Episode 28
You're Not Behind (You're Just Waiting for Permission)
You know what matters. You know your thread. So why haven't you started? The answer isn't that you're slow. It's that you're waiting for permission—and permission is disguised as strategy.
WHAT THIS EPISODE IS REALLY ABOUT
There's a pattern happening in your life and in the lives of everyone you work with. You're confusing two things that look identical from the inside but require completely different responses: stalling and seasons.
You call one of them strategy. It's not. It's permission-seeking. Permission-seeking is when you use a gate—a requirement, a prerequisite, something that needs to be true first—to delay having a conversation you're already ready to have. It feels smart. It feels protective. It feels intentional. But what it actually does is keep you building things in isolation, wondering why they don't land when you finally share them. It keeps you from the feedback that tells you whether you're building the right thing. And it keeps you stuck waiting for internal certainty that only comes from external conversation.
The cost isn't time. It's momentum, data, and the difference between guessing and knowing.
IN THIS EPISODE
- How permission-seeking differs from legitimate seasonal constraints
- The hotel room story: building an entire cohort infrastructure in isolation and getting zero enrollments
- The 3-1-2 sequence that most entrepreneurs default to (and why it fails)
- The actual 1-2-3 sequence that works in the real market
- How to recognize the permission-seeking language in your own voice
- The one-word test that tells you if you're stalling or managing a real season
- The Commitment Check: a specific three-outcome exercise that breaks the permission cycle
- Why permission only comes from other people, never from yourself
THE BIG IDEA
Permission-seeking feels like strategy. It protects you from rejection because you're not asking anyone yet. But protection that never moves is just hiding. And hiding keeps you from the data that tells you whether you're building the right thing. The only way out is to have the conversation before you feel ready. Permission doesn't come from waiting. It comes from moving.
MEMORABLE LINES FROM THIS EPISODE
"You know what matters. You know your thread. But something is keeping you from getting started. And we call it strategy. It's not strategy. It's permission-seeking."
"The cost isn't time. It's momentum. It's data. It's the difference between guessing and knowing."
"Permission-seeking feels protective. It feels smart. But protection that never moves is just hiding."
"Permission only comes from other people, and you have to go ask."
"Knowing and doing are two totally different things."
YOUR ONE THING THIS WEEK
Identify one conversation you've been avoiding—a pitch, a follow-up, anything you keep saying you'll do after you've built or earned or prepared something. Before you have that conversation, write down this one thing: if they say yes, here's what I'd actually do. Not the perfect version. The real version. The one where you already have other commitments and this adds to it. Get specific: what, when, where, and what they'd get. Then have the conversation. One of three things happens: you realize you can commit (that's data), you realize you can't right now (that's boundaries), or they say no (that's information). All three beat waiting in permission-land forever.
CONNECT WITH JESS
If this one landed, come find me at BigIdeasMadeSimple.com. That is where the newsletter lives, where everything I am building is taking shape, and where you can connect directly. One idea in your inbox every week, nothing else. And if you know someone who's holding back from starting something because they're waiting for permission to feel certain, send them this one. The right idea at the right time changes everything.
Follow Jess: @thejesswebber on Instagram, YouTube, LinkedIn, and Facebook
KEY THEMES
- Permission-seeking vs. legitimate seasonal constraints
- Infrastructure-first thinking and why it fails
- The 1-2-3 sequence (revenue, validation, build) vs. the default 3-1-2
- The permission signal: "I'm waiting for ___ before I can ___ because ___"
- Stalling requires movement through fear; seasons require rest and boundaries
- The Commitment Check as a permission-breaking tool
- Vulnerability in conversation as data collection, not weakness
Transcript
Hi, I'm Jess Webber, and welcome back to Big Ideas Made Simple.
Speaker:Today's episode is about something that I have been watching happen not only
Speaker:in my own life, but in the lives of a lot of people that I surround myself with.
Speaker:I'm noticing that we are confusing two things that look identical from the inside,
Speaker:but they require completely different responses.
Speaker:And there is a cost of not knowing the difference between the two,
Speaker:which usually ends up being your judgment of yourself.
Speaker:For the wrong reasons. So, this show exists to help you connect with the knowledge,
Speaker:tools, or resources you need to live your most impactful life.
Speaker:And right now, to me, that means getting clear on whether or not you
Speaker:are stalling or whether you're in a legitimate season where you need
Speaker:to potentially protect your bandwidth.
Speaker:here's what I'm seeing.
Speaker:You know what matters. You know your thread,
Speaker:your North Star. You know the work that you are supposed to be doing.
Speaker:But something somewhere is keeping you from getting started in it.
Speaker:And oftentimes we are seeing that called strategy.
Speaker:But it's not strategy. It's actually permission seeking.
Speaker:And what I mean by that is you use a requirement,
Speaker:a gate, a prerequisite, or something that needs to be true first to delay having
Speaker:Having
Speaker:a conversation or taking the next step that you're already ready to do.
Speaker:And we tell ourselves that this is smart or protective
Speaker:or we're being intentional. I've used air quotes twice,
Speaker:sorry y'all, but it actually does keep you from building the thing in.
Speaker:~ It feels smart, it feels protective,
Speaker:it feels intentional.
Speaker:But what it actually does is keep you from building the thing in isolation.
Speaker:I need to read my own words.
Speaker:But what it actually does is keep you building all the things
Speaker:in isolation and then wondering why when you put them out publicly they don't land.
Speaker:It's keeping you from feedback that tells you whether the thing that you're building
Speaker:is the thing that the market wants.
Speaker:And it keeps you stuck in a cycle where you are waiting for internal certainty that
Speaker:only comes from external conversations.
Speaker:So the cost here isn't time,
Speaker:it's momentum, it's data, it's the difference between guessing and knowing.
Speaker:So
Speaker:I'll take you back. ~ a year, year and a half ago,
Speaker:I flew to a four-day conference.
Speaker:And my plan for that event was really simple.
Speaker:Show up, pitch the cohort training that I had been thinking about,
Speaker:get some interest, come home and build it and launch it.
Speaker:When I got there, I felt scattered.
Speaker:I felt like I didn't have clarity on it yet.
Speaker:The framework was in my head, the gist of it was there,
Speaker:but I didn't have the s sales page,
Speaker:which I usually only build after I map the curriculum framework.
Speaker:I didn't have a payment link or ~ a wait list set up or anything.
Speaker:And so I told myself that I needed those things to have confidence
Speaker:in the conversations. So I did what I thought made sense at the time.
Speaker:I booked the first flight of the morning that was a direct flight,
Speaker:so that I could go lock myself in my hotel room for most of the first
Speaker:day before the event really got started and build the entire thing.
Speaker:So the 12-week framework, the landing page,
Speaker:the
Speaker:Payment link, all the stuff, because I convinced myself that I needed
Speaker:to know the details so that I could do everything else.
Speaker:It was the first domino that I felt like was necessary to make everything else
Speaker:happen and real. So I spent the whole day,
Speaker:I think it was eight, 10 hours in the hotel room building,
Speaker:and then I spent the rest of the trip pitching it.
Speaker:And the reactions were good, right?
Speaker:They were, that sounds great. That sounds awesome.
Speaker:that's so needed in the market.
Speaker:Yet nobody wanted to enroll. Not a single person was like,
Speaker:tell me more. I let's go to have the next step conversation.
Speaker:And the reason I'm telling you this is because I knew better.
Speaker:Years before, I'd done a different version of it where I invited people
Speaker:to a free experience, like the tasting menu before the full meal,
Speaker:got real-time feedback and figured out what landed and what didn't.
Speaker:And that gave me data, but it also gave me commitments to the next step.
Speaker:And I completely ignored that behavior.
Speaker:I completely ignored that way of operating.
Speaker:And
Speaker:Instead was so excited about this new thing that I'd built the whole dang thing just
Speaker:to see what happened. And I skipped the part where I talked to people
Speaker:to get feedback first. The cost for me in that wasn't just the infrastructure that
Speaker:I built. It was the conversations that I didn't have and the networking that
Speaker:I didn't do, or speaking or training gigs that I didn't follow up on.
Speaker:The one-on-one coaching commitments that I didn't secure because I was locked
Speaker:in a frickin' hotel room in Las Vegas building something that nobody
Speaker:had ever even asked for. And so I sat with the build for four days.
Speaker:And then on the plane home, I reflected.
Speaker:I thought first about what I had said on my flight there,
Speaker:which was what was the definition of success for myself?
Speaker:What would it look like if people had said yes?
Speaker:And so I knew that like delivering on it was not the problem.
Speaker:I would have been thrilled to have five people show up and sign up.
Speaker:But the metrics, the data of zero enrollments told
Speaker:me that I led with infrastructure.
Speaker:I led with parts and pieces and
Speaker:not the feedback and the
Speaker:answer to people's problems and the payoff in the way that I knew that they wanted.
Speaker:And so I sequenced my entire build completely wrong.
Speaker:And that's what a lot of entrepreneurs do.
Speaker:It doesn't matter whether you're in coaching
Speaker:training speaking ~ or any other business I find it happens
Speaker:all the time we have an idea we go build it with like the field of dreams
Speaker:we even delay to make it perfect sometimes if you're you've
Speaker:got those perfectionist tendencies and then you put it out there
Speaker:and you know if you're a movie buff this is this is a hundred percent
Speaker:the field of dreams play
Speaker:But I also think of it a little bit more tactically,
Speaker:and I call it the 312 sequence.
Speaker:So you build the infrastructure first,
Speaker:you build everything you think you need,
Speaker:and then you put it out there and hope for revenue because the revenue
Speaker:is going to validate it. And it doesn't work.
Speaker:But here's why people tend to do it.
Speaker:Building feels like progress towards that idea.
Speaker:It's something you can control and you aren't vulnerable.
Speaker:To the rejection because nobody's asked for it yet.
Speaker:And for people who think fast and move even faster,
Speaker:infrastructure feels like you're doing something instead of just talking about it.
Speaker:But we have to flip the script,
Speaker:we have to change the sequence to one that actually truly works in the market.
Speaker:So one is through the relationships:
Speaker:it's have the conversations, pitch the thing.
Speaker:It doesn't have to be perfect.
Speaker:It's getting commitments, booking gigs,
Speaker:~ getting down payments for a launch.
Speaker:It doesn't matter what it is, but you have to validate that people actually want
Speaker:what you think you're building.
Speaker:You have to get permission first from other people.
Speaker:Then you get validation from.
Speaker:through whatever it is. So it's that attraction event,
Speaker:like the free webinar I was talking about,
Speaker:a wait list, a pilot, a down payment.
Speaker:I don't care what it is. So people validate,
Speaker:you get it there, and then you can test it.
Speaker:And those conversations, those yeses that you end up with in
Speaker:the validation and testing phase,
Speaker:that is what is going to tell you what you actually need versus what
Speaker:you perceived you needed. And then that leads you to that third step because
Speaker:now you actually know what the demand is and it allows you
Speaker:to build the infrastructure. You know what language works and what people
Speaker:are asking for. And so you're not building.
Speaker:from an ~ perfect idea you're you're building from real data
Speaker:so the difference between one two three and three one two isn't just
Speaker:the order it's the difference between building something that people want
Speaker:and building something in hopes that they want it and so i'll tell you right
Speaker:now if you are hearing this and you're like ~ crud which one might
Speaker:Which one am I doing? Or there's no way I'm doing it the wrong way.
Speaker:I don't know what's going through your head right now,
Speaker:but there is a way to tell which way you're doing it very quickly.
Speaker:So here's here's the signal for me.
Speaker:Listen to the way that you talk about it,
Speaker:whether it's to yourself or to other people.
Speaker:Listen to the phrases you're saying.
Speaker:So stalling sounds like I'm waiting for blank before I can blank because of blank.
Speaker:I am waiting for the sales page before I can pitch because it needs
Speaker:to look professional. I'm waiting for the book to be further along before
Speaker:I can talk about the coaching business because I need to feel like I earned it.
Speaker:I'm waiting for my audience to grow before I can launch because I need there
Speaker:to be enough demand. I am waiting for the right time before I
Speaker:can start the conversation because I don't want to feel overextended.
Speaker:The because is that gate that I mentioned at the beginning of the episode.
Speaker:Permission always hides behind a gate that sounds reasonable.
Speaker:And so here's the caveat. Sometimes there is a real gate,
Speaker:and you do need to know that. Last November,
Speaker:my mom went to the ER, and turns out she had stage two lymphoma that we
Speaker:had no idea about.
Speaker:The entire first half of this year has been doctor's appointments,
Speaker:chemo, hospitalizations that included falls and sepsis.
Speaker:I mean, the whole thing, real stuff.
Speaker:And those were all bandwidth constraints for me.
Speaker:So when I tell you about permission seeking,
Speaker:I'm not saying that every reason that you have is a delay that is just built
Speaker:out of fear. Sometimes there is seasons in life that are actually too full.
Speaker:Sometimes the bandwidth actually isn't there and you're not supposed
Speaker:to be building the thing right now.
Speaker:And that is different from stalling.
Speaker:And so I want to tell you how to notice the difference because it is sometimes,
Speaker:like I said, hard, especially if you're in the thick of it.
Speaker:So if you remove the gate and if you just decide to have the conversation anyways,
Speaker:could you?
Speaker:Could you have pitched the cohort at the hotel without a sales page?
Speaker:Yes. Could ~ could I have pitched the cohort at the hotel without a sales page?
Speaker:Yes. Could I pitch it right now without a book being done?
Speaker:Yes. Could I validate demand without having a perfect,
Speaker:fully fleshed-out infrastructure?
Speaker:Absolutely. But would it feel scary or premature?
Speaker:Of course. Probably it would.
Speaker:Would it feel like you're asking people to connect with or engage with or
Speaker:say yes to something unfinished?
Speaker:~ yeah. But that the answer to those is stalling.
Speaker:When you say, I cannot have this conversation,
Speaker:that's not seasons. Seasonality is literally,
Speaker:I cannot take on one thing more right now.
Speaker:And I need to protect my boundaries,
Speaker:which is completely different and it's honest.
Speaker:One requires you to move through your fears.
Speaker:The others require rest. So I'll tell you what I think you should
Speaker:do and what I'm working on practicing doing,
Speaker:even though it's uncomfortable sometimes.
Speaker:And that's identify the conversation that you've been avoiding.
Speaker:It could be a pitch, it could be a follow-up,
Speaker:it could be a hey, I'm thinking about this offer.
Speaker:Would it be valuable to you? And the thing that you keep saying you'll do after.
Speaker:that conversation, you'll build,
Speaker:earn the right, get ready, prep,
Speaker:whatever language you're using,
Speaker:go write it down and say, if they said yes,
Speaker:here's what I'm gonna do. So it doesn't have to be the perfect version
Speaker:or the version where there's unlimited time,
Speaker:energy, and leverage. But what's real?
Speaker:If I had that conversation today,
Speaker:what could happen on the other side of a yes?
Speaker:The one
Speaker:where you have commitments and this thing adds to it,
Speaker:but you're being honest about what you can actually deliver and when.
Speaker:And do it specifically. So it's not,
Speaker:I'll run a cohort, but it's like this cohort starts on Tuesday,
Speaker:September ~ eighth,
Speaker:let's say, at 2 p.m.
Speaker:Central time and runs for eight weeks.
Speaker:And here's what's gonna happen this week,
Speaker:that each week. That's the type of specific conversation you need to be having.
Speaker:And you'll notice one of three things when you do this.
Speaker:So the first option is you realize you can commit to this even with everything else
Speaker:on your plate.
Speaker:And that's valuable. It's permission and it's not something manufactured,
Speaker:but it's based on honest capacity.
Speaker:So it's data, it's real, and you can use it.
Speaker:The second thing that might happen is you realize you cannot commit to it right now.
Speaker:The version you could deliver doesn't match the thing that you're wanting to build,
Speaker:and it's okay. It's not stalling its boundaries.
Speaker:That's your calendar,
Speaker:your
Speaker:Capacity telling you that right now it isn't the right time.
Speaker:And that's also feedback. It's also data.
Speaker:The third option that could happen is they say no.
Speaker:You have the conversation and they're not interested.
Speaker:And can I tell you something? You are going to survive this.
Speaker:It's feedback, it's information instead of the story that you've just been telling
Speaker:yourself, you have true data.
Speaker:All three of those outcomes, the yes,
Speaker:the you can't right now, and the no all beat waiting in permission land forever.
Speaker:And it matters because permission seeking feels protective.
Speaker:I get it, it's very protective,
Speaker:but protection never moves us forward.
Speaker:Protection is just hiding and it keeps you from the real information,
Speaker:the real data that tells you whether or not that idea is even worth your time,
Speaker:energy, or effort. And so the only way to get out of that space is to
Speaker:go have the conversation before you feel ready.
Speaker:And most high capacity people,
Speaker:I get it, you lead with infrastructure because it solves real problems.
Speaker:It's how we, you know, kick analysis paralysis in the teeth and
Speaker:we conquer imposter syndrome. We perfect it so we can put it out there
Speaker:and expect people will want it.
Speaker:But what actually happens is often we build something in isolation.
Speaker:And by the time it gets to real people,
Speaker:there's so much emotion and energy invested in the wrong thing that pivots feel
Speaker:impossible. So the people who are moving faster than you,
Speaker:they're not braver. They're not more confident or less thoughtful.
Speaker:They're moving faster because they got permission from other people.
Speaker:They had the conversation and they didn't set an internal standard first.
Speaker:Permission only comes from other people and you have to go ask for it.
Speaker:So you probably know the sequence internally or intellectually.
Speaker:Revenue, conversations,
Speaker:feedback before infrastructure.
Speaker:Validate it before you build it.
Speaker:Get certainty from the commitments.
Speaker:Knowing and doing are two totally different things,
Speaker:my friends. And if you're in a season right now where you're
Speaker:not launching shipping and you're holding something back,
Speaker:go be honest with yourself about what it is.
Speaker:Are you stalling or are you managing in a season that's already too full?
Speaker:Because the fix is different based on which one is true.
Speaker:And if you're stalling, the fix is a commitment check.
Speaker:Get real about what you can deliver.
Speaker:And then go have the conversation anyways.
Speaker:Move through the fear instead of waiting for it to pass.
Speaker:But if you're managing a season,
Speaker:then the fix is different. Say out loud,
Speaker:this isn't the time. Give yourself that permission,
Speaker:right? Then protect the boundary instead of feeling guilty about it.
Speaker:Because you can't do either one until you know which one's true.
Speaker:So this is your one thing this week,
Speaker:right? Don't launch, don't build,
Speaker:don't commit to another thing.
Speaker:Go have a conversation with yourself about what's true.
Speaker:And if it's stalling, then go have the next conversation.
Speaker:If it's a season, give yourself the permission to rest.
Speaker:Because remember, it doesn't come from waiting,
Speaker:it comes from moving. You are the only one who can decide whether it's time
Speaker:to move or time to rest.
Speaker:And if you're somebody who is looking for a little bit more feedback
Speaker:and more permission, find me anywhere on all socials.
Speaker:I am the Jess Webber, double S double B,
Speaker:and I would love to have this conversation with you.
Speaker:Because again, sometimes we can't see clearly when we're stuck inside of it.
Speaker:And that one extra conversation is all we need to define what is
Speaker:our next right move. So, as always,
Speaker:thanks so much for listening, and I'll see you next week.
