I did full-time telecommuting for 1.5 years. I have mixed feelings on it.
For starters, I like the idea of working remotely. I don't like actually doing it. I am not a self-motivated person & do not have a lot of self-discipline; I need the pressure of working around people & having deadlines in order to get stuff done. I also need the routine of actually getting up & going to work. I wish it was different, but that's just how I'm wired. I can just as easily sleep in til noon on Saturday, not shower, and go nowhere as I can go to a work site & have to have a more structured routine.
The biggest thing I learned from it was exactly that: I am a person who requires structure in order to be functional & to be useful to society. I don't think I can ever retire because I will probably die, haha. I am a total loaf without structure. With structure, I am great. I can build my routine around structure...I'll exercise in the morning, I'll cook & eat well, I'll shower & get ready for the day, I'll keep things clean. Without that pressure, I don't do well. I thought it would be a cakewalk, but for me, it wasn't.
There are people who do well with it, and there are also jobs that make it work. My cousin telecommutes for a major airline & handles reservations over the phone & computer. Hours are flexible & iirc the pay is decent for not being a super skilled job, like $12 or $14 an hour, which doesn't sound that high, but when you're not driving your car, sitting in traffic, buying fast food because you can cook at home, spending money on a work-accessible wardrobe, it's not that bad.
I have a buddy who does remote support & programming for a specialized software product. He is a very self-structured person. He lives by his routine & can make it work because he is able to live by the structure he chooses for his day. imo that's a rare talent. Not many people can provide consistent, constant structure for themselves. It's a great dream, in theory, but in practice, nearly everyone I know has found out that they don't do well with it. Most human beings do their best work around other human beings...for the pressure, for the social aspect, for helping people, for bouncing ideas off other people, etc. There's an old saying that goes "one person can do one thing, a team can do anything"...there's an awful lot of magic to working in collaboration with other people in meatspace.
Two things to think about are family & distractions. It's very difficult to work remotely if you have a family because hey, you're home! You're not "really" working, right? And like Carson said, you can never really escape...work IS home. Distractions are also a big problem. I have ADHD. If I have a work computer in front of me & a video game system next to me, it's awfully tempting to just put in 20 minutes of gaming time, which turns into 14 hours of gaming time. Sounds ridiculous, but if you weren't a super organized student growing up, remember back to the weekends of your youth & how much homework you really got done during them.
I've bounced between telecommuting, working a steady job full-time, and being a freelance contractor. Right now I'm back to being a freelance contractor. I get a little more flexibility in my day, but I also am required to actually show up to places to install stuff, make deliveries, troubleshooting, and so on. Keeps me more involved in my work since I'm doing the planning for the day, but also doing the work for the day, and I'm also seeing people on a daily basis.
The lure of telecommuting is strong because hey, who wouldn't want to work at home in their pajamas? The reality is a lot different, at least for most people. I thought I hated working with people until I started working from home, then I realized I hated working at crappy jobs, for crappy bosses, and having to deal with the public. Working at cool jobs with great bosses & colleagues & not having to deal with the public is an entirely different animal.
Best advice I can give you is to think long & hard about how you really behave under work-at-home circumstances & to honestly examine your track record of getting stuff done at home. And if you really want to do it, then definitely give it a shot, at least to get it out of your system. I telecommuted for work & also did a few semesters of college remotely & ended up hating both. I hated doing school remotely partly because I need those in-person deadlines and partly because a lot of school topics are better explained by a human being than a book. For example, math made no sense to me when I was reading from a textbook; I NEEDED a professor to explain the concepts.
If you do end up getting a job where you can work remotely, my suggestions are:
1. As soon as you wake up, shower, get dressed, and get your shoes on. I'm not kidding. Actually put your shoes on. Getting yourself ready for the day & ready for anything puts you in a way more productive mood. Again, there are some people who can sit around in their pajamas all day & still be productive, but I am not one of them & most people I know who telecommute do this because then if they do need to run some errands or whatever, they are ready to go. It's basically the same idea as putting on a uniform, whether it's a suit for work or workout clothes for the gym or whatever.
2. Have a dedicated workspace, and preferably, a dedicated room to work in. Have all of your tools setup: printer, office supplies, computer with UPS (or laptop), and so on. Have spare ink & whatever else you need so you're not running out to get supplies all the time.
3. Create a power routine. Same idea as a regular routine, but amped up a bit to the point where you clearly define what time you're going to work, what time you'll take breaks & lunch, and so on. People who are disciplined will get their work done regardless & can play for half the day & still do their work by the end of the day, so it depends on how you roll. For me, the more structure the better. It's easy to take two-hour lunches & not really get stuff done, haha.
4. Get your family onboard, if you have anyone at home during the day, so they don't bug you during your defined working hours. I know some guys who simply cannot work at home because they get the kids shoveled on them while the wife takes a break, which isn't a good environment to let you get your work done.
5. If you really need the extra help, create a timesheet broken down into 15-minute intervals. Keep track of what you do. It will let you see where you are actually spending your time all day. Again, very easy to get distracted at home.
TL;DR: Worked from home for a year & a half. Glad I did it for the experience & to get it out of my system, but would never do it again. A minority of people who have excellent self-discipline can be successful at it. If you're going to try it, set some ground rules like a defined workspace, a routine, etc.