I have gotten into the habit of reaching out to people who I admire. What I love about your exercise is that you are suggesting for us to have conversations with people who might be dead.. I have been thinking about your approach for a couple of days but I must say that I am far too practical for me to be ok with being hypothetical.
Thanks to the internet it's fairly easy to find people we can learn from. When I wrote my first book I approached freelancers who I admired for their careers. That really made a huge difference in my first year of freelancing.
Now with the second book, I've been trying to figure out how to turn my freelance career into a creative business while remaining the freedom freelancers have. Here are the people I've been talking to and who I've learned from:
I have approached all these women quite randomly and just asked them whether they would like to share their story with me. And they did! Transcribing and editing these interviews is really helpful for me to reflect on what they said. It's a long, exciting and simultaneusly a very painful process that makes me think about every single word they said at least millions of times.
I am actually really excited to publish what I have learned from them. I'm planning to go live on Kickstarter on the 4th of January. Nevertheless if I could choose anyone to mentor me it would be Tina Roth Eisenberg and Seth Godin. I approached Tina too unfortunately haven't heard back just yet.