First, thank you for given me motivation enough to post my first reply to slashdot in years!
The Past:
I could have written this very "ask slashdot" 2 years ago. I was around 30yrs old, weighed over 230 pounds. I have always thought my health to be "good", but I'm in a high-risk category for heart disease, and had been gaining weight steadily since late college. When my wife told me we were implementing family+=1, I became (for the first time) aware that my health was very important to the health of my family, and decided I should try to do something about it.
The Present:
I weigh about 180lbs. I'm in the best shape of my life (in the cardiovascular sense) though I probably wouldn't break my personal bench press records I had in high school. But then again, I can do 50 push-ups, which I guarantee I was never able to do in high school!
With similar thinking to the user who wrote this ask /., the breakthrough (for me) was to be able to exercise in my home. Career and personal obligations as well as, sure...personal insecurity, made me very unlikely to succeed in a fitness center environment. So, I bit the bullet and bought a midrange ($1500) elliptical trainer. I found this ideal for me because:
1. High calorie burning aerobic workout.
2. Fairly natural motion, very little fatigue (but I should mention it is crucial to try many different models from various manufacturers...I tested about a dozen and found all but a few to be awkward).
3. Privacy. Less important for me now.
4. Convienience (somedays, 5am is the only time, others, 8pm). I don't want to go to make a long drive to a gym (for me) on icy roads just to workout.
5. zone-out-ability. I listen to the radio, watch TV, or sometimes, just think about my life. Try doing that in a gym with activity all over the place. I literally "lose myself" during my 50 minute workout, and making the time go by quickly and painlessly is probably the most important reason it has worked for me.
At first, I started with 3-4 30 minute workouts a week (okay, at "very first" they were 20 minutes). At my peak, I was doing 5 50-60 minute workouts a week (that was insane!). Now, I do 3-4 50 minute workouts a week. My machine tells me, based on my weight, that I burn about 900 calories. I started this when I got to around 175 pounds (which I thought was as small as I needed to be) and have bounced back ever so slightly (but generally maintain 180) at this current level.
I have also been incorporating crunches/push ups/ and 5 or 6 sets of free weights a few times a week, just to get a little balance. The pushups and crunches definately have toned my chest and abs, and the increased muscle there makes me look a lot better without a shirt than I did even 5 pounds less ago. Speaking of that, the most positive unanticipated side effect was becoming more attractive to the opposite sex...I might be in a monogamous relationship, but getting a flirtatious look from an attractive, young woman stranger can turn a bad day into a great day!
The Future:
I've been starting to try to incorporate other things. On days where its nice, I might trade an elliptical session with a 40 minute, 5 mile jog. Bad knees run in my family, so I'll probably never try to run a marathon. Might try biking. I have also begun to try some yoga to help with flexibility and back pain issues I've had for many years...just started that a few days ago, as a matter of fact.
Anyway, this is what worked for me. I hope whatever you do, you stick to it. Once you see some results, you won't find that very difficult to do.