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I used to run 5-8 miles per day, with some various days I'd increase just to push myself. It got to the point where running anything in my usual range was easy.

I actually miss running. Stopped when I became so busy because I was working a time-demanding job, started a family, etc. Had such little free time that I spent what few moments I had just chilling. Now that I've dropped weight, I want to get back into running, but it was more fun before when it was so easy and I could run the 5-8 miles without hardly breaking a sweat (now, I feel like I look like I'm going to die while running).

Hood to Coast was a fun event - ran it one year. After I found out where the proceeds of the event really go, I became jaded and haven't run it since.
 
Did you slowly transition to them (as I've heard some people recommend, running maybe just a mile at first) or just throw them on and go out and run 5 miles?

Sorry, didn't see this, yeah, started off slowly, as bb30 said below. I'd go quarter mile or so, around the block, then stop at my house and switch shoes and continue my run. Then after like 3 runs of that, went 2 blocks, mile, etc.
 

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