Episode 115 | How to Pivot Your Career Without Starting Over

Table of Contents

In episode 115, I’m breaking down one of the biggest myths about career change: that pivoting means starting over. It doesn’t. Most people who want to pivot already have years of experience, skills, and credibility. The real challenge is learning how to leverage what you already have without letting fear keep you stuck. This episode is for anyone who has been thinking about a career change for months or years but hasn’t taken action yet. We talk about what’s actually holding you back, how to reposition your experience, and how to move forward without blowing up your financial or professional stability. Listen to the episode here: How to Pivot Your Career Without Starting Over

You Don’t Need to Start From Scratch

One of the biggest reasons people stay stuck is fear. Fear of losing seniority. Fear of a pay cut. Fear of judgment from family, peers, or coworkers. And for many first- and second-generation professionals, fear tied to financial security runs even deeper. But here’s the truth: pivoting doesn’t erase your past. Your experience still counts. The issue is rarely a lack of skills. It’s not knowing how to translate what you’ve already done into something new. When you can clearly connect your past experience to future roles, you stop seeing your background as a limitation and start seeing it as leverage.

Translation Is the Real Skill

Most job descriptions are written in corporate language that makes roles sound more complicated than they actually are. A big part of pivoting is learning how to translate those roles into plain English and then connect them to your own experience. This isn’t about inflating your resume or pretending you’re someone you’re not. It’s about telling a clear story. What problems have you solved? What impact did you create? Who did you influence? When you can answer those questions confidently, you stop feeling like you’re “starting over.”

Clarity Comes From Action, Not Overthinking

Overthinking is one of the most common ways people stay stuck. Waiting for certainty feels responsible, but it often leads to mental exhaustion without progress. You don’t need to pick the perfect path right away. You need to test one path at a time. Small experiments, like a 30-day focus on one direction, give you real data. Action creates clarity. Thinking alone doesn’t. Progress comes from trying, learning, and adjusting, not from finding the perfect answer in your head.

What a Strategic Pivot Actually Looks Like

A smart pivot doesn’t mean quitting without a plan. It means creating financial safety, identifying transferable skills, and gathering evidence before making a big move. That evidence comes from conversations, projects, and market feedback. When you talk to people already doing the work you’re curious about, you gain clarity and confidence. Networking becomes a way to test demand, not ask for permission. This process reduces risk and replaces fear with information.

Key Takeaways

– Pivoting doesn’t mean starting over. Your experience still matters. – Fear is often the real barrier, not a lack of skills. – Translation and storytelling are essential for career pivots. – Clarity comes from action, not waiting for certainty. – Small experiments build confidence and reduce risk.

Timestamped Overview

00:00 Introducing the career pivot mindset 02:51 Identifying fear as the main barrier 06:09 Translating experience into new roles 10:07 Taking action instead of overanalyzing 11:53 Planning a strategic and financially safe pivot 17:28 Validating pivots through market feedback 21:58 Outreach strategies and coaching support

Want More Support?

Explore additional resources and tips on my website or connect with me on LinkedIn for insights into building your network effectively.

Read the podcast episode transcript below.

Read the full episode transcript

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, any. And you can make moves that feel right for you. Whether you're climbing the corporate 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. Hi, how are you? Today we're going to talk about how to pivot your career without starting over.

Now, this topic in general was the topic that kind of launched me within this space a lot, like about three, three, four years ago. And the reason why I feel like it can be such a popular topic about pivoting careers or changing your career is because a lot of the times we are raised or we grow up believing that we can only have one set career, that we have to like, build momentum piece by piece, build our careers within one path. And then it becomes then very scary to try to change it to something new. And so I want to talk about how you can change your career. You can pivot your career without completely starting over. I think it's important for so many different lenses in the sense of life should not be all or nothing and you should not be tied to one thing just because that's what you started out with.

And it can be very, very scary to feel like you are restarting. But there is a way to do it without restarting. You have so much great goodness, expertise, experience within you from what it is you've done already, whether that's one year, to 10 years, to 15 years, to 20 years plus. And so we just need to kind of break it down into a plan of what that looks like. So we'll do that today. All right, I'm going to go ahead and jump in. If we have not met yet, you heard the intro, but I'm Danny Tan, I'm a career leadership coach and I myself have pivoted careers five times. PR, sales, merchandising, e commerce, you name it all, achieving 11 promotions in 11 years. I love career literature development.

From my corporate career of being a VP to multibillionaire company when it came to helping build out teams, hire teams, train teams, when it Came to looking at different kinds of tech and platforms to see what would best help an organization or a business to the volunteer work that I do with an organization called American Needs you, which helps first and second gen college students get internships, figure out their careers. And so this has always been a love and passion of mine. So let's dive in. So I have some slides for today. I would like us to go ahead and kick it off. com and you can check out where there are more episodes like this under the podcast page. All right, so here's the biggest thing.

It is fear that is keeping you stuck. So if you have been sitting on this idea of wanting to change your career for quite some time and you have not taken action on it, and I want you to take true inventory with yourself and be really honest with yourself. How long has it been that you have been sitting and thinking about wanting to change and you haven't. Has it been months? Has it been years? Because normally it is typically years that I hear folks say that I've always wanted to try this, this new thing, but they haven't necessarily gone after it. And the fear is going to keep you stuck. And here are some reasons why. And before we dive in, just in case it's not absolutely clear, I help everyone, but who I especially help are first, second gen women of color.

So if you are an immigrant to the United States, if you are first or second generation, if you are the first or second in your family to go ahead and graduate university or college, if you were the first in your family to pursue the particular career path that you're going out after, if there's any way, shape or form where you feel like you are truly the one, the only one of the few that is doing what it is that you're doing and you're trying to navigate changing your careers like you're in the right place, this is, I'm here for you. So just know that my own background, I'm Asian, Latina, I'm Puerto Rican, Filipino and Chinese. And so there's so much complexity that comes to these intersections of cultures and identities and how that has a ripple effect on how we take action.

It's not a bad thing, but it's just things to notice in general. And so if you are like me, you were very much potentially raised to be like you, pick one thing and you stick with it and you have safety and security through this job and you grow from it, and that's what you have to do. It feels really shaky to our nervous system, to our minds, to our bodies to try to make a change. And so there are so many professionals who want to make a change, but there is this fear. And the fear could come up for a couple of reasons. One, you feel you're going to lose seniority, you don't want to go back to junior roles, and you're kind of nervous about that, right? The other thing it could be you don't want to take a pay cut.

So you're worried about taking some kind of salary cut in some big way. You're worried about your financial safety and security. Hey, you pay your bills. You're like, I am my own plan. There is no one who I have as a backup to take care of me. There is no trust fund, there is no parent who will jump in and save me. And so that might be something that's important to you. Or you're like, hey, I have a family that I'm taking care of. And then wasting experience. You don't want all of your hard earned education, training, growth, development, years of putting your time in to go to waste, to have to start completely new. And then also, let's be real, you have a little fear of judgment. You're having a little bit of fear of how will people perceive me or think about me or judge me for starting over or for doing something new.

And so I just want you to know that these are all real things that come up when it comes to changing your career. And it is essentially what is part of one of these reasons is why you're probably staying stuck and not making the move. And so that's okay. I just want you to acknowledge that that's coming up for you. And how do you feel about that? Like, how do you feel about one of these reasons? Or maybe it's not on here, but how do you feel about what is driving you? What is driving you not to take the ch, not to take the step forward, not to make a change. And are you happy with that? Are you happy with what's driving that? So I want you to think about how starting over, the idea of starting over is not the way to go about it, it's not the way to frame it.

And like, let's kind of go into a little bit more. So the reality is, is that you already have so much experience. I was alluding to it before. And so the problem Is it is not about you going into something new and not having the skills. Right. It is not knowing necessarily how to leverage your experience and skills and translate them so it makes sense to the person that's interviewing you for your future boss, for your future organization. So it's not that you don't have existing skills, it's that maybe you don't necessarily have the. You haven't worked the muscle of how to translate those skills to a new position and then be able to showcase and tell a story of how you've done it and show your value.

So it's not like the. The fact if you're not capable it just being able to pull that out, translate it, and then share it. I always joke with my clients. I feel like majority of my job is translation. I feel like I'm constantly translating a job description, what it says in corporate gibberish, and explaining it in plain English so that way my client and I can tackle what their past experience is and how it lines up to what it is that they want to do. Listen, I grew up in a household with many different languages, with many different accents throughout my entire life and translating from this and this. So I don't know if that superpower translated over into this, but for some reason it became one of my superpowers too.

To one, listen to my clients and what their experience and their background is to take job descriptions that sound like corporate gibberish and then translate it into plain English. And then I'm able to connect the dots between what my clients do and what the roles that they're going after. And then I teach them how to do that skill so they're able to repeat it, so that way you're able to start to identify, okay, what does translating my skills mean? How do I do that? And so we do that by understanding what they're looking for, the inventory of what you already have, and then translating it and drawing the line by telling stories, sharing value of what you've done. So it drives that impact home.

So I want you to remember that you're not starting over. It's just about really learning how to position, reframe, and speak to the experience that you have and take inventory in it. And sometimes it takes an outside perspective to help do that, whether that's a family member, a friend, a colleague, a co worker, a former co worker, a boss. Sometimes we need somebody outside of us to be like, wait a minute, let's shine a light on this. Do you see and notice this? And so I just want you to Know, like, changing careers does not erase the past. It actually is an opportunity for you to take the past experiences and the present experience that you have and reposition it. And so people will get stuck still because of a couple reasons.

You start to re. You start to overthink. You're like, okay, well, I don't know, is this direction the best direction? Is that direction the best direction? Do I have this one thing, this other skill? Maybe I should talk to this person? And so you go into overthinking mode of scenario A, B, C, D, E. And I am an overthinker. Like, don't get me wrong, I love to overthink things. And for our safety and security, for our minds. A lot of us have overused the ability to overthink to protect ourselves, right? That's a protective mechanism. If I understand all the possible scenarios, then I'll be safe because I'm anticipating and understanding what could become potentially coming up and assessing risk.

And so that's from a place of safety. It's a protective mechanism. But what I want you to understand is that when we overanalyze for too much, right past, there's a past, a point, there's a tipping point of over overanalyzing and overthinking that then starts to create mental exhaustion and no progression. Right now you're actually not tackling what it is you want to tackle or taking action. Now you've actually also exhausted yourself mentally because you've gone through all these scenarios, and then here you are. So that will actually get you stuck before you even be. The other part is waiting for this certainty, right? So a lot of the times folks are like, I just need to make sure I'm. I'm 100% sure this is the right path.

If I'm not sure this is the right path to move forward with, then I can't redo my resume. Then I can't apply for jobs and I can't network. Then I can't start talking. People. I have to be so sure this is the right thing. Lady, how will you know unless you experiment? And so the biggest thing I have to say is this. If you have three paths, you're trying to figure out, knowing that you don't have to take the three paths and pick the one that's going to be the best one and go all in on it. There is experimentation here. You don't wait for certainty. You have to take action. Action helps you create certainty because you will then have more information, more data, more feedback to then know what is the path you want to move forward with.

So I always tell my clients, if you have three paths, then pick path A to start to explore. We do an experiment for. For 30 days, and then you start to see how you feel about it. If you're like, yes, no, maybe. So then we go to path B. You start to experiment, and then you see, and that is how you decide what path it is that you want to go down. If you're trying to wait for the aha, light bulb moment, you will not get it. You will get it from taking action and experimenting. And the last piece is there's this fear of, like, making the wrong choice, making the wrong move. Hello, recovering perfectionist here. So it's like, I want to make sure I'm picking the perfect choice when it comes to the optimal things that I want in my life, the optimal salary, remote work, these roles and responsibilities.

But I have to make sure it's at this timing in my life at this level. Okay, well, if we are so worried we're going to make the wrong move, then we're not going to make any move. Then we're going to be frozen, because we're going to be so frozen by our perfectionism will paralyze us, and we will not take a step forward. And so just understanding that there are ways to explore opportunities and learn from them and gather from them without having to make ourselves stop for making the wrong choice. And so I want you to think and remember this, that clarity comes from taking action, not from overthinking. Okay? Clarity comes from taking action, not from overthinking. And that any small step forward that you take is not permanent, does not have to be perfect.

And it helps you start to collect information on what it is that you want to do. So let's go ahead and talk about what a strategic pivot looks like and does not look like. So if you want to pivot strategically, what it does not look like is I am not recommending that you quit without a safety plan or an action plan. I always talk to my clients about having a smart transition plan or a quit your job plan before you go and make a big jump. Because the biggest thing that I've learned is that having financial safety and security, especially if you are somebody who has lived in financial scarcity or was grew up in a home that had financial scarcity, it is very hard to find a job if you are nervous about your finances.

And so the best way for us to help you show up with the best energy to your job search is, boy, you're doing this when you are not like with your, your back against the wall, but when you have the freedom and flexibility and the financial safety to do it. So we talk about what that financial plan looks like and then we also say it's not about starting from the beginning and losing all the years of progress. That is not the case. And it's not abandoning everything that you built. I'm going to work with you. And what we work together on is leveraging all the experience and skills that you have to help propel you toward is that you want to go. And so what a strategic pivot actually does look like it is identifying those transferable skills that we were talking about.

It's taking one, one path out of the three. Taking that and testing it to see through action if you like it. And then it's creating evidence through conversations and projects. I truly, truly believe in evidence based confidence. So how can you build your confidence through evidence and data collection, not just through like wishful thinking or mantras or meditation or positive affirmation. I believe in all those things, don't get me wrong. But I do believe especially, especially when you're somebody who maybe came from a background that feels a little bit shaky, where you need to make sure you're really sure about your next step. And all these decisions carry lots of weight. It's super important to collect data and evidence.

You can feel like it's real and build this self trust in yourself, this confidence you're in yourself and that you feel like you've really vetted the decision. And so I've had so many clients who have wanted to make a career pivot and they were scared. I have clients who were like in their 50s, in their 40s, in their 20s, who all wanted to make changes. And the biggest fear that comes up is, am I starting over? Will I throw everything out the window? Will I lose my finances? And let me tell you, they have pivoted and they have done it. And they have done it not just by taking something lateral. They've done it and taken two jobs up, two promotions up. They've taken it and doubled their salaries, gotten 50k in their salaries, 20k in their salaries increases.

And so it is possible. It does take time and it does take work. But you can either continue to sit at your job for more years questioning it and not being happy about it, or you can start taking action now. I mean, it's like it's up to you. It's truly up to you. But I have such a passion about this Just because I hate the fact that I feel like a lot of the times we're fed that you must just stick to one lane and that this is all you can be. And so the biggest thing that I find with folks who want to pivot their careers is that when you were little, when you were young, you wanted to do something and maybe, maybe a parent or a family member or someone in your life told you you should pick something that's more safe or pick something that's more secure or pick something that is a sure bet.

And so you picked something else. And now as an adult, you are unhappy with what it is. And a lot of the times I see that those clients end up going back to what they wish they wanted to be. And so I want you to know that it's possible. That's it. Period. I had a catch up call with one of my clients today. She pivoted careers two years ago. So she's been in that role for two years now and she's looking to get to her next level. And I have my clients for life. I always joke, I'm like, you know, so even two years later, I'm just catching up with her to see how she's doing. And she said to me, you know, I have a friend and she keeps talking about how she's not happy or job and she's been complaining and complaining and I keep telling her, you don't have to be that way.

And I keep telling her to go to you because, you know, I came to you years ago and here I am and she pivoted career, she has a higher salary, she's doing the work that she wants to do. And so I just say this because I want this for you. And I've done it myself many times over and I couldn't be happier with the work that I do now. So let's go ahead and talk about translating your experience instead of downplaying it. Here's the thing is that when you talk about like your skills, that is not necessarily going to drive it home for you. So the things that I want you to start to think about and brainstorm for yourself and your career pivot is translating what your experience is and the value that you brought, right?

So don't just list out the things that you've done, but how did it bring value? So let's say it's project management, right? So thinking about what was maybe the roadmap of the projects that you worked on overall, like did you were able to increase or decrease the timeline? What Was the, the goals for that project, were there different like revenue goals for it that you were able to hit or achieve once the project launched? Were there different stakeholders that you're able to influence and think about those things and how they're going to relate to that new role is how you start to prepare for networking, how you start to prepare for interviewing, how you start to prepare your resume. And just I don't want you to downplay because I feel like our go to is to laundry list what's in our job description.

And it's like, no, honey, that's like not what we are doing here. We were really going to beef it up, amp it up. And I then I think everyone defaults to, I don't want to be bragging. And it's like, we're not bragging. It's just facts, it's just data, okay? It's what you did. And so take ownership of it with some metrics. Don't try to, don't be lazy with yourself, okay? Like I'm sure you're out there like hyping up your bestie or your friend or your family member. Like do the same for yourself. And so when it comes to how we collect that data of ourselves and take inventory on ourselves, how do we go ahead and validate that data, huh? Here we go. Because for those of you who are like, great, I've, I've taken my skills, I've translated them, but that doesn't mean I'm getting a job.

Well then I want you to validate with the market, your experience. I do this a lot. This is how you create evidence based confidence. So this is what I work with my clients on is networking, relationship building, information, interviews, whatever you want to name it and call it, it is data collection. So I want you to use it to take the things that you know about yourself and go and meet people who are in that pivot who have either done a pivot themselves or in that role themselves. And I want you to talk to them about your experience and your background for them to validate and like reinstill in you and re believe in you so you can have this belief in yourself of, hey, this is possible based off your skills, this is possible based off of your background.

Now we're not looking for this for like external validation in the sense we need people to validate us. It is to validate your theory or hypothesis that you can make this pivot possible. Possible by getting the feedback on them. And then last piece, this helps reduce the risk because you feel like the risk feels less riskier because now you have gotten feedback from people who truly are living and breathing and doing that. And so this is why it's not about asking for favors, asking for a job I like. I feel like we think of networking in only one way. It is also about having the conversations validate what we're trying to do, the path we're trying to go, the experience that we have. And if there are gaps, it'll help validate it too.

And this helps react, eliminate this guesswork and this fear and this risk, and helps you gain confidence. Networking is how you test the demand and not how you beg for permission for something. So I have one client, for example, who's trying to make a pivot. She was trying to look at different paths. She had a path that was going to be for something that was going to be more creative, a path that was going to be something that was me more sales based and another path that was going to be more so like marketing based. She went and we validated it in the course of three months. She validated the three paths and then she figured out the path that she wanted to pursue. Ba da bingo. So then once she nailed down that path that she wanted to pursue, we went and reworked her resume, her LinkedIn, all the above, in order for her to go after it.

And that was through validating and testing it by having these conversations and her realizing, oh, I can do that job. But after I talk to like these 10 people, their day to day, not for me, and now I know versus I always kept wondering and wishing for years, is this my path? And did the same with the other two. So you don't have to keep sitting here wondering, wishing if it's possible. We have, you know, a way to do it with a path in front of you. So how you're going to know that you're going the right way when it comes to your pivot? Kind of like what I touched about on one of my clients is that you'll know that you are getting this clear feedback on, okay, on your background, on your experience and related to those who are currently in those roles.

You'll start to understand like, okay, what is feeling right when it comes to networking. Because now these, you're starting to build your confidence on how you talk about your experience, on how you talk about your background, about how you talk about yourself, how you pitch yourself. So you'll start to know that you're pivoting because now you're starting to build this belief in yourself. Oh, wait, yeah, I can do this. Look at all the stuff I've done, and you're going to build that through these conversations and get feedback on what is possible. And then it starts to fade. This anxiety and fear of, am I starting over? Am I messing up? Am I picking the wrong thing? Because you've built momentum and there's a noticeable shift that I see.

And then the best part is when the opportunities start to pop up. This is my favorite. So one of the clients that I mentioned before then, she was getting referrals for jobs so easy. That was not the intention of the conversations. I'm very clear of not having my clients lead with that intention because it creates nervousness, but it ended up leading to that because you're coming in with your best energy. You've practiced your pitch, you've practiced talking about yourself. You practice communicating your value and your achievements. So now you're coming at these conversations so differently. And now this person gets to see you for who you are and is realizing, wait, you could potentially be a good fit for this role.

So that's how you know you're doing it the right way. So these are the action items I love for you to take. If this is something you've been mulling on for quite some time, so you don't have to have it figured out, I want you to take very small steps towards where it is. I want you to pick one direction to test. So maybe you've had, like three, three paths you've been curious about for some time now. Pick one. Pick one that you want to explore for the next 30 days. Okay. And by exploring it, that could be like looking at job descriptions, something super simple like that. For that one path, don't get distracted. The second piece is I want you to look at three skills that you can talk about that transfer.

So look at that one path, job descriptions for it. Take one job description, look at what it's asking for. And I want you to think about, okay, what are three skills that I currently have in my job now that translate to this job description? And write them down. Okay. And the last piece, I want you to schedule one conversation with someone who's in that target role. And I want you to talk about your interests and pivoting careers. Now, I want, you know this. It's a numbers game. You can't just assume that if you reach out to one person on LinkedIn, you get a one response. It's not one to one. You're gonna have to reach out to a couple people. But at least if you get One phone call. I want to get one phone call.

Schedule. You're talking to somebody who's in that path and talk to them and say, hey, look, I'm looking to make a pivot. I would love to just learn about your experience and your background on that call. I want you to share where it is you're trying to go, the skills that you have that transfer and see what it would be like. See what it'd be like to pivot. So let me know how that goes. You can always Message me on LinkedIn or email me on my email list and reply back. All right, so I want you to know, again, pivoting does not mean starting over. It is truly about learning how to communicate what it is that you've already done and translate it for something new. And so if you have been stuck for a long period of time and you're ready to gain some momentum and make it happen, you just need a strategy and some support.

And so if working with me kind of feels like it resonates based off of some of the things you've read about me or from listening to this workshop, then know that I do work with my clients in private coaching. Private coaching is one to one. So we work together privately, just you and I, and that is from either three months or six months. And on there, what we do is we go ahead and create a customized coaching plan for you to help tackle what it is that you want to do. So if you're looking to pivot careers and you have no idea where to start or what path to do, I'm your gal. If you know what path that it is that you want to do, I'm also your gal, and we can make it happen. com that's-a n I t a n dot com.

And you can go to the contact tab, book a call with me, and on that call will happen is you'll fill out an intake form, and then on the call, we'll talk about what it is you're looking to do, what challenges maybe you faced, and then I'll give you a customized coaching plan of what it would be like to work together. Then you decide if you want to work together or not. And then when we start working together, I am helping you when it comes to all things of exploring a career pivot. What does that look like? Interview prep, negotiation, working on your resume, your length in being able to have a story bank of your stories, being able to learn how to translate your value and communicate the things that you do and so much more.

And my clients are amazing. They have gone multiple promotions in a year. They have gone 20, 50k, double their salaries. But the most amazing thing is that they are the most amazing women who are making a difference. So it's all about to me getting them in roles and seats that will help amplify their uniqueness, their expertise, so they can continue to make a ripple effect of change in society, especially in days like these. It's most important, and I love this work that I do. And just know, if you're a client of mine, you're a client of mine for life. And so I hope you have a good one and I hope you enjoyed this and I will talk to you soon.

Let's Work Together

Research and deep dives are just the first step (trust me, I’m the first one to dive in for months)—but having a plan and accountability is what leads to action. Book a call, and we’ll go over what’s working, where you’re stuck, and I’ll recommend a plan to hit your goals. Together, we’ll explore if private or group coaching is the right fit for you.

Book a Call

Leave a Reply

Your email address will not be published. Required fields are marked *

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.

Join My Weekly Email Series

Stay in the loop with exclusive offers, the latest blog posts, and updates on my most impactful coaching insights. Perfect for leaders focused on growth, team success, and mapping out their next big career move.

Recent articles