Dana Ortegón

Dana Ortegón has been making a living as a writer for nearly 25 years, a fact that still astounds her parents and routinely makes her feel pretty darn lucky. Starting in journalism, she’s expanded her skillset to include copywriting, content strategy, and branding. As a freelancer, she gets to work with some of the smartest, funniest, coolest people in the greater Boston area. When she’s not working, she tweets @xacerb8, valiantly attempts to finish her first romance novel, and spoils two children and a goldendoodle.

Published Thoughts

The Art of Self-Directed Learning

The title of this post is shamelessly appropriated from a book by Blake Boles. I heard him speak this week, after following his work for several years. Blake is a bit of a celebrity in the unschooling world.

In case you have no cause to know anything about “unschooling,” it’s pretty much what it sounds like. Not schooling. It’s a philosophy of education that says that kids (and adults for that matter) don’t need to be told what, how, or when to learn. And that, in fact, when they are, education becomes non-consensual and coercive.

Blake runs several successful programs for young adults, through his company Unschool Adventures. They range from semesters abroad in Latin America to 12-month Gap Year programs. But they all emphasize self-directed learning.

My interest in self-directed learning began when my son was about two. He was reading by then, though neither his dad nor I had any hand in it. One day he just blurted out, “No turn on red,” when we were stopped at a light. I was sure it was a fluke, but as the weeks went by, his reading continued.

Right about this time, most of the other parents we knew were busy applying to preschools. But when I thought about sending my son to school, I got a sick feeling in the pit of my stomach. He was bright, curious, and not a big fan of sitting still and doing what he was told. He was sweet, but not a people-pleaser. And I was pretty sure that if I put him in school, he’d have some kind of label by the end of his first week — and it wouldn’t be “student of the year.”

So, I decided to homeschool. At first, I was drawn by all of the workbooks and curricula. The flashcards. The audio collections. But when push came to shove, I realized that the philosophy that made the most sense to me was “unschooling.” I didn’t have to make decisions about what my son should learn. All I had to do was make sure he had the time, space and freedom to learn what he wanted to learn.

Our adventures in unschooling lasted until he was five. He needed something more than the Boston scene had to offer. Through friends, we found Sudbury Valley School. Founded in 1968, the school allows kids from 4-19 to control their own educations. No tests. No homework. No curriculum. No mandatory classes. No segregation by age. It was a match made in heaven.

Over the last 8+ years, I’ve seen the power of self-directed learning, up close and personal. Looking at it from a UX perspective, it makes perfect sense to me. Too many students today have suboptimal school experiences. We have a shameful school-to-prison pipeline that targets students of color. We have pressure-cooker academic expectations that drive high-achieving students to suicide. We’ve had a generation’s worth of helicopter parenting that’s resulted in young adults who aren’t prepared to live in a world that’s unmediated by Mommy and Daddy.

No Child Left Behind is being replaced by Every Student Succeeds. But succeeds at what? Filling in ovals with a number two pencil? Creating a persona that looks good enough to get into an Ivy League school?

If we looked at education from a UX perspective, I think parents would be clamoring for a radical shift.

  • We would recognize that “one size does not fit all.”
  • We would respect children’s natural curiosity and drive to learn.
  • We would give our children the freedom to choose what, how, and when they learned.
  • We wouldn’t be afraid to acknowledge that the traditional education system—public and private — is “failing our children and society.”

Ultimately, schools should be created to serve the best interests of their end users: the students. There should be focus groups, usability tests, and a massive move toward creating an experience that provides delight at every touchpoint — from the first day of kindergarten to Graduation Day. I believe that self-directed education is a basic human right. And I wish that every child would have the opportunity to experience it for him or herself.

I have a love/hate relationship with gratitude. It’s the raison d’etre of my favorite holiday. It’s 1/3 of Ann Lamott’s foolproof trinity of prayers. And, research shows that it can do all kinds of things for you.

It makes you happier, boosting positive emotions like joy, pleasure, and optimism. It strengthens your immune system and lowers your blood pressure. It helps you sleep better. It makes you resilient in the face of trauma. And it also makes you more compassionate. (Ask a scientist!)

There’s no doubt about it. Gratitude is awesome. It’s life changing. It’s magic, if you ask Rhonda Byrne. And yet, every November 1st, I brace myself for the month-long onslaught of hash-tagged blessings — the cornucopia of humble-brags disguised as heartfelt expressions of thankfulness.

Don’t get me wrong. Over the past six months I’ve worked hard to develop a gratitude “practice.” I write a gratitude list every morning while I drink my coffee. And every night before I go to sleep, I think back over my day, pick the best thing that happened, and say “thank you.”

Actively cultivating an “attitude of gratitude,” is nothing new. Over 400 years ago, St. Ignatius of Loyola came up with he called the daily examen. This daily practice of prayerful mindfulness includes reviewing the events of your day with gratitude. The Buddhist practice of Naikan asks us to reflect on the past 24 hours of our lives and ask ourselves these three questions:

  • What have I received?
  • What have I given?
  • What difficulties have I caused?

Notice what’s missing? Neither one of these practices includes a step that says, “Tell everybody around you what you’re grateful for.” They’re deeply personal contemplative practices. They’re not about making sure everybody else knows how thankful you are. They’re about making sure that you see all that you have to be thankful for.

Gratitude has become a spectator sport. And November is its month in the social media spotlight. But I suppose I should be thankful. Come December it will be replaced by the just-plain-creepy Elf on a Shelf.

It’s not what you say. It’s how you say it.

For the longest time, every professional bio of mine has included something along the lines of, “My superpower is taking complex concepts and making them simple.” A Creative Director once wrote that on an annual review, and I’ve loved it ever since.

Lately, I’ve been working on a project that’s shown me just how valuable that superpower is. I’m part of a two-woman content/copy team responsible for writing a wellness & weight loss curriculum.

My co-writer is super-smart — works-in-a-research-lab smart. But, she writes at graduate student level, and our curriculum needs to be at a 5th-6th grade level. So for the past few weeks, I’ve been “translating” her writing.

When we first started, I thought I’d be able to tear through her lessons. I was surprised to find out just how time-consuming this kind of “writing” can be. Because it’s not just about finding two-syllable substitutes for four-syllable words, or sticking to a simple sentence structure. Those are the easy parts.

The part I love is reading the dense, complicated explanations of biological processes — like aerobic metabolism — and figuring out how to describe them in simple language. I like taking a 100-word paragraph and distilling it down to its core meaning.

This is painstaking work. But it’s as satisfying as untangling a ball of yarn or a chain you find at the bottom of your jewelry box. Sometimes I’ll hit a paragraph that can take half an hour to work through. Reading the “before” and “after” gives me a thoroughly geeky thrill.

This kind of writing is like hiking down a steep trail after a rainstorm. You’ve got to step carefully, picking your way around newly exposed rocks. You’re forced to slow down. To stick to the trail.

And afterwards, when I sit down to write for another client, another project, there’s such a sense of freedom. All the clauses! All the words! All the loping, wandering, saying-words-for-the-sake-of-saying-them joy of expression.

It’s so easy to write when there are no “rules.” When you can use any word. Make up your own sentence structure. Hear a rhythm in your head and follow it, without caring whether anyone else hears it, too.

But great poets are bound by meter and they make magic. So do musicians. I want to be like them. I want even the simplest 5th grade-level copy I write to be well written. I want it to flow. And when it finally does, that’s when my job is done.

That time I did $150k worth of work for free

No, that’s not a typo. And I’m not exaggerating.

It was 2007. My marriage was unraveling and my days as a baby-wearing, attachment parenting, home-schooling stay-at-home parent were numbered.

I needed to find a way to support myself.

I had worked as a freelance copywriter until the day before my son was born. Wrapped a project, celebrated with a team lunch, and went home to wait for him to arrive.

I’d squirreled away enough money to take a 3-month, self-funded maternity leave. But just about the time when I would’ve had to go back, the Internet bubble burst. It was perfect timing. I didn’t want to leave my son, and now I didn’t have to.

And then, all of a sudden, I did.

So, I created a LinkedIn profile, contacted people I’d worked with, and haunted Monster.com and craigslist. I’d only been off the treadmill for six years, but it felt like I’d been gone for a lifetime. Everything had changed.

Back in 2001, I was working 50-60 hour weeks and routinely turning down gigs that offered me twice my regular hourly rate. Now, nobody was hiring freelancers, and half my old copywriting colleagues had given up and taken “real jobs.” The other half was limping along, cobbling multiple 10- and 20-hour projects into a living wage.

And then, out of the blue, I got an email from a guy I’d worked with at the tail end of 2000. He’d hired me to create a library of personal finance materials for what was, at the time, the largest bank in Boston.

It was a dream project. The topics were fun: “Planning for Retirement” and “Buying Your First Home.” We had an unlimited budget, and I was able to hire two of my friends to write content with me. We worked remotely, but met once a week in Cambridge for lunch and progress reports. It was my first experience as a content strategist, and I loved it.

Having this guy contact me at the exact moment when I needed a job felt like a gift from the Universe. We met for coffee and he explained the project. He and a few buddies had developed a proprietary “thing” that allowed them to predict a particular kind of consumer behavior with 90% accuracy. They needed a web site, sales materials, and a blog. Did I want to take on all of the content and copywriting?

Of course, I said, “yes,” feeling a wave of relief wash over me as I envisioned a regular check coming in for the next few months. That, however, never happened. I got a check after my first invoice. But after the second and third ones went unpaid, I got a call from “Robert” instead.

Money was tight. The team was looking for some VC funding. Prospects were great, but it was going to take a little bit of time. “Robert” offered me a stake in the company in lieu of payment. He explained some very complicated plans that involved our start-up being acquired, and incremental payments, and possible government backing.

And just like Fox Mulder, I wanted to believe. I wanted to believe that this guy thought of me as a friend, not just a freelance contractor. That he cared about me as a person, since I’d cried in front of him more than once when he asked me how things were going. I wanted to believe that he wouldn’t knowingly scam me.

I worked without a paycheck for the next year and a half, draining my savings account to stay afloat. Fantasizing about being acquired and how maybe my tiny sliver of the company would equal enough money to pay the mortgage off entirely. Or maybe pay for the kids’ college.

Over the course of those 18 months, I steadily lost confidence in “Robert.” The focus of the company seemed to change on a whim. Maybe he’d made millions on other ventures, but it clearly wasn’t happening this time. Without that sense of hope and possibility, it became harder to feel enthusiastic about changing our strategy — and all of our written materials — yet again. Plus, the job was exhausting. I’d get calls at 6:00 in the morning, on weekends, and late at night.

So why did I do it for so long? That’s the $150k question, right?

I call it “Bad Boyfriend Syndrome.” As in, even a bad one is better than being alone. Fresh from a heartbreaking divorce, new to the workforce, I was the poster child for low self-esteem — personally and professionally. I was just glad that somebody wanted me.

And then one day, after a particularly contentious phone call, I was done. I told him that I couldn’t continue to work for free and he very politely wished me well. That was almost five years ago.

And here’s where it all gets weird. Because not two days after that phone call, I got an email from a woman who’d gotten my name from a friend who’d told her that I had a lot of healthcare writing experience. The woman was Mad*Pow’s Amy Cueva. We talked on the phone, I showed her some samples, and she hired me.

At the time, I’d worked on one healthcare project. Robert’s. But I had a solid portfolio of work to show for it, and it was enough to convince Amy to give me a shot. That has led to years of collaboration with dozens of smart, funny, inspiring Mad*Pow people doing work that actually improves lives. And when I added that work to my portfolio, it attracted other clients in the healthcare sphere.

I didn’t set out to find a niche for myself, but somehow it found me. It’s my bread and butter. And unlike the me of 2007, I know that I do it well. And that the folks who hire me are as lucky to have me as I am to have the work.

That time I did $150k worth of work for free? I wouldn’t be here without it, and here is an awesome place to be.

A few weeks ago, I had the chance to read bedtime stories to my goddaughter, Jane. I sprawled on the floor in front of her crammed bookshelf, reveling in the assortment of completely unfamiliar picture books. (The last book I read aloud to my kids was most likely a dystopian YA novel.) I grabbed a few that looked promising and climbed into her bed.

After I read my two picks, a very giggly Jane handed me a book, saying, “You have to read this to me, Auntie Dana, ok? I get to pick a book, too.”

The book was B.J. Novak’s “The Book With No Pictures.” Cue internal eye-rolling.

I have an unseemly hatred for celebrity-written children’s books, born around the time Madonna penned “The English Roses” and fed by a growing list of authors that fill me with a stomach-churning mix of contempt and envy. Perez Hilton? Tori Spelling? Sharon Osbourne?

“Those people aren’t writers. They’re just famous, so they get book contracts. And write stupid books.”

So, even though my favorite podcasters at Pop Culture Happy Hour mentioned “The Book With No Pictures” favorably, I chalked it up to a momentary lapse of reason and continued on with my life. Normally, if they recommend something, I’ll at least check it out, but in this case, my bias was too strong. Until Jane thrust the book into my hands and demanded that I read it.

Although I started begrudgingly, it only took a few pages for me to realize that BJ Novak had nailed it — that thing that makes kids ask for the same book over and over. Or at least one of them. In this case, it’s the joy of hearing a grown up say absurd, vaguely naughty, and possibly forbidden words out loud. That’s the book’s genius premise: when you’re reading out loud you have to read every word on the page, no exceptions.

By the time I finished reading, Jane had laughed herself off the bed and onto the floor.

And that got me thinking about user experience. This book was more than just its content, the black words on the white pages. It was about the interaction between those words and me. And from Jane’s participation as a listener, hearing me read them. It came from our preconceptions, that grown ups don’t or shouldn’t say the word “butt.” And the thrill of breaking that rule. Whatever flaws I could find in the writing, they were trumped by the experience Jane and I shared when I read the book out loud.

Did I love the book? Not really. Lines like, “I am reading you this book with my monkey mouth in my monkey voice...and my head is made of blueberry pizza,” don’t seem all that inspired to me.

However, it was clear that Jane loved it. And seeing her joy made me happy, too.

Every few months, Ira Glass’s famous monologue about creativity surfaces on Facebook. You know the one, where he tells beginners to keep at it, even when they feel like what they’re doing is nowhere near as great as they want it to be.

Where was Ira when I needed him, back in 1989?

Fresh out of college, I moved to New York to become a writer. I answered an ad in the New York Times classifieds and within a few weeks was hired as a staff writer at a small Japanese trade journal that covered New York fashion, lifestyle, and entertainment.

That job paid the bills — barely — but the thrill of getting paid to write didn’t last as long as you’d think it would. It wasn’t good enough. I wanted to write for Spy magazine.

Spy magazine was my Everest. The pinnacle. It was the Saturday Night Live of magazines. Funny, cool, and exclusive. And I wanted it. So. Badly.

One afternoon, my coworkers and I lounged around the Upper West Side co-op that our boss illegally sublet as an office. She was out for the day, and we’d stuffed ourselves on our favorite $5 Chinese lunch special and expensed a stack of magazines. For trend spotting, of course. Vogue. Elle. W. Architectural Digest. Elle Décor. And Spy.

To this day, I have no idea what prompted me to sit down and write a letter to the Submissions department at Spy. Let me just say, I do not come from “horn tooting people.” I must’ve been high on MSG and perfume inserts — Calvin Klein’s Obsession, of course.

Possessed by freakish self-confidence, I poured my sarcastic, witty 20-something soul onto the page, sealed it up in a #10 envelope, and sent it on its way.

About a week later, I got a response from Spy: They would love to publish some of my work. Would I be so kind as to send them some pieces at my earliest convenience?

And here’s where Ira would have come in handy. Because, I never sent them any of my writing. Not one word. When push came to shove, I had zero follow through.

I wasn’t too lazy to write. I didn’t sit down in front of my comically gigantic pre-fingernail-sized-processing-chip computer and procrastinate the day away. I just went blank with fear. I had no good ideas. Who did I think I was? What could I possibly have to say that anyone would read other than to mock?

Life went on. I wrote for other magazines. I got married, moved to Boston, entered the realm of copywriting and savored the pleasure of being introduced as “one of our creatives.” (There, see, it’s real. I am creative! Because they said so.) I learned my strengths as a writer — I’m pretty good at making complicated things sound simple. And my weaknesses: “Dana never met an adjective she didn’t like.”

Copywriting was the perfect fit for me. I never had to worry about not knowing what to say. I had a creative brief, key messages, and concept copy right from the start. All I had to do was fill in the blanks.

I have made a career out of filling in other people’s blanks.

That’s not a complaint. It’s just an observation.

It’s been over 25 years since I got that letter from Spy. I have it in a box full of writing nobody’s ever seen. I’m going to take it out and put it above my desk. It can sit next to Ira’s encouraging words. Maybe it will remind me that I have my own blanks to fill.

“The most regretful people on earth are those who felt the call to creative work, who felt their own creative power restive and uprising, and gave to it neither power nor time.” (Mary Oliver)