One year ago I won the lottery.

1378617_10151721596898598_552650650_nOne year ago I won the lottery.

Ok, not really, but it felt like it. Juggling a full-time job I just wasn’t into with an ever-growing load of freelance writing gigs, I was at a breaking point. I couldn’t keep doing it all, not and also keep up a home life, workout routine and any semblance of leisure time. Plus, I just wanted to write.  I’ve blogged here since the pretty early days, and finally thought to try to make a little cash in 2008 when I was giddy to get my first paid blogging gig. For the sum of five(!) dollars a post, I churned out story after story for what I realized later was little more than a content mill. Oh well, at least my all-time favorite homemade pizza recipe is preserved for posterity.

I scrabbled my way up the ladder, snagging $12 a post for my next gig, and a whopping $35 for my first local Louisville work. A newspaper column was next (thanks to a timely introduction from a friend and supporter — thank you Erin!), then assorted and sundry other outlets — a brief stint editing a food magazine, smallish travel website articles, local and regional magazine columns — until I cobbled enough freelance income to support our travel habit. Not overnight, mind you. This took months and years of working at night and on weekends. And oh, the hustling, it took, the ceaseless pitches and the equally ceaseless rejections.

But every time someone said no I redoubled my efforts. I’m nothing if not persistent. And I pitched way outside my league, sending ideas to big-time glossy magazines as if I were somebody they should consider hiring. Then one of them did — I landed an essay assignment for Elle and thought my head would actually explode. And sometimes, to my great surprise and delight they came to me. Delta Sky magazine asked me to write their Louisville and Lexington city guides. Zagat asked me to edit their Louisville edition. And I could have fallen over the day Food Network magazine reached out to see if I could do a little assignment for them. Only 50 words, but hey, now I was in contact with an editor there (and down the road after a few pitches they gave me a bigger assignment).

Anyway, I was starting to seriously consider making writing full time my real job. But freelance writing and stable, grown-up income aren’t usually things you hear together. What was the answer? To keep busting my arse, and to get laid off, of course.  The organization where I worked held regular layoffs, and we all knew a big one was coming last January. If I could have gone before the decision makers to volunteer as tribute I’d have done it in a flash, but it didn’t work that way. I was blunt with the “consultant” they brought in to interrogate the department where I worked (Creative Services) but that didn’t necessarily mean anything.

I hoped and dreamed and wished but I never seriously entertained the thought that I’d get “The Package,” the absurdly generous severance package they handed out like so much candy to other people in the seven and change years I worked there.  January 24 — RIFday — rolled around at last, and I thought the suspense and turmoil would eat me alive. I couldn’t do a thing all day but sweat it out. They waited until after lunch (as if we could eat!) before they started calling people. When my boss got the call I was wrecked. I liked my co-workers, and the only reason I’d managed to hang on as long as  I did was that I worked with a fantastic group of smart, talented, fun, and generally awesome people, led by a woman I was privileged to learn from. I’d sworn I wouldn’t cry that day, but losing my boss and keeping my job was the worst possible scenario so I stormed into my work brother’s office, slammed the door and howled.

Back at my desk a few minutes later, as I  typed furiously to my husband about this insanity, my phone rang. You hear people say their heart stopped, but I swear, mine did. It was the guy mowing down the staff. “Can you come upstairs?” he asked. Calmly, oh so calmly, I answered yes, and carefully replaced the phone. Then leaped up, exhilarated but sick with worry for my remaining co-workers. “I got the call, I GOT THE CALL!” It had to be a dream, a hallucination brought on by anxiety. I went upstairs, sat down as cool as you please, and signed the paperwork terminating my service. I was to leave immediately and come back for my things later. My parting gift? My paycheck and benefits would continue for another nine months.

I’d won the lottery. The shattered team that remained — down to two from the original eight when I started — wasn’t so lucky. (They both quit within a month.) I left, forcing myself to not smile as I walked out — just because I was overjoyed didn’t mean everyone was, and met my boss, and later others from our team, at a bar where we drank many drinks and a smile never left my face.

When I woke the next morning and didn’t have to go to work I had a tilt-shift sensation that I was still in the midst of a good dream, but one I didn’t have to wake up from. It was time. This was my chance to see if I could make it as a full-time freelance writer. My early morning post on Facebook read:

When I went on the camping trip last year in Oregon, I joined a group of the more intrepid hikers one day on a pretty scrappy hike to get back to this amazing natural rock slide over a pristine, clear spring (though it was dark because of the shade of all the ancient trees around it). You had to climb a rope up a slippery rock wall to be able to go down the slide, which was a narrow little carving in the face of the rock with a trickle of water, a straight shot to a few feet above the pool. Of course I wanted to climb that rope, and once I did there was no turning back. I was flat terrified – there was no control, people just flew down it. I went last, I was so scared. But I did it – I flung myself down the slide. And I popped back up out of that spring like an otter, laughing my head off. It was one of the best things I’ve ever done.
I feel like I’m standing between the rope and the slide right now.

Meeting the captain of a cruise ship while on assignment in the Mediterranean

Meeting the captain of a cruise ship while on assignment in the Mediterranean

One year later, I’ve survived flinging myself off the slide. It’s no less terrifying or exhilarating than it was then. Some days I can’t believe my luck. I get to talk with fascinating, smart people and ask them all the questions I want. From time to time I get to travel to amazing places and relive the experience by writing stories about them.  I’ve interviewed Paul Theroux (!) and gone on assignment to places like Istanbul and Tuscany. I’ve written about pizza in Naples, Italy, and a sensory deprivation tank in Portland, Oregon; I took my mom on a Mediterranean cruise and traveled Eastern Kentucky with my dad on a motorcycle; I’ve judged the Jack Daniels World Barbecue Championship for a story and landed an NBC News byline; I interviewed a Belgian scientist about a corpse flower and got a food tour of the Lions’ Ford Field. I even fell in love with Detroit. I marvel sometimes that I get to sit down, for instance, with people who make bourbon and listen to their stories, and write about them, and someone pays me for this. How can this be?

Then some days I get a ‘no’ from an editor that I really wanted to write for, and no response from five others, and I have a fantastic story idea and nobody wants it or they do, but not from me. Actually, that’s most days. I send emails inquiring when I can expect to be paid, and I wake up at night wondering if this is crazy. I couldn’t get insurance when mine ran out thanks to a pesky case of rhabdo (though I have it now, thank you Mr. President) and my taxes — oh, I dread going to the accountant. Every day I’m hustling and it will always be this way.


Courier Journal travel feature

Courier Journal travel feature

I’ve been exceedingly fortunate, and it’s flattering when people ask me for advice. But I honestly have very little.  Unless you can arrange to get a financial cushion like I enjoyed, and have a partner with a steady income, it’s not easy to make the leap to full-time freelance work. And it’s not easy to hustle. It’s hard hearing no. It’s hard being ignored. It’s hard to constantly put myself out there knowing I’ll most likely be rejected again. But when people ask, I try to share whatever I have in the way of advice. This is nothing earth-shattering, but here’s what I’ve learned in the past year.

  • “Sometimes writers not as good as you get the job because they have bigger balls.” — An editor leading a panel at the excellent Book Passage Travel Writing Conference I attended in 2012 said that and it stuck with me. When you give up after one no, somebody else will keep trying. I’ve landed (good) assignments after six months and countless pitches with an editor. Don’t be a bunny cooker, but don’t give up, either.
  • Know your worth. If I’d kept working for $5 a post I’d have had to go straight from my lay-off to another day job. Now I turn down low-paying work because my time is better spent hustling for work that pays what I deserve.
  • On that note, don’t be afraid to turn down work. Every rulebook will tell you to never say no to an editor, but I do it all the time. If I don’t have the bandwidth, if it’s not a fair wage, I politely decline with a reason. Sometimes the deadline is extended or the offer is raised, but if not, that’s ok too. Better to do good, solid work where it’s a fit than compromise and resent what you’re working on.
  • Know who to pitch. It’s worth the $50 a year for Media Bistro’s Avant Guild membership solely for their How to Pitch section, which comes complete with assigning editor’s emails.
  • Get out and get to know people. I get assignments now from editors I’ve met in person. We’re all just people, and we like working with people we know and like.
  • This is obvious, but do good work. Understand the assignment. Give the editor what they need. Make their job easy. Be reliable. Respond to emails. Stay in word count (ok, that one I have trouble with), and never miss a deadline. This is a real job, as fun as it may look from the outside sometimes, so treat it like that.

Thank you, may I have another?

The past year has been frustrating — maddening sometimes — and scary, and I’ve questioned more than once if I shouldn’t just throw in the towel and go back to a “regular” job. But then I get a great assignment, or a nice email from an editor, or a message from a reader, or interview an especially intriguing subject, or even way once in a while cash a big check and I remember there’s nothing else I’d rather be doing. Here’s to one year after another. And hey, why not go read something?


11 responses to “One year ago I won the lottery.

  1. “I’d sworn I wouldn’t cry that day, but losing my boss and keeping my job was the worst possible scenario so I stormed into my work brother’s office, slammed the door and howled.”

    As an ex-coworker of Dana’s I can say that I will NEVER forget that “RIF” day, more important that very moment. I felt the aftershock.

  2. You definitely inspire me, Dana!!

    I am one of those talkers who would love to do something else instead of what I’m doing, but don’t have the resources (or make excuses for) why I am not.

    I love to blog, love to write, love to help people.. yet stuck in the cubicle rat life.

    I always love your stories and think it is so amazing that you are doing something you absolutely love to do!

    • Thanks Jennifer! I truly was fortunate to have a chance to jump start the writing career. Most people don’t get a break like that and have to work even harder. But I have no doubt if you want to do it you can – you’re one of the most motivated people I know :)

  3. Thank you for writing this post, very inspiring! Gives me a better understanding of how to find my own path as a writer, which you know from personal experience can be difficult! Thank goodness I’m a hard worker at heart :) so I’ll take your advice with me everywhere I go!

  4. Hey Dana,

    I really do hope you are okay, in some country exploring and having a good time.. I read this and one of the comments and thought to myself, I am a cubicle rat, sitting in a cuibicle with so much down time, I could cry. As I write now, I have been waiting on a call in this call centre to come in for the last 30 mins, and I am not allowed to browse sites, listen to music or even turn around to talk to my friend. Yet what I would love to do is travel the world, though I may never be a travel editor or a travel blogger but I want to be a Goodwill Ambassador, traveling to different countries helping to implement policies, offer my services through volunteerism and being a advocate for social welfare, child protection, and human development. Sometimes I see red cross relief or even the UN volunteers and say to myself I want to be there doing that but I think of my financial resources and I sink back down in the cubicle and wait for a call. I volunteer now at different organization and I pray and hope that the Lord will provide me with an opportunity to give back. I wish you all the best and continue to write, you have inspired me. I also read your article on Elle, it was good.

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