Thanks for the reply, Steve! Nice to meet you.
a 2.5-4 hr commute to the day job (an hour, fifteen each way with no traffic, which never happens) in Chicago each each day
I think you should stop working on your product and solve this issue first. Can you get into or start a car/vanpool? Can you move? Is there a public transit option for much of the commute? Can you work from home some number of days per week? Find a different job? Right now it seems all you can do safely on your commute is listen to podcasts or use a voice recorder to talk out ideas for your product, neither of which is the most efficient use of your time. Even being able to sit on a cramped bus with paper and pencil would help you make progress. I had a 1-hour commute each way by bus for 4 years, and it could be very productive, even those times I didn’t have room for a laptop.
I’ve been lucky; just as I was in negotiations with my employer to allow me to work from home more often, Jason Freid and DHH released their book Remote. I bought two copies, one for me and one for the boss.
Luckily, a combination of my heartfelt, candid discussions with my boss, and the compelling support from the contents of the book, I’ve been given permission to (A) work from home two to three days per week (as weather and project timetables dictate), and (B) I got to write our company’s remote work policy.
I’m second in command in this 20-person web dev consultancy, VP Business Solutions, so him allowing me to work from home was huge. It basically means he now has a senior manager who he physically only sees two to three days per week. It was a huge shift in my boss’ mental paradigm on the matter, so for that I’m thankful.
We use Hipchat to mimic the old watercool chats, a brand new RingCentral phone system that seamlessly routes calls from clients no matter where I am, Google Hangouts for facetime and staff meetings, and GoToMeeting for screen sharing.
So far, this arrangement has yielded many extra hours of freedom per week that I’ve been able to throw at my business.