Writing Plan: Going Pro

Eden Typewriter

About 2 weeks ago my friend Sonny bought me the book The War of Art:  by Steven Pressfield. It’s about the struggle to create. I read it in 3 days. It’s a short read and I already have started it over again. I’ve started writing a book about a month ago but have been struggling with consistency, inspiration, discipline, fear, and a million other things that Pressfield refers to as “Resistance.” In the intro there’s a section  titled “What I know”. This is what it says: “There’s a secret that real writers know that wannabe writers don’t, and the secret is this: It’s not the writing part that’s hard. What’s hard is sitting down to write.” I concur. So, while reading the book I put it down and scratched out the following plan.

Writing Plan – Going Pro

1. Find a professional writing coach – Do what they say. 

2. Buy and read my favorite authors* (buy one book at a time)

  • Philip Yancey
  • Steven Pressfield
  • Jon Krakaur

*These are authors who are not necessarily brilliant in their philosophy or background but who’s writing style and hard work have inspired me. Most of them I have read anything they publish from theology to experiences on Everest, to US Military scandals.

3. Be Inspired by classics for their content

  • Hugo, Dumas, Doestefosky, Dickens, Tolestoy, Twain, Chesterton

 4. Create a schedule – This was the hard one for me

  • 1 hour inspiration – reading (30 min classic / 30 min favorite author)
  • 3 hours perspiration – writing
  • Start at 9am
  • 6 days a week

5. Create the location

  • Clear the space (mostly all the crap on my desk and office)
  • Set it up – Buy a lamp & blanket

 6. Follow Rules

  • No computer/phone allowed in the room
  • Show up on time
  • One month trial
  • Share this plan immediately with Sonny & the kids
  • DO NOT leave the upstairs for the 4 hour block.

Some Tips:

  • The Resistance is a bitch and I am less focused on quality, quantity, or a million other variables/excuses that are outside of my control and just focusing on overcoming the things that keep me from productivity and creative risk taking.
  • For an entrepreneur freedom is defined as being your own boss. But, freeing yourself from the limitations of a regular job does not mean that you will automatically do your best work. You have to understand yourself and the nature constraints so that you can create the limitations that unleash your best work. This is why you would struggle if I asked you to write about your city but if I asked you the top 10 things about your city you would pound it out. Good restrictions are good.
  • Limit distractions but allow loops to be closed. I got rid of all internet because looking up on word can lead to voyeurizing high school friends on facebook. I keep at least 2 notebooks on my desk with me. One for to do lists and the other for ideas. If something strikes me and I want to close the loop I take 30 seconds and write it down so it doesn’t keep on distracting me.


This was written on the plan from Vegas on 2/25

I started this on Monday and faced the Resistance immediately. My desk was a mess so I got to my office at 8:55am and shoved everything outside my door. I didn’t let it stop me. Monday through Thursday fluctuated from feeling great to wanting to burn everything I had written but I’m ok with that. I did it. At one point I contemplated for 10-60 minutes the benefits of recording my voice and then transcribing but I think that was just to get out of writing since I’ve never considered that before or since in my entire life. Friday I was flying out around 5 pm so that made a good excuse to take the day off but I didn’t. That was a victory. Saturday I will be taking off for Shabbat. Sunday, Monday, and Tuesday I was working for 12+ hours each day so did not write so I pick it up again Wed morning. I’m actually kind of looking forward to it. I have a monthly board meeting at noon but instead of flaking on the writing I’m going to wake up early and get my 4 hours in before hand. Also I have my first writing lesson tomorrow which I’m excited about. We worked out a sweet trade of writing lessons for Financial Training. SWEEET! Thanks Rachel!



Met with my writing coach yesterday. It was awesome. She told me to start scrap the 40 or so pages I had written and start over. So that’s what I did this morning. Because I’m viewing this as a process of learning and personal development it really was not a waste although it did take a while to re-formulate and get momentum from a section that I had mentally moved on from.