I’m trying to avoid duplicating the excellent advice already given. But picking up on the goal thing. Obviously there’s the sportive type route already mentioned. You might want to consider time trialling or cyclo cross racing or even BOTH. I suspect the danger of having just one event to aim for like a sportive, could cause you to hang up your wheels after and undo all your hard work. Unless you are particularly motivated or have a number of sportives lined up. Sportives are also pretty expensive comparatively. Whereas having a series of regular events to participate in would maintain the impetus and enthusiasm. You’ll be able to see real tangible, quantifiable gains. Cycling is one of those sports you just keep chipping away at. It never gets easier you just go quicker!!
Both time-trialling and cyclo cross are blooming marvellous. They are both very accessible, in the case of testing super cheap and both disciplines are incredibly friendly. Best of all perhaps is that they are perfect for any level of cyclist, unlike some other disciplines like road racing where if you haven’t got the fitness = BOOM straight out the back and race over. If you have children and they’re up for it, you could easily turn it into a family passtime!!
Time trialling is a race against the clock over a set pre-defined distance/ course. Most cycling clubs will run their own events most weeks from April - March. They are advertised through your local club - you can find your local club through the British Cycling website. These tend to be ‘closed’ events open to club members only. With my club you can join the club for a few quid, buy a TT pass for £20 which gives you ‘free’ access to all their own TT’s (3 per weeks) OR you can PAYG. Entry is £1 per event if PAYG. Sign up on the line. They have a league and other competitions like a club 10 championships annually. Anyway. You can watch your times improve and compare yourself to others (if you do wish). We get all abilities turning up, from the local pros to youth riders, to 70/80 year olds. All shapes and sizes. All abilities. All sorts of bikes!! I’ve turned up to race on my heavy winter bike, with rack, mudguards, etc. Nobody cares. I’ve also turned up in a skinsuit, TT helmet and best bike (I don’t own a TT bike). There’s a ‘sport’ category for those not on TT bikes.
Cycling Time-Trials (the national governing body) also list hundreds of events. Take a peak on their website and you’ll likely find local ones and it’ll explain how to enter. Again very cheap! As a rule of thumb if I can’t ride to it from home or work to the start/finish I won’t do it. That’s how many local events there are.
In terms of cyclo cross. You’ll have a local league. It’s raced from September - Jan/ Feb. On a Saturday or Sunday. Check out British Cycling and Cyclo Cross. You’ll race on a set out off road circuit which you ride as many laps of in a given time (usually an hour). There’ll likely be obstacles to negotiate like planks to jump over or sand to ride through. Don’t worry about this!! The bigger leagues have separate kids, women’s, youth, vet men and senior men’s races. Because you are riding off road (races are usually held on school playing fields or at country parks) and it’s an autumn / winter discipline courses tend to be muddy. So it’s an awesome way of improving your bike handling skills and confidence all directly transferable to your road riding. When I started I couldn’t mount/ dismount quickly, I practiced a lot and now I can leap on and off during the race to negotiate the planks and other obstacles. Because it’s such a friendly open to all discipline there’ll always be others with minimal skills, but it really isn’t an issue. Again this is the beauty of cyclo cross racing, it’s for all. You’ll get pros and the very serious show up down to complete beginners. I did my first ever races on a hybrid!! Now I have two specific cyclo cross bikes. But they were a worthy investment as it’s my ‘hobby.’ Again you see all ages, shapes and sizes, fitness abilities and types of bike there. The only downside is because of its popularity it’s become quite expensive. Although that’s more my local league - others are cheaper and more relaxed. So I have to be a league member (cost involved - although I get free membership through my club), then I have to pre-enter and pay in advance for races. It’s normally about 15 per race 😫 and annoying if you come down with a cold or something as there’s no refund. You used to be able to just enter on the line. Other leagues are much smaller though and don’t have this policy of pre-entry only. I guess if you enter a sportive (never done one!) you have to cough up a large sum in advance with no refund. If you turn out to be really good at cross, there’s prize money. Not enough to retire on but I’ve covered my race entry and diesel.
I love the camaraderie and community with both disciplines and I too am an anti-social bugger! Typical cyclist really. I like to ride in a big bunch, but not really say anything and love spending hours flogging myself on my own on the road.
Having a coach is definitely a good idea if you want to maximise the time to train you have available and you have a specific goal eg a sportive, or a cross season. Goals can be anything vague or specific eg you want to knock out a century (100miles) on your own this summer or knock 2 mins off your Personal Best on a particular TT course. I don’t think it’s remotely necessary for just riding for pleasure though. It depends on the type of person you are, but riding to a plan can utterly suck the fun and enjoyment out of riding a bike. It can also be an added source of stress in your life as you aren’t ‘switching off’ whilst you ride, but trying to constantly ride at a particular intensity. That really depends on your personality and reasons for cycling though!!
One thing to really remember with cycling is that no matter what discipline you do, it’s predominantly an endurance sport. So the vast majority of your riding tends to be (or should be!!) at a fairly steady pace. Building cycling fitness is like building a pyramid or house. You need super deep, wide, strong foundations (lots of long steady rides) in order to then start going quicker (building the rest of it). Prior to having DS I road raced for several years - I spent the majority of the winter doing long steady paced rides. I didn’t start doing harder paced work until February ish. I didn’t do my speed work until March/ April just before I started my first race of the season. Throughout the season the bulk of my riding was at this steady endurance pace or ‘zone 2’ (based on heart rate zones).
Happy peddling.