Breaking Up Is Hard To Do

Portland, Christine & Stephanie

We are basically this ridiculous all the time.

This week, Christine and I are in Portland, Maine speaking at Grow Brand Camp, a sweet boutique conference filled with some pretty awesome creative minds.

Those who know me know one thing I like best is a neat and tidy ending – a lesson, a silver lining, a happy moral of the story. (It makes writing blog posts way way easier!) In ending my partnership with Christine, I’ve struggled to find one. There is nothing at all neat and tidy about ending your business partnership while still maintaining your friendship. But I still kept looking and looking for that message.

The running joke has been that people continue to pull Christine or me aside, lean in with a comforting hand on our shoulder, and ask “Are you and Stephanie/Christine okay?” And our responses are always at once lighthearted and reassuring. We’re fine. We’re good. We’re better than good.

Which has been nearly entirely the truth for me. On the one hand, after my initial shock, I’m excited at the huge opportunities presented by getting to step out onto my own path, exhilarated at the future.

On the other hand, I’ve struggled with some overwhelming moments of guilt, fear, and worst of all – jealousy. Jealousy is a lousy beast because it shows up in the sneakiest ways. Wariness, anger, a sense of betrayal – are all just jealousy in disguise.

Like in all breakups, even the amicable ones, seeing your former partner move on without you is especially difficult, Now imagine that you’re your former partner’s go to confidant – as they start seeing new people, they want to tell you all about their first dates, and second dates. It’s strange and painful and awkward all at once. And it feeds jealousy like no other.

Christine and I have had a conversation that addresses that strangeness. She felt weird telling me the exciting opportunities she was finding, and I felt weird hearing them. We both know we had to carry that weight on our own. But that didn’t really make that weight any lighter.

Yesterday, I was asked to introduce Christine before her talk. Given about 2 minutes to decide what I was going to say, I wasn’t even sure where to start. How to do justice to a friend and partner without whom I would never have been standing in that room at all? What I said in the end doesn’t really matter (though I did call her my life partner at one point) but it was there introducing her to speak that the the message I’ve been seeking started to quietly nudge at me.

The jealousy and hurt and anger which would suddenly, unexpectedly come bubbling to the surface, was all tied up in my own fear – Would I be okay? Would I succeed alone? What if I didn’t? How could I find a way to be happy for my former partner moving on without me, going forward without me?

As I introduced her, I realized that we never really go forward alone. She’s not going without me, nor I without her. We’re still side by side, even on diverging paths. There was a peace in watching her speak, and no small amount of pride. I’m proud of my brilliant, inspiring friend. Proud of her that she’s making her dreams come true on her terms. Proud of myself that I am, too.

Christine and I are fine, even sometimes when we aren’t. Because that’s the nature of relationships, both personal and professional. Sometimes, it’s hard. Sometimes, it hurts. But ultimately, after all is said and done, after the jealousy, anger, sadness and other crap we haul around inside our own insecurities fade away, what we’re left with is a genuine desire to see each other fly. What is left is love.


Stephanie Ostermann

I’m the sort of girl who you meet for coffee and end up pouring your entire heart out to. The friend you come to when you need someone to call it straight. No bullshit. No extras. Just truth.

I’m a communicator. That’s a PC way of saying I like to talk, but I also spend a lot of my time listening, and over the years, I’ve developed a sense for subtext – how one or two words can change your entire message, what people are really trying to say and how to weave the varied layers of your story into one cohesive brand message that your clients fall in love with.

When I'm not acting as editor in chief for Vivid & Brave, you can find me geeking out over words here.

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