In college football, the practice of scheduling cream puffs is both much reviled and much practiced. Football powers pay smaller schools to act as sacrificial lambs.
Seeking out weaker competitors is a contemptible trait in football, but it's good strategy when it comes to business. There's no BCS formula to give you extra credit for tackling tougher opponents.
Some of this principle is apparent in the practice of market segmentation--finding a niche you can dominate. But where segmentation is about customers, this is about selecting a competitive set where you can shine.
When I was a student at HBS, one of the companies that visited campus was Progressive Insurance. When asked the secret of their success, the managers there admitted, "Frankly, not that many smart people want to go into the car insurance business. Nothing we do is that advanced, but it's more advanced than anyone else in the industry."
In my own life, I've had a lot of success with my writing simply because most other business writing is that bad. When I was a Creative Writing major at Stanford, I struggled to get any of my stories or poems published. Today, I can get my articles published in some of the top outlets in the world.
It's not that my writing is that much better; I used to spend upwards of 40 hours writing and editing each of my stories. Today, I usually don't bother with revisions, and can write a piece in less that two hours. The difference? The competition. The average PR flack or business executive is much weaker competition than a dedicated fiction writer.
Want to shine? Find a competition you can win.