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And Then This Happened...

Sarah Preston Gorenstein

So there’s some good news happening in my world, but probably not the good news you were expecting: I got a new job!

I left Playboy back in December—it was a departure I knew was coming months before it did, ever since I learned that its Chicago headquarters were likely moving to L.A. You know when people say breakups are mutual, but you know they really aren’t? It's usually one person prompting the breakup conversation… That was sort of the case here. A lot of things had changed at Playboy my last year there, not the least of which was new management of the digital division—to make a long story short and not get into too much detail that could get me in trouble, I was offered a great opportunity to walk away, and live the life I had dreamed about for years.

I’ve fantasized about being a full-time/work-from-home freelance writer since I had Preston. Actually longer. For 10 years I was essentially working two jobs—a full-time job at Playboy, and a part-time job at Chicago magazine, People magazine, Michigan Avenue Magazine, DailyCandy, BlackBook, etc. I was working my butt off juggling two careers simultaneously, so that one day—when the full-time job was over (whether by my choice or not)—I would have a writing career to fall back on, which is a great career for a mom. Writing is what I love. It’s a passion I get paid for. I’m a lucky girl that I get to write about topics I care deeply about, and interview people I admire. And I will continue writing till the day I die.

When Playboy and I parted ways (very amicably), I thought this would be the perfect time to pursue my dreams, and I wouldn’t have any guilt about it, because technically I didn’t have a choice in the matter. So for the past four months I’ve been writing this blog, writing additional articles for Parenting like this one (and more to come!), and writing regularly for Michigan Avenue Magazine—and I’ve loved it. I have other projects in the works too.

But I’m not gonna lie: I've missed the corporate culture a little. I've missed being part of a team. I’m a writer and editor, but I also appreciate the business side. And being a freelance writer doesn’t allow you opportunities to contribute on that level usually.

Being a freelance writer is a hustle, there's no other way to put it—there are people making a good living doing it, but fewer than you think, and everyone knows you work many more hours than you actually get paid for when you're on contract. It can be stressful: You might have five assignments due within a two-week period, and be totally overwhelmed, and then some weeks your inbox is empty. You pitch and pitch and pitch editors relentlessly, and sometimes you don’t hear back for weeks. In my world, you’re only as good as your last article. 

You have to have very thick skin when you’re a freelance writer—you can spend months researching and pitching a story to an editor, just to have the idea rejected. Then you'll see that very same article in a competing publication, and think: "If only I were running things!" It happens to the best of us, though not with anyone I'm currently working for (I love you, my dear editors!). Anyway, I've been on both sides of it for years and, admittedly, there's still a big part of me that wants to be the one "running things." 

Once I finally hired a part-time nanny two days a week to help me out, and got Preston into a new preschool two mornings a week, my new schedule settled into a nice rhythm. Mondays and Tuesdays I’ve been working out of my parents’ house or Starbucks (where I’m writing this blog right now); Wednesdays are my days with Preston (I’ve been taking him to a mom-and-tot class he LOVES); and Thursdays and Fridays I take him to school in the morning, and then I’m there to pick him up, have lunch with him, and put him down for his nap. And I’m there when he wakes up.

The first month was hard—I was still in the mindset that I was “in between jobs,” and we didn’t have our childcare situation worked out. I was having a difficult time letting myself sit still for a minute. (That’s a whole other blog topic.) So I kept my eyes out for good opportunities and told myself that I’d be picky and only pursue the jobs that were worth my time. I saw a great opportunity come up in January that I applied for immediately, and after almost two months of interviews I was finally offered the job last week. Not to be mysterious about it, but I want to keep things separate so I’ll just say this: It’s an opportunity of a lifetime. I’m getting to do what I love, on a level I have worked very hard to achieve, for a company I respect that treats its employees well. It’s a new industry for me, which presents all kinds of new and exciting challenges, and I’ll be working with some of the best in the biz.

But I’ll be perfectly honest: The idea of going back to work full time after I’ve had a taste of “the good life” for four months is a little terrifying. Not to mention, it’s been 80 degrees in Chicago—why couldn’t this have happened in the winter!?

One of the things that sold me on the job, other than the job itself, is that the office is about six blocks from my house, and about seven blocks from Preston’s preschool. It’s in my neighborhood! I can literally walk him to school, and then walk to work on a nice day. That’s pretty unheard of in the city. I can see Preston for lunch some days, which would be amazing.

I worked hard to get this job, but when the offer came I had a bit of an identity crisis again—I had finally settled into my lifestyle as a work-from-Starbucks freelance writer; the life I had been fantasizing about since I became a mom was starting to come true. This was a head vs. heart decision, and in this case my head won.

Some people might not understand why I’d go back to work, or why any mom would work, especially while I’m going through infertility and trying to focus on growing our family, but when it came down to it, I made this decision for Preston and for our family. It will give us—most importantly, Preston—opportunities we might not have otherwise had.

I wrote a short non-fiction piece about this for a cool writing project I’m a part of, called the3six5 (365 days as told by 365 different people). The underlying theme of my entry was that being a working mom is hard, and it doesn’t come without a lot of sacrifice. I love my son more than anything in the world—deep down I know I’m making the right decision here, but it’s going to be a big adjustment for both of us. This might be harder than going back to work after my three-month mat leave when he was born. In fact, I know it will.

Even if you don’t work full time, do you have mom friends that do? I’m always amazed when I meet women with one, two, three or four kids who have big-time careers. It makes me think I can juggle this—so many women like me do these days. Most of our friends are two-income families. And when I think about the opportunities this will afford Preston, I know the sacrifices will ultimately be worth it.

Follow me @spgorenstein. Friend me on FacebookEmail me. Read my entry for the3six5 project.