“Be Your Own Boss, Do It From Anywhere, and Make a Lot of Money”

“It’s difficult to watch— other people’s successes.” – Donald Pollock in The Devil All the Time

This guy became a writer when he was 45. He’s now 56 and has published 2 books. He said that during 32 years of working at a paper mill he didn’t think about being a writer. That all changed when he watched his father retire from that same plant.

Donald resolved to be a writer because he assumed:

During the interview they laughed at that last point, but I wouldn’t. I identify with Donald’s story because being an artist who wants their work to be seen by others is very similar to being an entrepreneur. As an artist, your team doesn’t scale and the distribution channels are for the most part apparent, so you focus your energy on work that scales (writing, painting, songs), and ideas that get passed on by your audience.

Toward the end of the interview, Donald was asked if his self image changed since he became a published author, and he said it really started changing over a decade before he got published. Here’s the sequence:

  • He stopped drinking alcohol. Things like alcohol, health, being a part of destructive relationships and so on often have the potential of being “lynchpin” habits. If you can address them directly and aggressively, a broad range of other things can fall into place.
  • He became a responsible employee and started taking his work seriously. A job is a great barometer for your ability to go out, work hard, and drag it home. If you aren’t excelling in your work as an employee, and you think it’s going to be easier as an entrepreneur, you could be wrong. It’s not so dissimilar from thinking that if I could just move to Thailand my life would be better.
  • He got an education. Robert’s story involves him going to a university, probably in part subsidized by the union he was a part of. Nowadays, I would not say to go back to some state university if what you want to do is grow a business that helps you earn from anywhere. If you go to university to learn this stuff, you’ll be just like everyone else there— clueless on how to get it done. Get an apprenticeship with somebody doing exactly what it is you think you want to do. Then you should work as hard as you can for them.
  • He copied successful people who had done exaclty what it is he wanted to do. I love this part. Donald said that he didn’t learn to write during his college education (go figure), instead he started typing out— verbatim— his favorite stories from authors like Hemmingway, Flannery O’conner, and others. Who says we don’t have the opportunity to learn directly from the best and brightest? He did this for a few years.
  • His highest expecations always remained with the work. Donald told his wife that if he could just write one short story that was good, he would consider himself a successful writer. I like this point. I like the feeling of finding work you value in and off itself. For me, that’s earning $1,000 a month by writing and helping others. When I decided that’s all I needed to be successful, my career took a major turn.

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I gravitate to stories like this one because my lifestyle is similar. Many people who meet me in person are surprised to find out that I don’t spend my days barking into phone receivers (only my mornings ;). I live a writer’s life. I wake up most mornings and walk to a coffee shop, where I gather the notes I made the day before. Almost every day I sit down I write 1,000 words (often more). So little of it gets published at this blog because I’m still learning how to write. My stuff ends up all over the place:

  • On this blog.
  • As outlines and key concepts for podcasts.
  • As emails to my friends, our staff, and to my business partner.
  • As documents to help my friends and fellow entreprenuers.
  • As posts or responses in the DC.
  • As actionable ideas and concepts in my head (which very often get communicated to my friends and team members).
  • As a lump of un-published raw material that will form my first book.

“In this dark and wounded society, writing can give you the pleasures of the woodpecker, of hollowing out a hole in a tree where you can build your nest and say, ‘This is my niche, this is where I live now, this is where I belong.’ And the niche may be small and dark, but at last you will finally know what you are doing.” – Anne Lamott

That bit about creating concepts— that’s the most fun for me. I don’t do it often, but every once in a while I’ll stumble on a thought-framework that helps our business or one of our students change their future.

And it’s a weird thing to actually believe about writing. That if you are smart about it, and work very hard at it, you can be your own boss, you can do it from anywhere, and you can make a lot of money.

What’s more likely: that it isn’t true or that most people aren’t willing to work hard enough to make it happen?