I committed my November to writing a 50,000-word novel inspired by the NaNoWriMo project.

I’m a very self-conscious writer. Writing is a puzzle where the pieces—story, grammar, flow, context, and voice—shift when I add or change a word. If I follow the rules, I can be a decent writer, but I don’t want to spend my time simply telling decent stories. This month was about conquering voices of doubt in my head…and writing a story.

At the end of the month, I emerged with 50,000 words and a first draft of a novel. How did I temporarily fight my writing demons? I set a goal to write 2,000 words everyday. On November 8th, 15th, 19th, 21st, and 28th I didn’t write a single word. I never wrote more than 3,000 words in a day.

I’m sifting through my first edits of the book now. I’m still a self-conscious writer, but one armed with a few more tools that might help others along the way:

— I Did it My Way: You people out in the world expect a lot from me, so I ignored all of you when I wrote this first draft. I decided to focus on process rather than outcome. Something that resonates with me might have an impact on others. It’s also easier to edit a story I like.

Prison Building: I created a set structure for my writing practice. Writing was my first task each day. If I only wrote when I felt like it, I would have managed about six days of writing in November.

What if?: This was my first project where I put a couple of characters into a world and asked the question, “what would happen if?” Instead of an outlined plan for this book, I wrote through the story. I experimented like a scientist—the story was a vague hypothesis fueled by confusion and exploration.

—  Relief in Writing: Each word I put down on paper was one less word swirling around my head. Relieving myself of that burden gave me some peace of mind throughout the rest of the day.

No Free Samples:  I decided to stop giving the story away. People’s feedback started to shape the way I wrote when I tried to explain a detailed plot summary.

—  Those Stories with Intention: I wish I had addressed my intention at the beginning. My creativity supported my fears because I never stated my goal beyond “write 50,000 words.” I think it’s important to understand what type of work you want to create—it gives the mind a direction. My book currently lacks the humor and wonder I try to bring to my work.

—  Edit later: First drafts are terrible. Creating is about refining. That’s not something I can do at close range. I wrote a rambling version of my novel and walked away. Only now, as I begin to read my draft, can I see the size and scope of the story I created.

Newsletter: From Denver to Chicago to New York and Now What?

Live from New York…

Friends, Romans, Coloradans, lend me your ears:

Welcome to my first newsletter. Why am I writing a newsletter in 2015? Apparently, newsletters are still very popular. Social media hasn’t killed the email and people spend a lot of time reading emails (at work). There’s a Bernie Sanders joke here somewhere, but Larry David beat me to it.

Now, you may think I am going to start spamming your mailbox with emails, but since it’s taken me almost two months to write this first one, I think you’ll be okay.

I want to take you back to August 22, when I first tried to compose this newsletter on a flight to Chicago. I ended up spending the whole flight writing what turned into my first Blog Post: In All Seriousness, the reason I joined Experience Institute.  Then, I spent the next couple of days worrying about what Experience Institute would be like before it began.

Luckily, I met a lot of great people, especially my classmates, and learned a few things about myself. The biggest leap I made came courtesy of Eric Staples, who did a workshop on personal motivation. Eric has a system of archetypes that allowed me to realize that we all make decisions based on our feelings. In Eric’s words, I’m a heart person. I found out that my goal in the world is to be a caregiver to others. I want to achieve this by being a magician.  A magician, from Eric’s presentation, “creates transformation; changes how we see the world, presents new realities; delights with imagination and cleverness.”

Eric’s talk led me to my goal for the year. I want to create places of inspiration, humor and wonder through storytelling.

With this new understanding, I moved again, this time to New York City for an apprenticeship. For ten days, I made the commute from my apartment near Columbia in a nice part of Harlem to an apprenticeship in Soho with the hope of telling stories. Unfortunately, the apprenticeship wasn’t what I had hoped for and I wasn’t the best fit for the position. To put it simply, it was a mutual breakup.

My second blog was all about the lessons I learned from the apprenticeship.

So, now I’m in New York, listening to a song written in a Chelsea hotel by Bob Dylan “Vision’s of Johanna,” planning my next moves. Now that we’re all caught up, I’ll try and figure out what I’m doing with this newsletter before next time.

Thank you for your support and time,

Derek Kessinger



My first apprenticeship was not the right fit for me and it ended, on mutual terms, two weeks after it started.

I learned a lot from the experience and will use that knowledge moving forward. I want to share my thoughts on picking the right apprenticeship. These principles can apply to any new partnership, consulting position, internship or job.

1. Put Yourself First: A host company is only bringing you into their network if they believe you’ll benefit their long-term success. You’re the only person that can put your learning goals and needs first. You want to understand what assets both sides bring to the table.

2. Be Specific About Your Needs: Communicate the things you need in this relationship. If they’re unwilling to address your needs initially, that likely won’t change.

3. Your Supervisor is More Important Than Your Company: Figure out the relationship with your supervisor heading into the apprenticeship. A boss’ interest in an employee’s work is perhaps the most important part of a job. Make sure your supervisor wants to guide you through the apprenticeship.

4. Understand the Daily Process: Ask the following questions. What’s the office culture like? Do people interact with fellow co-workers frequently? What are the expectations for my time? What are the working hours? How will I receive feedback? How much autonomy will I have?

5. Contact Other People in the Company: This is a trick I learned from my friends who work in local television news—if a news director is a tyrant, reporters will tell you. Ask around to make sure that your boss is not a tyrant.

6. Trust Your Instincts: If something doesn’t feel right in the interview process, press for answers about your concerns. If they don’t have the answers, make sure you are okay with that going in.

7. Ask Why They’re Interested in You: Verify that your potential host company does its initial research on you. You want them to value what you bring to the company and make sure that they aren’t just hoping to fill a random position.

8. Create Personal Time: If you’re burned out, stressed and exhausted, then you will not be in a mind frame to learn a lot.

9. Change Course (Quickly): If the situation is not working for you, be willing to speak up early and make a plan with your supervisor. If it’s still a bad situation, be willing to leave. Remember to “put yourself first.”

10. Don’t Force an Apprenticeship: You have a strong community of support, and you can always employ your own curiosity. Don’t take something just because you’re afraid of being left behind. There are lot of teachers in the world and a lot of ways to gain experience.