Holding Yourself Back Is Exhausting: Why Women Play Small in Business

Holding Yourself Back Is Exhausting. So Why Do We Keep Doing It?

I went into Canva to resize a photo. That was all…just resize it, export it, move on.

Forty-five minutes later I had completely redesigned my podcast cover art, and I was sitting with a much bigger question than I expected to be sitting with on a Tuesday afternoon. Oops!

That’s what I explored in the recent episode of Business Like a Mother. You can listen to the full episode below or keep reading.

The Moment I Almost Played It Safe (Again)

When I was setting up to relaunch the show, I needed to resize the original cover art to fit some new specs. The old cover was fine. Black background, a photo of me in a pink blazer, shirt that said "mom and more" on it, a touch of a slight ‘Don’t fuck with me.” grin.  On brand, not embarrassing, looked like approximately ten thousand other podcast covers in the women's entrepreneurship space.

Which is exactly the problem.

I went into Canva telling myself: don't create more work, Jen. Just resize and export. But I found myself thinking, is this still right? Can it be bolder? Can it actually be MORE Renegade?

There were two little Jens on my shoulders having, as my Bluey obsessed kids would say, ‘a squabble’ about it.

The recovering perfectionist Jen: 

“Your cover is FINE. Stop avoiding other real work. Resize and get the hell on with it.

The recovering playing-small Jen: 

“Ummmm yeah. This cover is safe AF. It's you trying to look like everyone else. Push it.”

I decided to try to meet in the middle. I gave myself a 30-minute time limit and dug through old photos where I found the winner taken almost eight years ago, back when my oldest was a baby. And when I dropped it into the template I just knew. This was the real deal. 

If you've seen the new cover, you know: I have a pacifier in my mouth. I do not look like a mom who has her shit together and that's the whole point. This mom wants to grab a lovey and a paci and take a long nap. The right person is going to see it and think, okay, “I feel seen!” 

The wrong person is going to scroll past and that's fine too. I am not here to be for everybody and neither are you.

What Playing Small Actually Looks Like in Business

The cover art thing sounds small and in the grand scheme of shit we do everyday in work and motherhood and life, it kind of is. And it’s also exactly the kind of moment worth paying attention to, because it shows up everywhere.

You're about to hit post and you go back and edit the caption for the tenth time. You have a draft sitting in your inbox for weeks because you're worried what people will think. You have an idea for a new offer but you're not doing anything with it because what if people don't buy it. You really want to do live speaking but something stops you every time you think about getting on a stage.

I know that last one well. I spent about 15 years pursuing a musical theater career in DC and New York City. Hundreds, maybe thousands, of auditions. Most of the time you get ten seconds and never hear anything. Sometimes you get a callback, put in more work, and still never hear anything. There was a point I was going to 10 to 12 auditions a week.

That experience built real resilience. It also left a part of me, that inner child, that still fears rejection and actively plays smaller to avoid it. Even when I know what I'm doing matters. Even when people are telling me to keep going. Even when I genuinely want to grow.

I still find myself holding back.

If you're nodding right now, you're not broken. You're human.

Why Women Play Small in Business (And Get Penalized Either Way)

Here's the part I think about a lot. Women are conditioned, in both obvious ways and a ton of subtle ones, to stay palatable. To not take up too much space. To keep it toned down. And then we're told we're not living up to our full potential.

When we do something bolder, we're told to dial it back. When we don't, we're told to put ourselves out there more. Damned if we do, damned if we don't.

I've had hundreds of conversations with members inside Renegade Motherhood and the same fears come up over and over: I'm afraid of being too much. I'm afraid of alienating people. I'm afraid of losing clients. I'm afraid of what happens if I actually let people see me.

And underneath all of that is something that doesn't get talked about enough. We're not just afraid of failure. We're also afraid of what happens when we start playing bigger. Can we handle the success? Will our families suffer? What if it goes away?

I don't have a clean answer to any of this. I'm not going to gaslight you and say just be more yourself, because if it were that simple there'd be no coaches left. But I will say: start noticing the moments. The caption you edited ten times. The email in your drafts. The offer you haven't launched. Notice what the common thread is, because that's where the real work is.

The Thing That Actually Moves the Needle

Here's what I've seen make a real difference, and it's not a course or a framework.

It's being in community with people who let you be yourself and also call you on your bullshit when you're shrinking. Who celebrate you when you step into your magic. Who make you feel like the bolder version of yourself is not just acceptable but necessary.

Every time someone inside Renegade Motherhood steps out of their comfort zone and into their real, full self, everyone around them feels more encouraged to do the same. It's a ripple effect and it is genuinely epic to watch.

Holding yourself back is exhausting. The version of you that's been playing it safe has been working overtime, and she's tired. So is mine.

That's why I changed the cover art. And why I'm back. It's also why I think talking honestly about why women play small in business is worth an entire show.

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