Nowadays, I am growing a bike between my legs. Carrying heavy objects, switching between bikes and ride positions, rushing through traffic, gasping for air up on a narrow mountain passes. I ride ! When something is off, I feel it. A screw is not tight enough, the seatpost slid down 0.05mm, the saddle bag strap came loose, a break cable is rusty or the chain needs some lube.
I find, that the most significant feeling comes from a single speed bike. When you lube it up, whommm, it goes way better. Immediately it is more ridable, more pedal-able and no noise or link blockage is present. On geared bikes however, this is not always the case. The grit build up between the links can act like grease and it might not give out any noise. Your shifting might mess around only for two sprockets, what is not that disturbing if you rode as a messenger, you just shrug it off.
When more than 2 sprockets got skipped, when dropping a chain often enough, when not going down to the last little one, well, lubrication is necessary. You might have to even change chain. A badly lubed up non-functional chain can damage, not only your cassette and front rings, but your jockey wheels and your frame too. Yes, when dropping a chain, or when badly changing gear, it can hit your BB or chain stay, chipping of paint and carbon. If you had a front derailer, it can rub a whole on it.
Weather of course is a biggy, but environment too. The age of the chain and the quality level too. Of course the type of use, the weight of the rider, the frequency, the intensity and so on.
Weather
Rain, mud, dirt, snow, dry, sandy, salty. You need different lubrication.
Wet weather lubes are necessary, if rode every single day in rain. However, they are mostly oil based and makes everything very messy ! Also hard to clean it up ! Often people prefer to use WD40 in wet weather. Why ? It is cheap, easy to apply, easy to clean ! It doesn’t perform half as well as a proper oil based lube, but when have to apply, clean, reapply every single day, people still use it.
When rains, snows or just very damp, I lube up every single day with Green Oil. Wipe it off with no chemicals, just a piece of textile.
When dry, depending on the chain’s characteristics, I lube up twice / 3 times a week, basically every 300km.
Environment
Riding in the city, in the mountains, on dirt roads or single tracks. Different kind of dirt has different effect on your chains link-mobility and link-health. Natural road dust might build up from passing through mountain cols, but it does not nearly as bad of a damage, than constant breakdust, fumes, oil and chemical filled water spills from constant city riding.
For my messenger bike in dry weather, I lube up every second day, what is 200 to 220km.
For my training bike, if went out 2-3 times a week, I lube up once a month. Each 800km. I only train in dry weather. I ride for work too much in rain, so it is just not fun getting out on the bike again in hammering rain. I still lace up the running shoes though !
On my MTB, for dry weather, I might ride 2-3 times a month, so I lube up not more often than once a month, but more likely once every 2months.
I use Squirt !
Shim, Sram, Yaban, KMC, KCNC, Wipperman, Taya, Izumi ?
I tried all of them, but I just stick to Shim and Sram. I find that you must go mid-high end, if you wanted already a great factory lubrication. Also, for rust resistance. 105 or under does just not cut it. For dry weather, they are okay, but two rainy days and they are orange ! So XT/Ultegra or Force/Red. I find the factory lube of sram chains are slightly more resistant and smoother feeling for longer. If paired up a Force cassette with a Red chain, that is a perfect combination for me personally. I don’t buy a Red cassette ! Either ways I have the change it after the same exact time, like the Force ! Also these mid-high end chains hold and handle bike lubes better, than low-end ones.
I lube the first time on a chain after 500km in dry weather. Squirt !
After 2 or 3 days in rain, on a new chain, I start lubing up with Green.
Intensity and frequency factor
Bigger riders, putting out more watts, smaller riders with extremely high cadence, electric bikes ? Lube more often. Riding every single day the same bike ? Lube up each 300km. Riding 3 times a week dry ? Lube up each 500km. Riding easy chill, flats, no rain, not a lot of gear changes, maybe each 1000km. Sprinting, climbing, descending, using all your gears and all intensities, big gear or high cadence ? You might clean off and lube up every single morning !
How to lube up !
I use a degreasing chain cleaner “machine” time to time. It works, but I feel that after a deep cleaning like this, the chain is never the same. It needs lubrication way more often afterwards. I simply use Citrus cleaner . If I really had to clean fast I might go with the Speed degreaser. That is great for the cassette too. I never use water, wet cloth, kaercher or anything to clean off chain.
On my training bike, I lube properly. Pin by pin, top and bottom. Run through 100 turns in both directions. Wait for an hour, run another 100. Wipe it off. I keep the bike inside, so cold doesn’t affect the penetration.
On my work bike, I don’t care. Run the lube on the top, next time on the bottom. Done in 20sec. Why ? It doesn’t make any difference ! I am out so much, got rain and dirt, every single week. Adding 1 week to the chain’s life, is not a measure ! Summer, it holds up for 4 to 5 months, winter, 2months top, but often only 1 ! After 12hours of messenger shift, you arrive home, the last thing you will do, is to dry your bike ! I just go down to the basement, wipe of the road grit and clean the rims. Bedtime ! Also, normally, when chain is changed, cassette is changed ! Not gonna happen ! I am working to gain money, not to spend. I change cassette twice a year on my work bike, once a year on my training bike, and basically every two years on my MTB and E-Bike. I ride for pleasure and not doing any crazy shit on them.
Confused ?
One easy tip. Have two bikes ! One for wet, one for dry. Use a white wax on the dry one, every second day. I really like Squirt, but go with anything. White Lightning is great too. Use an oil based on the wet one, every single day. Problems solved !
PS: I tried at least 20 different lubes and never really found any better than Squirt. I have to state though that never got the chance yet to go with the TOP 3 of Molten Speed wax, Silca or Smoove.
Want to geek out ?
https://bike.bikegremlin.com/1986/bicycle-chain-lubricants-explained/
https://road.cc/content/feature/227757-seven-best-chain-lubes-should-you-go-wet-or-dry-lube
https://www.cyclist.co.uk/buying-guides/1773/the-cyclist-guide-to-chain-lubricants
https://www.velonews.com/2017/09/bikes-and-tech/the-who-what-why-of-chain-lubes_448772
Boundless Runner 
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