Update: Saturday 13 August 2022

Don’t!

That’s right! The first step in learning how to cycle commute is to avoid doing it! Whenever you try to do something new, you have to brace yourself against two sorts of people: those who un/wittingly gnaw into you by asking you why you’re doing it; and those who jab at you by saying that you should do more! And, much like vegetarianism/exercise/dieting/etc, bike commuting too suffers from this.

My advice is to ride on only a few sunny/comfortable days, in your first summer. If that goes well, do a few more nice days in autumn. Then resist till the next nice season, at which time you could do a bit more.

Most people do too much, too soon. They start with 15 km commutes, each way! And perhaps even tackling rain!

While achievable, this is not sustainable. It is analogous to what happens to gym memberships: most people get great results, but drop out after three months! The delta is achievable, but is not sustainable. Instead of a sharp, step-change in their habits, they should aim for a very gradual curve, almost imperceptibly rising.

As such, your most important task is to resist doing more! To hold yourself back from biking every nice day, or from biking the full distance that you can! Change of habit has to be imperceptible; it comes about over the _long_ term, not in a short spurt.

It has to be the smallest delta over whatever it is that you’re doing currently! Don’t ‘cut meat out of your diet’ entirely! Just sort-of dabble a bit, and don’t tell anyone–lest the zealots of either side pounce upon you!

Update: Sunday 24 July 2022
My perspective has primarily been shaped by riding year-round in Vancouver, Toronto and Montreal, with a few years of the same in Taiwan, and some experience in the U.K. and the U.S.

Pace

This is a personal choice, of course, and it will vary with the conditions. But some clarification is called for.
The notion tacitly held at the back of too many people’s minds is that of bike-commuting as exercise. “It’s good for you”, and all that! This is not how I view it.
Done right, it will be only the slightest delta over whatever your body is comfortable with. No huffing, no puffing, no sweating, no struggle, no break-all-land-speeds, no fighting traffic, no podium!
Laziness is a virtue.
As I’ve repeated elsewhere on this site, your only struggle must be against those who say you’re not doing enough, and those who say ‘Why are you doing it?’!

I’m not one for feel-good fables, but the turtle definitely wins this one!

Route Selection

On a bike, the longer route might often be the better route.

Uphills

Gradient is a major factor.
A long, flat route could be faster, and more comfortable, than one with slopes. A route with a short uphill may be more comfortable than a longer route with a shallow uphill, even if the total climb is the same. Long, shallow uphills can be very exhausting–much more so than a sharp climb that gets it over with, quickly. On the other hand, how sharp is that climb?
A route with many ups and downs may well be worse than one with a single uphill, for the same elevation-gain.
I’m not a morning person. I prefer descents in the morning, and climbs at the end of the day. My route-selection will factor that in, taking different routes to, and from, work, if possible.

Traffic

Traffic is another factor.
After decades of urban cycling, I no longer have any tolerance for traffic. Simply, I take the longer route to avoid cars. In Vancouver, I often have a choice and, so, avoid main streets as often as I can. Bluntly put, drivers’ mentality lags far behind the change that’s been requisite for decades, with most tacitly assuming that they have prerogatives.

Bike Paths

And then there are the bike paths.
Nowadays, I exhibit the same intolerance for bicycle and pedestrian traffic as I do with car traffic! While there is much to be said for the protective envelope of a critical mass of cyclists biking together, daily commutes demand a different approach, for me. There are too many ex-drivers and newbes conditioned by the media that cycling is a free-for-all. Or, because many laws make little sense for cycling, some of these riders ignore common sense as well.
And then there are the cars taking shared bike-paths to avoid rush hour traffic!
Add to this the fact that too many bike paths are in door zones: They are alongside parked cars, forcing you to play Russian roulette with your life.
With too many dysfunctional, disproportional electoral-systems in the West, municipalities desperate for sane, sustainable transportation have to ease micro-mobility into the urban infrastructure, without riling up the middle-of-the-road electorate (who then frequently get mobilized by a media whose most significant source of income stems from carcentrism). Too often, this results in a series of disjointed part-paths that take you through door-zones then land you at an intersection cars obliviously turn into.
Then there is the distinction between recreational paths and commuting paths. Cities love to jack up their stat’s by tagging any stretch of path they can as a ‘bike path’, no matter how out of the way, how disjointed, how meandering! Often, only a subset are of use for daily commutes. (And I’m not even thinking of the utterly dangerous ones in London, U.K., where they are trying to restore bikes and people into a city that evolved for them, after seven decades of squeezing cars into it!)
So, I take less popular bike-paths, or side-streets, when possible.

Remember: Bicycle-path design is a political decision. The fight is electoral, not engineering. Solutions abound for cycling, and even for Climate Change; the obstacles are electoral.

Maps

Good cycling-maps are rare, but very useful.
When I start a new job, I study the available maps to determine the route options. As time passes, further refinement, or outright change, takes place. Traffic, pedestrians, cyclists, gradients, surface conditions, the season, etc go into that calculation.

Safety

Of vital importance, of course. But, I placed it last because the above had to have been discussed beforehand.
It overrides _even gradient_ in importance! My route selection is primarily determined by safety, with periodic re-assessments as the conditions (traffic, season, encounters, etc) change. Bluntly speaking, I just want a peaceful ride, nowadays: no stress, no ‘encounters’, no near-hits, no getting pushed into door-zones! I want to arrive at the same peaceful heart-rate as I left, with no bad memories lingering.

Layering

Layering, for bike commuting, is the single most important determinant of your comfort. It determines whether you are going to continue commuting, or not! If done well, you will find yourself wondering why everyone else is not bike-commuting! If not done well, you’ll be huffing and puffing, changing clothes at the destination, showering at work, or some other nonsense!
Of course, nowadays. with e-bikes, e-scooters and e-skates, it has gotten far easier. It is not as much of an issue as it used to be, unless if you pedal as well.

The Bike

This is a personal choice, of course. If you don’t have a bike already, don’t buy a new one; used would be a better choice, so long as it’s a well-functioning bike that’s not very heavy or bulky. A hybrid bike would do for most people. If your commute is a long distance, then folding bikes + multi-mode would be a better option. If you’re just starting, then don’t over-spend; as emphasized elsewhere, _ease_ into this. A road bike (i.e. light-weight, racing bike) would be uncomfortable for most people. A cruiser would be too heavy and bulky. A cargo bike would be best for families/kids, but an electric motor will be called for. A mountain bike is too heavy, bulky and slow; you’d sweat a lot! A folding bike is a great option, but see below.

Folding Bikes

This is a great option for commuting. It allows you to multi-mode, and is light- and small-enough to be unobtrusive into your life and work. You should be able to take it into your work-place, so theft won’t be a concern during that time.
But, folders are like laptops: higher-priced than desktops, more finicky/delicate/vulnerable, and pricier to repair, with their parts not being generic. They’re fantastic for commuting, but your appetite may expand beyond them after a few years.
In my experience, the Brompton is the single best option in folders, by far! Simply, they have the best folding design, which makes it indispensable to multi-mode commuting. Unfortunately, it is far too over-priced in North America, especially in Canada. Still, it’s IIRC cheaper than most, if not all, ebikes! (N.B. the last time I tried it in snow, which was 15+ years ago, its hub-gear had trouble with sub-zero temperatures.) The basic model was only 3-speed, which is actually great: it forces you to take a break from pedalling, thus coasting periodically! 🙂
Frankly, I would not bother with most/all other folding designs. Not if you’re multi-moding.

Hybrid Bikes

A good, all-around choice for commuting. Upright position, the tyres are not too fat or knobby, nor are they too hard+thin. The bike is not a heavy beast, and it is easy to add racks, panniers and what-not as needed.
Why would you not want fat tyres? Too slow, though they _are_ comfy!
Why would you not want thin tyres? Too uncomfortable, despite being fast.
Why would you not want knobby tyres? Too slow. Their greater traction is perfect for downhill, single-track, off-road, mountain-biking though.
Why would you not want hard tyres? Too uncomfortable, despite being fast.
Why would you not want soft tyres? Too slow, and very vulnerable to punctures.

Confusing? Hybrids are your answer. They strike the perfect balance.

Cargo Bikes

Popular with families. Too much for a single person, even if shopping for groceries after work. Families use them to take the kids to school, shops etc. As I’ve said elsewhere, they are too heavy for the task, and are particularly vulnerable to theft. Still, they’re more fun than a car, and will be even better when, inevitably, manufacturers make lighter ones.

Road Bikes

Unsuitable for commuting, except for the hardcore. If you’re new to bike-commuting, or to bikes, this is not the option you should seek. If, on the other hand, you’re a natural roadie, then you won’t be reading this article anyway! 🙂
Cons: non-upright position; hard, skinny tyres make for an uncomfortable ride; ought to wear gloves when riding, and likely padded-shorts.
Pros: fast and light. Highly efficient. A joy to ride if you know what you’re doing.

Mountain Bikes

No.
It’s in the name! Ignore all the people riding their big-box-store suspension-bikes in cities.
Fat, knobby tyres are not for cities, unless if you’re dealing with ice and snow.

Single-Gear, or Fixie

They _can_ be cheap, and they’re certainly light.
But, fixies are for only the hardcore.
Single-gear is more common, but I’d not at all recommend them for commuting. A mismatched uphill, and you could be struggling; a mismatched downhill, and you’d waste time by coasting excessively. It really depends upon the gearing you installed on the bike. Again, this is not for the average commuter.

Recumbents

Surely, you jest! How far is your commute? And how/where are you going to park it?

On a serious note, hand-operated trikes and the like _are_ used by those who need them.

Multi-Mode Commuting

Also known as sensible commuting.
To illustrate by example: You live in a suburb, but work in downtown; you bike to the suburban train/bus/metro/LRT/whatever, take your bike onto the latter; when arrived in downtown, you bike to your office/shop/destination/whatever.
In other words, long distances are covered by other means; short ones by bike.
Hardcore types will peck you into biking the whole way, and others will whittle away at you by gnawing repeatedly, “Wouldn’t it be easier by _car_? Then you could run other errands after work! Isn’t it too cold? Isn’t it too slow?”. But, ignore the former, and watch the health-issues of the latter in old age.

Gear Shifting

Most people have trouble with shifting gears!
I expect that there are videos on youtube for teaching you how to do this. My suggestion would be to practise in a park or empty parking-lot, aiming for the gear that provides just the right amount of resistance (not too hard, and not too loose) for the slope/flat you happen to be on at a given moment. And don’t worry about the front gears, for now; leave that on easy, then just focus on changing the rear one. After a while, it’ll become muscle-memory.
Alternatively, ebikes are an option. And there is even automatic transmission for bikes!

Repairs

The most frequent problem is flats! The softer you keep your tyres, the more likely that an inner tube will get punctured. Personally, I use a very efficient bicycle-pump, so that I’d never postpone inflating the tyres. Without that, pumping would be a hassle, resulting in my postponing it to ‘the next time’, which occasionally leads to a flat and its larger hassles!
What happens if you find a flat tyre, first thing in the morning, as you’re about to head to work? There is no easy solution to this. You’d need a plan B: a second bike, public transit, a car, e-scooter etc. Frankly, I’m too lazy to be arsed to check my bike every night! …As if!

Other than that, a tune-up at the local bike shop is a good idea–at least twice a year, if you ride regularly. Simply, the bike rides better afterwards! But do beware of larger shops which bundle their service-levels (Bronze, Silver, blah blah): Not only are they up-selling things you don’t need, the poor mechanic will now be back-logged with a large queue of unnecessary checks, on a lot of bikes, causing you to wait even longer for your bike!

Plan B

As hinted-at earlier, you ought to have a plan B, if you end up bike-commuting regularly. An e-scooter would be a good idea: You’ll likely use it not only as a back-up, it also offers different usage scenarios.
Unlike a car–which is a catch-all tool, whether you’re going to the office or to camping–you can have multiple tools. For less than the price of a set of winter tyres, you can have an additional tool, for different purposes! You can have a folding e-scooter for when you don’t feel like pedalling, or when you want to multi-mode at a time when the local metro doesn’t allow bikes on.

Accessories

Bag

The main accessory is for carrying your stuff.
If you’re just starting, a backpack should do. Nothing big; just enough for whatever you need to carry–lunch, spare clothes, etc.
Soon thereafter, you ought to change to something better.
A messenger bag would be an improvement, since it can leave your back free to breathe. (Backpacks result in a sweaty back, even if you’re not exerting yourself much. Simply, the don’t allow air circulation.) But, they’ll periodically slide over to one side of your body, so you’ll need to push them back!
Panniers are the best option, suitable for when you’re sure that you’re going to carry on cycling. They’d need a rear rack on your bike. One should suffice for most people. If you need more room, I hope that it’d be for groceries, not for a change of clothes: Most people should not need to change, or shower, at the destination; if you do, then you may be doing it wrong!
Lately, it’s become popular here, in Vancouver, to use dry sacs. It’s unnecessary overkill. If you do spend hours outside, or there is a heavy downpour, then a liner would suffice. Admittedly, clear, plastic bags of a suitable size are surprisingly hard to find. If I can’t find thick ones, I nest multiple ones into each other. Unlike the delicate dry sacs (yes, there are rugged ones), they’re cheap, and easier to repair (if you don’t want to generate waste by tossing them). And they’re much more configurable.

Disc Brakes

Arguably not an accessory, but I have no better place to put this info: Disc brakes are not necessary. Plain caliper brakes suffice for riding in rain. And they are cheaper, and easier to maintain.
Disc brakes cost more, and are much more difficult to maintain: They require periodic cleaning, and ‘bleeding’, and are much more difficult to adjust, let alone install.
“But they stop better in rain!” No, they don’t. I’ve not had such trouble with caliper brakes since the Eighties! Your bike’s probably too old; get alloy rims, and better brake-pads (if not better caliper brakes).

Lights

Definitely crucial.
There are lots of takes on this. Mine is that the reason why there are lots of takes on this is because of the outdated laws governing cycling!
You see, the laws that demand that bicycles have lights are not for the cyclist to become visible; they are for the path ahead (of him/her/per) to become lit!
Do they think that this is the horse-and-buggy/carriage era, with potholes in the cobblestones? Or is it the usual carcentric mentality, thinking ‘Well, bicycles are now legally considered _vehicles_, and proper vehicles have headlights, and so bicycles must have headlights!’?
Talk about deckchairs on the Titanic! The single largest threat to cyclists, the most lethal object that could come onto the path of a bicycle, is the automobile–a living-room on wheels, with a person inside with less than 100% command of his/her/per surroundings. Add to this a little bit of rain, in the dark of the return commute, and every single droplet of water on its windows turns into a bicycle headlight to be ignored–and that’s if the car is not approaching the intersection from your left/right side, with your light being even less visible.
The outdated law results in cyclists pointing their lights forward, thinking that it’s best, instead of pointing at what needs to become visible: Their own presence!
Then round up the cattle onto bike paths, and the lights (each more powerful than the next, in the futile hope of making the rider more visible to cars) blind the oncoming cyclists.

It is the cyclist that has to be made visible, not per path forward.

My current approach is to point a light forward, for compliance, and mount another, pointed at my torso! In addition, I wear a reflective vest.
Reflective straps on wrists are very useful, but I custom-make mine, to allow air circulation onto my forearms when I’m wearing rain gear.
Reflective straps on ankles could augment, but they stop air flow into my pants, when it’s raining.

Rain

If you’re just starting bicycle-commuting, don’t do rainy days.
Leave that for the next year.

Rain is a very lengthy topic! But it really has to do with only/mainly layering. In Bicycle commuting, managing your layers makes all the difference between taking on rainy days, and not. The choice of shell is not nearly as important, especially now that there are many clones of Gore-Tex available.

Snow

As with rain, layering is crucial here. But, surface conditions and ambient temperature are much more so.

While a casual ride on a pleasant, snowy day, in a park or some such, is easy enough, daily commutes are a different animal altogether. It is one thing to go for a brief ride in perfect, fluffy snow, it is another to head out on a daily basis, no matter the conditions, on a specific route, to arrive at work on-time!

At least here in Canada, this requires extensive experience. You have to have mastered your layering (or at least have become comfortably skilled), and daily riding in cold rain, plus masterful control of your bike.
Of course, as always, there is a sensible short-cut as well: Just do comfortable days, leaving the harsher days to the following year(s)!
More practically, though, a lot of experience is needed.

(This is a very lengthy topic. I will write a page on bike commuting in snow.)