Dear Future Experiencer

Dear Future Experiencer,

Here we cross paths on this journey. You are heading into the uncharted wilderness, and I am on the path home. As a fellow experiencer, I wanted to impart a few pieces of advice on the terrain ahead.

I cannot give you my map because the path I took is no longer available. This territory is always shifting. Even though I walked with care, I seemed to find uneven ground, dead ends and blind turns. When deciding the path you should take, trust your instincts.

Many people will try to tell you otherwise. A lot of people, on a different journey from yours, will try to give you their own map. Do not use it. Their advice will bring you frustration and take you wildly off course.

Appearances and first impressions need further investigation. A spot can look great from a distance and end up being nothing more than quicksand. Investigate all destinations ahead of time and do not ignore warning signs.

Ask questions to make sure each camp is the right fit for both sides. The person running the camp may be more talk than substance. They may ignore you and your growth for their own gain. If this happens, change directions. You must have difficult conversations and make decisions based on your own long-term goals.

You are on this journey to learn. Never lose sight of the goal. Sometimes no bridge will appear to cross a raging river below. It is natural to want to shut down in these moments, but take this time to learn something new. What can you learn on this side of the canyon as you search for the bridge?

The further into the wild you go, the more your body will want you to turn back and run. It will rebel. Your mind will be at odds with your will. You will feel crazy, lonely and destructive. Taking care of yourself takes willpower, but you need strength to finish this journey.

Do not forget to laugh. This is not that serious. The fate of the world does not rest on this journey. This is a journey you should enjoy. You should make fun of yourself. You should find ways to laugh with others. When the world seems to be turning against you, call it on its joke and laugh to the heavens. The journey is easier with some irreverence.

Just like the map of this journey, the map of success is always shifting. You will create blind spots if you do not vary the trails you travel searching for success. Some maps lead quickly to a solution, but perhaps less often to the right ones. The person who stops looking around cannot see the hidden poison ivy. The person eager to try a new way should be aware of the roaming wolves.

Do not lose your humility on this trail. Holding your head too high will cause you to miss the traps before you on the path. Confidence should come from within, not because others think you should be confident. A bird attempting to keep his head in the clouds must constantly flap its wings. A bird aware of its surroundings may glide in the current.

You will get through this year—one way or another. All roads lead to the end of this journey, but not to safety. This year will not solve your problems. It will cause you to ask more questions. A time will come for you to venture into the wilderness again. This journey will allow you to navigate with a quiet confidence in yourself.

All the best,


I Have Witness. I Have Documented

I wait for the time machine that will transport me back. Sometimes it takes me to the day I committed to Experience Institute last summer (Ei). It has transported me to the first day of Meetup to start Ei. I have found myself in November, on a random rainy day in New York.  Now it will take me to my first day in Seattle, where I am starting my final term with Ei.

Each time a mass shooting rockets through the media, I travel back in time.

Some days I wake up and fear checking my phone. What if something happened last night? This time, however, I woke disgruntled about my current living situation. I was having trouble finding a temporary place to live in Seattle. Sunday morning I woke up in a frat house. While it had no affiliation, the house was full of University of Washington bros living in a space far worse than anything I experienced in college.

On this Sunday, I checked my phone without reservation, and immediately saw the headline:

Attack on Orlando Nightclub, 50 Dead.

The time machine kicked in. I was taken back to the feeling of that night, July 20th, 2012, when the Aurora theater shooting rocked my world. A gunman murdered my friend Jessi among others. It was a night that split apart the world around me.

Here’s the thing about a random murder. Your brain can’t make sense of it. How can someone’s life be taken at an elementary school, a midnight premiere or a nightclub? How can someone pull the trigger on strangers? Your brain can’t categorize it—this is loss without explanation. So the thoughts ricochet around your brain until you feel disconnected from the world.

The first time I traveled back to that feeling—the void—was six months after Aurora. I was getting ready to take a college final when reports of Sandy Hook hit my phone. For me, the media part is important. I remember staying up all night watching coverage of the theater shooting before I found out about Jessi. So the pain grows through increased media attention or when it occurs close to home.

It makes me sad to think that I can’t feel every gun death, but how could I? There are thousands a year.

I am rocked every time. I felt despair at the first reports of a shooting at Arapahoe High School that happened when I was near the school in winter of 2013. I felt the pain when a white terrorist shot up the church in Charleston the day I accepted Ei’s offer last summer. I felt the pain as people in my profession, a news reporter and her cameraman, were murdered on-air when I started Ei last fall. I even felt it with the coverage of the terrorist attacks in France in November. There was San Bernandino, Colorado Springs, and Kalamazoo.

So yes, I felt Orlando. I felt like we failed Jessi. We failed the 12 who died in Aurora. We failed the more than 10,000 people who are murdered by guns in this country every year, excluding the astronomical suicide rates.

As Edmund Burke said, “The only thing necessary for the triumph of evil is for good men to do nothing.” We let the evil win again. We failed all of their memories by not stopping this attack.

I waited to turn off the coverage until President Obama gave his address. He delivered it with a kind of numbness everyone affected by gun violence can relate to. It comes when you feel unable to comprehend why more people don’t care enough about gun violence to stop it.

“This massacre is therefore a further reminder of how easy it is for someone to get their hands on a weapon that lets them shoot people in a school or a house of worship or a movie theater or a nightclub,” President Obama said. “We have to decide if that’s the kind of country we want to be. To actively do nothing is a decision as well.”

After his words, I turned off social media for the day. I knew the pain and hurt without reading about it. I knew the anger and futile arguments that would come. I didn’t want to see the hate spewed towards my friends who advocate for gun safety. I didn’t want to read the bigotry directed toward my Muslim and LGBT friends.

So I walked. I walked out of the frat house and down Greek Row to the University of Washington. I walked through parents arriving for graduation and down to the light rail. I rode it to Capitol Hill in Seattle.

I continued to walk. I walked to the Space Needle and Lake Washington and Pike Place Market. I noted the people smiling and playing. I listened to music and an audiobook and didn’t check the media.

Hours later, I took the light rail back to the University of Washington. As I walked through campus, I noticed all of the families posing for different pictures marking graduation day. Their joy was a refreshing reminder. I was so happy that they were taking the time to take these pictures. Even when the process was messy and unorganized, like so many families, I knew someday they would want to look back at these pictures.

I have documented my year in a lot of ways—in pictures and videos and conversations. I’ve documented my year in long walks and great books. I’ve documented this year as a quest to bring light to places that will never fully escape the darkness.

Each new city in my year comes with the same directive. Document the smiles. Witness the laughs. Prepare the time machine.

Term 2: The Chicago Experience


I build a lot of walls. I build walls made of strong moral beliefs. I build walls between the best parts and the worst parts of me. I build singularly-focused walls when hard work is required. I build walls for personal comfort. I build walls to make the world seem easier to manage.

Most of my walls fell down around me by the end of my second term of Experience Institute (Ei). After several weeks of sifting through opportunities, I began an apprenticeship with Ei in Chicago—balancing a complicated role as a student and a staff member. The term included team collaborating, strategic planning, marketing and video editing.

Continue Reading on Exposure… 

Newsletter: The Email Debt Forgiveness Day Newsletter

Email Debt Forgiveness Day (April 30th) is a holiday made for this newsletter. We all know that this newsletter has been as sporadic as a Colorado Rockies’ winning streak.

Events that happen with more regularity than this newsletter: Taylor Swift music videos, superhero movies, Tom Brady suspensions and me changing apartments.

Today, that doesn’t matter, because it’s EMAIL DEBT FORGIVENESS DAY.

All the details are here.

And if you’re not listening to the podcast, Reply All, PJ and Alex are the friends you always wished you had in half-hour increments. They tell interesting stories about the internet and work for Gimlet media, my dream company.

I even get a merit badge for this… No joke, listen to the episode, which includes a great love story and some heartbreaking emails.

Term 2

The highlights of the term have existed outside of my main work, video editing and copywriting. I’ve enjoyed conversations and brainstorming sessions with Victor, Eli, Aaron and the Ei team about the direction of different aspects of the organization. It’s also been great to be involved in interviews for next year’s Ei class.

Here’s my latest post about my year.

I’m still working out third term, but it’s hard to believe that I’m two-thirds of the way through this year.

The DK Chronicle

Since Leap Day, I have written a lot. I have posted on my website every weekday since the start of a project called DK Chronicle. The inspiration came from the Leap Kit and it’s pushed me to share personal pieces that make me uncomfortable.

The project will end on Friday, May 6th with my 50th post. I will have a final project to share at some point. This is not the end of me sharing my work, but the beginning. This is an area where I’m in my element and want to continue to create projects that interest me. I hope that my work will increase in scope and influence.

 Thanks for all of your support!

The Error in Justifying Your Work

Harvey began telling me what I should be doing with my life. I had known the guy less than five minutes and now he lectured me about how my mistaken approach. My attendance at this mixer was to support a friend, but seemed like another place where I needed to justify myself.

Harvey (not his real name) boasted about his own success. He told me about his nonprofit, how helpful he was to others, and how well his life was going. I listened as he shared his philosophy on life in great detail before he asked about me.

“I’m a writer and journalist. I’m at an alternative school called Experience Institute looking at different ways to tell stories.”

This was my two-sentence answer refined over 1,000 tellings. I iterated away from terms like “creative storyteller” and “alternative storytelling” to simply “writer and journalist.” Next, I explained to Harvey about designing my own education around apprenticeships.

“So what have your apprenticeships been? How are you going to do this in the real world?”

My apprenticeships, of course, have been a bit messy. For those just tuning in, I began at a startup in New York City that fell through. Then, I wrote a novel, but I am nowignoring the book because I don’t like the story. I’m currently working for Ei, helping them with the Leap Kit (another term I have to define for Harvey).

Once we get through this introduction, conversations of this type follow a general pattern. Harvey asked how I could do this in real life. Without letting me answer, he told me that I should think about marketing or copywriting. He was oblivious to the idea that I might have given my year some thought.

Harvey explained how I’m mistaken on the term storytelling and he had figured out my life for me. He repeated the mantra I’ve heard so often about how “everything is storytelling.” I bit my lip and nodded along politely.

Finally, I extricated myself from the conversation. I just told the next person who asked that I’m a journalist and work freelance—a fallback with short follow-up answers. I find myself in the same conversations over and over at these events:

What do you? What are you trying to do? How have I done something similar?

I worry about overexposure to other people’s feedback and opinions. Learning and making connections through discussion is important. However, the Harvey-type interactions are not about me, but about validating someone else. People eager to share ideas without considering me only adds to my burden of proof, rather than eases it.

This influences how I approach conversations. I try first to understand where the person is coming from and create a sense of empathy early. It turns out that not everyone needs my help. Giving unsolicited advice is a lot less valuable than trying to learn what the other person knows.

If I have helpful suggestions I add those later without challenging the person’s philosophy. Who am I to say what works in an always-evolving world?

I want to get to a place where my work speaks for itself. I’m not there yet, but I know I can’t get there by chasing the approval and ideas of everyone. I’ll work on my craft, continue my personal projects and learn where I can. My justification can come later.

How Will You Survive Experience Institute?

I can hear the concern when people ask me questions about Experience Institute. I understand why people worry how my year is going to turn out. They’re concerned about me being safe and finding a place to stay. They picture my path becoming derailed or people taking advantage of me. They cannot imagine surviving a year like mine. They’re imagining the following scenes:

I feel the apprenticeship is slipping away from me me. Instead of learning about storytelling, I’m dealing with an uncomfortable situation. My boss is demanding I deliver things that are outside of my current skillset, while ignoring my educated warnings about this path. Showing up everyday to this tension will not lead to long-term learning.

I’m sitting in an Airbnb room in a converted dermatologist’s office; the room is not what was advertised. I’m exhausted from moving, unsure what my next move is and afraid I will run out of options.

I’m lost in a big city. It’s raining and I can’t make my phone work because I got water in the case. I have no idea which direction to go, so I start walking – in the wrong direction.

The Greyhound bus doesn’t show up. Not prepared to stand outside for two hours, I’m starting to think a popsicle might warm me up because the temperature has dropped. I’m having problems with my contacts and can’t really see. I’m overcome by the resolve of movement and need for stable footing. I wonder if I’m going to survive the year.

These are the scenes from my year that likely won’t show up in my capstone Experience Institute video. I didn’t document them, and the lessons feel shallow and self-defeating. Sometimes you have to wait for the bus—perhaps this bus is never coming.

It’s in these struggles that I see the secret of Experience Institute’s success. This program is not just about creating connections or becoming better storytellers. I see great value in finding the ability to continue onward.

We all face roadblocks in our lives. Sometimes they make us pause and reevaluate what we’re doing. A lot of times we try to navigate around them or we turn around and look for a less obstructed way. Experience Institute forces you to go through them.

The school’s secret to success is instilling in its students a sense of quiet confidence. This confidence is not worn as an emblem on your chest or a degree hung on a wall. This confidence is felt, but not seen.

Look for the signs in Experience Institute students and alumni you meet. It’s the hint of a smile when people ask a student if they worry about what might happen next. It’s the mischievous shrug of the shoulder by alumni when someone asks if they are worried about where life is heading. It’s the pause for air, just before I dive into the depths of another battle.

If you’re worrying about someone’s dark moment this year, take a second to reconsider. I certainly am becoming better by building this confidence. This program is sharpening me, rather than shutting me down. If this bus doesn’t show up, I’ll find the next one.


An author’s greatest asset is the ability to shape what details the audience can see. This insight came to me during a talk by Experience Institute all-star photographer Kevin Von Qualen. Kevin showed my class how a great photo really comes down to choosing your focus. A creator, in any art form, must decide what stays in the frame and what is cropped out.

A skilled storyteller narrows the frame of view to just the important details. Imagine taking a picture on your phone of a fire juggler from 100 feet away at a crowded outdoor mall. In your mind, you’re about to take a great picture, but the result is a haphazard mess of people and stores. The blurry orange of fire in the distance holds none of the brilliance of the performer. For the best picture, you need to move closer to the subject or find better equipment.

Now imagine you’re up close to that fire juggler. About to take the shot, you notice excited audience members’ faces lit by the flame in wonder. You include them in the picture and it tells a story of an emotional reaction to the fire juggler.

Stories resonate when edited toward authentic emotion. Authenticity is the result of credibility, trust and delivery. Each detail should support the story’s mission to elicit the desired response.

Left to its own devices, a story loses form depending on the details. A teenager tells you his day at school was simply “fine.” A first grader details every moment of the day without reflection. The best story lies in the middle—a story of authentic feeling and reflection supported by details.

George Washington understood the power of authentic emotions in storytelling. At the end of the Revolutionary War, General Washington’s work was not over. His disgruntled officers met in secret to discuss overthrowing the Continental Congress. Washington showed up unannounced, but with a prepared speech.

The speech was not well received. Washington moved onto a letter from a congressman, but only got through a few lines. “Gentlemen,” Washington said, “you will permit me to put on my spectacles, for I have not only grown gray, but almost blind in the service of my country.”

Washington never wore glasses in public and his admitted vulnerability shocked the men. He leveraged his own weakness to support the Continental Congress’ cause. Instead of explaining away the glasses, he used the detail as a source of vulnerability. The moment of emotion was key to Washington’s persuasion.

I first heard this Washington story from my high school history teacher, Mr. Hughes. Mr. Hughes used emotional stories to help draw students into his lectures. Invested in the story, Mr. Hughes acted out the scene, pretending to pull out the glasses. He paused for a moment and with a choked up voice of emotion, delivered Washington’s line. The authentic delivery still gives me chills.

On the opposite end of the spectrum, my facts-based history professor in college failed to compel me with the same Washington story. The man droned on, everyday, without emotion. Instead of using the Washington speech as a great story of history, it became merely facts. He listed the event as one of the ways the Continental Congress survived after the Revolution.

It’s important to me that I deliver my Experience Institute year in an authentic story. I hope I will be able to gain meaning from the story of my year and inspire others. This process begins when I get beyond the facts of the program and talk about moments of struggle and triumph. After all, my year is about more than three terms of experiential learning. My year is also about capturing both the wonder and wounds of juggling fire.

Where’s the Book and Did You Really Write One?

Dear Friend,

Should all acquaintance be forgot, allow me to reintroduce myself in the New Year. I am Derek Kessinger. I hope your holidays were wonderful. This is my latest newsletter as I continue my year as an Experience Institute student.

What do you do when your plans lay discarded on the New York City sidewalks like crumbled umbrellas? Here’s a piece on my first term in NYC:

Term 1: The Write Umbrella

Have you ever tried to create something, but struggled with your process? We all work in different ways, but I think I have a little insight. So let me address the question… I leveraged my work to bolster my own creative habits. First, I told people that I was going to write 50,000 words. After sharing my goal, I had to either write, or risk disappointing my confidants. I played against my own need to please people.

I never found an easy, secret writing formula. Paragraphs did not organically sprout after I planted the seeds of my first few words. In fact, the last few days of my project were the most difficult. Despite frustrating moments, I’m glad I completed a challenging project without shortcuts.

Throughout the month, I tried to simplify my process for the most consistent results. My first task each morning was to sit down with a cup of coffee and write 2,000 words. The day was a success as long as I sat down and avoided distractions, even if I struggled to write. Just remember, the first draft is not the final edit.

I struggled through days of feeling isolated and lonely. These feelings sometimes endured despite a trip to a place full of people, such as Times’ Square. In the trenches of writing, I felt attacked by my own thoughts of ineptitude and doubt. In hindsight, I am able to see my growth through the month. I now know I have better days when I write in the morning.

Just like most things in life, we become what we spend our time doing. I became a better writer by writing. It can still be a struggle. Some days the writing process feels like this Avett Brothers song:

Ten thousand words swarm around my head
Ten million more in books written beneath my bed.
I wrote or read them all when searchin’ in the swarms
Still can’t find out how to hold my hands.

And I know you need me in the next room over,
But I am stuck in here all paralyzed.
For months I got myself in ruts,
Too much time spent in mirrors framed in yellow walls.

The book, after its first draft, is a jumble of images and characters, but I can share a few themes:
  • Ulysses S. Grant and Frederick Douglas discuss modern day New York’s sovereignty.
  • The main character tries to find his footing in the city before meeting a Central Park tree sprite named Johanna.
  • A Coney Island circus boss leads an army of mischievous men to create chaos in New York.

My first goal was to write the book. Now, the editing process is underway. I’m now exploring pieces of this novel’s world that I glossed over upon first telling.

Term 1: The New York Experience

The defining moment of my term came when I was walking the streets of New York just before a rainstorm. I stopped and bought my third umbrella of the week. The first two umbrellas, torn apart by rain and wind, lay crumbled in Manhattan trash cans.

Much like the umbrellas, the schemes for my first term lay abandoned 20 blocks back. After serving just ten days as an apprentice at a startup, I had walked out a free man. I left the startup‘s office in a bizarre scene best described as a mutual parting of ways. In my boss’s eyes, I failed because I asked questions. I left the anxiety-filled experience without regret.

Continue Reading On Exposure…


Newsletter: I Brought Stephen Colbert to This Update

Hello again,

Sorry it’s been so long since the first newsletter! Thank you for your support.

This newsletter is all about you and Stephen Colbert.

In my first newsletter, I was deciding on a new course of action for my term. I decided to focus on a personal project and spent November in New York City with the goal of writing 50,000 words by the end of the month. Inspired by theNaNoWriMo project, I wrote a 41,000-word novel and a few essays. I’ll have more on this journey in future newsletters.

In the last newsletter, I linked to the wrong blog post. Please read the real version of I Learned How to Pick Better Experiences So You Don’t Have To.

Now, let’s talk about this newsletter with a segment I like to call…

Stephen Colbert is the master of word play. If you missed his podcast this summer, or his wordplay on camera, Colbert’s personal title for his CBS late night talk show is:

The Late Show With, Starring: Stephen Colbert.

While the inclusion of “with” and “starring” is obviously a joke, I think there’s a second motive.

Colbert wants to perform a show that resonates with his audience. More than any of his contemporaries, Colbert is willing to become the joke for laughs. The real title of the show should be, “The Late Show, With Audience, Starring: Stephen Colbert.”

That’s how I am approaching this newsletter. I want to share thoughts about my year that are interesting to you, my newsletter reader. This year is a grand experiment. I hope that pieces of what I learn will benefit you and even lead to a couple of laughs.

Please, if you have questions/comments/observations, let me know!

On next week’s segment of Word Play With Stephen Colbert, I look at how the word play in Stephen’s book, I Am America (And So Can You!), further polarized America.