Productivity & Time Management

Episode #429 – Breaking the Maybe Mindset

January 13, 2026

I’m Cherylanne.
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Ever find yourself circling around a decision, stuck between yes and no, with a big “maybe” holding you back? This week, I’m pulling back the curtain on the “maybe mindset”…that quiet habit of postponing meaningful choices and playing it safe.

I’ll share why it’s so tempting to linger in indecision, the real price we pay for not committing, and practical strategies for finally breaking that cycle. Expect honest recollections, a fresh perspective on why clarity doesn’t require perfect certainty, and a powerful invitation to make bolder, more confident choices.

If you’re ready to stop living in limbo and start moving forward, don’t miss this episode. 

Show Highlights:

  • Have you spotted your euphemisms for “maybe”? 00:51
  • The true costs of the “maybe mindset.” 04:30
  • Paralysis of options and how to overcome it. 05:56
  • The comfort zone conundrum. 08:11
  • The illusion of abundant time. 09:53
  • Ask “What would have to be true to say yes?” as a clarifier. 13:23
  • Weighing the cost of a no. 15:56
  • The power of breaking big choices into small steps. 18:05
  • Why embracing uncertainty leads to growth. 19:37
  • Clarity through a clear yes and a clear no. 20:50

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Follow Cherylanne on Instagram: http://www.instagram.com/cskolnicki

This is episode 429 of the Brilliant Balance podcast. Today, we’re talking about breaking the maybe mindset.

Well, welcome back to the show. I’m so glad that you tuned in today. I don’t know if you heard the song “Maybe” from Annie in your head as you read the title of today’s episode. It’s all I can ever think when I hear that word. It’s always, like, the first thing that comes to my mind—and today’s episode is going to dig into the word “maybe.”

This is actually a re-air from a couple of years ago. But as I listened back to it recently, I was really struck by how relevant it is today. Because if there’s one thing that I see just over and over again with the women that I have the opportunity to connect with inside of Brilliant Balance, it’s this:

We really don’t struggle to make all decisions, but we struggle to make the ones that move our lives forward in a meaningful way. Right?

Those are the ones where we have that word surface—right, that “M” word—and we say all the euphemisms for it. Like, “Oh, maybe not yet,” or “Not now,” or “I’ll think about it.” Right? The total kiss of death. And sometimes we say that for years and years.

So in this episode, I’m talking about what I’m calling the maybe mindset: why we get stuck there, what it’s really costing us (which is a lot, by the way), and how we can move toward having a clearer, more confident yes—or no, for that matter—without needing perfect certainty to get there.

So if there is any decision in life that you have been circling—about your work, or something in your home life, or within your personal well-being—this conversation may really resonate with you. So let’s dive in.

So I want to start this episode with a confession of sorts. True story.

I have been trying to install outdoor lighting in our home for almost seven years.

We bought this house. It had very limited, kind of older-style landscape lighting, and I kind of, you know, fell in love with some of the more architectural lighting— a little bit more elaborate outdoor lighting.

And so, a few years into owning our home, I called someone, had them come out and give us an estimate to install the lighting, and I told them I was going to think about it.

And I did think about it off and on for months. And then a year or two later—still no landscape lighting installed—I called another company to come and talk to us about landscape lighting and architectural lighting.

They came and did a beautiful job kind of rendering what it might look like, gave us an estimate—which I told them I would gladly think about.

And here we are seven years later, and I still don’t have this upgraded outdoor lighting installed in our home, which is embarrassing. Right? Talk about a true confession.

But I know that we’ve all been there. That kind of “Well, you know what? Let me think about it” moment to end a conversation.

It’s so normal. We’ve normalized this behavior. Right?

We’re just looking when we’re in the store at the mall, or we’re just browsing at the farmer’s market, or we’re just not sure yet at the furniture store.

And all of those examples that I just gave you are shopping examples—and shopping is certainly one place where this shows up, kind of an innocuous place for this pattern to show up.

But there are other areas of our lives where this same kind of behavior truly impedes us.

So today, we’re going to get into the world of decision-making, and making commitments, and the power of getting yourself to a clear yes or a clear no.

And we’re going to look at why, if you’re living a life kind of filled with maybes, it might be holding you back from a level of transformation or growth that’s really possible for you.

So this isn’t really about landscape lighting, or the new handbag that you’ve been eyeing, or the latest skincare product. Right?

This is for decisions that could genuinely move you forward. Things like career changes, right, or educational pathways—advanced degrees, maybe—or bringing in some kind of support structure to your life, like a caregiver for your children or a housekeeper. Right?

It might be decisions about relationships: starting them, changing them, you know, working on them, ending them.

It may be about social opportunities that you are watching from the outside in, wondering what does it take to be a part of that—or even mindset patterns that, you know, you can see maybe that there is change available if you could just get yourself to think differently, but you don’t know how to get there.

So I really want to talk about why we stay stuck at maybe—and some things that we can do about it.

And the first piece of this is: Why do we stay stuck at maybe? Right?

Why are we so tempted to end an evaluation process with “Maybe I will, maybe I won’t,” or “I’ll think about it”?

And the first reason—I’m going to talk about three here—the first reason that I think we stay stuck there is the paralysis of options. Right?

If you’ve ever found yourself stuck in that cycle of indecision—that point where you’re presented with an opportunity, but instead of embracing it, you say “maybe.” You know: “I’m just going to keep looking.”

Especially when you say, “I’m just going to keep looking,” this is what happens when we are so afraid of making the wrong decision that we don’t make a decision at all. Right?

We tell ourselves that it is safer to keep looking because, I don’t know, something better might come along—or because maybe this is the first option that we’ve considered.

And it’s like we get into this pattern where we owe it to ourselves to do exhaustive research and to really understand all of the options that are out there.

And, of course, what that leads to is a place where, you know, we’re building spreadsheets and comparative documents of all of the different options that are available to us—and then we’re completely paralyzed. Because while one option looks better on one vector, another option looks better on another, and that can keep us in gridlock.

So we get into this gridlock or paralysis when we start evaluating options candidly because we’re living in a world where there are so many.

Any decision that we try to make is empowered if we can limit our set of considered options. If we can just shrink the consideration set to something reasonable, we are more likely to get to the other side of the decision and actually have the thing. Right?

So if you find that you’re really stuck in the “I’m thinking about it” through the lens of “I’m going to keep looking, I’m evaluating my options,” then this is a place where what we have to acknowledge is: all of that time that we’re spending looking at options is not time that we’re spending implementing the change. Right? We don’t have the thing.

We haven’t enrolled in the degree program. We haven’t engaged in the relationship. We haven’t shifted the career. All the things I was talking about before—we’re just kind of stuck at the starting line.

Okay?

Which brings me to the second reason that we sometimes stay stuck at maybe, and that is—I’ll call this—the comfort zone conundrum.

So the comfort zone conundrum is where something in our brain knows that staying where we are is survivable. Right?

It’s where we know that even if the situation we’re in isn’t one that we love, we’ve already proven to ourselves that we can survive it.

So because our brains are wired to seek comfort and avoid risk, saying “maybe” can be kind of a sneaky way that our brains keep us within our comfort zones. Right?

It’s like your brain knows that if you buy some time and you say “maybe,” you’ll just kind of hang out where you are.

And that can keep us in a place where we’re sort of in the dull gray version of our lives instead of the Technicolor version. Right?

We’re not making the bold choices that could actually change things.

So we’re kind of hanging back, saying, “Maybe I will. I’m thinking about it. I’m evaluating my options. I’m toying with the idea.”

All that time, what we’re really doing is just wrapping ourselves up in that big blanket cocoon of comfort.

And comfort is sort of the opposite of growth. Right?

In order for us to grow, we have to get out of the situation that we’re in. We have to at least dip a toe in the water. We have to try some things. We have to run some experiments.

So we don’t have to dive headfirst into something new, but we do need to find a way to get ourselves moving. Okay?

Which brings me to the third reason we stay stuck in maybe, which is the illusion of time.

It’s really, really easy for us to talk ourselves into the idea that we have an abundance of time in which to make a decision.

Right? How long do you need to think about this decision?

Sometimes when I’m talking to people about coaching, I’ll say, you know, “Well, how long do you think you need to process this decision?” And the answers would astonish you.

I mean, plenty of people—by the time we’re in conversation about coaching—are at the point of “I am evaluating: is this the next step for me?” Right? And so for them, it’s a fairly expeditious decision.

They can kind of get the information that they’re missing, make sure that there’s a strong connection, and then they’re ready to go.

Other people might say a month. They might say a year.

What are you going to be doing for a month of thinking about this decision? What is the process of getting more sure? Right?

Or people will say, “Well, maybe I’ll do this when the kids are out of school. Maybe I’ll do it when the house is paid off. Maybe I’ll do it when this big project at work is completed.”

You know, this time dimension is expansive.

Sometimes something as brief as a week can feel like a long time, and sometimes we’re stretching decisions out over years—back to my landscape example. Right?

It’s like, if you would have told me the first time that we had someone come and give us an estimate for lighting that seven years later I still wouldn’t have installed it, I would definitely not have believed you. Right?

I would have said, “Yeah, I might think about it for a little bit, but there’s no way I would ever let it go on for seven years.” And yet, here we are.

So it’s so easy to fall into this trap of feeling like we have an abundance of time—but time is a finite resource. It’s actually our only finite resource.

So maybes really squander precious moments that we can be using to move toward what we really want.

And that’s why it’s so important to learn how to harness the power of now. Right? It’s a really important skill.

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So let’s look at some techniques that I’ve seen people use—and that I try to use—to banish the maybe mindset.

We all fall into this trap in certain places.

What we want to do is keep those maybes for kind of innocuous, don’t-matter-that-much decisions. And when we’re really dealing with something that could change our life, we want to learn how to say yes. Okay?

Or say no so that we can move on to an alternate option.

So whether you’re setting goals, whether you’re really visualizing, like, what do you want your future to look like—you want to think about how decisions are the pathway to achieving that vision.

So the first technique that seems to be very powerful is to ask yourself: What would have to be true to say yes?

What would have to be true?

There is a mindset shift needed to transition from this life of maybe, right, to a life that’s filled with very clear yeses and noes.

And we need to rewire sort of the lens through which we’re looking at decisions.

So this question—“What would have to be true to say yes?”—starts you on a path of thinking about criteria.

Right? What are the criteria that would enable me to say yes to this decision?

To feel really clear about it—maybe even excited about it.

Like I could manage the risk involved in it.

Like the investment, if there’s one required, is worth it.

Right? Investments of money. Investments of time.

So Shonda Rhimes famously wrote a book called The Year of Yes, and she challenged herself for an entire year to say yes to almost everything.

And I’m not recommending that you go that far, but it is sort of resetting your default position to yes.

Okay. If my default were going to be yes to these things that I’m genuinely intrigued by, genuinely interested in—what would have to be true for me to say yes? Right?

So you’re kind of raising the bar on what it takes to talk yourself out of things.

Because for many of us, I think our default is set to no, and we hold a really high bar around how we would give ourselves permission to say yes.

By the way, there’s a paradox in this.

I think some things are easier for us to say yes to and harder to say no—and those are things that are about supporting other people.

Right? Giving our time in service to others—then we all of a sudden have a really hard time saying no, and we’re much more likely to say yes.

And also, things that are like cotton candy in terms of their pleasure for us.

So, you know: yes to the dessert, yes to the coffee Starbucks treat, yes to the TV show.

Like, it’s easy to say yes, it seems like, to some of these real little, like, snackable treats—and harder to say yes to things that actually move our lives in the direction we want them to go.

So for the purposes of this episode, that’s why I’m trying to keep us in that frame around: What would it be to default to yes on those kinds of things?

Which may require you to say no to some of those littler kind of treats and pleasures.

Second thing that can help you banish the maybe mindset is learning to weigh the cost of no.

When we don’t make a decision—when we take a look at an option, right: “I’m thinking about going to grad school. I’m thinking about starting this particular endeavor. I’m thinking about changing careers.”

When we’re in that space where we’re thinking about it and we don’t make a decision, we are essentially saying no.

It’s a silent no, but the act of non-decision is essentially a no.

And that no has a cost. Right?

Because through that no, we stay where we are—which means it’s the cost of doing nothing. It’s the opportunity cost. Right?

It’s the cost of foregoing grad school, foregoing the career change, foregoing whatever the thing is on the other side of the decision.

And it’s really easy for us to overlook that because it’s hidden. It’s silent. Right?

So, “Oh, I’m thinking about going to grad school,” if we use that example. “I’m thinking about changing jobs.” Okay.

I’m not coming to a clear decision means my decision is no. Okay? And that no has a cost.

The cost is: we can’t have the thing. We’re stuck where we are.

So a clear no can be useful.

It can be useful to say, “I have evaluated this option, and I am saying no.”

And the reason that no is helpful is because it shuts off the open loop in our brain that is pondering that decision—that’s still wondering, “Should I or shouldn’t I?”

And as soon as we close the loop with even a clear no, we can get to closure.

Our brain is immediately able to consider other options.

So as long as this particular loop is open, it’s hard for us to even allow other options in the door.

Okay?

So clear yes or a clear no—those are the things that move us forward.

Which brings me to the third point of how do we get ourselves out of this stuck place, right, in the maybe mindset—and that is to use small decisions to build momentum.

Because, look: changing your life ultimately is a journey. It’s not a one-time event.

So an initial yes or no sets the stage for building momentum and sustaining positive change, like, over time.

Small decisions stacked together can lead to big transformations.

So I think James Clear’s book, Atomic Habits, has gotten a ton of attention over the last number of years because of this—because of this idea of small decisions that stack together to lead to big transformations.

You essentially build momentum.

So if you are looking at a decision that you cannot bring yourself to say yes to, right—but you also kind of know, “I don’t want to say no”—

One tactic is: Can you make a smaller decision that’s like a precursor to the bigger one?

Instead of enrolling in a degree program, do you just take one class?

You know, instead of committing, “I’m going to change my career,” do you update your LinkedIn profile?

Do you have some informational interviews with people in a field that you’re interested in?

There are many, many, many ways—and this comes up a ton in coaching—to take a big change that you’re considering making and essentially break it down into something smaller so that you can get started and you can build some momentum.

And that’s what I want to leave you kind of thinking about today as we wrap up this episode.

So I just want you to remember that a life of maybes is kind of a life half-lived. Right?

And in order to get yourself to a yes or a no, you’ll have to embrace a little bit of uncertainty.

You have to hold the tension of not being completely sure and make the choice anyhow—which will help you to transform your life.

We can’t change our life with a maybe.

We really need the power of a yes or a no to unlock our true potential.

And I see it every single day in my practice. I see it every single day in my personal life.

So I am personally recommitting to being more clear-minded about decisions—to moving things to decisions more quickly, right—even if that means tolerating some uncertainty in order to build that momentum.

And I would invite you to do the same. Okay.

As we wrap up today, here’s what I want to leave you with:

A maybe is always going to feel safe. It is.

But quietly, what it is doing is quite the opposite. It is keeping your life in exactly the same spot.

Right? Maybe keeps us exactly where we are. We don’t have to move in either direction.

And clarity doesn’t really come from waiting longer, or waiting to gather one more data point or ten more data points.

Right? It comes from movement.

Clarity really comes from choosing—from being, like, willing to hold a little bit of uncertainty so that you can build momentum.

It is a clear yes that will move you forward, and a clear no will free you up to go look elsewhere. Right? Both can be powerful.

So if this episode stirred something for you—if there’s a decision that you’ve been postponing—I would just invite you to ask yourself: What would it look like to decide even without perfect certainty?

Because that’s where real change begins. Okay?

If you found today’s conversation to be helpful, would you please share it with someone else who might need it in your life?

And also be sure that you are subscribed to the show so that you don’t miss an episode and you don’t miss what’s coming next.

Alright? Until next time: here’s to confident decisions, to meaningful momentum.

Here’s to the chance to really enjoy the life that you’re building.

That’s all for today, my friends. Till next time—let’s be brilliant.

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