Jen Cooper

image credit: Dave Cooper

Oh – this is a GOOD one.

Like Melanie, Jen is part of my original group of blogging friends. And – like Melanie – she has changed paths, and bravely faced fears and risk of failure to tap into what matters inside.

ANNNNND – like Melanie – she has appeared on these pages before. For her blog, her partnered project with her husband, and for a lovely collaborative e-book she created with other talented bloggers a few years back.

As I so adore and admire Jen on both a personal and professional level, I’ve watched with respect and anticipation as she’s shape-shifted over the past few years, embarking on some truly unique projects. She’s graciously agreed to take the time to answer my many questions, and I think you will find her journey as inspiring as I do.

Let’s go (all images courtesy of Jen Cooper)!

Jen Cooper

image credit: Dave Cooper

Since – at this time anyway – no one “goes to school” for blogging, how did you come to create Classic Play? Specifically, what were you doing before, and how did that inform your decision to start the site?

Okay – let’s see if I can get from point A to B in as straight a line as possible – even though that line is anything but straight:

When I first entered college I wanted to be a writer. Then I had a professor who loved her red pen a lot. Like, a LOT a lot. I figured, well, guess that writing thing ain’t for me. So I switched to education. That wasn’t right either. Then I found psychology. It was perfect! Ack! This is already too much info. Deep breaths, Jen. Find the thread here. Let’s try this again……

I went to work in early intervention after college; eventually working my way up the ladder to glorious middle management. It sucked. When I got pregnant with my second child I dropped out of the traditional work force. But because I’m a bit bonkers I started a small business called Ellie Bellie Kids. We made toys based on my knowledge of childhood development. Somewhere in 2006, while I was running Ellie Bellie Kids, I caught the blogging bug. Probably because I secretly hoped my old college professor was wrong and I was actually a writer. But mostly because I had two young kids and no friends. Blogging was my way of reaching out. It wasn’t a successful blog but it gave me an idea. I could develop a site that would be a companion to the toy one. We had no money so a blog was pretty much my entire market strategy. Over time I realized I liked writing more than I liked manufacturing. It was cheaper too. And so that‘s how Classic Play was born. In a nutshell? I started a blog as a marketing strategy for my small business. Seems so simple when I strip the history from it.

Jen Cooper

image credit: Dave Cooper

Yet it’s the history that is so important to the story! For most of us there IS no straight line, especially for we who create, and I think that’s where the real story lies. I met you as the writer of Classic Play – one of my favorite sites, as you know. And as your friend I watched as you began easing away from it to explore other pursuits. What was going on at the time? And how did you decide on your next step?

If I recall correctly, I was having your garden–variety identity crisis. My kids were getting older and I felt like I had either accomplished all the things I set out to accomplish or was able to with the resources I had.

Also, I think fatigue set in. I just needed to do something new. And so I sat and cried and ruminated and eventually it became clear I needed to do something else. I knew I wanted to do something outside of the “kid” world, but didn’t know what. I knew I wanted to share stories, and assessed all the resources I had. And so, after several late night strategy conversations with Dave, we started South of Brooklyn.

Jen Cooper

Dave, being Dave Cooper – for those of you who don’t know Dave he is a very very talented photographer and your husband! I really – REALLY – loved South of Brooklyn. I loved the look of it, loved the fabulous stories and the creators you introduced me to, loved the mix of traditional story-telling and film. Did you have any inkling when you started ruminating that your next step would be a collaboration with your husband? What did you learn from that experience? Is there more to come or was South Of Brooklyn a limited run? Were you doing anything else at that time?

Dave and I already had a history of working together. He was the photographer for Ellie Bellie Kids and we had created videos for ClassicPlay and later a PBS series. Oh, and we created two pretty awesome kids, so it seemed natural to work together. In terms of what I learned from that process: a) It’s really, really hard to turn down paying work for a passion project (South Of Brooklyn was a passion project), b) I was fully capable of stepping outside of the kid/family world, and c) There are so many incredibly cool people in my area! But, we also knew that we couldn’t sustain it on our own. If we wanted to really make the site a go, we would have had to find investors and frankly, we aren’t good at that part of the business. So we work on it here and there when we can. There are so many stories I want to tell on South Of Brooklyn. So many!

Jen Cooper

image credit: Dave Cooper

That makes me sad – South Of Brooklyn is something really special. I found “b” to be such an interesting take-away. When I think about my last profession prior to blogging (it was landscape design), there would have been no indication that blogging would be the next step. And when I think about the last 6 years of writing donuts, dresses and dirt, MY biggest takeaway is the pride I feel in creating something brand new that bore no relation to what I had done for the last 10 years. Which leads me to my next question – these last few years, as I’ve watched slashed stalked you online, I’ve noticed that you have turned more inward in terms of what you share, and are also juggling a few different personal projects. Can you tell me more about the genesis of those, and were you needing to find paying work outside of the creative field at that time?

It’s so interesting to hear that observation about turning inward! I guess I haven’t felt like I’ve turned inward as much as I’ve stepped out in front. I’m probably not explaining this well, but I think it’s less me hiding behind something like a brand or image or being an expert in something (or even, if I’m being really really honest, my kids or husband), but more me being me. Last summer, I started a personal project. And that was pretty much a changing point for me. It started out with feeling the impulse to do a ballet jump. I had taken ballet as a kid and loved it. Looking back, I know I felt powerful when I danced. I would say carefree as well, but at the core of being carefree is power, right? Like you feel empowered to be your most authentic self. Anyway, I had Dave take a picture of me doing this leap against a wall of green. And I don’t know, it just felt so fresh and alive and joyful, even though it was drizzling outside, and so I posted it.

Eventually I turned it into a personal project. I wrote about it on my blog and started a new Instagram handle, @101jumps. I would jump 101 times in public spaces, without fear, with only strength in my conviction to let go of all the invisible shit I was holding onto that weighed me down.

I’m more than halfway through and the change in my life has been tremendous! I think it was tapping back into that power I felt as a kid:

I had four pieces published in a magazine – a dream come true!

I had my illustrations appear larger than life on a jumbotron in Times Square.

And I broke back into the traditional workforce after 12 years of being away.

Now we’re in the middle of trying to move our family from Baltimore, which has been our home for 16 years, to Los Angeles!

About going back to the traditional work force… I wanted to make money again. And to have health care.  And to have that reliability. Working as a freelance is nice in theory, and blogging is a beautiful outlet, but I was never able to monetize anything all that well. That was a failure on my part.

Jen Cooper

image credit: Dave Cooper

When I said “inward”, I meant that you were now sharing more of your own personal journey and challenges. It’s amazing how – by tapping into “you” – you can affect so many profound changes in your life!

I ADORE @101jumps. And the new paths you’ve forged for yourself have had an effect on me too. When I see your posts it reminds me to “check in” and make sure that I’m sticking to the promises that I’ve made for myself since starting blogging – am I happy? Am I fulfilled? Am I still doing this mostly for me? Could I see myself doing ANYTHING else? And of course the images are just pure joy.

Last question! Your move! So exciting – and scary, I bet. Are you going with a game plan for yourself, or are you going to let your new surroundings guide you?

Jen Cooper

EEEEEEE!!!!! I do not know what we’ve gotten ourselves into with this move. It’s something we’ve talked about off and on for years. And now that we put it out there for reals it’s like, WHAT WERE WE THINKING!?

So yes, exciting, terrifying, all the emotions.

Because we have kids (one going into seventh and one going into her first year of high school, how did that happen??), good public schools are important. So that is helping guide us a bit. Other than that, the only other part of my game plan is to find a decent job that covers the rent. I’m aiming high with my LA dreams, yeah!

Jen Cooper


I think you’re aiming DAMN high just by the virtue of your big move!

This was amazing Jen; I could talk to you forever. By now it’s clear to anyone who’s read this that you are someone who is as open to the idea of uncertainty as you are to sharing the journey with ease. What can you offer as some parting words to those of us who know – deep down – that we’ve not quite landed where we belong, but just don’t know how to make that first step toward getting there?  

Trust yourself.

Take one step each day.

And remember that for 99% of human history we’ve been nomads. Change is tattooed on our DNA. So, to steal a line from Cheryl Sandberg, lean into it.

Jen Cooper

image credit: Dave Cooper

It still blows my mind when I think about the group of incredible women that I call “friends” – that I would have never ever known had it not been for blogging. Take a look at all of the places Jen creates – Classic Play, South of Brooklyn and Jen Cooper – and follow her on Instagram at @heyjencooper and @101jumps.

Thank you Jen! xoxoxo

More of my favorite bloggers and creators can be found on my Pinterest page!

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