I got my first writing job out of the University of Oregon in 1981. That was as a general assignment reporter for the little Lake Oswego (Ore.) Review. I’m happy to report that it’s still being published, by the way. Since then, I’ve worked as a newspaper reporter, a corporate communicator and, for the past 20 years, a freelance writer. I've completed one (unpublished) novel and am working on another. I’m still learning, but here are 10 things I figured out in that time.

1.     Don’t be afraid to look dumb. When I first became a reporter, I was simultaneously excited and terrified. I am an introvert, and I wasn’t used to asking complete strangers about their lives or their work. I soon discovered that the worst thing I could do was to pretend to knowing anything. It was liberating. Gradually, I became comfortable jumping into any story or subject and knowing little to nothing. I realized I wasn’t supposed to know this stuff. Eventually, I would disarm my subjects by saying, “You’re the expert. Now I’m going to ask you a bunch of dumb questions.” Of course, this was a sly strategy on my part. The interview subject would invariably take pity on me and explain everything.

2.     Don’t be afraid to admit you don’t get it. This is a corollary to #1. I’d be in the middle of an interview, and invariably I’d become distracted and realize I hadn’t heard a thing this person had said in the last 10 to 30 seconds. Or the person said something that I didn’t understand. As I became more comfortable in my own skin, I realized this was not a sin and could in fact be used to build trust. I remember once apologizing to a rep from my company’s ad agency. “I’m so sorry,” I said. “Could you just repeat what you said? My mind was wandering.” She smiled and said, “I often can tell from a person’s eyes that they’re not listening to a thing I’m saying. You’re the first one who’s ever admitted it. I find that refreshing.”

3.     When you think you’re right, you’re probably wrong. I never covered the courts or the cops, but I do remember plenty of times when I was writing a story and I thought I had enough information to draw conclusions. This happened especially when reading official reports. After making my share of mistakes (fortunately, never to anyone’s great loss), I realized the worst conceit a writer can make is to pretend to know the truth about people’s actions or intentions. You can do that if you’re a fiction writer. Or maybe Tom Wolfe.  

4.     The truth still matters, even in public relations, marketing and advertising. Journalist friends sometimes confided their worry that if they switched to being a “hack,” their bosses would make them write lies. That never happened to me, and I’m thankful. As a corporate communicator or a copywriter, though, you will at times get information from your clients that, absent any way to independently check its veracity, you will have to accept as their version of the truth.

When I worked for the local utility company, management decided to permanently shutter the company’s nuclear power plant. This decision followed by only two months a tense campaign in which the company spent millions to defeat a ballot measure that would have closed the plant. Nuclear opponents rejoiced and took credit for forcing management’s hand. Management called it purely a financial decision. Even though I was skeptical, I accepted and translated management’s explanation to the company’s shareholders.

If you suspect something is a lie, though, you have a choice. You can ignore it and chalk it off to “just doing your job.” But if that doesn’t sit right with your conscience (and it shouldn’t), you have a obligation to inform the supplier of this false information. At minimum, providing false information can damage your company’s credibility (remember, this is not politics). At worst, it can land you or your boss in jail.

5.     Garbage in, garbage out. You can make stuff up. It’s called fiction. But when writing non-fiction, or even marketing copy, you must start with a solid foundation of facts. I’m continually amazed at clients who expect me to create diamonds out of fairy dust. Say, a case study without any details of how the customer solution solved the problem. Or what the problem was. As writers, we can sometimes make silk purses out of sow’s ears—as long as the sow’s ears are ragged facts that can be rinsed, spun, dried and pressed. But we can’t pull rabbits out of hats unless the bunnies are in there to begin with.

6.     You can’t cook by committee. You can try, but the result won’t be palatable. The quality of writing is inversely proportional to the number of reviewers. One of the funniest, most exasperating exercises I ever participated in was sitting around the table with lawyers and accountants who picked apart my copy for the annual report. But at least I could interact with them.

The worst exercise is one I call Track Changes Roulette. Faceless people whom you will never meet, and who’ve had no part in a project, get to throw rocks at your copy. They make indecipherable comments and vague, blanket statements that leave you wondering if you’re just supposed to ignore them or throw the whole thing out and start over. My peers who are successful freelance writers run the other way when they hear that there will be “three, possibly four” rounds of copy approvals.

7.     Avoid tyrants, dictators and people who don’t know what they want until they see it. We can dispense with the tyrants quickly, executives who use and abuse their underlings like medieval Medicis. Off with their heads! But a close second are those executives who seem to take glee in their inscrutability or their mercurial mindset. They approve a creative brief (or never look at it) and then trash copy that fulfills the brief to a letter. If that sounds like Steve Jobs or Elon Musk, I guess I’m saying I would have had a hard time working for these brilliant, flawed leaders.

8.     To wait is to die. I love working with marketing directors who are empowered. They know what they want, they appreciate my ability to get it done, and they get my copy out there fast. This usually happens in small, nimble organizations. The bigger the organization, the longer the wait. And the longer the wait, the greater the chance that your brilliant copy (and indeed, that brilliant project or even product) will never see the light of day. Priorities change, teams get reshuffled, or budgets dry up. The one bright spot (not to be dismissed, especially for freelancers and agencies) is that, most of the time, you’ll still get paid for your time in.

9.     Writing is a process of discovery. E.L. Doctorow said, “Writing is like driving at night in the fog. You can only see as far as your headlights, but you can make the whole trip that way.” As much as I try to plan any piece of content, I still find that I have to sit down and start writing. I love the advice of Anne Lamott in her wonderful book on writing, “Bird by Bird.” After explaining that almost no writers write with ease, she explains that the only way she can write at all is to “… write really, really shitty first drafts.” Writing is an act of faith. You have to believe that somehow, despite all the inner and outer voices telling you that you suck and have nothing to say, you will show them all wrong.

10. I love freelance writing. I have been doing this for 20 years. And I plan to keep doing it. For two decades, I haven’t known where my next paycheck is going to come from. I have suffered bad years and recessions, not necessarily at the same time. And yet. This life has given me great flexibility and satisfaction. I write fiction most mornings. I play guitar in two bands. I have evolved my writing business so that now I write mostly about clean energy and clean technology—areas I’m excited about and believe in. And I can take time to travel without having to get permission from anyone but myself. (Of course, that means that I generally take the work along with me.)

Thank you to all who have helped me learn and grow—and eat—along the journey.