Stuck

Last week when I wrote Downward, I looked back on my life and found quite a few places where I felt stuck.

This post is inspired by Startup Edition’s question: “What advice would you give young entrepreneurs?”

I was stuck in a job after college. I was trained to be a Chemical Engineer, but really wanted to be a software developer. When I graduated, I got a non-developer position at an information technology consulting company, Accenture, recording meeting minutes and documenting requirements. I hated it.

What’s interesting about ruts in my life is how often writing got me through them.

I was bored with my job, so I’d email tons of Accenture partners ways to improve business or ideas for clients. I worried a little bit about looking stupid. I’m 21. A complete newbie. I kept doing it anyways.

Most people ignored me. But, eventually, some didn’t. And I got promoted to a position where they finally let me develop software. I was unstuck.

We felt stuck when we started Inkling 8 years ago. We went six months without any revenue.

Writing helped there too. I wrote a stranger, running a company where people would submit ideas, and the crowd selected what got made. Since Inkling was a technology platform to solicit decisions from a crowd, I thought he could use us. Just another email. Most likely ignored. But it wasn’t. It turned into our first paying client and $30,000.

Life goes on and I got stuck again. I wanted to create my next business, an attempt at branded games - Cityposh. I completely failed. Then I repeatedly banged my head against a wall, trying to figure out the next project. Nothing worked.

How’s writing going to help?

I escaped the struggle temporarily by joining the Obama re-election campaign. But once the election was over, I was back. Stuck.

After the Cityposh fail, I had little confidence I could pull off another business again. I was envious of my highly employable colleagues getting great jobs.

Am I being an idiot? Am I missing an opportunity to strike while the iron’s hot and get a great job? I gave more than one serious look at the jobs out there.

But I just couldn’t let it go. I had to try again.


From 13 to 21 I worked at the Chicago Park District’s golf courses. When I was 16, my boss decided to sell hot dogs and soda to people in the public park near the golf course. My friend Peter Gagliano and I sat near the baseball diamonds peddling our concession stand food.

I remember salmonella lady.

“I can see the salmonella! I can see the salmonella,” she kept yelling, as I tried handing her a hot dog.

That’s odd, because, first, the hot dogs are already precooked, from a fresh package, and been heating in ridiculously hot steam. I’ve already eaten one, like I’ve done for years. And I’ve never gotten food poisoning.

And second, I’m pretty sure salmonella is a microscopic bacteria you can’t see with your eyes.

But, there is no convincing our potential customer I’m not trying to poison her.

The best part of the day was getting to know Pete. He was a little older than me and a writer. (Pete went on to become the highest student-rated teacher at Lane Tech High School in Chicago. He also wrote a couple novels I enjoyed: The Other Side of Green and The Rosary Roulette.)

Pete gave me some writing advice that day: Keep a journal. Write in it often and consistently. One day it’ll be incredibly valuable.

What do you think a teenage kid did with that advice? I completely ignored it.


After the Obama campaign, I finally created a product I hoped I could turn into a business. It came from an aggravating personal need to make writing and blogging easier. I built Draft.

The time arrived to see if other people wanted it.

I sent it to groups of people I belong to online. The feedback was useful, but Draft didn’t reach very far. If this was representative of growth, I’m in trouble. How was I actually going to get people using this?

The solution was the investment Pete tried to get me to start years ago.

 Write more

The process advice that makes sense to me is to write. Constantly. At length. Often. Don’t publish everything you write, but the more you write, the more you have to choose from.

Seth Godin, The Writing Process

Pete was right. I should have written more. I regret not having more stories journaled closer to when they happened.

I finally started writing with consistency a couple years ago, and just kept at it. Every week I’d show up to add at least a little something. Even if it was just a photo of a weird truck I saw on the street or a neat way a cafe was improving customer loyalty.

The investment grew. My Twitter followers and web traffic increased. Would this be enough to help launch Draft?

I took a lesson from 37signal’s ebook: Getting Real.

To build up buzz and anticipation, go with a Hollywood-style launch: 1) Teaser, 2) Preview, and 3) Launch.

I started previewing Draft in a series of blog posts before launching. The blog returned on its investment. I had thousands of people signing up as beta testers.

A common argument I hear, when I recommend blogging to people, is that they don’t have anything to say yet. Bullshit. You’re squandering the best time to start. It’s ok to write about your learning process. Someone’s going through the exact same thing, and they’d love the company.

And write to more people. Send emails to potential mentors asking them questions. Send emails with ideas helping other people. You’ll be surprised where those take you.

 Write less

Someone I’ve admired for a long time is mentoring me on Draft. How’d I get their help? I sent him a 420 character email. That’s it.

We’re too verbose. Practice editing.

Revising Prose is a fantastic book on the subject.

Use active voice to get to the point faster. Remove adjectives and adverbs. Eliminate prepositional phrases.

Use a word and character count in a text editor like Draft to pare your prose down. If you’ve written 1000 words, try it with 500.

 Write better

Don’t rely on the dull approach to writing essays you may have learned in high school.

Seek out great writers and study how they get people’s attention. How do great speechwriters do it? Often, a speech is just as impactful on the page as it was spoken. Learn how they use things like triplets, rhythm, and metaphor. How do screenwriters create great movies? How do they glue people to their seats? How do comedians write jokes and keep people laughing?

A secret you’ll find: they’re all great storytellers.


I’ve got miles to go before I’m the writer and entrepreneur I want to be. But don’t repeat my mistake. If I had followed Pete’s advice from 20 years ago, I’d be so much closer.

Write more, write less, write better.

P.S. I’d love to meet you on Twitter: here.

Read other perspectives on this topic from an awesome group of entrepreneurs at Startup Edition.

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