Which is "easier"?

I just read some people's blogs about losing 60, 100, 140 pounds, etc. For me, I've never been in the same boat. The most overweight I've been is about 20-30 pounds, depending on what my "ideal" weight is. I've had doctors tell me to lose a little weight or to exercise more, but it's never been a life or death sort of thing (or overwhelming risk of diabetes, blood pressure, etc. sort of thing).

So, I started wondering: for people who are considered obese, is it "easier" to jump right in and change a lot of habits and take off the pounds because there are more of them? Or is it "easier" for someone my size/health because I'm already closer to reaching the goal?

What do people think?