Episode 104 | You’re Not Failing—You’re Leading Through Uncertainty

Table of Contents

In episode 104, I’m talking about something that every leader, founder, and high achiever faces at some point: the feeling that you’re falling behind. But more often than not, what you’re calling failure is actually growth in disguise.

You’re not failing, you’re leading through uncertainty.

Listen to the episode here: You’re Not Failing, You’re Leading Through Uncertainty


Understanding Uncertainty vs. Failure

When things feel unclear, when milestones are murky, metrics are fuzzy, or progress feels slow, it’s easy to think you’re failing. But uncertainty doesn’t mean you’re doing something wrong. It often means you’re stepping into new territory, building something that doesn’t yet have a map.

One of my clients, a founder, once told me she felt like her business wasn’t “real.” But the truth was, she wasn’t failing, she just didn’t have clarity on direction yet. We worked together to define her mission, set quarterly priorities, and create a simple framework to make faster decisions. That clarity helped her move from second-guessing to leading with focus and confidence.

Reflection prompt: What are you calling failure when it might just be a foggy phase of growth?


Creating Clarity in Leadership

Leaders don’t always get a playbook. We’re often building something that’s never existed before, and that can be uncomfortable. The pressure to “get it right” can block creativity, limit strategic thinking, and cause us to lose trust in ourselves.

Progress doesn’t come from perfection. It comes from imperfect action, taking one clear step forward, even when things aren’t fully defined.

One of my clients transitioned from a manager role to an executive position and felt lost without clear direction. Once we clarified her leadership priorities and created a plan for how she wanted to show up for her team, everything shifted. She didn’t need to know every answer—she needed to lead with clarity rooted in her values and goals.


Taking Imperfect Action for Progress

You don’t need to wait for certainty to move forward. In fact, waiting for the “right” moment can keep you stuck.

Ask yourself: What would you change if you stopped waiting to get it perfect?

If you’re launching something new, lead with experimentation. Pick one idea, one channel, or one next step, and test it. Clarity comes from movement, not overthinking.


Leading Through the Unknown

Clarity doesn’t mean having every answer, it means knowing your values, your direction, and what’s needed most right now.

You can lead yourself and others through uncertainty by grounding in your priorities and communicating them clearly. This might look like:

Building a weekly structure that aligns with your long-term vision

Delegating with intention to free up time for strategy

Making small, aligned decisions that reflect your values

Progress often looks quiet before it looks visible. What matters is that you keep moving forward with intention instead of reacting to every new challenge.


Key Takeaways

Uncertainty often signals growth, not failure.

Progress happens through imperfect action, not perfection.

Clarity is a leadership skill, lead with values, direction, and focus.

You don’t need a playbook; you can create one as you go.


Timestamped Overview

00:00 Welcome to the Pivot and Promotion Podcast
00:33 Understanding uncertainty vs. failure
03:52 Creating clarity in leadership
07:39 Taking imperfect action for progress
11:53 Final thoughts on leading through growth


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Read the podcast episode transcript below.

Read the full episode transcript

Dani Tan: Hi, I'm Dani Tan and if you are here, you are in the right place. Welcome to the Pivot and Promotion Podcast where we say forget the rules because they weren't written for us. I'm Dani Tan. I'm your host as well as career and leadership coach and a proud advocate for redefining what success and leadership looks like. And here's what I know. You can lead at any level. You can pivot at any age and you can make moves that feel right for you. Whether you're climbing the perfect ladder, starting something completely new or just figuring out your next step, I've got you covered with strategies, stories and straight up inspiration. So let's make some moves. Hello, so today we're going talk about how you are not failing, you are just leading through uncertainty.

And so this is for you if you are a high performer, if you are a leader, if you are somebody who is just really ambitious, but you kind of just feel like you're falling behind. I just want you to realize and understand that you're not necessarily falling behind. You're probably and most likely just leading through ambiguity and growth and the unknown and the uncertainty. So let's go ahead and break it down. So phase one, this may hit home for you, we identify with this, but what you think is failure might just be uncertainty. So maybe you're not failing and you're not dropping the ball, but uncertainty has just come and has arisen. So what does that kind of feel like? It feels like the milestones are maybe murky.

You're like unsure what you're supposed to be hitting and targeting the metrics of like, okay, did this work? Did it not, are not always clear. And you just kind of feel like you're in uncharted territory. You're not sure where you are, where you're supposed to be. So it can feel like failure because when you are either growing or things are uncertain or things are evolving, that uncertainty kind of can sometimes make us feel like we are failing or make us feel like we're behind. But in reality, it's just like that lack of clarity and understanding. So this uncertainty can sometimes show up as like you're overthinking, you're on the same loop, you're kind of obsessing over these things of like, did I not get it done?

Am I not doing it right? Then this self doubt starts to creep in of like, am I the right person to be doing this? Can I do this? Am I have the expertise and experience to do this? And then you start to like hide from the things that you probably are the things you need to tackle, whether that's like visibility, whether that's marketing, whether that's just having a plan, whether that's doing that outreach, you start to hide. And so this is what I say when really it may feel like failure, but in truly it is probably just uncertainty that is coming up. And that's when these things feel murky or unclear and they start to have the self doubt creep in the overthinking come in and kind of makes us creep away.

And so I just want you to know. One of my clients, they are a founder and they started to feel really stuck. And like, they're like, I don't think my business is real. I don't think my business is like really a solidified thing. It kind of just feels like it's just something that I like to do for fun, but it wasn't because they didn't want to see a business, but it was just because they felt really uncertain. They're like, I'm not hitting these goals that I have set up for myself. And I said, okay, well, let's like talk about that. Well, we started to kind of like dig in of why she felt like her business wasn't real and why she wasn't able to hit these goals as the bigger issue was that she didn't necessarily know what direction she wanted the business to go in.

She had set this monthly target for herself of what she wanted to hit for like revenue and sales, but she never really like sat down and was like, okay, what is my mission for this business? How do I want to break that down in the work that I'm doing? And how is that reflecting in my day to day of like, do the things that I do day to day, these tasks, these actions, do they actually, you know, layer up into what it is that I want to do? And so we clarified her vision. Okay. And we made it sure that whenever she was feeling stuck, how can we give her a step-by-step framework of how to make faster decisions to get her where she needs to go? Because here's the biggest thing. Once you had a better understanding of like what her overall vision was and how she wanted to break that down into steps by a month, then we could layer in the part of like hitting civic revenue goals by month.

But it's always bigger to look at what's the biggest plan that you want to go ahead and hit and then break them down by quarter. So you give yourself some grace every single quarter. You're not like, I didn't hit it this month, so I'm a failure. You can give yourself like a quarter, which gives you a three months grace period to kind of figure out how to action and tweak. And then also she felt like she was getting it like this decision fatigue or just in all honesty, she was just like freezing on it. How can we give her a framework? That's like one, two, three for support system of how to make a decision. So that's something that we worked on too, which I usually work with my clients when it comes to doing a time audit of how are you using your time?

Is it alignment with the things that you're trying to achieve? And then what would be your ideal? Then how we start to edit and tweak. So that way every single time you have to make a decision, you're actually going through a filter of how you want your weeks to be shaped out based off what you want your goals to do. So that was something that was really helpful for her. So I would say the reflection question that I have for you is what are you calling failure when it's actually just a foggy phase of growth? So maybe you're trying to get to that next part within your project, your business, your life, and it kind of feels like failure, but in reality, it's just like a foggy phase where you just need to create some understanding, some clarity and a plan for yourself.

And so the next piece that I would say is that when it comes to that you're not leading, but you're not failing, excuse me, you're just leading through ambiguity or uncertainty is leaders just don't always get a map. Like you don't get a map, especially if you are a founder, a business owner, or even just building things out for your team with an organization, leaders don't always get a map. They have to build it themselves. And so when you know that there is no outline, there was no blueprint, there was no playbook insert word, and you have to do it yourself and you're building something new or you're stepping into something new there is this immense pressure to feel like you have to get it right.

And when you have this pressure on yourself, if I have to get it right, it starts to block your creativity. It starts to block your ability to use the part of your brain that helps create strategy. And then you start to stress on yourself because you're like, my gosh, I have to get it right. have to make the perfect decision, the perfect choices, pick the perfect tech, make, the perfect clients, have the perfect marketing and just get it all right. Cause if I don't think I'm going to fail and if I fail, it's not going to work. And then what have I done? And so here's the thing you putting this pressure on yourself of having to get things right or do them in a certain way is blocking your ability to think creatively, blocking your ability to be strategic because you're in this survival mode of trying to perfect things.

And then you start to lose trust in yourself and your ability to do it. So what's more important than anything is progress. Progress is going to be much, much, much more important before anything's going to be visible of what your plan or outline should be. So how can you take imperfect action? How can you take messy action just to create some progress for yourself? So then you can start to lay out what that plan looks like for you and knowing that you're allowed to change edit evolve any way you see fit. had a client who was going from being a manager level to a bigger executive leadership role. And she kept second guessing herself, honestly, like she was really, really sure at her job at the manager level.

She knew what to do. She knew who to hire. She knew how to train. But when she got to the executive level, she was like, I don't know. I feel like. I'm the youngest one here. I feel like I'm one of the only women here. I don't know if my voice is gonna be heard. I don't know if my ideas are gonna land the same way they did before. But you just started second guessing yourself, like left and right. And it was because she didn't feel like she had a playbook or a map out in front of her. So the biggest thing that we did was we mapped out her priorities and clarified how does she wanna lead, right? What's most important for her for her leadership and how she wants to show up. What are her priorities and her plans and her vision for her team, for herself and for her organization?

And once we had those ideas and thoughts and beliefs laid out and what was important to her and those priorities, we mapped them out into a plan. When we mapped them out into a plan, it allowed her to understand, okay, how do I engage with myself? How do I check in with myself? How do I engage with my direct reports? And how do I check in with them? And how do I show up within the executive team when I'm in board meetings? This was a big change for her because she didn't have a plan given to her on how to do this. And we don't get that when we are either co-founders leaders and we're going into different spaces where we had not been before, we have to create some kind of outline and structure for ourselves to create security in our brains, which allows us to be able to open up space and time and remove the pressure blocks that we have for us.

So we can, can be more strategic and more creative answer to build trust in ourselves because we have built something out for our brains to feel safe about it. So the question that I would have for you, and this is the prompt would be, what would you change if you stop? You know, waiting for certainty. If you started waiting to get it right. So what would you change and how can you get that started now? So is there something currently that you are just waiting for the right answer? If so, how can you take messy imperfect actions to have progress towards that now? That is a question that I have for you. So a thought could be if you're building a business and you're super worried about marketing and you don't know where to start and what is the right channel for you.

What can you do to take one simple step forward with that right now by picking one and just experimenting to see how it goes. That's the biggest thing is like getting the reps in by taking the bandaid off and just getting started. So the last piece when it comes to you're not failing, you're probably just leading through uncertainty and growth is you can lead with clarity, even the unknown. What does that even mean? So clarity doesn't mean that you have to have all the answers. It means that you're making decisions based on your values, your direction and what's needed most right now. I wanna repeat that one more time. Clarity doesn't mean having all the answers. means making decisions based on your values, direction, and what's most needed right now.

So leaders can create certainty for others and for themselves by showing up in their process, grounded, and what their values are and the direction that they have as a vision. So progress is often, it can be quiet, it can be slow, it can be steady until it's not, but here's the thing you have to take those steps forward. So versus feeling like you have to have all the right answers, just knowing that if you know what your values and your direction is and your goals are knowing that as long as you're trying to take steps forward towards that, you are going to be able to get to where you want to go, even if it feels a little bit unfamiliar. So I had a founder who was struggling to balance strategy and execution.

She kept trying to not trying to, but she kept falling in to the execution piece. We really needed her to lead into the strategy, please, because she had built out a team that could help work through this, but she felt a little scattered and unsure. And so the biggest thing was, again, like building, what is the weekly structure that prioritizes the vision and the direction that she wants the business to go into? When she did that weekly structure, it helps her understand, OK, then what are the things you should be working on every single week that helps move that forward? Right. What are the different check-ins she can have with different team members that can help move that forward? t To help overall move forward her values and direction.

So even if like the clarity doesn't feel there, like what is the perfect marketing for you? Or if the clarity doesn't feel there, like what is the perfect client archetype for you? Or the clarity isn't there, what is the perfect piece of tech for you to use? It's just being able to make sure that you're structuring your week that has the elements that can help continue to help you move and progress forward towards that. And then you'll start to shoot the clarity of what is working for you versus not from a marketing piece or a tech piece or a client piece. But you have to get started and begin with a place of intention, not reactivity. Because a lot of time we are reactive about the things that we need to do, and we're just jumping to the fire drills and the fires that are coming up every single time.

And the reality is we have to be like, if this is my goal, what are the intentional steps that I can kind of take and experiment towards that? So for you, how can you create a sense of structure or clarity, even when you don't know what's next? How can you create some structure or clarity for yourself? So for example, if you're trying to find a new job, but you're not sure where you want that new job to be, because you're trying to do a pivot or a career change. How can you put structure and clarity in your life right now? Could that just be by making sure every single week you're dedicating one to two hours on Friday where you're researching different roles or taking inventory on what your interests are?

If you're somebody who is building an app or building a product and you're kind of unsure of what should be next, how can you be taking some, building some sense of structure or clarity for yourself, whether that is going to meetups or groups to just make sure that you're having conversations about what it takes to build an app or how to build a product. These are different ways that when you are growing, you can see that it's not that you are failing. You're just going through a time of uncertainty and growth and change. And this is how you can go ahead and create some safety around it. So you feel less like you are failing and more so that you're making progress for it. So I hope you found this helpful.

As you can tell, this is something that I do many times over with my clients and that's something of interest to you. com. com and learn more about coaching and working together, but hopefully. This had a little nugget in here that you can take away to know that you are not a failure. You are just leading through some uncertainty and some growth right now. And there are some steps that you can take to create some clarity for yourself. So amazing and have a great one.

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About me

Hi, I’m Dani Tan

I’m a first-gen Asian-Latina with Puerto Rican, Filipino, and Chinese roots. I went from a sample coordinator to VP at a billion-dollar company, pivoting careers five times with 11 promotions in 11 years. Now, as a Leadership Coach and Speaker, I’m traveling the world and helping ambitious women of color lead boldly and make a lasting impact.

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