Self-esteem? Tell you what, I started 2 years ago with huffing and puffing for 3 miles one way commute on practically flat which drained me by end of week... (okay, I was really sedentary for over a decade...) I think you are doing much better than me by far I actually really like the profile of your ride. If you sweat, and you will with that hill, you can take shower and have nice beer/water/soda at end of ride at home... no big deal. You probably won't sweat at all going to work no matter the temp... being presentable! I think you got wonderful commute for getting fit, saving time, and manageable as you get better. Pretty soon, you won't be happy with that 5 miles and start figuring detours around to lengthen it