Making Meeting With Yourself Even Better With the Help of Others
Making Meeting With Yourself Even Better With the Help of Others

148: Making Meeting With Yourself Even Better With the Help of Others

It always starts with a meeting.

When you first get the idea for your business or want to revamp it or add something new, you plan a session to strategize. And you might be doing this alone.

But while meetings with yourself to strategically plan and think ahead are good, they aren’t the most effective way to strategize. If you want to be a big thinker and create growth in your life and business, you need a guide along for the ride.

In this episode of Time to Level Up, you’ll learn about the three reasons why meeting with others is better for you and your plans. I’ll teach you the value and benefits of strategizing with others and where I often see clients struggle the most.

What’s Covered in This Episode About Making Meeting with Yourself Even Better

3:22 – How meetings with yourself might differ from meetings with others

5:21 – Why you find yourself spinning your wheels after your solo meeting

9:30 – Why meetings with others open you up to bigger dreams you may not realize you have

13:39 – The second reason why communicating with others while strategizing is so important

15:52 – Why reason #3 for planning with others might be the best one of all

18:32 – The challenge you face even as things become super clear in meetings with others

20:22 – What happened when I went through this exercise recently with two business leaders

24:02 – How support helps you separate fact from fiction

Mentioned In From Making Meeting With Yourself Even Better With the Help of Others

She Thinks Big by Andrea Liebross

Andrea’s Links

Quotes from this Episode of Time to Level Up

“Meeting with yourself is just not going to cut it, because it’s so easy to break a commitment to yourself.” – Andrea Liebross

“We as women especially have a really hard time dreaming. We can’t get ourselves past today.” – Andrea Liebross

“Your brain doesn’t really like planning what’s next. It likes where it is right now because right now, it knows what it’s doing.” – Andrea Liebross

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Welcome to the Time to Level Up Podcast. I’m your host, Andrea Liebross. Each week, I focus on the systems, strategy, and big thinking you need to CEO your business and life to the next level. Are you ready? Let’s go.

Hello, my friends, and welcome back to the Time to Level Up Podcast. How are you? How are you doing today? Are you having a good day? I’m having a pretty good day. I’m recording this the day before my book launches. By now, you should have your hands on a copy of She Thinks Big.

If you don’t, then you need to head over to and get yourself a copy, plus get access to a couple of bonuses. One of which is the Think Big Insider Session that is happening on the day that this is being released on October 10th.

If you’re listening to it on October 10th, you still have time to get inside that Insider Session where I’m going to show you really how to take what you’ve read and actually implement it, actually do something with it. If you’re listening to this after October 10th, that’s okay because I bet you could go over there and get the replay. I had to bet. Haven’t decided yet but I’m pretty sure.

You can also get a handwritten message from me, a bookplate, I will mail it to you snail mail, I will put a little personal message for you in there, and you can stick that inside your book, kind of my gift to you.

Here’s what we’re going to talk about today. We’re going to talk about why meetings with yourself are not good enough, why meetings with other people, specifically meetings where we do some strategic planning and think ahead, meeting with yourself on this is not good enough. It’s good but it’s not good enough if you want to be a big thinker, if you want to create some growth in your life and your business.

Meetings with yourself are good, planning with yourself is great, but it’s just not great enough. I am bringing this up today because at the end of that Think Big Insider Session from October 10th through the next week, you’re going to have access to an amazing offer, which is going to include a meeting not just with yourself but a meeting with me.

Part of the offer is a Vision to Action Intensive and I think this is super valuable for a couple of reasons. What I want to talk about today are the three things, the three reasons why strategic planning with yourself, a meeting of one, or even a meeting of two, is good but it could be better.

Here’s what I mean by this. When you started out in your role in your business, you probably sat down and had a meeting with yourself. At that point, you were customer service, you were marketing, you were web design, and you were graphic design, and you were finance, and you were sales, you were all those departments, and you were meeting with yourself and you were writing stuff down, you were fiercely writing things down.

I’m sure at this point when you’re having meetings with yourself even if you’re still having them, which you probably are, you make some big long lists, maybe you craft out a sentence or two about where you want to go, but it mostly looks like a big long list.

Now, if you have upgraded and you have now meetings with your team, you still may be making lists, but you are using that meeting also as a form of communication to create some accountability, to make sure “everybody’s” on the right track, I will argue that there is no right track, and everybody’s on the same page. I might argue why do they have to be on the same page? You might actually want them to be on a different page and tell you what they’re reading. But we’re not here to argue, we’re not going to talk about that today.

What I want to talk about today is the value and the benefits and what happens when you have a strategic planning meeting with the help of another person. Why are meetings with yourself not necessarily the most effective?

Now, think back to these meetings with yourself and think back to your big lists. You probably say to yourself, “Okay, I’m going to do these three things today, and I’m going to do these three things tomorrow, and I’m going to do these three things in the next month,” and then you might take out your planner and you might put them in there, and you might look at your Google Calendar and figure out when you have time.

Now, the things that you’re putting down on your list, this meeting with yourself, chances are, you’re not really looking long-term, you’re not thinking, “Does this align with where I want to be three years from now as I’m having this meeting with myself?” You don’t. But you’re getting everything out of your head, which feels awesome, you’re putting it on a piece of paper, and then you can see it, and then you’ve got a chance to relax and you’re going to trust yourself that things are going to happen.

But what I see my clients often do when they do this is that I see them spinning. A week after them meeting with themselves, they are spinning because they just don’t know what to do with their time even though they have their list, and they always are thinking they don’t have enough time because everything on that list feels very urgent and when they do have a little pocket of time, they really don’t want to do any of it. They would rather empty the dishwasher, check emails, or go on a walk.

Those meetings with yourself, if you want to grow yourself and your business, if you want to achieve different things, if you want to create more time, money, and energy, and have freedom, the meeting with yourself is just not going to cut it. Because it’s so easy to break a commitment to yourself.

If you put something in your planner that you’re going to do, it’s so easy to just not do it, to just say, “Forget it, I’ll do it tomorrow.” The deadline is like an elusive deadline like you made the deadline? So it’s not really there, it’s not really real.

Again, everything on the list though feels very urgent like it has to happen today or by the end of the week. I have had that experience recently in planning for this book launch, there were so many moving parts, so many I cannot even imagine, you don’t even know how many moving parts, and about a month ago, I made a big long list, I had a meeting with myself, I made a big long list and I felt like everything had to be completed that day.

But now that I am right here at the launch 24 hours, or not even before launch day, I realized that everything didn’t need to be done then but that is how I felt. I’m going to give you a framework for this, here are three reasons why the meetings with yourself are not as effective as they are when you’ve got someone there with you.

I see this a lot when I do these Vision to Action Intensives, VIP days. I see my clients come to me, “Oh, we’ve already thought about this.” They’re bringing things to the table which is of them, they’ve already thought about some of the stuff that we’re going to discuss, but they haven’t thought about a lot of the other things that we’re going to discuss, and even if they have thought about something, they probably didn’t go too deep on it, it’s still very surface-y or they haven’t looked at what they thought about and put on paper in three years.

Here’s the number one reason why meeting and having a guide to facilitate a meeting when you’re talking about your business strategy or your life strategy, why having that guide is so, so helpful. Here’s number one. Number one has to do with big thinking.

I could count the number of times when I’ve been doing one of these types of strategy and planning Vision to Action Intensive meetings that someone had said to me when I asked them, “Where do you want to be in 10 years?” first of all, they struggled to answer this question. This is hard. We as women especially have a really hard time dreaming. We can’t get ourselves past today, it’s just like we don’t have the brain space for it, and honestly, it feels like we don’t have the skill to do it.

There’s a roadblock. It’s like we’re not even allowing ourselves to go there. But when you have this guide and I’m pushing you and asking you, “Where do you want to be in 10 years?” and I say, “What else?” and you say, “Oh, I want to be traveling a lot. I might want to be living at our lake house. I want to be working three days a week,” and I say, “What else? What else?”

Eventually, that else comes through with a lot of talking. Someone said to me, “What I want to do is I want to speak on a national stage and share my message. I picture myself in Carnegie Hall sharing my message. But that’s never going to happen.”

Here’s the thing, if you put off that dream of standing on a stage in Carnegie Hall, you’re right, it is never going to happen. They might say, “I’ve been thinking about it for five years.” Well, do you want to be thinking about it for five more or do you want to be working towards it?

Sometimes people say, “I really don’t like what I’m doing right now, but it seems to be paying the bills and I’m pretty good at it. I’ve developed this business and it’s going well but it’s not really what I love doing. But at this age of mine at 45, is it too late to make a switch? Should I pivot this business? What will people think?”

But here’s what I want you to know, you should be pivoting if this isn’t what you like, we need to find what you like to do because do you want to spend the next 45 years doing it? Now, if you were to ask yourself, “What are my dreams and goals?” you might come up with one sentence, “Maybe.” But there’s power in a meeting because meetings are about communicating, and I am communicating with you in that meeting and asking you the whys, even why do you want to get up on that stage.

Why do you want to switch careers? Why do you not love what you’re doing? Why do you think you’re going to love this more? With all of that dialogue in communication, that big thinking happens because without it, we stay in our small thinking. We stay with what’s comfortable, we bring that that’s impossible how it would happen, which brings me to the second reason why communicating and sitting around a virtual or real table with someone when you’re strategizing is so important, and there is a second reason.

Let’s say we do have this vision, now what are you going to do? Now you have to take some action steps. You’ve got to plan what’s next. Your brain doesn’t really like planning what’s next. It likes where it is right now because right now, it knows what it’s doing.

But when we come to those next steps, they’re hard, they’re uncomfortable. They’re probably things that aren’t necessarily easy for you, let alone fun, although I am big [inaudible] of how can we make this fun, which is one of the reasons you need someone asking you that, “How can we make this fun?”

But planning the steps and which steps to take, our brain wants to shut down because it doesn’t see how it’s going to get from here to there. We get stuck in the how. I see so many of my clients falter in the how. This is where they get stuck. But I also see my most successful clients knowing that all they need to know is the next best step, not all the steps, but just the next best step.

In order to figure out that next best step, we’ve got to ask a lot of questions about where you want to go. We’ve got to look at how all of the pieces of the puzzle fit together.

First thing is it’s really hard to do big thinking on your own and you will keep your dreams in a box and not let them out if you’re meeting only by yourself. Number two, figuring out what the action steps are to turn that vision into action, really, that’s where people get stuck. That’s the second reason why meeting with someone else is super important.

Then the third reason is being able to see all of the tentacles of what you want. This I think is almost one of the most, maybe the best reason why meeting with someone else, having a strategy, and planning a meeting day with someone else is so, so, so important. Because here’s the thing, if you said to me, “I want to go speak on the stage in Carnegie Hall,” I might say to you, “Do you know what you want to talk about?” “Oh, yes, I know what I want to talk about.” “Do you know how you want to talk about it?” “Well, not really.”

So I might say to you, “Okay, we’ve got to get help and we’ve got to solidify and tease out exactly what you’re going to say. But once we do that, then we’ve got to figure out how we’re going to get you on that stage, how do we make inroads there.” Then let’s say you get on the stage, do you know where? Who do you want to be on the stage?

Then once you’re on the stage, so many people are going to see you. What are they going to do? How are they going to connect with you? Do you have a platform that you can send them to? How can you continue to help them?

When we talk about next best steps, I also want to look at all the tentacles of a dream, all the things that need to happen in order to make that dream come true. You might even say to me, “I want to get a forklift to help move things around in my warehouse,” and that’s kind of a short-term dream but it’s a dream. So what do we need? We need a forklift, we need a driver for the forklift who has to have a special license, we need to have a place to store the forklift, we need to be able to maintain the forklift, and we probably need another operator of the forklift, is one person enough?

See all those tentacles? We need to explore what all the tentacles are in order for you to know the next best step. That is a lot for one brain to handle. But when we talk about it and communicate about it and we tear it apart a little, things start to become super clear, that next best step emerges because we’re breaking things down and looking at all of the elements.

Now as we break things down, here’s something else that’s challenging, you have to stay in the belief that this actually can happen. We’ve got to put your belief plan and very quickly as you see all the tentacles of these things, that belief plan can get thrown out the window. It’s really hard to keep the belief plan front and foremost.

Because here’s something that happens, we’ve figured out all the tentacles, we talk about next steps, probably it’s going to take some resources to make this dream come true. It’s going to take time, which means that you don’t have all the time, maybe we’re going to have to hire people to expand our time capacity.

That, my friend, is going to take money and then you’re like, “Oh, my gosh, I don’t know if I can afford this.” Then it’s going to take brain power, energy to find people that can help you. Then the fear factor kicks in. Hiring people is scary. Wondering if we have enough money is scary, thinking about managing them is scary.

This goes full circle. We can go back to my first thing which is it’s really hard to think big on your own. Once you think about all these things that you might have to do that are new, that are hard, that are uncomfortable, that you’re not really efficient or proficient at yet, the big thinking, in order to stay in that space, it’s super challenging.

I just did this, I’m recording this on a Monday, on Friday, I went through this exercise with a team of two leaders. They have a business and their business is growing exponentially. They came to me having thought through where they wanted it to go. They had thought through that. But as we dove a little deeper, we realized that action steps, how they were going to get there, really weren’t what they thought or the easiest way really wasn’t what they thought it would be.

Although it might be the easiest way, it also comes with some fear because it’s something they’ve never done before. They’ve created a lot of content in service to their clients in short little bursts, but they have never created what I like to call recurring revenue. They have never created something where people are paying them month after month, time after time, and that scared them.

I understand why it scared them. But I had to keep reminding them of their big thinking. I had to keep going back and saying, “Yes, but if you want to create a business and lifestyle,” because this business they’re going to create would allow them to have a lifestyle that they wanted, “if we’re going to do this, then we have to get super clear on the dream, we’ve got to figure out what our next action steps are, and then we’ve got to break those action steps down into pieces.”

Fear, go back and listen to my podcast on the nine common fears of entrepreneurial women, fear comes to the surface. That, my friends, is really why you need that other person there. That is why doing this work together in a small community or with a coach is of utmost importance. We want to stay in our peanut butter jar.

Here are the three things we want to do: We want to stay in our peanut butter jar, we’re in our peanut butter jar, and it’s so sticky, we can’t get out and we can’t see what’s going on around us.

Number two is what we want to do is that we want to stay in the familiar. Our brain, remember that frenemy brain back there, it tells us, “Hey, you really sure you know what you’re doing? You’ve never done this before.” And you have to say to it, “Yes, thanks so much but I’m ready to face this and I actually have support.”

Then the third piece of the puzzle is that our brain, also remember, likes to do the easy things, the motivational triad, our brain, we like those things to be easy and doable. The motivational triad kicks in. It kicks in and it keeps us in that safe spot.

This is why this is so hard. It’s not that you just should be able to do this, or it’s not “by now you should be able to do this,” you’re a human, so these are human things that happen to us that create roadblocks, that prevent us from thinking big, from making these things come true, from turning our vision into action and then into a reality.

You’re human. Your humanness sometimes gets in the way. That is why you need to secure some support in the form of another human. That is one of the things that big thinkers do. Let me just end with this, and in the process of securing that support, and teasing all these pieces out like where you are and where you want to go, you’re going to recognize what the facts are and the fiction is.

A lot of stories that you’ve been telling yourself are going to come to the surface, things like, “No one’s bought this before.” Is it true? No one has bought this before? Three people have bought it before and you wish it was 30.

The story of “I don’t have enough money to do this,” that’s truly just a thought. It may be a fact that you don’t have enough money today to pay for it today but we’re doing this to create more so you will have more in the future to pay for it. That’s you staying in the belief.

But beliefs are thoughts. Beliefs are stories that you are choosing to believe. Going through this process too, if you’re someone that has trouble separating out fact from fiction, this is also super helpful.

Okay, my friends, meetings with yourself are okay but meetings with someone else are a whole lot better. Strategizing with yourself is okay but strategizing with someone else is a whole lot better. Looking at your future by yourself is good, I want you to, but looking at your future, doing big thinking, accessing future you, and believing it all can happen with the help of someone else is awesome. It turns you into extraordinary.

Head over to, get access to that Insider Session live or replay, and be on the lookout for the book offer that I am making after this Insider Session just in the month of October. It’s going to include a Vision to Action Intensive and a ticket to my live event in January, and having access to a course that I am going to create in 2024.

It’s an amazing, amazing offer. I think you’d be crazy to pass it up. You need this just for the Vision to Action Intensive alone. Everybody should be doing one of those. Everybody listening should have a day for a Vision to Action Intensive. It is transformative and I’m doing my best to try to explain to you why. It’s hard to explain to you why because some of it is a feeling that you’re going to get. It is very empowering.

But just think about this, three reasons why meeting with yourself is not always amazing: one, you can’t do that big thinking, two, figuring out those action steps is hard, breaking it all down and seeing where all the tentacles go is very important, and if not done will lead you to not creating the reality. But if done, and staying in that power of belief, we’re definitely creating something extraordinary.

Head over to She Thinks Big The Book, head over to, you’re going to find all the details on this. In the meantime, take a screenshot of this episode while you’re listening to it, share it with someone else, direct message me on Instagram, let me know you’re listening, and let me know what you’re big thinking about.

Alright, my friends, right now is your time to level up, to upgrade you and your business, and I would love to do it with you. I’m here. If you don’t have a coach, I’d be happy to be your coach. Let’s do this together. See you next time.

Hey, listening to podcasts is great. But you also have to do something to kick your business up a notch. You need to take some action, right? So go to and take the quiz. I guarantee you’ll walk away knowing exactly what your next best step is to level up.

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Who_s the Best Business and Life Coach in Indiana -

I'm Andrea Liebross.

As a business and life coach specializing in helping unapologetically ambitious women entrepreneurs from a variety of industries level up their businesses and personal lives, I provide strategies to boost clarity, confidence, productivity, and profitability while teaching you how to transform obstacles into opportunities. I’m also a speaker, host of the Time to Level Up podcast, and author of the best selling book She Thinks Big: The Entrepreneurial Woman’s Guide to Moving Past the Messy Middle and into the Extraordinary. If you’re ready to drop the drama and achieve time, money, and energy freedom, you’ve come to the right place. It’s time to combine Big Thinking with solid systems to unleash your success. Let’s do this!