From Corporate Leader to CEO: Building a Thriving Business with Dorothy Yiu S5 I Ep1

Welcome to Season 5 of the Career Transitions podcast! We’re launching this season with an inspiring guest—Dorothy Yiu, CEO and Co-founder of Engage Rocket, a leading people analytics platform that helps organizations drive real-time insights into employee engagement, performance, and development.

Dorothy’s career journey is nothing short of extraordinary. From starting out in banking and consulting to making the bold leap into entrepreneurship, she co-founded Engage Rocket to address one of the biggest challenges in HR—how organizations leverage data to build better workplaces.

In this episode, we explore:

• Dorothy’s transition from corporate leadership to startup founder
• How people analytics can transform workplace culture and performance
• The key challenges companies face in driving employee engagement
• Why culture-building requires intentionality, consistency, and empowerment
• Dorothy’s experience as a working mother of two and her advocacy for Down syndrome awareness
• Her top lessons on resilience, adaptability, and building a portfolio career

Whether you’re navigating a career shift, looking to create impact as a leader, or curious about the future of HR and workplace analytics, this episode is packed with insights, strategies, and inspiration you don’t want to miss.

Connect with us on LinkedIn:

· Vanessa Iloste (Host)

· Vanessa Teo (Host)

· Aaron Wu (Producer)

Transcript

Vanessa T: [00:00:00] Welcome to Season 5 of the Career Transitions Podcast. In this episode, we had the privilege of speaking with Dorothy Yiu, founder and CEO of Engage Rocket. 

Vanessa I: Dorothy is an inspiring entrepreneur who made a bold transition from a successful corporate life to start her own award winning tech startup. The journey as an entrepreneur is filled with challenges and Dorothy shares her inspiring story of building a company from ground up, focused on a strong culture and values.

Vanessa T: We hope that you are inspired by her journey and your own career transition.

Welcome everyone to the next episode of the Career Transitions Podcast. The podcast where we explore what it takes to successfully navigate through career transitions, no matter which stage of [00:01:00] life or career you're at. 

Vanessa I: In this episode, we are thrilled to welcome Dorothy Yiu, the CEO and co founder of Engage Rocket.

Engage Rocket is a leading people analytics platform that empowers organizations with real time insight into employee engagement, performance, and development. 

Vanessa T: So what really got us curious was the fact that Dorothy transitioned from a successful corporate leadership role into founding one of the most successful startups in its field.

Alongside her professional achievements, Dorothy is also a proud working mother of two young children and a passionate advocate for Down syndrome awareness. Welcome to our show, Dorothy. 

Dorothy Y: Thank you very much. You know, I'm such a big fan of both of you and the way you lead in the HR space. So I'm very happy to be here and I look forward to our conversation.

Vanessa I: Dorothy, let's start with your inspiring career transition. After graduating from the Singapore Management University, you started your career as an investment [00:02:00] analyst at a local bank before moving to Gallup where you had operation. But then you made a very bold move and went from your corporate leadership role to then start Engage Rocket.

Tell us more about how you began to consider starting your own venture. 

Dorothy Y: Starting a business has actually always felt like a very natural path for me because I grew up in a family of entrepreneurs. Both my parents ran their own businesses and many of my uncles and cousins are also in the business world.

So I grew up surrounded by business talks and also having the front row seat to what it's like being an entrepreneur. Interestingly, my dad actually advised me not to start a business. He thought I would have a much easier life working for someone else. And eight years, nine years into this journey, I, I think there's some truth in that.

As they say, the apple doesn't fall far from the tree. So eventually I found my way into the business world as well. But I knew I wanted to gain some work experience before starting on my own. So like any SMU graduate of my [00:03:00] time, I obediently started a career in banking and finance. And after a year or so, I got an opportunity to move into the world of consulting, and specifically HR consulting.

And that's really where I discovered my passion for the HR space, and also identified the problem that Engage Rocket solves today and the problem really is employee disengagement and the fact that there's a lack of data driven decisions on this topic within the workplace. And solving this problem is very meaningful for me, mainly because of two reasons.

The first one is that if I solve it well, it actually drives very tangible business outcomes, right? There is a wealth of research showing that engaged and motivated employees, they don't only stay longer, they perform better, but they are willing to go the extra mile, right? They actively contribute to a stronger culture.

They deliver better service. They add to the brand value and in times of crisis and change, which we just recently came out of, right, the pandemic, they are also more resilient. And the second reason why it means a great deal to me to [00:04:00] solve this problem, and most likely it means a great deal also to actually everyone that works in Engage Rocket, is also because we believe that we are making a huge difference to the life and well being of these employees.

You know, we spend so much of our waking hours, you at work and if we can enhance our experiences at work by creating more opportunities for people to feel valued, to feel supported, to build meaningful relationships and to be empowered, right? There's a positive impact not just on their overall happiness or well being, but also on life satisfaction.

And honestly, I always tell new hires who join Engage Rocket that we're not just impacting these employees but their families as well because how often do we go home after a bad day of work and, you know, risk spreading that negativity to our families. So Engage Rocket is an employee experience platform.

Today, we're very proud to be working with a lot of organizations and it's just been an incredibly rewarding journey to be able to address this meaningful problem. 

Vanessa T: Dorothy, I really love how Engage Rocket gets to the heart of [00:05:00] many of the issues I believe as HR that we face. When trying to build data driven informed decisions that ultimately impact business.

And what I love about what Engage Rocket does is that it really helps business to make better, more well informed decisions on how to elevate the employee experience. Which as you said, is so, so crucial to today's world. And so the ability to use data driven information becomes even that much more critical.

You've had quite an incredible journey building this organization over the last eight to nine years. And I'm very curious if you could just share a little bit more about this journey of building this great organization and share a bit more about that. 

Dorothy Y: Well, we were founded in 2016, right? So I'm not going to lie, it hasn't been the easiest journey.

So there's some truth in what my father had said, but you know, when we first started, we very quickly realized that it was at a time where most of the HR leaders that we were speaking to weren't quite sure what people analytics meant or how to even [00:06:00] begin. And when they weren't sure, it also perhaps meant that there wasn't a budget allocated for it yet.

And this is especially prominent in Asia. Right, so I do feel that in the last eight years, it has almost been like we're growing alongside our customers. We are educating them a lot along the way, but at the same time also educating ourselves because the needs of organizations are evolving very quickly for the future of work.

So one thing that I felt really proud of is that we managed to gain a lot of trust from organizations that we work with. Even though Engage Rocket was the very first venture backed HR tech company in Asia to be focusing on employee experience. Actually, until today, we're still the only one, right, that is born from this part of the world.

And it hints to the level of maturity here. And we are very often also the underdog. In a lot of the deals that we're in, but I think one key strength that we have is that we are always putting our hearts out there, right? We have a genuine interest in trying to solve our clients problems. One of the things that we do is we are constantly [00:07:00] listening to our customers and we are actively asking them for feedback.

And these feedback don't go into a black box, right? We act on them. So when organizations work with us, we really want them to feel heard and to see tangible results that come from their suggestions or their input. If you think about it, it's like an engagement survey, right? Because you want to close the feedback loop from the data you collect, and we kind of apply the same, uh, philosophy to engage with our customers to build trust and engagement that way.

And many of our clients have stayed with us for, you know, since we start. Some boomerang. They left us for whatever reason, and they came back. Some carried us to the next organization that they have joined. One thing that I've learned as the CEO and as the leader is that for me as an organization to enable that business outcome for my clients, I need to commit to creating an environment within Engage Rocket where innovation can thrive.

So this means that I need to ensure there's as little bureaucracy as possible. I have a zero politics policy, like everybody knows I'm very low tolerance for [00:08:00] politics. Everyone within Engage Rocket needs to feel empowered that they have the psychological safety to try new things, to experiment, to do something different for our clients.

And I believe that is so important because it encourages creativity and it encourages Innovation, and I'm very intentional about even the culture that we build within EngageRocker. It's funny because we're in the business of helping clients build better culture, then all the more we need to hold ourselves to very high standards.

So a lot of what we do, being customer centric, this isn't a buzzword for us, right? It's very embedded in our DNA. So much so that I do believe that every day I can actually find examples of my team going above and beyond for our customers. And it goes down to even the people that we hire, right? We want to make sure that everyone that we hire, regardless of the role they're in, that they genuinely care about making a difference.

And we also embed things like, we want to keep our values alive. So we have very regular value alignment assessments [00:09:00] within Engaged Rocket through 360s. We have three key values and I make sure that. You know, regularly our team actually get assessed on behavioral statements that align to these values.

Vanessa I: This is very interesting, Dorothy, and there is something a little bit counter intuitive in the way you have positioned your company. Most of the time, when Vanessa T and I, we work with external providers, we are supposed to hire people who know. And people who have expertise into a field and the more expertise, the better what you're describing is a very, very different approach, which is you almost acknowledge that this is in the making, you acknowledge that this is a field that is growing as we speak, and you engage into the journey with your partner.

So can you tell us more about that? 

Dorothy Y: Yeah, absolutely. I think I understand that perspective because I came from HR consulting too, right? My entire job is to convince my clients that I knew better than them and they should procure my services so that I can tell them what to do. But I think within EngageRocket, it's not about [00:10:00] us not being experts, right?

We come from domain expertise too. We do have in house people science teams. We do hire ex consultants. So these people, it's not that we don't know what we're talking about, but I think the mindset that I want my team to have, and also hopefully my clients to have, is that the needs of every organization is gonna be different from everybody else.

I think with HR, it's a lot, there's almost an unhealthy obsession with best practices and with benchmark. And I constantly find myself repeating this when I build enough trust. with my five partners that I can actually share this, right, that these best practices and, you know, these benchmarks is a good reference point, but let's really talk about what is the organic problem within your organization and how can we design a process that can address it.

And a lot of times, I mean, even at Engage Rocket, we are also a technology company. I think we're a good hybrid. We are a technology and advisory company, but on the technology side, Very often, they will come to me with a laundry list of [00:11:00] features that they want. And again, I will start the conversation again.

Okay, great, but why do you need this? What does this help you achieve? I don't know. It's just your competitor has this. So can you provide it too? So what I'm trying to help my clients and some of the best experiences I've had. Also like you on the other side with our clients is those that actually work with us to design new features that will actually help them solve a real problem.

It's almost having to shift their mindset away from, let's just follow what other people are doing. But almost having the creativity and curiosity themselves to try to come up with a solution of what they truly need.

Vanessa I: That's very powerful. And I think this is what the future of partnership is going to look like.

Vanessa T: We love how you dig in to really get to that root problem of what organizations think they know, or sometimes they need to find out more about what they need to know. And that really helps them to really get to the root cause of some of the problems that we may be facing with employee engagement. We'd be very curious as you've [00:12:00] had so many of these different conversations, what are some of those patterns that you see with organizations and what do they struggle with when it comes to employee engagement?

Dorothy Y: I think there are a couple of things, right? One is the lack of intentionality. I do feel that really good companies, when they are building culture, they don't just leave it to chance that, oh, culture is something that will happen. They are very deliberate about building it. And I think I don't see that enough in organization. Good companies, they know that culture building isn't just about having the right perks and the policies or how fancy the organization or the office look. It's not even about the employee engagement score, right? It's about embedding values into every part of the organization and creating an environment where those desired behavior that align with these values are encouraged.

Be it the hiring practices that you put in place, to how decisions are being communicated, to holding leaders accountable in modeling those behaviors that you want to see. I think all of this [00:13:00] has to be designed to be intentional with culture in mind. I mean, I use ourselves as an example. I kind of mentioned it just now, right?

That we run a very regular 360 engagement because it has three values and on a regular basis. I basically assess everybody within Engage Rocket, including myself, on all these behavioral statements that are aligned to our values, because not only does it regularly serve as a reminder to everyone that this is expected, but it holds them accountable because there will be results that will be reviewed.

Right, they're not held to it. It's not a performance thing, but there will be a conversation around it. The other thing that we do is we have a culture fit round in our interview for all roles, right? For all roles at the final interview, it's always a culture fit round and we deliberately pull a diverse group of what we call rocketeers, people who work in engaged rocket, we call them rocketeers, to interview the new hire and to assess innately whether this candidate is a fit for our culture. 

I think the other thing that I also find lacking is consistency. You know, actually one of the reasons why Engage [00:14:00] Rocket was founded is because we wanted to create an opportunity to be more consistent with data gathering.

Why consistency is important is because it builds trust. And I firmly believe that trust is a foundational ingredient to a good culture and a good workplace. And one of the ways to introduce consistency is actually through regular pulse surveys. And I know, every time I talk about pulse surveys, I always, nine out of ten times, get that question, like, oh, but wouldn't there be survey fatigue?

And I always challenge that notion because truly, it really isn't so much about survey fatigue as it is about lack of action fatigue, isn't it? If I give feedback and I see that feedback translates to a positive outcome, the next time I'm being asked for my feedback, I will definitely give it, right? The reason why people are tired of surveys is because they don't see any changes.

Worse, they don't even get communicated about the results, right? So I think the power of pulse surveys is that you can then break down And the scope into something that's smaller. And you can [00:15:00] enable more feedback loops to be closed. And this create a consistent and regular improvements to be made. And these improvements doesn't have to be big.

It can be small and it can be incremental. But what it does is that it then builds trust because people feel that their voices are being heard. And they also see that the company is actually progressing in the right direction. And I'll say one last thing. It's the lack of empowerment. I do believe that there's still a very big misconception that culture is a very soft thing and it's owned by HR.

It isn't. It's a collective effort across everyone, all departments, all levels, all employees. And the most powerful and successful companies I've seen really tries to empower their people. 

Vanessa T: Dorothy, you bring up some really great points about building of this employee engagement and the evolution of our workforce.

And as a result of that, the deliberate actions that we as leaders need to make. I'd like to go back to the point that you made earlier about how Engage Rocket really uses data to help organizations make better business decisions. [00:16:00] And I was wondering if you could just share some practical strategies of how organizations can use some of the data that we could gather from Engage Rocket really to help the rest of our organization to address some of those engagement related matters.

Dorothy Y: I think what sets us apart is that beyond being a tech platform that enables all this, we also put a layer of advisory, right? So one of the things that we often start with It's actually helping companies understand those critical moments that matter in the employee journey, right? A lot of people come to us and they start with the employee engagement survey and it's going to happen once a year and it's going to be during September. The next one is going to be September. 

So we like to challenge that thinking sometimes. I know it's not always possible, but we do try to widen our client's mindset sometimes to think beyond that. So what about other moments that matters throughout the employee journey? What are you thinking about onboarding?

Right, the new hire experience. How are you thinking about work anniversary? How are you thinking about promotion? How are you thinking about, you know, an employee that's returning from long [00:17:00] leave and may be anxious about coming back to work? There are actually a lot of moments that we can collect useful data on because these are moments where employees experience may be challenged, right, and may need to be looked at.

So what we do is we walk on a journey with our clients very often to go beyond the traditional annual engagement survey to see how it can evolve towards a more continuous type of listening. I know continuous listening ruffle feathers in the wrong way sometimes because people think like, Oh, I have to listen to my employees all the time.

I think it's not about let's run a survey every day, right? It's about how do you collect a stream of data regularly, so that you're constantly tweaking and improving people policies and people decisions that you're making. One very important thing that I think Engage Rocket does, and we don't do enough, unfortunately.

It's not because we cannot, it's just we don't get enough opportunities. It's actually tying those HR metrics. We call it HR metrics, right? Like Employee [00:18:00] Engagement Score. It's a HR metrics. It's actually also tying those to business outcome that truly matters with predictive analytics. If you say that retention is important, or if you say that customer satisfaction is important, Or if you say that patient care or whatever outcome that matters to your organization is, it's one of the top API for this year, right?

Let us do the math to show you how engagement can actually drive that, right? And there's so many drivers of engagement. Let us tell you which one actually drives it the most because it can then focus your resources. It can focus your intervention to make sure that you're doing things that reach the highest ROI.

Oh, by the way, on the topic of ROI, let us calculate that for you, right? Let us tell you whether or not it's actually returning on the investment. And if it's not, then you have the data to then go back to your management and say, this is the reason why we are tweaking our strategy now. I think one of the very big thing That keeps me doing what I'm doing is that I generally want to change the [00:19:00] position HR has in the senior management table.

HR is such a strategic function, but it's not always seen as one. And I do believe that we are not always seen as a strategic function, primarily because of the lack of data usage. Oh, this person say this. We think that we've done this in the past, so we're repeating it this time. So I mean, after a while, people just don't listen to you anymore.

But if you're going to the table and say, look, if I'm going to be spending a hundred dollars on improving development programs this year, it will directly translate to 10 percent increase in sales revenue for you within a quarter. You think the business leaders won't wake up? You know what I mean? 

Vanessa I: Thank you on behalf of the HR community, Dorothy.

Vanessa T: Indeed. 

Vanessa I: We need more people like you around us. I wanted to ask about the way you share the dual demands of running a successful business as a CEO and raising, uh, two young children. I know because you shared with us that one of your son has a Down syndrome. We wanted to ask you about this very important part of your life.

Oliver and Nathan are your [00:20:00] children and how do you make sure that you balance all of that?

Dorothy Y: I think I'm still a work in progress. I have my good days and I have my bad days. But I think over the years, I mean I'm someone who is always very driven to self improve. So I think over the years I've realized that there are two non negotiables for me.

Sleep and family. So let me start with sleep. I was deeply influenced by two books. The first one is Outlive by Dr. Peter Attia. I'm not sure if you have read it before. If you have not, I highly recommend it. And the other book is Why We Sleep by Matthew Walker. So these books actually really completely changed my perspective on how important it is to rest and sleep.

So much so that, you know, I will self admit that I do enjoy a good glass of red wine. But unfortunately I have to cut back significantly on drinking because it actually impacts my sleep quality, right? I do wear a watch to track my sleep quality. And now I know that getting seven hours of sleep is a non negotiable for me because it really does [00:21:00] affect everything, physically, mentally, emotionally, how well I operate the next day.

So this means, literally, even if I'm out on an engagement, be it work or with my friends, at 10, I'm just going to make a move. Yeah, because I need to prioritise me and I need to prioritise sleep. You know, my friends have called me, oh, you're such a grandmother nowadays, and I'll be like, yeah, I am. Just knowing that that's a non negotiable has really changed my perspective on how I lead my life.

And then I think the second thing is about family, and it's because we're parents. We can so easily get distracted by our kids. So by family, I really mean my marriage. I want to make sure that my marriage is always strong. I'm a firm believer that if my home front isn't stable, I can't focus on the work front.

And interestingly, I laugh about this a lot because a lot of the concepts that I apply at work, I apply at home too, right? So things like, oh, good communication, psychological safety, teamwork. I repeat this to my husband too, and he's like, oh yeah, I definitely married a HR wife. But my husband and I prioritize these things to a point where, you know, like psychological safety, right?

[00:22:00] We can talk about absolutely anything, including constructive feedback for each other. Because when we got married, we committed that we want to help each other become the best version of ourselves. So that commitment means mutual respect. If I have a feedback for you, I love you, but listen to it. And yes, the other party has to listen to it and to really make it a point that we work as a team.

So if I can't make it to the kids, right, can you do it? I'm sorry, I can't make it again next week. Can you do it? And it's not a, Hey, I've already done it last week, it's your turn. So it's not about a transaction, but we will operate as a sole unit. So I think having that focus that it's my marriage, even before my kids, it's also another non negotiable for me.

Vanessa T: Dorothy, you sound like you almost at the point of using a survey for your family as well. I would use that at home too to see. Measure my engagement score at home. 

Dorothy Y: Yeah, I have a funny story where on my second date with my husband, I made him do the Gallup StrengthsFinder. 

Vanessa T: Oh my goodness. Wow. 

Dorothy Y: Yeah, I took out my laptop.

I paid [00:23:00] for it. I was like, you know what, I'll just order a beer and I'll have my beer. And then you can check through the, I want to look at your results in 20 minutes. 

Vanessa T: Oh, that's fantastic. Maybe I should do that at home. Check out what my score would be like. Dorothy, you have a great sense of humor about that.

We're also very curious how your advocacy for Down syndrome has also impacted, kind of, the way and shaped your perspective as a leader, as a mom, and as an entrepreneur. 

Dorothy Y: So Nathan, my older son, he is four this year, and he has Down syndrome. Down syndrome is essentially a chromosomal abnormality where they have three copies of the 21st chromosome instead of two.

So as I was raising him and as I become more and more active in the community of special needs, there are a couple of things that I've learned along the way. And the first one is really, ignorance is the biggest barrier. And knowledge is the most powerful enabler. Many people, I think when they approach a topic or something that they're unfamiliar with, they default to [00:24:00] assumptions or worse, they will just fear the unknown.

Advocacy for me, I think it's very important because it's really about educating and helping people to move from a place of misunderstanding to one that is empathy and empowering because it's enabled by knowledge. So in many ways, I think it parallels the work that we do at Engage Rocket because we're using insights and data to deepen understanding of the body and to break down those barriers and assumptions in the workplace that could lead to ineffective people's strategies and initiatives.

A lot of what I do now is to try to invite conversations about Down syndrome because I think there's a lot of misconception out there. Even when I was pregnant with Nathan and I knew of his condition, I did face a lot of difficulty and resistance even from family members because they didn't know what they are signing up for, right?

They're like, oh, you know, your life is going to be greatly impacted. Oh no, oh no. Everybody's just super worried. One of the very first thing I did, which is also, I mean, now that I think about it, I think it's quite funny. I created a PowerPoint slide and I put in, you know, all the [00:25:00] knowledge that I knew about Down syndrome to the behaviors, right?

What kind of desired behaviors I would like to see around my child. And I literally sat down with my family, my husband's family, with our closest group of friends. I even did this presentation with employees within Engage Rocket, just to make sure that the closest community that Nathan will be exposed to, these people are armed with the knowledge that they need to interact the best with Nathan.

So that was one. The other one that I've learned is to really celebrate small wins. In parenting Nathan, what I've learned is that, you know, progress really doesn't look the same for everyone and that's really okay. Oliver, my second son, he is neurotypical. Not to compare the two, but Nathan learned how to walk when he is two years old.

Where else? Ollie started walking even before he turned one. And it came so naturally to Ollie. With Nathan, it's really week after week of therapy. Because of his low muscle tone, even lifting up his head when he was a baby was a [00:26:00] challenge for him. Because babies with Down Syndrome, they call them wobbly.

Like they are just, they don't have enough muscle tone to be firm. So his head used to flop down, even try to fold his head up required a lot of therapy sessions. But in those therapy sessions, you see how hard a baby is working, right? A three month old baby is working. And when the day came and then he was lifting his head up, well, we celebrate a heart, this mindset influenced me very strongly because even when I'm now leading Engage Rocket and I've built a company, it's not about celebrating big.

Oh, we hit our revenue milestones or we won a big deal. I think it's really about recognizing those daily efforts. All the times that my team went above and beyond and worked overtime just to make sure our client get something that they needed or the resilience that they displayed that made those bigger wins possible.

It's really about calling those out and recognizing them. That's so important. And again, back to really building it within the DNA of the company. Every Monday morning, we actually have an all hands meeting and we always dedicate 10 [00:27:00] minutes at the end for recognition. And it's a beautiful segment because we always go over time and it's cross functional.

Like people are recognising each other from different departments. Oh, thank you so much for doing that because you did that. I was able to do this. And the recognition just flows. And it's nice because we have this meeting on Monday and it just starts everyone on a very positive note for the week. 

Now I'll just make one last point. The last point I've learned is that people really respond to the energy project to them. So if I approach the discussion about Nathan or Down syndrome with positivity and with confidence, what I realize is that people tend to mirror the energy and then they will be more willing to ask me questions, which is exactly what I want.

I want that opportunity to raise awareness, to educate people about Down syndrome. It's taught me the value of just being very intentional as a leader. What kind of energy I'm bringing into every situation. As a leader, if I react to a difficult time with fear or with negativity or, you know, with a lot of anxiousness, then it trickles down.

That stress trickles [00:28:00] down to my team. But if I'm projecting optimism, hey, okay, you know what? We can do this. Let's, you know, figure this out together. Don't worry about it. Even in difficult time, I think it inspires. confidence and I can see that my team is a lot more focused on action and focused on, okay, what can they do then to, oh no, oh no, oh no, something bad happened.

Yeah, so that's probably a couple of things I've learned. 

Vanessa I: Well, you're very inspiring to the two of us and I think you're very inspiring to many more people. When we went to your office, we could also see. The smiles and the eye contact of your team members and how much they are actually in awe of everything you do.

So please continue everything you do because I can see the impact and I can see, you know, the way they actually embrace all the things you are doing intentionally. So great job. Congratulations. 

Dorothy Y: Thank you. Thank you. I try my best. 

Vanessa I: We wanted to talk about the resilience and the importance of building a portfolio career.

What would you say are the key elements of building a portfolio career for yourself and staying adaptable [00:29:00] through the challenges?

Dorothy Y: I always think about what this quote by the futurist Alvin Toffler. You must have heard of it, right? The illiterate of the 21st century will not be those who cannot read and write, they will be those who cannot learn, unlearn, and relearn.

I mean, I love that. And I think it just captures the essence of what's needed to succeed today, which is learning agility. Having the mindset and the willingness to not just challenge the status quo, but just as importantly, to be open to be challenged, right? It's really gonna allow us to adapt and grow and to continuously evolve our skills.

I think building a portfolio career requires a very diverse range of skill sets and you can't develop those skill sets without curiosity, without commitment to lifelong learning. Both my parents went back to school in their 50s and 60s. My dad got a master's in counseling and when he was, I think 62 or 63, and my mom just got her license to become a traditional Chinese medicine practitioner.

It's funny because she always wanted me to be a doctor, and I didn't. [00:30:00] So I guess she ended up having to fulfill that dream herself. But I do think that it really starts with having the courage to step out of your comfort zone and just having the openness to let go of what you knew and just to be challenged and to keep up with times, which I think is a very big struggle with a lot of leaders, particularly leaders today.

I think the cycle of learning, unlearning, relearning will never end. And it's going to keep us adaptable because the world will just keep changing. So that's one key thing that I would say is important. 

Vanessa T: I think Alvin Toffler's quote about the ability to learn, unlearn, and relearn, I think really resonates with me too, because I truly believe that as we progress into the careers of the future, the ability for us to constantly be looking back at what we've done and thinking about how we can do things differently, be open to challenges, innovation, will really help us to build much, much, longer, more sustainable and more interesting careers.

Now, Dorothy, we've [00:31:00] talked so much about your journey as an entrepreneur, listening to how you go about building your career as an entrepreneur, and also balancing that with your family life. For aspiring entrepreneurs who are navigating career transitions, what would you say are the top lessons that you've learned about building resilience and perseverance?

Dorothy Y: I think when it comes to resilience, what is not talked about enough is this key ingredient of grounded optimism. And I don't mean unrealistic, overly cheerful, like an energizer bunny and for positivity. I don't mean that. I mean making the deliberate choice to always see the cup half full. Even when the odds are stacked up against you.

And I think this mindset is critical because it allows you to bounce back from setbacks and to continue to move forward. The reality is that the path to success or to goals, whichever path that you're on, is going to be riddled with obstacles and failures. I think social media paints a very unrealistic picture.

The reality is everyone's struggling somewhere, somehow, on something. And one of my favorite [00:32:00] example of resilience from an organization standpoint is actually the story of Netflix. Back in the early 2000s, they were the underdog and they were competing against corporate titans like Blockbuster. And Netflix actually journeyed from a very small DVD rental business to now obviously a household name.

They are a leading online streaming platform. But that journey wasn't smooth, right? Even though they were quick enough to adapt to the rise of online streaming that was brought on by YouTube, they still faced challenges because in the very early days, even though they went into online streaming, their content library were old movies that nobody were interested in.

Instead of giving up, they actually pivoted and they started to take risks to build their own in house production team to do original content. Have you heard of House of Cards? So these are one of the, one of their very first original series that it brought to consumers. And obviously now there's just too many to count, right?

So for me, I think the Netflix story is a testimony to resilience as well, because it shows [00:33:00] that you really cannot give up at every no that you hear or you retreat after every single failure, even if you're on the right path. And Netflix was on the right path. They moved into online streaming, but still, they were faced with a roadblock.

It is really about seeing every failed attempt, not as a mistake, but what can I learn from this? How can I pivot? How can I move forward? So choosing to always focus on what you can learn, deliberately choosing to see the cup half full, I think it's really key to building resilience and to really build that strength to adapt and to grow and ultimately succeed. 

Vanessa I: Thank you Dorothy, for sharing your inspiring story with us. Your insight on entrepreneurship, advocacy, and building great workplace cultures will be something that we will keep for our research and we'll continue studying. 

Vanessa T: Thank you, Dorothy, really for sharing with us your incredible journey and you're such an inspiring ball of energy.

Thank you so much for all the things that you've shared with us today. We hope that your journey will truly [00:34:00] inspire our listeners to think of their careers as a portfolio and also how to go about being bold in experimenting and to embrace their challenges as they come along. And with that, thank you so much, Dorothy.

We have truly enjoyed speaking with you today. 

Dorothy Y: Thank you so much and congratulations again on five seasons of Career Transitions. What an incredible platform and it's just been a privilege to be able to contribute to it. 

Vanessa T: It has been such a pleasure speaking with you today. Thank you for tuning into this episode of the Career Transitions podcast.

And we look forward to bringing you more inspiring stories in the weeks to come.