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The Lipstick Gospel

No Longer A Lazy Spectator

I'm Stephanie May Wilson!

I'm an author and podcaster and my specialty is helping women navigate big decisions, life transitions — creating lives they love.

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I don't love playing games.


I’m not great at team sports and what used to begin as an effort to impress a boy usually left me sweaty and defeated — not the impression I was hoping to leave.


I’m also not the hugest fan of board games. My family loves them and when they're feeling particularly “Leave it to Beaver”, they pull one out of the game cabinet, excited and ready to bond.


I rarely join in.


Somehow over the years I've cultivated this habit of sitting on the sidelines. I'll watch, be a fan, or read a book while everyone else is laughing and having fun.


I think it’s because I don't want to put a lot of effort into something I: 1. May suck at (sports) or 2. May not particularly enjoy (family game night).


But in the process I think I've been missing out.


I went to Mexico with my family and boyfriend recently and at our resort there was a whole team of staff members dedicated to games. They had pool volleyball and beach volleyball, dance classes, and tennis courts. And my family was all about it. They participated in all but the dance classes and I’m pretty sure they would have joined those too if there weren’t older men in the pool filming on their iPads.


And for the first several days I opted out of everything. I'd scoot close to the court and watch my family play, but I'd always stay a safe distance away, glancing up from my book occasionally.


I got roped into a game of tennis one day and as we were packing to leave, I grabbed my iPad. My boyfriend asked me what I was doing and I told him that I'd probably just watch and read some. “On the courts?” He asked surprised.


One of the staff came by my lounge chair later, convinced that he was going to recruit a gigantic pool volleyball game. He asked me and I shook my head.


I don't play volleyball.


But as I watched my family gear up, I took a pause. Everyone else was going to play… and they weren’t all great at the sport.


And that changed the offer a bit. It wasn't a question of playing volleyball, it was a question of engaging with my family and boyfriend–doing something on a team with them and choosing to make the most of every moment we had together.


And so reluctantly but resolutely, I hopped into the pool.


I touched the ball maybe once, and tried to quit halfway through the game — once again resigning to the sidelines. But as I watched them dive and high five, I jumped back into the pool, recommitting all over again.


At the end of the game I still had touched the ball only once, but I got to high-five my team members and laugh as we reenacted highlights. My boyfriend pulled me into a slippery pool hug and whispered in my ear, ” I'm glad you played.” And u know what? So was I.


Throughout the week I had several more chances to join in. Sometimes I played (tennis) and sometimes I watched (beach volleyball).


But each time I chose to engage. I watched with rapt attention and cheered loudly. I played my hardest in tennis and then watched my sister take on my boyfriend in a face off—I couldn’t decide which side to root for.


I was the biggest fan of their beach volleyball games—cheering happily and genuinely when one of them scored a point.


I went from a lazy spectator to someone who was all in, giving each moment everything I had, even if it wasn't much.


And that is the way I want to live. I'm fine with a challenge as long as it includes travel or languages or food or my job. But I'm uncomfortable diving into activities that don't look like me—things that I've never been good at or have never really loved.


But regardless of the activity, I love my people. And sometimes that means learning to love certain things so I can join them as they do the things that they love.


My family loves board games and so I want to play with them—joining in completely instead of standing on the sidelines.


And I want to do this in life too.


I want to be all in, making the very most of each moment that's offered to me, not just the ones that seem comfortable.


I want to live an “all-in” kind of life.


Don't you?


How do you step out of your comfort zone to live an “all-in” life? 

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  1. emilydtuttle says:

    Love this Steph. I think it’s much easier to fully engage in things we’re not good at when we can completely trust that the people in our lives know us, accept us, and love us for who we are. Then who really cares is we suck it up on the tennis court? They’re going to love you anyway, maybe even more for having played with them:)

  2. Christy says:

    I love this a lot Stephanie May! Beautiful! thanks for sharing your heart lady!

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