238: Why Six-Figure Women Still Feel Trapped By Their Calendar

Welcome to the She Thinks Big podcast. I'm your host, Andrea Liebross, coach, speaker, life balance architect, and strategic thought partner for high-achieving women who want to think differently, lead confidently, and create success on their own terms.

As an entrepreneur myself and the bestselling author of She Thinks Big, here's what I know: You've been at this for a while, but somehow you can still feel stuck in the day-to-day. And running your business like a to-do list does not fulfill the vision.

So around here, we're not about more hustle, we're about smarter strategy, bolder thinking, and leading a business that fits your life. Each week, you'll hear the mindset shifts, real-world tools, and CEO-level conversations that help you reclaim your time, grow with intention, and elevate your leadership. Now, let's dive in.

Hey friends, welcome back to the She Thinks Big podcast. Let's talk about something that's likely familiar. Even if it feels a little taboo to admit, this is something that comes up a lot with my clients.

I sometimes feel this way too myself, where you've built the business, and you've hit the six or maybe even seven-figure mark, and yet your calendar still feels kind of like a straitjacket. I will admit, I am feeling some of this today because I am recording this at about five o'clock on a Monday, not a usual recording time. I am about to head out of town later this week, and I have jam-packed my calendar for the next three days.

Here's the rub. We think—you thought, I think, I believe—that success equals freedom. I guess I wouldn't have the freedom or feel comfortable heading out of town and taking a couple of days off at the end of this week if I wasn’t in the place that I’m in in my business. However, for these next three days, I feel really booked and busy and even probably a little burnt out.

Today, I want to name what’s really going on here and offer just a new way forward. If you haven’t subscribed to my revamped, revised, renovated newsletter called Friday Forward—get that? We have a new way forward. The newsletter’s called Friday Forward—I want you to make sure you head right now to the show notes and click the link to get on our list, because we have revamped this so that you are going to get some real nuggets of wisdom.

It’s a real newsletter every Friday to help you move forward into the next week with a little bit of sass, a little bit of energy. I digress. Literally, go get yourself on that Friday Forward newsletter email list if you're not there.

Today, what we’re going to explore is really hidden time poverty, the hidden time poverty that women experience, even if these women are "at the top" or are feeling successful. We talk about the mindset behind your calendar a lot. We talk about tools. I kind of want to put it all together here. I want to talk about mindset.

I want to talk about tools to shift it, to shift this hidden time poverty, and the space you must reclaim, not just for doing things, but for thinking and not thinking. That’s kind of how I see this week a little bit for me. These next three days, I’m trying to get a lot into a little amount of time.

However, the end of the week, I am reserving time for thinking and not thinking, if we want to look at it that way. I’m okay with that. If it was this way all the time, if it was all busy and no time for thinking and not thinking, I think we’d have a problem.

Here we go. Part one: the success time trap. Here is something that women are not talking about on the soccer fields. They are not talking about it at the networking meeting. But we are going to be honest and talk about it here. Success creates demand.

With every level you reach, more opportunities appear and more people want your time. Because you’re smart and you’re capable and you’re responsible, you say yes, until suddenly, your calendar looks like a reflection of everybody else’s needs instead of your own vision.

This is something I personally have been working really hard on. I want my calendar to reflect my vision of who I want to be and my business, not everybody else’s needs. I have reached this level where I am saying yes to more opportunities because more opportunities are appearing. These are the opportunities I’ve worked to create.

But I don’t want to suddenly feel like my calendar is just a reflection of everybody else’s needs. One of my clients recently said to me—and I took this quote directly from a coaching call—“I thought I would feel free once I got the business to multiple six figures, but instead I feel more trapped than ever.” I think that is the success time trap.

If we want to name it something, let’s name it the success time trap. It’s not just you, because according to a Gallup poll, high-income earners are more likely to report time stress than lower earners. If your revenue is up but your breathing room is down, you’re not alone.

I want to say something here on the podcast that I often say inside what I am rebranding as Ascension. Now Runway to Freedom Mastermind is going to be called Ascension, because we are ascending into a new level of leadership. More on that later.

That’s just a little hint. I say this often inside that group: your calendar is really a mirror.

If you don’t like what you see in the mirror, then it is time to look at who’s doing the designing. Who’s designing the calendar? What are you wearing, so to speak? Your calendar is a mirror. If you don’t like what you see, it’s time to look at your outfit, at what you’re wearing.

Let’s talk about that mirror for a second. You might be familiar with systems like the Full Focus Planner or the Ideal Week. I have a whole bunch of episodes on time where I talk about those things and others.

I use this kind of thinking—this Michael Hyatt, Full Focus style of thinking—with my clients all the time. I use it in my own business. But knowing how to use the tools and trusting yourself to use them are two very different things.

The gap between trusting yourself to use them and knowing how to use them is what I want to call the calendar confidence gap. It shows up when you keep accepting meetings that drain you, fill your week with shoulds, not really CEO-level work, and never really block time to zoom out and think strategically. I have gotten really good at saying, “No, I don’t need to be in that meeting. You guys can handle that yourselves.” I’ve gotten really good at saying, “No, I don’t want to be on your podcast.” I don’t want my calendar to feel like shoulds. I want it to feel like CEO-level work.

Here’s something that’s often overlooked: you need time to do the work. You also need time to think and time to not think. You need white space. You need margin. You need breathing room. That’s not laziness. That’s leadership. Michael Hyatt calls it margin. I call it oxygen.

Let me tell you what this has lately been looking like in my own life. I have made a lot of space this year to play golf regularly. Not just casually fitting it in. I have really designed my schedule around it. When I am golfing, that’s time to think but it’s also time to not think. My business has not suffered. I think it’s actually gotten better.

Because I have designed my schedule to do something I enjoy. I joke with my friend Jenny, who I play golf with often—If you follow me on Instagram, go follow me on Instagram. You’re going to see a lot of photos of Jenny and me playing golf—we joke that we solve more before we get to the sixth hole than we do in a whole day. She owns a very successful business. Oftentimes, we talk about business problems. We solve a lot of things.

That’s time for me to think but it’s also time for me to not think. I’ve seen the same thing happen with my clients.

One woman inside Ascension told me—in what I now call in my back office "white chair testimonials," Last retreat, I had everybody answer a few questions about their experience at the retreat and in the mastermind. They were sitting in a white chair.

Now I call them the white chair testimonials. She said, “Here’s what’s happened since I started working with Andrea. I’m finally doing things with intention, not just out of habit.”

“I’ve stopped measuring my worth by how full my calendar is.” That moment—her realization there—that’s what this is all about. She stopped measuring her worth by how full her calendar is.

She’s being way more intentional. She’s closing that gap. That’s the calendar confidence gap. She’s closing that gap between knowing how to use the tool and then trusting herself to use it.

How do we begin this shift? I think it starts with what I’m going to call a calendar detox. Using the four D’s. I’m going to give you four D’s—four verbs that begin with D. If you can do these four things effectively, then you’re going to close that gap.

You’re going to detox from that feeling that your calendar is ruling you and that hidden time poverty. You’re going to start to make time to do the things you want to do, to think and not to think.

Here’s the first D: Delete. What can we cross off completely? What is outdated? What’s draining?

Me being on other people’s podcasts that only have created 10 episodes, I’m not doing that. Me fielding calls for people who just want to pick my brain, I’m not doing that. Delete.

Number two: What can you delegate? We’ve talked about delegating on this podcast numerous times. What are you still doing that someone else could own if you trusted them to? That’s delegating.

Next, third D: Diminish. What can be shortened or simplified or scaled back? I don’t know if you’ve noticed, but I purposely have shortened the time, the length, of some of these podcast episodes. I don’t think they need to be 45 minutes long.

I’m really aiming now for 15 to 20 minutes. I’m shortening. I’m simplifying. I’m scaling back. I think you get just as much value.

Then the fourth D is Designate. What doesn’t need to happen now? What can be pushed forward with intention and time can be designated for it later?

Delete, Delegate, Diminish, and Designate.

Here’s a practical exercise. I want you to go look at last week’s calendar. Print it out if it’s digital. I want you to grab two highlighters. Use one highlighter, we’ll call it green for the tasks that gave you energy. I want you to use another highlighter—maybe hot pink—for the tasks that drained your energy.

Okay. So look at your calendar. Highlight what gave you energy and what drained you using these two different color highlighters.

Then ask, "What would the future version of me, the $1 million CEO, never ever put on her calendar again?" Never put on her calendar again. That's question one.

Question two: I want you to not forget to think about next week's calendar. Do you have time to execute on things? Do you have time to think about things? Do you have time to not think about things?

Again, in one of those white chair testimonials from Ascension, another client described this perfectly: "I finally have a calendar that reflects my future, not just my past."

Now she really starts her week with a strategy block. She keeps Fridays free. She doesn't take meetings after 3:00 PM. None of that happened by accident. It happened by design because she didn’t like what she was seeing in the mirror previously. So she redesigned her outfit.

All right. Here’s what I want you to take away from today. You don’t need another productivity hack to create more time. You need the confidence and clarity to protect the time you have, to protect what matters.

Second takeaway: Time freedom isn’t a reward you get after the hustle. That’s what I don’t love about my week this week, to be honest. I feel like I’m waiting till the end to have some time freedom. I don’t like that.

Time freedom really should be a leadership decision you make now because it’s how you lead your next level. So this is a leadership decision I’m making. So I can buy into this.

I’m being intentional this week. Nothing’s perfect here. Notice.

Third: You didn’t build this business to be booked solid. You built it to breathe and to lead and to think big. And I built it to play more golf. You didn’t build the business to be booked solid. You built it to breathe and lead and think big.

So your homework this week is to do that calendar autopsy. Print last week’s calendar.

Highlight what gave you energy in one color and what didn’t give you energy in another color. Then ask, "What would that next level version of me do differently?"

I want to invite you—if you want support to redesign your business and calendar kind of from the inside out—this is exactly what we’re doing inside the Ascension Collective. We’re getting ready right now to do an enrollment push because I want you to be at our next retreat, which is in November.

The next retreat for Ascension is in November. This is the kind of stuff we talk about in there. We talk about redesigning our businesses and calendars from the inside out. We create space.

We protect margin. We help you go from operator to CEO with a calendar that really reflects who you are becoming.

So who are you becoming? And are you inside a support container that reflects who you’re becoming? Or does it just reflect who you are right now, or your past you?

I’m inviting you. Here’s my invitation. Go book a call with me. Go to Andrea’s Links, andreaslinks.com. Book a call.

Let’s talk about what that looks like for you. Let’s talk about you having a calendar that reflects who you’re becoming. We can do this, my friends. Okay. Until next time, keep thinking big. I will see you right here next week.

Thanks for listening to She Thinks Big. I know you’re committed to yourself and your businesses because you listened all the way to the end of this episode. But this isn’t really the end. It could be the beginning of your next power move.

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