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

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

“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.

*  *  *

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?



Published on 08.20.12
  • “Creating concepts”, “thought-framework” … I feel these are perhaps an under-emphasized area within entrepreneurship / leadership. People are believing creatures and operate according to the frameworks they have. It’s not just about knowing what to do, but to be able to communicate an fresh operative paradigm, convincingly, to others… phil majors ftw! :)

  • David

    “Be your own boss, do it from anywhere, and make a lot of money” great words Dan! Today I cancelled my job contract and I’m free man after December! So I hope these words will be true for me and not these ones: “Find new boss, work from different office and be happy with whatever they pay you!” :)

  • “if I could just move to Thailand my life would be better.”

    It’s easy to say that when you lived in San Diego lol

  • Andrew

    Thanks for introducing me to Donald Pollack, who I hadn’t heard of before. I find stories like these and people like him truly inspiring. People often make excuses for why they can’t accomplish certain goals (myself included). Then you hear about a guy like this and it makes you say to yourself, “If someone at his age can start a completely new career, especially one as competitive as writing, then what legitimate excuses do I really have for not making my dreams a reality.” It just goes to show you that it is never to late to create the life you want.

  • Dan, thanks for highlighting Donald Pollack, who I also hadn’t heard of before. I also gravitate toward stories like this – they’re exactly the types of stories that I want to share on A Congruent Life (www.acongruentlife.net).

  • That idea of linchpin habits is great. There’s a whole host of transfer benefits that accompany stuff like that. Same goes for working out, stopping smoking, eating healthier, waking up early, etc. In fact, in my experience, creating good habits and overcoming bad habits almost always create unexpected side benefits.

    There’s always the thought “If I can do that, what else can I do?”

  • I’ve noticed that when I get up early and am on a regular workout schedule, I’m easily twice as productive. No doubt about it. I’ve changed my habits and seen results. Thanks for this killer post!

  • Tim Bonner

    Thanks for sharing the information on Donald Pollack. I’d not heard of him before.

    It’s remarkable the way he turned the direction his life was going around. An inspiration for all of us.

  • Agree about getting an education, whether its apprenticeship or university or a collection of online courses from iTunes and Coursera. This is especially effective when you have an end in mind, because you can identify the courses that move you toward the end, rather than whatever courses the program requires. Best strategy: find a mentor to guide you through the courses to choose the right ones, and immediately apply the learning to something, whether its a job, a non profit, or your own startup. In five years this will become a standard, but you can get five years ahead of everyone else.

  • Dan

    word I can dig that!

  • Dan

    Cheers Tim. I love these turn-around stories. I think I’m still holding out hope that I can turn it around for myself! :D

  • Dan

    Agreed John! I love playing chess with my own brain like that. You are a boss at this stuff.

  • Dan

    Cheers Ben anytime!

  • Dan

    Cheers Andy your new venture wasn’t on my radar! I just jumped on the launch list.

  • Dan

    yeah man totally. I love the simplicity of the whole thing, also the poetry of him seeing his father do something that he didn’t want for himself, and then he (punchline) started working….

  • Dan

    if your implication is that San Diego is an insanely cool city, I agree sir!! :)

  • Dan

    Best of luck to you David!!!

  • Dan

    haha we are starting to assert ourselves in the world!

  • mattjohncanty

    Hey Dan little off topic but whens that book coming out? I think it will be a huge success and I for one would like to get my hands on it! love the way you think about life and business in general. By the way I feel blessed to have started my journey so young unlike Donald. I started my first business when I was 20 years old and now i’m here in The Philippines jamming away on some cool stuff while most people I know are stuck in a job back home. I may not be a millionaire but at times I already feel like one.

  • Dan

    Hey Matt thanks for that! Book is planned to come out by year end but could be finished way earlier. I really appreciate the support there and feel the same way you do RE: millionaire. We are lucky guys to do what we do.

  • Great article. Love to hear inspirational stories of off the beaten track people sometimes who followed their own beat. Keep these coming. It is refreshing.


  • Dan

    Hey Turner thanks for the support!

  • Some Guy

    Not writing new articles for the Blog anymore?

    Be careful, people will forget quickly about you if you don’t update regularily :D

  • Dan

    gotta get back on the horse! :)

  • Nice post about MBA

  • One of my favorites, have to create yourself, and those linchpin habits are hugely important if they’re negative influencers.

  • Just one question. At some point, don’t folks become so successful that they really can do it from anywhere on not just cheaper places? Where is the lifestylers who lives in Paris for example?

  • Dan


  • Dan

    Absolutely, it’s just a cash thing. When a business runs out of cash, it’s over. So one of the best strategies for staying in biz is to radically reduce expenses, and the “lifestyle” crowd are finding ways to do that and put a long term time investment into their businesses by moving to inexpensive places. But yea, if you’ve got big time cash it’s sort of a moot point.

  • Nuno Poço

    Hi Dan,
    Today while searching for posts about working remotely, i found this blog and this post caught my eye.
    I recently developed an idea that there are more jobs that could be remote and simply aren’t due to attrition.
    My background is in sales and so I found interesting to gather info on the possibility of remote sales and ended up creating this article on LinkedIn: https://www.linkedin.com/pulse/making-case-remote-inside-sales-nuno-po%C3%A7o
    Could you share your opinion on it?
    Do you see sales as a possible do-it-from-anywhere and make-a-lot-of-money job?

  • Sonny Tee

    I live in Paris … this is your answer 5 years later … I bought my Home for CASH and live here FULL TIME ..

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