Define “successful”


I’ll be back for 2020 as well…


By Caitlin Kelly

So there I was last Sunday, wearing my black dress and chartreuse silk scarf, all dressed up to attend an annual holiday party in Manhattan at the home of a man I’d met a few times at conferences. He’s had a career studded with highly visible and well-paid success, including becoming the first digital director of the Metropolitan Museum.

The room was packed with people, some of whom have Big Jobs at places like CNN and The New York Times and many teach at local journalism schools.

At one point, when it was a bit quieter, we were all asked to briefly introduce ourselves — like many, when I said “freelance writer” I heard some laughter, (kind? unkind? sympathetic?) as this is where so many talents now work — nowhere.




A legendary writer and war correspondent — much of her life was spent frustrated by overwhelming, unfulfilled ambition. Makes me feel better!


Thanks to social media, other people’s BIG and quantifiable successes are in my face every hour: a book deal, a TV series created from their book deal, an award, a grant, a fellowship. It can feel completely overwhelming as I work, alone, more slowly and quietly.

I do have a major piece of work that will appear nationally in late January — that I worked on between August and October.

But for now…crickets.

People are fired daily now in my industry, with even well-funded and highly regarded places like the magazine Pacific Standard disappearing overnight.

So when you’re surrounded by people with visible, credible “success”, it can feel stupidly intimidating.

So I mostly, I’m embarrassed to admit, sat in the corner of that party, eavesdropping. I really enjoyed the great Indian food, but didn’t engage in much conversation. I’ve never been a fan of chitchat — and a NYC journalism party can present a heinous pecking order.

I don’t have children or grand-children, the traditional default place to park your pride when work fails.

I’ve been full-time freelance since 2006, when I was laid off from a well-paid job at the New York Daily News. I’ve applied for staff jobs since, rarely even getting an interview. I’ve stopped applying for fellowships and had two grant applications refused this fall.


So “success” is a moving target for me, and maybe for some of you as well.


By necessity, if not desire, I look beyond work, visible accolades and high payment to my thriving marriage (20 years together, nine married); deep friendships across oceans and generations, a lovely home, generally decent health instead.




This was my most recent New York Times story, about a sailing program for New York students


I’m already booked to speak in 2020 at two major conferences (unpaid, but smart, interesting audiences, one in the U.S. and one in Canada, where I do hope to find paying clients) and we’re planning (let’s do it this year, dammit!) a three to four week holiday in England.

Thanks to a link on the blog Small Dog Syndrome, I found this powerful insight, from American comedian Jenny Slate — who was hired into the cast of Saturday Night Live (never one of my favorite TV shows but considered the pinnacle of comedy success)then later fired.

Her take:

First, I just felt really, really embarrassed and terrible. … Hardly anyone gets kicked out of a cult, because I guess they want you to stay…But suddenly I just couldn’t imagine anything worse than getting fired. And then I just thought: I have to keep going. And no one can ever take away the dream.

And nothing will ever dim the lights of that experience, which was like: getting the job, leaving 30 Rock, calling my parents and saying “I am going to be on Saturday Night Live“? That is what it is. It’s such a beautiful achievement. And it’s real and I did it…

But what had also happened at the time, and what always happens, is that: Until I eventually croak, I will not die. I truly will not lie down. And you can be kicked out of a place; I definitely believe that. But I also believe the opportunity to find self-love and creative fulfillment is not a hallway with one door guarded by a super-old man. Actually, it’s spherical, and you just have to hold it between your legs. Just look down, find your opportunity.



18 thoughts on “Define “successful”

  1. Based only on the achievements you mentioned in this post (and I know there are others) you sound successful to me. Congratulations and if you love what you do, just keep doing it.

  2. Robert Lerose

    As a freelancer, I have been in your shoes–that is, being surrounded by people who have staff positions. Who have weekly paychecks. Who, because they work for the XYZ Company, have instant credibility and status, while the self-employed writer is seen, somehow, as less worthy. I have been in those situations where I have to introduce myself to such a gathering. Unless I list ALL my credentials and awards–in short, unless I give them my resume, which is impossible to do–they really have no idea who or what I am. They know nothing of my talents and skills. They know nothing about why I CHOOSE to freelance. They know nothing about my personal responsibilities (you know what I’m referring to) that I shoulder doggedly. And right now–at this moment, as I write these words–I don’t care what they assume. They don’t know me and they never will. So, like you, I go about my business day in and day out, trying to get a little better every day at what I do and moving forward with the same kind of quiet competence that was on display this week by some of the officials who testified at the impeachment trial.
    One more thing that this discussion of success reminds me of:
    There is a scene in Kramer vs. Kramer where Dustin Hoffman is desperately looking for a job days before Christmas so that he can fight for custody of his son. He’s just made a pitch to a creative director and he’s waiting for the word. He sits outside the office while a raucous holiday party is in progress. Looking at him sitting there disconsolately amid the festivities, you’d think he was a loser. But they have no idea that the only thing he’s thinking about is hanging on for his son’s sake. That’s success.

    1. Thanks. It’s become very Us and Them. If our health insurance wasn’t killing us financially, I would care less. But the American system privileges those with a staff job with affordable healthcare. That’s appalling.

  3. I moved in the very old family, wealthy east coast American social circle for a few years (I was a married-in, my husband at the time was the one with the connections) and met journalists, bankers, and business people. Many of them didn’t “have” to work, but did. Honestly, Caitlin, I found it puffed up and full of itself. Arrogant, no-one-is better-than-us, total bs. I became very aware of how Canadian I am and how I little patience I have for the type condescending behaviour you were exposed to. You have earned a lot of respect Caitlin. Don’t let the bastards get you down.

  4. Similar situation as a freelance musician.
    I always enjoy your writing and constantly professional stance. Thank you!

    Thanks also for the clips of Gilda and of Jenny Slate doing Marcel! Love Jenny Slate’s comments elsewhere about not wanting to lose the sweetness in her characters or her comedy… All of us holding onto the love of what we do despite obstacles or difficulties in making a living at it.

    1. Thanks!

      That Marcel video is the BEST thing I have seen in a long time. Truly sweet.

      Yes, it’s not a culture that usually rewards creativity or artistic skill in dollars, that’s for sure. Journalism gave me a nice living for a long time, but not now — and not at an age that’s giving me a lot of better options.


  5. I’ve known “Successful” people who can give you sunburn just by walking through the door. They have heard the saying that “If you’re the smartest guy in the room, you’re in the wrong room”, they just don’t believe it. They wear me out with their tales of how they beat the odds, beat the system, beat the eggs, saved the world and saved a quarter on a gallon of gas. Tedious, to say the least.

    1. Ugggggggh.

      Journalists combine the worst qualities — we can be really shy (!) and insecure and then brag to overcome it. The worst question, always is: “Who are you with?” (i.e. who is your Big Fancy Employer?)

      I donated several hours of my time a few years ago to guest lecture at a NYC journalism school and one of the teachers there asked me that — HELLO I was there to discuss freelance. I told her that and she persisted with: “Who did you used to be with?” HOW RUDE IS THIS?

      Ugggggggggggggh. The guy who had invited me to speak (former NPR exec) eye-rolled in sympathy.

  6. Whew. The eternal question, and one in a lot of flux for a lot of people I know. At many ages, income levels, professions, backgrounds, and more!

  7. life is a series of ups and downs, ins and outs, and often unfair. from what I know of you, you have always been an ethical, diligent, professional in all you have chosen to undertake. while it is often not rewarded, I would say you have been very successful in life, and your work is just one part of your success.

  8. I hear you on chit-chat. I can do it, but the older I get, the more I want to have a real conversation. Have always been that way, but we become more of who we are as we age, right? Love Jenny’s commentary–thanks for sharing.

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