Interesting thread. I'm 6'3.5, 42 years old.
2011, in March, I hit 248. Too much. I started weighing myself every time I used the master bathroom. I cut volume of food, but I didn't change the diet -- just focused on 2,000-2,500 calories a day, and one nice meal a day. I love food, I love cooking, and I like wine. It took about 3 months to not be hungry any more, but it worked. I would also replace about half of the additional calories burned exercising.
By the late summer I was in the mid 220s, and figured that was pretty good. I was much stronger on the bike and had a lot more stamina. I started seeing abs. I finished a hilly century in late September in 6 hours flat; my goal had been 7 hours.
I added a core workout 1-2 times a week. Exercise ball, free weights, lots of planks and pushups and pullups. I would do planks, front and side, during commercials when I watched TV at night. I also started trying to run 10 miles a week in addition to the cycling, and signed up for a 10-mile running race to motivate myself. By the time I got to the race in April 2012, I was 212. I ran 10 miles in a respectable group, finished in 91 minutes. No knee pain. Felt amazing, and very proud.
I was very ill as a child, and very asthmatic. I never thought I could run.
I'm now about 205, and my waist is down from a tight 39 to a true 35. I am not trying to lose any more, but I am trying to keep up a high level of fitness. If more weight comes off, so be it. To celebrate my birthday yesterday, I ran 5 miles in 44 minutes, then did a core workout and went to work. Oh, I was on a business trip; got home at midnight.
The most amazing thing is not the weight loss. It's my stamina. I can function well on 2-3 hours of sleep. I am much, much stronger. And very little hurts, ever. It's been over a year since I have injured myself exercising.
The key, I think, is in the relationship with food. I love it. Always have -- it is a great pleasure to me. I could not bear the diet described above with mostly cabbage and beans. But you can love food for its taste and quality and all the rituals that come with preparation and eating, and not get too caught up in the volume.
On plateaus -- yup. I have had several: 232, 220, 212 and now around 205. The other thing is that my weight varies quite a bit -- whether I've been good or not on volume, exercise, etc.