Should we do it?

We've always had this family dream of traveling across the country together. Jared and I want to share our favorite places in Boston and NYC with our kids. We want to experience new places together. We're pretty good at road trips and love the adventure and together-time they offer - and the kids are really good in the car.

I've got to be out in New Hampshire to conduct a Power of Moms Retreat Oct 21-22.  Jared has a flexible schedule as he looks for the right new job. We both can do our work just about anywhere as long as we have our laptops and the internet. So I got this idea that maybe we should ALL head out to New England in October and Jared agreed that if he didn't have a job by the time I would need to buy a plane ticket for the Retreat to get a good fare, we should hop in the car and make the trek across the country.

Well, I'd need to buy a ticket in the next few days if I'm going to fly out for the Retreat so now's the time to make the decision.  Should we drive that 35 hours each way?  

The kids would have to miss some school but they have a few days off for fall break during the time we'd be gone and I've always embraced my parents' philosophy - "never let schooling get in the way of your education."  And we'd have plenty of car time to do the kids' school work that their teachers could give us.

We don't really have extra money right now but when we do have money, Jared's generally working at a pretty non-flexible job and wouldn't be available to go with us. Plus this would be a business trip so we could expense a lot of things and we're very good at keeping things cheap on road trips - we eat from a cooler in the car and just need a basic motel room or a corner of someone's living room where we can roll out our sleeping bags for the night. Plus we've had requests to do a Retreat in Chicago so we could do that on the way or on the way back and that would generate more revenue.  Maybe we could even do a mini-Retreat in NYC...

We might have to miss some basketball games for Eliza and the twins - we just signed them up to play starting in mid October.

It might be hard sometimes trying to get work done on the road while helping kids with homework and keeping everyone happy in the car. I do have quite a few big projects I'm in the middle of for Power of Moms.  But I got tons of work done during our last road trip all over the Pacific Northwest (love that you can create a "hot spot" with your phone and use the internet almost anywhere now) and Jared and I could trade off driving and working and doing stuff with the kids (plus they like time to read or watch a movie and don't need attention from one of us all the time).

The kids are at great ages for a road trip. They are all old enough to be good in the car and really get and remember what we'd be visiting. They are young enough to think trips like this are super cool - they don't yet worry about missing friends and they still think family time is a treat.

So, what do you think?  What would you do if you were us?