I will encourage you! :)
I’m quite anxious, I cycle as my main form of transport, and I really love it. The sense of freedom and never needing to wait for a bus/train or look for a parking spot is the best.
I do hear you on the fear of cars, because cycling around cars can be genuinely risky, especially in places where the cycling infrastructure is not great. So I don’t want to dismiss that caution but at the same time, we don’t want to exaggerate the dangers.
As far as not feeling like you’re in control of the bike … hmm, it could just be a familiarity thing, but could it also be that the bikes you’ve been using aren’t the best style or size for you? For example, I always find mountain bikes super uncomfortable. Do you prefer a twisting or a clicking gear shift mechanism? To be further forward or more upright in your posture? How straight or curved do the handlebars need to be to feel comfortable? What kind of saddle works best? And, of course, are the bike’s proportions appropriate for your body? Maybe the person you mentioned could help you experiment with trying out some different types of bikes and seeing if any of them make you feel more secure?
There are many cycling promotion/advocacy groups, and I would suggest trying to find one that offers some tips or courses on defensive cycling. I think that might make you feel a lot more confident getting on the roads if you know that you’re controlling what you can in terms of your own safety. Also, remember you can always pull over and step onto the footpath/sidewalk if you feel freaked out!
In terms of very practical stuff I can think of (apologies if anything seems overly obvious) …
Personally, I always wear a well-fitting helmet — I know there’s a lot of debate on this but the risks and benefits shake out in favour for me.
Check up on the exact road rules for cycling (e.g. how you are supposed to handle left turns, if you ride/drive on the right), and for how motorists are supposed to interact with cyclists, in your area. They almost certainly won’t be followed all the time, but it’s good to get a sense at least of what other road users are expecting.
In general, just err on the side of caution. Don’t rush. Leave yourself extra time so you don’t feel pressured to rush. Check your own blind spots carefully before braking, turning or overtaking. If you’re crossing or turning across an even somewhat busy street, just take the extra time to stop and look both ways.
Don’t speed up to get through an orange light, and be aware of situations where cars might be speeding up to get through or complete their turn before the lights change and might not see you. Again, better to hang back than charge through even if you should have right of way.
Be extra careful when passing cars or *especially* larger vehicles that are turning right when you’re going straight (again, assuming right-hand driving direction here).
Be extra careful when passing parked cars — leave plenty of room so you don’t get a door opened onto you (been there, it hurt!).
Also, if you live somewhere where the cycling infrastructure is such that there’s no separate bike lane or the bike lane is largely obstructed by parked cars, don’t be afraid to ‘occupy’ the middle of the ‘car’ lane so that cars can see you better, rather than weaving in and out around the parked cars. This is an example of defensive riding. If the road is really busy with parked cars and there’s only one lane, such that cars going the same way as you can’t safely overtake you, it’s courteous (and probably also safer for you) to pull over when safe and let those cars pass you.
If you’re riding in the dark or weather with poor visibility, do deck yourself and your bike out in lights, reflectors, high vis etc. Honestly, more is more — it really does make a big difference to drivers being able to see you. You can actually get some quite cool/fashionable options nowadays!
If you want to listen to music or podcasts, consider keeping the earbud out of the ear closest to traffic, so you can still hear the cars etc as well (or be aware that you need to be extra *extra* careful with visual checks if you’re missing the audio cues).
Hills and sweatiness can definitely be a challenge, if you’re riding for transport rather than exercise — the ideal is being able to shower and change at your destination (or at least a little freshen up with deodorant and change of underwear, maybe). Otherwise, I would recommend trying to wear light and loose clothing and going a little slower. I’ve never tried an e-bike, but I imagine it would help quite a bit :)
I personally also *strongly* prefer to have a basket on my bike, because I usually need to carry stuff and I really hate the sweaty back from wearing backpacks. Makes riding way more comfortable, for me at least!
Start small and build up your confidence with rides on more familiar streets and quieter places and times before you tackle rush hour or busier roads. There are actually some apps/services that will map routes specifically for cycling where you can try to optimise for most bike paths/quietest streets/fewest hills, rather than the most direct route. I think one is called Komoot. The cycling navigation option in Apple Maps is also pretty good for me.
If you don’t already know your routes by heart, you can get nifty little accessories that go on your handlebars and hold your phone so that you can use GPS navigation. I think it’s great because you can just use your peripheral vision or flick your eyes down for a second when you’re stopped at a traffic light — way safer than having your phone in your hand, and I would argue also safer than needing to scan around with your head looking for street signs, landmarks etc while you’re riding. Even easier if you have an earbud in with a voice narrating the route as well.
Well, that’s all I can think of, but I really hope that you do get out on your bike and have a great time! Wishing you the best!
