First, awesome site! I just found it today, so I’m totally stoked to get more ideas from you. As of a few hours ago, I honestly didn’t know how to put a name to what I had been thinking. I tend to be a pretty big picture kind of guy, and I find difficulty in sorting everything out and focusing on one thing. That being said, my absolute *biggest* challenge is focusing. It’s no secret that I have a lot of interests, and I take pride in the fact that no two jobs I’ve had could be related… not even remotely. I have difficulty knowing how much is too much, and I fear that because I cannot give an elevator speech to friends/family, it sounds a bit… crazy.

I’m in the DC area, so I’m fortunate to have a rather large network of people to bounce ideas off of, but I don’t think any of them have ever mentioned “lifestyle design.” I’m intrigued by the possibilities and would definitely like to learn more!

Thanks again for offering this… it’s totally stellar!

In service,
Stephen

My biggest challenge right now is confidence 1) that I know enough to get started on my business plans and 2) that even if I fail this time around I can pick myself back up and start fresh. I’ve got the outline of a report/small ebook I want to write, but I’ve got some kind of mental block on starting the actual writing.

The other thing that occurs to me now is my desire to remain somewhat quietly in the background, while still being successful online. I have no desire to be a major player in online marketing with hundreds of thousands of people on my email list. The downsides of that life are too large for me to want it. So I think I’m pulling myself in several directions at once – I want to be successful and I want to be somewhat anonymous.

My biggest challenge is that my current family direction seems to contradict my vision of a nomadic lifestyle. While my wife and I were never truly “white picket fence” people, we have cherished the last 18 months of raising our daughter around a great group of friends. We love having a nice home and inviting guests over to share it with us. We enjoy growing a garden and having pets and everything else that comes with a home base.

It’s difficult to picture all this alongside a vision of traveling the world with family in tow, working in coffee shops to support us. While that sense of adventure thrills us, we know we would miss our home and everything (and everyone) that comes along with it. So many nomads talk about how they ditched their mortgage and possessions and took to the road. While that is definitely the easiest way to go, I’m not sure we could do it. So, not being able to afford both a mortgage and travel, we opt for a house and frequent 1-2 week trips.

I’d love for someone with an outside point of view to ask me the hard questions about what I truly want in life. Or maybe if I want both, can it be done?

Great idea, awesome services. I’m really enjoying following you progress from taking 6 months off to being a strong voice, coach and entrepreneur in the lifestyle design realm. I’m not really putting my hat in the ring for a strategy session as I’ve engaged in enough of them over the years past. Success is a matter of trial and error…most people just don’t trial…I hope you push 5 lucky individuals to always follow their ideas and try them out. Our ideas are like a box of damp matches….one will catch flame if we go through the whole box.