Why You Keep Asking for Permission in Business (And How to Stop)

I can tell you the exact day I stopped asking for permission. I remember it in my body. And I wish I could say that the clouds parted and everything got easier, that it felt like pure freedom. It did not, not at first. It felt like standing in a room full of people where everybody goes quiet and all eyes are on you. That's why this isn't just the story of the day I stopped asking for permission. It's also about what that cost me, because it did cost me a few things first. And I think the more we have this conversation honestly, the more women will hear themselves in it and realize they can stop asking too.

🎧 Prefer to listen? This post began as Ep 606 of the My Aligned Purpose podcast. Listen on Apple Podcasts or listen on Spotify.

What Permission-Seeking Actually Looks Like for Women in Business

Nobody is literally standing over you saying you're not allowed. We're grown adults here, and every one of us is capable, resourceful, and whole. The permission-seeking I see in women in their 30s, 40s, 50s, and 60s is sneakier than a permission slip. It wears a disguise, and it sounds really responsible.

It sounds like "I just want to run this by a few people first." Then you run it by five people, your partner who isn't an entrepreneur, your parents from a different generation, your sibling who doesn't understand how you're wired, and the idea that felt so alive in your body gets completely watered down. It sounds like "I'm just going to wait until I feel more ready." Who decides what ready is? What's the criteria? I have watched women sit in almost-ready for years. It looks like pricing your offer based on what you can justify or defend if somebody questions it, instead of what the transformation is actually worth. And my personal favorite: softening the big, bold version of the thing before one single person has even seen it. The post was fire when you wrote it, and then you added the disclaimers, or you never hit publish, or by the time you did, it didn't sound like you anymore.

None of this is a character flaw. Women especially were raised on this. We were the good girls, the high achievers, the teacher's pets. We got rewarded for being agreeable, for checking with other people first, for having our work approved before it went up on the fridge. Permission was built into our DNA long before it ever became a business problem. So the question to sit with is this: who am I still waiting on to tell me it's okay? There's usually a face. A parent, a partner, an old boss, a mentor, or the invisible jury of high school. We are not basing our financial and business decisions on Sue from high school. It's time to move on.

The Day I Stopped Asking (And What It Cost Me)

It's 2016, and on paper I have done everything right. I'm a teacher. Respectable job, benefits, pension, summers off, the whole package everybody nods along to at family dinners. I'd been approved. And I was dying in it. Not a dramatic, visible death, just silently dreading every part of a life everyone else approved of, while nobody checked in on how I actually felt.

I had a vision with zero proof behind it. No podcast yet, no stages, nobody in my family is an entrepreneur, none of my close friends were entrepreneurs. There was no one ahead of me saying "yes, this is realistic, I've seen this work for somebody just like you." So who exactly was I supposed to ask for permission? There was nobody qualified to give it. And thank God, because it forced me to see the truth: there is only one person whose permission I ever needed, and she was staring back at me in the mirror.

When I told people I was leaving teaching, I wasn't met with congratulations. I was met with questions. "Is this realistic? What about the pension? Shouldn't you be settling down at 30?" Every one of those questions was an invitation to hand my decision back over. And then came the moment that made it real: my teacher's license came up for renewal in the spring of 2020. That little piece of paper was my plan B, my backdoor, my just-in-case. And a plan B is, energetically, one foot out. It's telling your own nervous system you don't fully believe in this. You cannot build a delusional life while holding the receipts of your old one. So I didn't renew it. That was the day. Not the day I quit, but the day I stopped asking what other people thought about it, stopped waiting to be congratulated, and just decided.

Here's the cost, because there's always a cost. When you stop asking for permission, some people lose their favorite, predictable version of you, and not everyone knows how to hold the new one. I lost relationships and friendships, and it was so uncomfortable. One past friend recently came back into my DMs to explain why she ghosted me four years ago, and it turned out to be jealousy of where my business and lifestyle were going. I wish I'd known then, because I would have said, "What? Let's rise up and do this thing together." But that's the price tag: you have to be willing to walk out of the room even if nobody follows. There is no comfort in your growth zone, and there is no growth in your comfort zone.

Three Ways to Start Giving Yourself Permission This Week

First, check your patterns. For the next week, catch yourself every time you hear "I'm just waiting until..." or "Do you think I should..." or "I just want to run this by..." Write it down, no judgment. You can't change a pattern you can't see, and I promise this pattern is running more of your business than you think: your pricing, your content, your offers, all of it.

Second, ask the question underneath. "Can I really raise my prices?" is not a pricing question. It's "Will I still be liked if I take up more space?" Catch the fear underneath and name it, because when you name it, it starts to lose its power.

Third, take one unsanctioned action. Do one thing in your business without running it by a single soul. Draft the email and send it. Set the price and post it. Ask for the sale. Then tell people after it's done. Make your moves in silence and let them find out when it's real, just to prove to yourself what you're capable of.

Gathering Wisdom Is Not the Same as Asking Permission

Before anyone DMs me asking how coaches stay in business if nobody should ever get input: Kaila and I run basically everything past each other. That's partnership. There is a massive difference between gathering wisdom for a decision you are making and outsourcing a decision you're afraid to make. You can feel the difference in your body. Gather input from people who are in the arena with you, people who are where you want to be or have been where you're going. If they're up in the nosebleed seats, they don't get a say.

Everything you've watched Kaila and me build, the podcast at 600-plus episodes, the stages, the events, the book coming in September, all of it lives on the other side of that one decision. None of this was available to the version of me still checking whether other people were okay with it. You don't need one more person to tell you it's okay. You're out of the permission business.

Ready to surround yourself with women who clap when you share the big dream instead of questioning it? Take the free quiz to find your fastest path to more money in your business, come join us inside the Aligned CEO Method, and sign up for our newsletter for weekly strategy and soul.