I think you should just go for it.
I did a similar thing a couple of years ago, going from an entirely sedentary lifestyle to an 18 mile one way commute.

I do have a couple of recommendations:
1. Try the route at a weekend first.
2. If possible, commute once a week until your body acclimatises.

I'm in the just do it camp, but leave yourself 2x the time you think you are going to take. You're only 50 once!

The flats will be easy, try to ride as fast as possible on those, but make sure you have enough power left for the hills. In percentage, how steep are the hills there?

I agree with just do it (especially if you drive part way) though don't punish yourself. When I started (though shorter trip than yours) I would actually stop twice and get off the bike to drink some water. It only took a few minutes to rest up and be ready to get going again. Don't hesitate to take breaks. Within a few weeks you won't need the break.

I disagree with this. Don't ride as fast as possible. Just keep a steady pace and save your energy for the hills!

And later with more experience on your route you'll know how fast you can really go on the flats.

Besides, you don't HAVE TO ride the bike each day of the week when you start out.

When I first started out riding I only rode for 2 days a week. My legs would be on fire at 10 miles, but still had to go 5 more. It turned out getting easier in just a few weeks and when I got me a better bike last month, I would only need 55 minutes for 15 miles anymore. It gets easier, you get faster. Last week I rode 3 days in a row, and again on Saturday. Makes 120 miles a week. Had a fun ride today again since I had a day off, and again took a 12 mile ride. You just can't help it, you get addicted. REALLY addicted

I drive part way every day. I have different parking spots that make my bike anywhere from 5 to 11 miles. Right now I'm doing 7 each way.

Park four or five miles from work and try that. I'll bet you move further away within a week.

Wow, this place is GREAT! Thanks for the continuing advice.

So I'm thinking tomorrow I drive the bike into town and ride from there, making it about a 10 mile commute and knocking out one killer hill. Depending on how that goes, I'll do it again one more day this week, either Thursday or Friday, and maybe the whole 14 miles (unless Tomorrow tells me otherwise). Then go for 2 or 3 days per week thereafter for a while. We'll see ...

I hear what you guys are saying about food and aqua. Question, how much should I eat BEFORE the morning ride? I'll have just woken up, with nothing in my stomach since dinner the evening before. Should I have some fruit? Cereal? Maybe just some juice? Basically, is it better to start the ride on a semi-empty stomache then stock up at work? Eat before the ride? Split breakfast between before and after?

About eating: I don't usually eat a tremendous amount before a ride, but I will eat during a ride. But that's how my body works. You might be different. I would say to start by eating a healthy breakfast, but don't stuff yourself, and see how you feel during the ride. If I have a heavy, greasy breakfast before a ride, my body makes me pay! (But luckily, you'll only make a mistake like that once.)

Take a few things to munch on as you go. You will learn which foods your body processes well while riding, and this really does differ from person to person. For example: lots of folks like power bars and stuff like that. If I eat one of those, it feels like a softball lodged in my stomach. I react well to peanut butter sandwiches and light cereal bars, and beef jerky on very long distance rides. So take it slowly, listen to your body, and learn from the first few weeks. In no time, you'll have an on-the-bike nutrition program dialed in.

As always, stay plenty hydrated too. If you find yourself getting thirsty, start drinking more frequently --- well, that's my policy and so far so good.

Unless you take off and try the round trip on day one. Build up to it a bit with some training rides around the neighborhood. It will only take a couple weeks until the 14 miles isn't scary. Then take a saturday or sunday and ride in to work, take a break and ride home. At that point you'll prove to yourself that you CAN do it and you'll be good for daily round tripping.

By the way. Don't worry about the rain, you are going to be wet. Accept that and you don't care anymore.

Have fun.

I eat a peice of toast with peanut butter and drink a glass of water before heading out (my morning routine from getting out of bed to riding away is 30 minutes). Sometimes I'll add a banana to that but if I eat much more before riding it bothers me. OTOH, I can easily do 15 miles on an empty stomach (and often do) but it is easier for me to eat before I leave and it's enough to hold me till lunch.

14 miles by bike is longer than you think....when I started, I took two weeks and increased how far i rode by a mile on the way out until I was easily doing half of my expected daily commute. Then I went for it, of course I'm only doing 14 miles (roughly) total.

Either way it is your rear!

For breakfast, I have a package (just one) of instant oatmeal. YMMV as I only go about 7 miles. As for water, I don't take any for anything less than 10 miles (flat).

It's stupid. Ride on the weekends until you can do a 30 mile ride without a long (more than a half hour) break. You could just keep trying to do both halves of your commute at once. When you can do that you're ready for the show.

14 miles is too much to jump into if you're not already in good condition.

When I started cycling I did a few short 10 mile rides then I did a 55 mile ride. I had someone's wheel to follow for the whole ride and a big break in the middle. I thought I was going to die by mile 50 and I was 22 at the time.
I was in decent condition at the time.

Eating: I like to eat after rides. I can *usually* run on fumes for dozens of miles and I enjoy the food so much more if I eat it after I ride. I must admit, I often ride to eat .

DO IT. but first buy a really expensive bike so that you'd hate yourself if you didn't ride it. It's easy to not ride a junker.

I am not 50 (only 45) and last year I was busy over analyzing all of my options on a 23 mile one way commute...

I took the bike to work and did a couple 4-7 mile rides at lunch a couple times. The next week
I found a spot about half way and rode in two days a week for awhile and worked out what I needed and didn't need in the pack. I then drove to the bottom of my hill and rode the last 18 miles to work. Later in the summer I got too lazy to load up the bike into my truck and just rode the whole way.

Each time I increased the miles it took a couple days to have my body adjust. My goal for this year is to be able to go on consecutive days and figure out how to haul the zillion pound laptop to/from work.

Why are you doing it? Lots of opinions on here and some may agree or disagree with each other. For me: I ride because it is good for my health, I enjoy the social part of clubs, my wife and I can do it together, a great way to see places, it relaxes me, and so on. Most of all I ride because I enjoy it. If you do this make it enjoyable. If it doesn't relax you and you work too hard at it you won't do it. Take your time and build up to it.

First, I'll give you my stats. Just turned 39. 10 miles each way. Hills both ways, but more uphill on the way home. Rode all of last winter, and not at all (two times) this winter. My schedule is brutal this semester.

My advice would have been (in case you start before you read this) to do the ride on a weekend first. Even 1/2 way and back to see how you do. You will suffer after the first day of the full ride if it has been awhile since you ridden (trust me- done it). If you have to take a day or two or three off after the first one, take it! Don't push yourself if your body says "NO!".

But if you work into it, you will be fine. It really does get better after you get used to it. You will amaze yourself after a little while.

As for eating; you have to find out what you like. I personally don't eat anything in the morning before I go. I usually try to drink a cup of water. I can drink more when I get to work.

Good luck to you! Keep us updated on your progress.

If my post made no sense, I am sick... LOL

That desk-jockey scenario is ideal IMHO.

I sort of ease into my day once I get past the ride, the locking up of the bike, the toweling off, the change of clothes, the quick intake of 8 to 16 oz of water, the draining of some V-8 for salt and the munching on a peanut butter or almond butter on hemp bread sandwhich. After all that, I usually play around on BF and daydream about my ride home. Before you know it...it's time for lunch.

Enjoy

Yeah, just do it.

One thing I do sometimes, when I've been off the bike for a while, is one-way commutes for a week or two. Ride to work on Monday, leave the bike at work Monday night. Take the train to work Tuesday, ride the bike home Tuesday night. It lets me get my lax muscles back in shape before hitting them with the entire 26-mile round trip.

Just starting out and out of shape, 1.5h sounds to little. Two hours sounds more like it. But it really depends a lot on the kind of bike that you have. I can be twice as fast on the good road bike than on the x-mart mountain bike.

You'll need a bike odometer if you don't have one already. Calculate how slow can you be allowed to go for the time you have. For 14Mi in 1.5H you could not go slower than 9.3Mph. And that does not take into account stops at traffic lights and rest stops. When I started biking, anything above 7Mph was pretty hard.

And the often overlooked detail... is your saddle comfortable enough for a 14mi/2h trip?

+1

Go for it. Your body will tell you pretty quickly whether you can handle it. If you find it's too much at the start, drive part of the way or don't try to cycle every day.

I was already cycling quite a bit when I started commuting, but still had to adjust to the routine of riding every day. Plus my commute route is very hilly. One thing I learned is that you can't ride hard every day. Most days I ride at a very moderate pace and that keeps my legs fresh enough to ride to work most days. Af first, I tried to keep a fast pace every day and got burned out pretty quickly.

Also, be safe. Get some good lights, front and rear, as well as brightly colored jerseys and jackets. I see too many occasional commuters dressed like ninjas and they probably get scared off of commuting from close calls with drivers who don't see them.

I'm another person voting "go for it"

I got on my bike at 325 pounds, started with a couple of 2-mile neighborhood jaunts on my dept store cruiser. One day I thought I'd try to bike to a bus stop 7 miles away to increase my threshold. Missed the bus, still had to get to work, ended up going the full 16 miles on my dept store cruiser, with some major hills and an interstate bridge crossing to boot.

Getting there won't be the hard part. You may find your fatigue setting in for the way home. Plan a different ride home for the first week or two.

But 14 miles where the majority of it is flat is certainly do-able if a 300+ lb asthmatic can handle it and have FUN doing it - I don't imagine your age being an impediment.

Why not on your day off try the ride one way and see how feel. If you need call for a pick up for the ride home.