56/300: The Best Advice I Know

Last night, I had the opportunity to give a guest lecture to a group graduate and under-grad students at DePaul University in Chicago. Okay, I couldn’t get up to Chicago, so I was technically sitting in my basement office and talking to my computer, but they were on the other end, so it still counts, right?

The class was on content strategy, something I have been doing for the last six years in an official capacity, but my entire adult life as a writer, journalist and editor. After my presentation, which was presented full-screen with my disembodied voice coming through speakers in the classroom, I clicked on the webcam and did a Q&A. There were the usual questions about what I see as the future of the field, what kinds of strategies I like (I forgot to mention Reebok’s ‘Be More Human’ experience. Look it up class.) and those I don’t like.

But, near the end of my time, I was asked – or maybe I assumed I was asked – if I had any advice for students getting started in the field. I’d never been asked a question like that so I didn’t have a canned answer to draw upon. My brain tends to thrive in moments of pressure like that and I arrived at two things that have, I realized, impacted my life and career more than any others. The more I thought about them, the more I realized that they are appropriate for more than just landing a job in marketing and can be applied to life in general. I learned both, but I’m not sure where or from whom. And I thought I would share them here this morning (don’t worry, I’ll go back to writing about my dog soon).

Three Useful Words

Throughout my career in its many forms, inquiry has been a consistent through-line. As a writer, a journalist, a strategist, a speaker, a consultant, asking questions and getting at the answers have been the watermark on my work and the basis of most of my thinking. And if there is one question that has been most useful to me, it is this three-word gem: To what end?

To what end is different than a simple why? Why can be related to motivation, it can be related to physics and chemistry and philosophy and religion. Why is nebulous and is neither specifically forward-looking nor backward-looking. Why is a big question without a specific answer. To what end, on the other hand, is about specificity of intent and is always future-facing. To what end is about motive and intent. To what end is about goals and objectives.

To what end forces you to consider not just that which is in front of you, but that which follows. It’s a great question to use in almost any circumstance. Training your dog – to what end? What is the ultimate goal of the training? If you can answer that, you can inverse your way toward a plan. Writing a book – to what end? If it’s fame and glory and riches and acclaim, you probably won’t write a literary criticism of Chaucer.

To what end, perhaps more than any three words, have had the biggest impact on my life, my work and my career. I think I might have heard my dad ask that question once and it has always stuck with me. I’m grateful that it has.

Reach Out Boldly

When I was in fifth grade, I fell in love with Air Jordans. The shoes. The shoes. I read an article about a guy named Tinker Hatfield, who had designed the most popular models of the shoes and followed an impulse to reach to him. I looked up the address for Nike’s headquarters on the back of a shoe box and wrote him a letter. He didn’t write back. I tried again. He didn’t write back until, after several letters, he did.

That early experience cemented something in my mind- that curiosity is only as good as the action it inspires. Over the years, I’ve reached out to hundreds of people I admire from a distance and have been pleasantly surprised at how many have contacted me back. I went through a phase a couple years ago of being fascinated by the work of author, blogger and human guinea pig Tim Ferriss. I found his contact information and reached out to him, knowing he was busy. But I really wanted to ask him a couple of questions. Not only did he write me back, he posted my message¬†on his website as an example of how to contact busy people.

Some of the best experiences I’ve had in terms of growth have come from sitting down and searching for a way to connect with someone I’d like to learn from. They have come from formulating my questions, from focusing in on what I want from them and from reaching. You get rejected. You get ignored. But there’s value in learning that too. There’s value in understanding – through trial and error – how to connect with a stranger. I’ve been on the receiving end of some of these contact and I’ve got to admit, it’s a thrill.

There is always value in following the instinct to reach out.

I’ve reached my allotted time for today, but I thought I would share these thoughts because they seemed to resonate with the class last night and it made me think they might be useful to others.

We’ll chat tomorrow.


1 Comment +

  1. Your presentation last night was fantastic, and thank you so much for taking the time to speak with us! I was in the class by the way. I believe the secret pass-phrase is “Caleb is sexy”.

    I really appreciate the followup blog post and I am excited to read your recommended books and follow your blog and insights.

    Many thanks!

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