.

While it’s easy to attribute this year’s increase in Conservative polling entirely to the tarnished image of Trudeau, I also think some right-leaning voters see fewer pressing social issues than they did 4 years ago. The absence of a socially conservative government has taken topics like abortion and same-sex marriage out of Canada’s national conversation. Meanwhile, increased attention on – and, in some cases, support for – extreme right-wing and/or authoritarian governments worldwide makes a politely Canadian Conservative government with a vague social agenda seem like a reasonable option.

Heading up the Conservatives this election is Andrew Scheer. Like Singh and Trudeau he’s in his 40s, bringing a youthful energy to his party. Also like Singh and Trudeau, Scheer doesn’t seem to have inspired a lot of enthusiasm from voters this election. As boring as their leader may be though, Conservative voters are enthusiastic about getting a progressive PM out of office.

One serious complication for the Conservatives this election is the newly founded People’s Party of Canada, which hopes to split out some Conservative votes with its more right-wing, populist message. Where in previous years the Conservatives’ obvious strategy would have been to moderate their message to mop up disaffected Trudeau voters, this new threat from the right has pulled the Conservatives back into conversations about things like same-sex marriage – battles lost that are hardly worth revisiting, but if ignored entirely could lose them their most conservative voters.

All that said, the biggest challenge for Conservatives is probably on the climate file. While Scheer has smartly maintained that climate change is important and that Canada should meet its Paris carbon targets, the Conservatives’ platform is very critical of carbon pricing, an approach that originated as a conservative market-based approach to global warming. Absent a carbon tax, the Conservatives are rather vague about how we might otherwise reach those targets.

You should consider voting Conservative if:

1. You’re a dyed-in-the-wool conservative, and you’re just reading this article to look for things to disagree with
2. You lean Conservative and couldn’t stomach voting for Trudeau again, especially if you’re not very concerned about climate targets or the potential of Scheer enacting a few socially conservative policies
3. You live in Beauce, Quebec, and have the irresistable chance to deny the People’s Party from getting a single seat in parliament.

The People’s Party

A natural consequence of a unified Conservative party is that there will, on occasion, be politicians who are too conservative, too extreme, to be part of a big Conservative tent. This election, we have somebody wild enough to try to out-conservative the Conservatives: Maxime Bernier.

Bernier says he would do “nothing” about climate change, thinks Canada’s “extreme multiculturalism” is a problem, called Greta Thunberg “mentally unstable”, wants to reduce funding for healthcare, called diversity a “cult”, and is overall a one-star clown.

That said, we’ve learned from elections worldwide that it’s too easy to dismiss populists as being idiots.

If you are considering voting for the People’s Party of Canada in any riding other than Maxime Bernier’s, you’re probably just splitting the vote and hurting the Conservatives, the party with an actual chance to advance your views. While in the short term it may be better for progressive politics in Canada to have a split conservative vote, I think legitimizing this kind of rhetoric sends a terrible message to the country and our children. Please just don’t.

Addendum: Vancouver Granville

By sheer luck – or lack thereof – this election I happen to live in one of the most interesting ridings in the country: Vancouver Granville. As such, a few people have asked me for some context for this rather unusual race.

Vancouver Granville’s incumbent MP is Jody Wilson-Raybould, who was the Minister of Justice and Attorney General of Canada until the SNC-Lavalin affair resulted in the Prime Minster ejecting her from the Liberal Party. She is now running for re-election as an independent.

While it’s rare for an independent candidate to win a federal seat, it’s also rare for a candidate to be the former Minister of Justice and Attorney General, the incumbent MP, and only be independent because she recently took the sitting government to task for a breach of ethics. Which is to say, she seems to have a serious shot.

Making things hard to call, though, is the fact that in 2015, the riding split very evenly on either side of the Liberals: 26% Conservative, 44% Liberal, and 27% NDP. A result like that should predict a stable Liberal hold this year, but now those Liberal votes will likely split, one way or another, between Wilson-Raybould and the new Liberal candidate – meaning whoever wins the riding could have fewer than 30% of the vote.

Given that, Vancouver Granville is a headache for strategic voters and pollsters alike. 338Canada’s model projects a tossup between Wilson-Raybould and the Liberals, but if enthusiasm and turnout become the deciding factors, it could become be a race between JWR and the Conservatives. While strategic voters crave projections, 338’s estimates are based on national data, and seem to struggle with the complexity of this riding.

For example, when Wilson-Raybould was added to the 338 projection as an independent in June, the model oddly semeed to think this would primarily hurt NDP and Conservative results, but somehow increase the Green vote. Meanwhile, in real life, Green leader Elizabeth May has endorsed JWR over her own Green candidate in the riding.

While that may seem odd for a recently Liberal MP, the Greens and the Liberals aren’t far apart on most issues – and the issues Wilson-Raybould outlines on her website mesh pretty well with the Green platform.

And although an independent might not necessarily have much power in our very party-dominated parliament, there is a tiny but fascinating chance that an independent MP could affect the balance of power in a very close minority government situation. Whatever your politics, it would be hard not to appreciate the irony of Jody Wilson-Raybould holding power over a weakened Trudeau government.

All that said, one huge benefit of living in a “riding to watch” is that there are some surprisingly in-depth recent profiles of the race in places like The Globe and Mail, The Huffington Post, and elsewhere. Which is good, since this is one riding where a few votes could make a real impact.

Actually voting

To vote on Monday, October 21 – or during advance polling until Monday, October 14 – you just need to:

• Have ID that proves your address
• Be 18, and a Canadian citizen
• Vote at your assigned polling station in your riding

If you’ve registered to vote you should have received a voting information card that will make voting faster. If you don’t have a voting card, you should still be able to vote, as long as you find your assigned polling station.

Voting hours vary by province, but are 7:00am to 7:00pm in BC, and are 9:30am to 9:30pm in Ontario.

Learning more

If you have any feedback or (especially) corrections on this guide, please get in touch!

While I hope this guide is a helpful starting point for people, I’m just a lone designer and developer from Vancouver – if you’re able, it’s great to do your own research, and spread the word about what you learn. Some starting points for doing your own research:

• 338Canada, a rough but valuable trove of polling data and projections
• The CBC Poll Tracker, which isn’t very useful for strategic voting but is nicer than 338’s
• Justin McElroy, CBC Vancouver’s local affairs reporter and professional ranker of things
• Party Platform Guides by the CBC and Maclean’s
• The Vote Compass, which is a neat tool even though the issues this year make its results kind of uninteresting and at times misleading
• The Oct 7 Leaders’ debate, made available in full on Youtube by CTV news including, inexplicably, hours of preamble
• A variety of political podcasts, including the CBC’s Party Lines and BC’s PolitiCoast

When I was a kid, we had a kitten named Rab. She was thus called because she was small, fluffy, white, and tail-less – like a rabbit. She was endearing and snuggly and prosh, or at least she was when she wasn’t drinking from the toilet bowl. Even as an adult, she stayed small and roughly spherical. To us, she was still a kitten.

One day, our kitten had kittens. So turns the circle of life. The litter was scrawny and stumbly, and blind enough that they’d attempt to suck milk from the olive green strands of our old shag rug.

As they grew, they got a lot cuter and a little less clumsy. As cute as they were, though, they weren’t the least bit cuddly. You could get one second of snuggle in, perhaps two, before they’d promptly mew and squirm – all they wanted to do was climb and play.

A few weeks into this, very late one night I was woken by a mewing pile of kittens in my bed. A pleasant surprise! As I blearily moved to let Rab lead them under the covers, I discovered that they were distinctly cold, wet, and shivering. Confused but dutiful, I did my best to help her warm them up, and soon fell back asleep.

The next morning, it promptly became clear what had happened. Rab, in her wisdom and stubbornness, had decided to drink from the side of the toilet in the middle the night. The kittens, in their curiosity and adventurousness, jumped up – and directly into – the bowl. Mama then taught them a critical lesson in leeching body heat from an unsuspecting human.

Disgusting, but endearing. Like much of parenting, I suppose.

As a parent, I do my best to teach my daughter well, and to keep her from harm. From time to time though, I slip up. I notice her copying behavior I wish I hadn’t modeled. I get overconfident in her climbing ability and she knocks her tooth on the pavement. Or, most recently, I give in and let her watch a cartoon that’s a little too scary. (Apparently we’re not born with the innate knowledge that “the floor is lava” is not likely to actually occur.)

If there’s a way to totally prevent these transgressions, I don’t know what it is. Nor is that a goal worth having, honestly. Letting kids slip up is a fundamental part of their education.

What’s important is, when that happens, we take care of them. We lead them to warmth, and give them comfort. Even if it’s a little gross.

And with luck, seeing my habits and mannerisms reflected in my child will continue to give me the perspective to better myself. The strength to choose my words thoughtfully, and be the person I’d like her to one day be. To stop drinking from the toilet.

Rab, mind you, she was unstoppable. Still, she was a good mom. You could just tell.

One of my most hated things is when someone over-fills a garbage bag.

You see, an almost-full garbage bag is a small task to deal with – you just close it up and pull it out. But an over-full garbage bag is a problem. Suddenly, you can’t just pull it closed anymore – dealing with the bin now involves biohazardous juggling, something nobody is inclined to do anytime soon. The resulting additional procrastination leads to, in most cases, an unstoppable garbage snowball that eventually destroys humanity itself.

Everybody has their irrational pet peeves. As long as I can remember, this has been one of mine. For years I always tried to prioritize the task of emptying the bin before it got over-filled. Sometimes I succeeded, but other times I failed, and a stupid garbage can would put me on tilt.

One day, when I attempted the task of emptying the bin, I found it over-full. And instead of emptying it, I left. I left for Home Depot, on a different task that would change how I thought about prioritization forever: I bought a smaller garbage bin.

It may be obvious to you, but for years I ignored the root cause of my age-long grief. I did nothing about the thing that actually enabled people to pile in more garbage than the bag could hold: the bin was bigger than its bag. By buying a smaller bin, the same bags simply couldn’t be over-filled. Even the most precariously over-filled bin could be wrapped up swiftly and neatly, using the specially reserved portion of bag draped on the outside of the bin, ready and waiting for duty.

It was glorious.

The quietly worthwhile

There is a lot of stuff you should get done.

Or, more accurately, there is a lot of stuff you feel like you should get done. My OmniFocus tracks 860 actions that, at one time, I felt like I should do. Many of them won’t get done. But there are some things in there that I truly should do, and if I do them, I’ll be very glad.

The question is: which ones?

Some actually-important things are urgent. If you don’t renew your passport, you can’t go on your upcoming trip. If you don’t empty the garbage before garbage day, you’ll be stuck with old garbage for two weeks. The task needs to get done, you need to do it, so you just gotta do it. It’s kind of obvious, because it’s both urgent and important.

More interesting, though, is the non-urgent stuff that is nevertheless very worthwhile. The tasks that are easy to defer, tempting to procrastinate, but actually more important than the supposedly urgent tasks: the smaller garbage bins, waiting to be bought.

So, when I’m looking at things I should do, I keep an eye out for certain kinds of tasks: work that isn’t urgent, but can multiply time. Things that could pay off for months or years to come.

In particular, I try to consider if I can:

1. Automate. Can you spend 1 hour simplifying or automating something that would then save yourself 5 minutes a week? If so, then I have an incredible investment opportunity for you: you can invest time – the most precious resource we have – at a 430% annual interest rate. The busier I get, the harder it is to get around to tackling these automation and simplification tasks, but the more worthwhile it is.
2. Teach. If there’s somebody who’d be willing to do this task in the future, but they don’t know how yet, then you have a big opportunity. The long-term payoff for teaching someone how to do a task can be massive. Even in the case of successfully handing something off only for it to “boomerang” back later, having taught still improves your understanding of the work and makes you a better teacher for the next attempt. If you’re in a leadership position of any kind, you don’t have the time not to be teaching people.
3. Calm. Like many people, I have a certain amount of tolerance for frustration and stress in a given day. At a certain point further annoyances, even small ones, cause disproportionate reactions and sap energy from me and those around me. That’s why I find it useful to prioritize fixing anything that is a persistent aggravation or stressor. In OmniFocus, I keep an ongoing project “Make Life Calmer”. Doing work today that will make tomorrow calmer and more focused is a great investment, and will let you use your future “stress budget” on something more meaningful than the fact the damn kitchen drawer is stuck closed again because the saran wrap and aluminium foil boxes got pushed on top of each other again and god DAMN it why do I have three different sets of measuring cups in here augghhhh.
4. Improve. It is extremely easy to procrastinate making yourself better. It takes motivation to build new habits, learn how do to something “right”, or to address a longstanding problem. But this work is profoundly worthwhile, since small investments here can have huge payoffs. After 35 years of using a computer like a dumb animal, I’m finally learning how to sit, type, and work in a way that doesn’t permanently injure my wrists and shoulders. Reading books about RSI or learning better posture aren’t necessarily my idea of fun, but I’m going to benefit from the investment for decades to come.

Diamonds in the rough

Next time you’re cleaning up your todos, considering a new goal or theme, or just feeling over-busy, consider how you can be multiplying your time. What things, once done, will have an impact that pays off for years?

What is your smaller garbage bin?

I try to be nice to people.

While being nice is relatively popular here in Canada, being nice is not necessarily popular in the business world. There’s something about business that makes some people feel like it’s a license to be a heel. “Well, that’s business, kid.”

Well, that’s not the kind of business I want to be in. Over the years, my team and I have made a point of making nice things and being nice to each other while we’re at it. It’s pretty simple, and it makes for a nice work environment. It’s great.

A few years back, I was at the excellent XOXO conference in Portland. Some friends and I were sitting in the sun, enjoying our cereal from a van or whatever weird-ass Portland breakfast we were eating, when an acquaintance came over from a nearby food cart with a delicious-looking free-range egg sandwich.

Now, this was a developer I’m friendly with and am always happy to see, so we quickly got to chatting. And as I talked and my acquaintance ate, he had the misfortune of getting some egg on himself.

I noticed, but I hesitated to call attention to it. To call out somebody’s appearance in a public setting, that’s not very nice, is it? So I did a rather Canadian thing – I acted like nothing was wrong.

This was a miscalculation. You see, I hadn’t considered that eventually, inevitably, my conversation partner would realize my deceit. Indeed, before long he noticed that, in a very literal sense, he had egg on his face.

Upon discovering this, he asked mournfully, “Why didn’t you tell me?”

It was a very good question. I may have felt like I was being nice, and perhaps by some shallow definition I was. But I was definitely not being kind. Immediately, I felt like the one with egg on my face. While I can only hope my friend has long since forgotten this minor cruelty, that moment has stuck with me.

Being kind vs. being nice

The distinction between niceness and kindness can seem subtle. While being nice might involve acting polite, positive, and pleasant, being kind is deeper – it’s about being caring, sympathetic, and helpful. In many circumstances the kind thing to do is simply to be nice. In some circumstances though, the kind thing to do is to be direct. Or clear. Or firm.

In learning to run a business, I found early on that however nice you are, you still need to set distinct boundaries and limits with clients in order to, for example, get paid. And when it comes to close friends and family, it can be second nature to prioritize kindness, even when it means having a less than nice conversation to help fix a problem.

The difficulty comes, I find, with acquaintances and colleagues that I’m not necessarily close to, where I can easily get away with just being nice. It can be too easy to just have conversations that are pleasant but shallow, avoiding the more uncomfortable but more helpful line of discourse. Kim Scott’s Radical Candor and countless other feedback systems are built around the idea that over-prioritizing niceness – what Scott calls “ruinous empathy” – is a short-term salve that causes long-term pain.

So, recently, I’ve been working to have deeper conversations with the people around me. I’ve been trying to ask myself: does this person necessarily care how polite I’m being, or would they rather I just prioritize being clear? It’s a bit more work, but often – especially in person – you can still do both.

I feel lucky to work somewhere where people are nice to each other, and I definitely don’t want to lose that. But there’s another notch above being nice; the next step on Maslow’s Hierarchy of Teams. Where you need to get is a culture where being nice is the default, but being kind – including having hard but helpful conversations – gets priority over always being pleasant.

That is to say, a place where you can trust that somebody will speak up – even if you have egg on you.

On an episode of Fun Fact back in March, I shared “one weird trick” for how to be an MC. Listeners seemed to find it helpful, so I wanted to write it up in a more referenceable format:

The trick to MCing an event is to control the silence.

Over the years I have MCed my fair share of conferences, meetups, weddings, and other sundry events. Any article on how to MC an event will orient you to the core requirements pretty quickly:

1. Tell people what to expect.
2. Keep things moving.
3. Make it fun.

So that’s the idea. But in order to tell your audience what to expect, you need to know what to expect. As such, a lot of MCing (or emceeing if you’re gonna be like that) involves running around collecting and confirming information about shifting plans.

How long is the break? How do you pronounce the next speaker’s name? Is there wifi? Why should we care about the rando you’ve dragged up to give a demo, toast the groom, or extol the countless virtues of immutable value types? The MC has to know what’s coming.

The next level up is about keeping things moving. Flow. How can you make this event flow smoothly, steering the audience’s attention to where it needs to be? What’s where the idea of controlling the silence becomes really useful.

May I direct your attention

You see, people are going to want to talk. Socializing is a lot of why people come to events, especially those blowhards way at the back. That’s why you need to make it clear to the crowd when it’s talk time, and when it’s pay-attention time.

If your event is well run, they will have some house music playing in the background before and between presentations. If not, you can often rig background music up yourself. House music is nice for getting folks to start talking to one another.

House music is even nicer, though, for getting people to stop talking. When it’s time to intro the next speaker or deliver a status update, just fade out the house music – or, ideally, have a sound tech do this on your signal. The sudden silence will draw everybody’s attention, and your intro blurb (or glib rhetorical question) will shut up the remaining verbal stragglers. You then say your bit, and hand that hard-won energy off to the next speaker by introducing them by name.

The reverse flow happens on the way out: you thank the speaker by name, tell people what to expect next, and then get the house music back on. By controlling the silence – by ensuring there’s only dead air immediately before something interesting is about to happen – you can control the room.

The smooth handoff

There are a couple sub-tricks to keeping folks’ attention as an MC. If it’s time for the next presenter and you jump into introducing them, you might realize post-intro that they’re not actually ready. “Oh, uh, I need to get my laptop set up.” Cue 2 minutes of awkward silence as your speaker fumbles around, inwardly panicking, while the audience slowly starts to talk amongst themselves again. Bad MC, bad! By the time things really are ready to go, the energy and attention have been lost to the wind.

Luckily, there are two simple ways to prevent a botched handoff:

1. Check with your next-up speaker if they’re good to go before you get the audience’s attention.
2. If you realize you’ve gotten the audience’s attention too early, and you can’t shuck and jive long enough to fill the gap, just give the attention back. Instead of letting things get awkward, explain that you’ll need a few more minutes and we’ll be going shortly – then get the music back on.

MCing an event isn’t rocket surgery. It does take a bit of practice, but the biggest requirement is simply caring about how things flow, and putting the work in to make them flow well.

Being the steward of an audience’s attention is a privilege. If you treat that attention as a precious resource, then they’ll be willing and ready to give it when you need it.

Once upon a time, Apple debuted an application for playing music.

Yes, an application. That’s what we called apps back when dinosaurs roamed the Mac. And one of the most-loved applications back in that ancient era was for playing your MP3s. It was called iTunes.

iTunes brought together a shiny interface and powerful library management that Just Worked™. What we didn’t know in 2001 was that iTunes was the first piece of a “digital hub” strategy that would change Apple forever. From its humble beginnings as a nice way to play music, iTunes quickly became the core of Apple’s push into consumer electronics: first the iPod, and later the iPhone.

Two years after its debut, iTunes was already at version 4. The addition of the iTunes Music Store turned a trusty utility into an internet marketplace overnight. The Store completely overturned the music industry and overturned Apple itself, kickstarting its shift from a computer company to a device and services company.

As fortuitous as this path would be for Apple’s business, the frenzied shoehorning of network and sync features into a large existing codebase – inherited from the aquisition of SoundJam MP – brought about the end of iTunes’ golden era.

Later that year, iTunes arrived on Windows. Apple quickly gained a foothold on millions of Microsoft PCs; a base they could add to every time they had the need to support something across platforms. As penance for this, the iTunes team was sentenced to maintain and add functionality on Windows every time Apple launched a new product or service.

And add functionality they did. Over the years, iTunes accumulated features for local music, playing and burning CDs, the iTunes Store, iTunes in the Cloud, iTunes Match, Apple Music, TV, movies, Smart playlists, Genius playlists, podcasts, network library sharing, device backup, internet radio, ratings, iTunes Extras, iTunes U, device software update and restore, media sync, ringtone sync, contact and calendar sync, AirPlay, queueing, Ping, Connect, literally rearranging the icons on your iPhone home screen and – most importantly – displaying a bangin’ visualization of the Hootie and the Blowfish track you just purchased for $0.99.

As the central device and platform hub, iTunes became a leaf on the wind of Apple’s strategic moves. The refined focus of the app’s early days gave way to an era of ever increasing complexity and power.

Of course, with great power comes great technical debt. As iTunes became a mammoth katamari of features tangentially related to media, it failed to become a robust front-end for Apple’s increasingly complex network of media services. UI oddities – ranging from weird modal dialogs to an often complete inability to handle network problems – often belied iTunes’ status as a tired legacy product.

Undeterred, Apple marched forward towards streaming music, introducing iTunes Match, iCloud Music Library, and iTunes in the Cloud – which, believe it or not, are three separate things. While Apple’s marketing team may not have struggled to keep up with this growing array of services, iTunes itself certainly did.

While building the UI for many of these new features using web technology might have been a pragmatic move, it exacerbated iTunes’ struggle to provide a polished and seamless user experience. A move from store pages powered by XML to one fuelled by WebKit never stopped the background drumbeat of glitchiness that often ground the app to a halt.

By 2015, it was time for a reset. With great fanfare and a remarkable performance by Eddy Cue, Apple Music was born. With Apple Music, the iTunes team was finally given the time and space to fully overhaul the app, ditching 15 years of legacy chaos once and for all.

Just kidding, it was just stuck on top of what was already there.

Of course, a focused and clean music-only app for Mac is still the endgame. The real question has long been: when?

Retiring iTunes is a hard thing to do, given the wild web of legacy things it enables. Building a ground-up replacement for music on the Mac is a tall order, especially if they wanted to bring across the powerful library management features that made Mac users fall in love with it all those years ago.

Alternatively, Apple must have at least experimented with bringing the much-maligned but generally more modern Music app from iOS to the Mac. Perhaps they could use some kind of almond-flavoured confection to ease the transition.

Regardless, replacing an app the size of iTunes is a big job.

So we waited. The world turned. Users slowly shifted from iTunes to Spotify. A movie came out about a gumshoe Pikachu and it was somehow not horrible. That is to say, it’s taken a very long time – so long that one might assume there has been a false start or two along the way.

But if the rumour and leak mill is to be believed, iTunes’ end is finally nigh. In macOS 10.15 we will finally see a Music.app for Mac. Surprisingly, this new app is said to be based not on the iOS app or a new codebase, but on the venerable iTunes itself.

There will surely be naysayers that claim iTunes should have been tossed entirely. And admittely, if the new Music app ditches iTunes’ interface but can’t cure its deep and baffling love for obtuse modal error dialogs, I too will bemoan its preservation. But arguing for code to be rewritten just because it’s old has never been the right way to build systems that work.

And whatever the composition and fate of this new app, you really have to hand it to iTunes for getting this far. Seriously, this app has been keeping the beat for almost 20 years. It has survived a veritable hurricane of scope creep and strategy taxes. It was a key part of Apple’s growth from charming underdog to singular goliath.

And now, it can finally lay down its burdens and get back to its roots. It can cash out its stock options, and once again be a music app. What better way for a vintage app to spend its retirement?

So let’s pour one out for iTunes. Farewell.

Writing is meant for reading.

Sometimes, the reading doesn’t matter that much. We might dash off a quick text, toss out a laugh line, or send a rote confirmation. Our emoji are leaves on the wind.

Other times though, the reading matters a lot. Occasionally we need to write something that must be understood, absorbed, and acted on. The more important it is that readers understand and act, the more time you should spend refining the writing.

There are a lot of things you can do to make an email, blog post, proposal, or process document clearer. For example you can keep it short, make it engaging, or have a colleague refine it before sending it out. These can all help a lot.

However, if it’s critical to you that your writing is read – especially by busy people – you need to make it skimmable.

There are a few ways you can facilitate this.

You can use short sentences and paragraphs, for example. That helps a lot because folks tend to primarily read the beginning of each paragraph. It’s kind of a hack, but it works.

There is one core approach though, one workhorse of the skimmable document, that is worth mastering: lists. Lists are rightly derided in the era of Buzzfeed, but the same principles that drive engagement on social media also drive engagement in a Google Doc or email. So today, I’d like to share one weird trick to quickly writing a clear and useful list: The Bolding Trick.

The Bolding Trick

1. Draft a bulleted list, whether it’s the key goals for a process, the main principles in a design, or whatever. Rather than trying to make it perfect on the first go, just get it out.
2. Your list should only have 3-8 items on it, with each item 1-3 sentences, which should keep it readable and digestible. Still, unless each item is extremely short, the resulting block of text can still be a slog to read, appearing monotonous and causing your audience’s eyes to glaze over, or – worse – cause them to decide to read it later.
3. For each point in your list, find and bold the key phrase in the paragraph. For example, the key phrase in this point was “bold the key phrase”. This will make the list far more skimmable.
4. If it’s an important list, it’s worth also pulling those bolded phrases up front. Once the core points are bolded, run down the list again and pull the bolded part to the beginning of each item, making it the heading/summary of the item.
5. Your eminently readable and skimmable list is now ready to be absorbed and acted upon, and easily maintained.

A thing I love about this process is that when you pull out the key phrases into headings, it also naturally drives you to edit the prose to be clearer:

The Refined List

1. Make a bulleted list. Hammer out the key goals for a process, the main principles in a design, or your weird trick for making lists.
2. Include 3-8 Items. Make the list clear and focused by keeping it to 3-8 items of 1-3 sentences each.
3. Bold each key phrase. Go through the items you wrote and mark in bold the 1-4 words that matter most. This would be often be a verb phrase in a process document, or an adjective phrase in a list of goals.
4. Make the phrases headings. While you can stop after bolding, it’s often worth also pulling the key phrases into inline headings. Rewriting your list this way also helps you refine and repeat the key points.
5. Share and maintain. The formatting will make your list much easier to read, update, and act on.

I find this approach faster than trying to come up with the headings first, and it has the added bonus of being incremental: after each pass you can stop and you have a useful document.

Once upon a time, when I would try to document a process or a project, I’d approach it like a blog post. I’d spin a narrative, write pages worth of context and detail, and really get to the heart of the matter. Once the resulting tome was complete, it would be read once, and then left to the sands of time. That was fine for battle stories and manifestos, but not so much for process or design documents.

Now, I write short docs consisting mostly of lists and bolded key phrases. They get read and maintained.

It’s a lot better.