When Armoire CEO Ambika Singh founded her clothing rental company, she had no idea how much grit she was gonna need to source.
It turns out it was a lot.
I had the opportunity to sit down with Ambika and talk about how much Armoire has grown in the nine years since she had the idea to reduce fashion waste with a rental company.
In this episode, Ambika shares openly about the challenges she had getting funding for Armoire, and the key thing that helped her source confidence and grit along the way, especially as a woman of color in a male-dominated industry.
She also shares about how parenthood changed her perspective on work and creating more balance in her life. And that while she has had to be super tenacious to get here, she still is working on not being so hard on herself.
This conversation is so rich and powerful, you don’t want to miss it!
“How do you balance a full, ambitious, purposeful life with all of the dreams that you have, including having a family?” Nicole Tsong
“You can build things and especially if you don’t like things, you can change things, but it’s on you to figure out how to do that.” Ambika Singh
“One thing that has helped me is having my little children. I was very afraid of how I was going to balance everything. …. It gives me an end to the day that I care about more than just work. I want to see them in the evening and be present.” – Ambika Singh
“I use that as a mental trick on myself when I’m not feeling super confident about myself or the business. The {Armoire} mission feels so significant that it gives me confidence, strength, and grit. But I certainly didn’t have a good sense of how hard this was going to be.” Ambika Singh
“With many of the women who work for me, my job is often to remind them of all the great things they’ve accomplished and the positive impact they’ve made. I know they’ve already been hard on themselves before our one-on-one meetings.”- Ambika Singh
“Entrepreneurship…is like the biggest personal journey and personal growth journey you’ll ever go on because you have to confront yourself daily, multiple times, hundreds of times a day sometimes to stay true to it.” Nicole Tsong
“One of the unlocks a friend who kind of acts as, like, a mentor and coach to me gave me was that you can’t have your personality be one way and just lose all the downsides… The yin and the yang don’t sit together.” Ambika Singh
“If at the end, the thing I will be most proud of is like, did the people who are closest to me—did I add value to their lives? And feels like at least this award is telling me that I have.” Ambika Singh
NICOLE
Hello, dear listeners! I’m coming to you with a truly special update. As a former journalist, this feels very newsy to me. I kind of wish I had some news sound effects in the background, but I know better than to bury the lead. So, I’m here to share that I am having a baby! If you haven’t heard, this has been a long-time dream of mine, and it is a really special moment for me and my husband, Michael.
We are making a few adjustments here on the School of Self-Worth to give me the time and space for maternity leave. We will be moving to a schedule with a new episode for you once every two weeks. You’re still going to get incredible interviews with powerful, inspiring Asian American leaders. I mean, these are some of the best interviews we’ve ever had on the show! You will also receive new mini-episodes from me, just a little more spaced out than usual.
I am so, so grateful to have a life where this is even possible—to take maternity leave and to be supported by all of you and my team. It truly is the dream I’ve always had: to balance my personal life, the people I love, and the work I am so passionate about. I cannot wait to come back because I know I will have so much to share with all of you. But how do you balance a full, ambitious, purposeful life with all of your dreams, including having a family? I am so grateful to you, my dear brilliant listeners, for being part of this journey. I know I will have so much to share when I return, so please stay tuned.
We have remarkable episodes lined up for you! Today’s episode is particularly special, and I cannot wait for you to hear from our guest, Ambika Singh. Ambika is the CEO and founder of Armoire, a clothing rental company she founded nearly a decade ago. She is incredibly smart and thoughtful about the entrepreneurial journey. As a mom of two, she has navigated how to stay true to her vision while running a growing company. I learned so much from what she shared about staying on track for herself, and I truly love our conversation because we delve into the details of what it takes to sustain a company for this long while remaining true to yourself.
Before we get started, if you are a high-achieving Asian American corporate leader who wants to feel valued and visible to nail the next promotion cycle, DM me “visible” @NicoleTsong on Instagram. I’ve got a bunch more details over there for you.
Okay, friends, let’s dig into this extraordinary conversation with Ambika Singh. Welcome to the School of Self-Worth, a podcast for ambitious women who know they are worthy of an astoundingly great life. Join us weekly as we get on the right side of your intuition, redefine success, and reclaim your self-worth. I’m your host, Nicole Tsong—an award-winning journalist who left it all behind to become a bestselling author of three books and a work-life balance expert helping ambitious women unlock their intuition and step into a life of fulfillment and radical joy. Every single week, I will bring you diverse and meaningful conversations with successful women from all walks of life who share insights about what it takes to be brave, joyful, and authentic every day. Each episode is thoughtfully designed to leave you feeling empowered with tangible tips and advice that will lead you to your next breakthrough. Ambika, it’s so good to have you here on the School of Self-Worth. Welcome!
AMBIKA SINGH
Thank you for having me! I’m really excited to get the chance to talk to you.
NICOLE
It’s so fun! I’m going to take you way back because I don’t know if you remember this, but years ago, we both went to Dartmouth, and they asked us to present at an entrepreneur forum. I laugh looking back because I was in no way an entrepreneur back then—I was teaching yoga and writing books. But I remember you were there presenting, and I think you had just started Armoire, maybe just a year in. I was really impressed by everything you were doing, especially since you were getting funding before rentals were even a thing. I don’t know if you remember that conversation; it was in an Amazon building in downtown Seattle.
AMBIKA SINGH
I do, very vaguely! And I will correct the record: you are very much an entrepreneur. It’s all connected, especially those early challenges of how to take an idea and turn it into something.
NICOLE
I’d love to start with that because, for me, the entrepreneurial journey has been a significant self-worth journey. I’m curious about your experience. You went to business school and were surrounded by a lot of people in tech who were focused on funding. I’m interested in where your journey began. When did you start to think, “Hey, I am the person who’s going to start this new thing, and I’m going to go ask a bunch of guys in Silicon Valley for money”? Have you always been entrepreneurial? Where did this all start for you?
AMBIKA SINGH
That’s a great question! I love the next generation’s focus on intentionality because I think I had very little of that. To your point, I was fortunate to grow up in a really entrepreneurial household. My dad has been a multi-time CEO, and my mom is very entrepreneurial in her own right. In middle school, I attended a choice school in Washington. These schools, which might be similar to magnet or charter schools elsewhere, are publicly funded but run very entrepreneurially. I was lucky to be in the first class to graduate from one that now has a great reputation.
The charter called for the creation of the school to involve one-third teachers, one-third parents, and one-third students. There was a lot of empowerment at an early age from those two influences—my school and my family—that you can build things, and if you don’t like something, you can change it. But it’s on you to figure out how to do that.
Fast forward, I was fortunate to go to Dartmouth and gained exposure to people who had run interesting businesses and thought about things differently. However, I didn’t leave undergrad thinking of myself as an entrepreneur. I went to work at Microsoft, as many do in Seattle. There, I gravitated toward a job that put me in front of student entrepreneurs who inspired me.
Another part of my background is that at Dartmouth, I wrote a thesis about microfinance and spent a good amount of time in India with women running businesses funded by microloans. I witnessed the transformational power of entrepreneurship firsthand.
So, I learned about entrepreneurship from many different places and began to build my own conviction. I went to business school thinking I would like to start something, but I didn’t have a specific idea. Many people lovingly tried to dissuade me from going to business school, suggesting that women often over-credential themselves. You’ve probably heard that men apply for jobs with 40% of the credentials, while women apply with 110%. They said, “If you really want to start a business, do you need this academic stamp?” For me, it was valuable because it gave me time to focus.
It would have been hard for me to create that time for myself. During my two years at Sloan, I tried all kinds of different ideas—from working on elderly loneliness to an idea about a shoe company that would offer two different sizes since many people have mismatched feet. My ideas were all over the place, but the concept of a rented closet really stuck.
It felt important from a lasting legacy perspective. The fashion industry is tough on the planet, and there’s not much awareness at the consumer level. While it’s great to consume less, we need to address the supply chain because we’re building an industry that treats waste as free. We might be overproducing by about 30 to 40% annually, and these clothes never go away. You can imagine we could dress the entire planet for 50 generations if we never made another piece of clothing.
NICOLE
I hadn’t heard that before—that’s crazy!
AMBIKA SINGH
Yeah, we have too much stuff.
NICOLE
Absolutely, we do!
AMBIKA SINGH
It felt really important to me from that perspective. I was deep in a part of my career that was particularly painful regarding gender inequality—what was expected of me professionally versus what was expected of me appearance-wise. I was at peak frustration with that. It felt essential to figure out something for professional women.
Lastly, I realized it was really fun for me. I had never had a chance to work with female consumers, and I was looking at women who represented me—working women with real problems. I thought, “If I could do something important here that would help their lives, this would feel really significant.” So, my entrepreneurial journey started from there.
That’s what I mean about being intentional versus unintentional. The stuff that came after it was unexpected; I never signed up to spend 100 hours pitching to guys who had no idea what I was talking about.
NICOLE
Especially when you started! Now, rental is more common—there are multiple companies, and I know many people who rent. But when I met you, I don’t think I knew anyone who was renting, probably because it wasn’t even available back then.
AMBIKA SINGH
Exactly. The oldest version of rental in America is tuxedo rental, which has existed for a long time. Remember the first Sex and the City movie? In the early 2000s, there was a highlight of a bag rental company called Bag Borrow and Steal.
NICOLE
Oh, I do remember that! I never borrowed from them, but I recall hearing about it.
AMBIKA SINGH
Hopefully, you didn’t steal from them either! It was an interesting name, and I later got to know some members of the team who were very helpful in getting me started, but they definitely regretted that part of the name!
To answer your question, there weren’t many people doing it. Coming from tech, I had worked at Microsoft and at two different web startups—one in the travel industry and one in dog boarding. My lens was, “Let’s find a place with white space.” It didn’t occur to me that white space has real challenges that spreadsheets don’t tell you about. The spreadsheet might indicate your business will thrive because there are no competitors. So Hockey Stick is going to be amazing.
NICOLE
But nobody knows what it is.
AMBIKA SINGH
Nobody knows what it is, but they want to do it.
NICOLE
Yeah, so a lot of your work was about generating that awareness. I mean, would you say, going back to the self-worth piece, did it occur to you as a worthy endeavor, or were you just thinking, “I’ve got an idea, and I’m just going to go for it”? And then as challenges came up, you had to keep coming back to yourself through all of that since it’s been many years now.
AMBIKA SINGH
Yeah, I think it’s a combination of both. The ultimate mission has always felt really important to me. I use that as a mental trick on myself when I’m not feeling super confident about myself or the business. The mission feels so significant that it gives me confidence, strength, and grit. But I certainly didn’t have a good sense of how hard this was going to be.
NICOLE
What would you say about your journey? I always tell my clients who are building their own businesses that entrepreneurship is the biggest personal growth journey you’ll ever go on. You have to confront yourself daily—multiple times, sometimes hundreds of times a day—to stay true to it. There’s no boss; you are the boss. You have to look at yourself and realize, “I made that decision, and now I have to deal with it.” Where would you say your biggest challenges were, and what did you learn about yourself through those experiences?
AMBIKA SINGH
I think my biggest challenge—and probably my biggest strength—is that I’m pretty gritty. It’s a combination of feeling like I have something to prove and being competitive. However, I haven’t made peace with the fact that I’m tough on myself. At the end of every day, it’s more about what more I could have done. I tend to have a lot of anxiety about whatever the proposed end of my day is. To your point, nobody really ends your day except for you because there’s no one telling you it’s time to go home. So, these late nights can be tough.
On the flip side, I feel like my drive is a strength because I believe I can solve problems. But I need to figure out how to give myself peace. I wish I could end my day feeling, “Bika, you did a great job today. You’re all done now, and you did good. Here’s a gold star.” I almost never give myself that end-of-the-day feedback.
NICOLE
You actually need a chart where you can give yourself a gold star every day. That would be fun!
AMBIKA SINGH
I really should!
NICOLE
Gold star for today!
AMBIKA SINGH
Exactly! One thing that has helped me is having my little children. I was very afraid of how I was going to balance everything. Knowing that I’m so obsessed with my company, I wondered if there was room for me to scale to these other things that people seem to be obsessed with once they have them. This has actually been really good for me because it gives me an end to the day that I care about more than just work. I want to see them in the evening and be present. They’re still very little, but they’re starting to be proud of me. Maybe I won’t ever be able to properly do that for myself, but maybe they will.
NICOLE
That’s a big thing for many of the women who listen—high achievers trying to juggle so many responsibilities. How do you figure out balance? There’s no definitive answer, but what are some ways that have worked for you? Taking maternity leave while running your own company must have been scary.
AMBIKA SINGH
Absolutely. It’s interesting to see how I handled it the first time versus the second time. I clearly learned something along the way. The first time, nobody forced me to go back to work, but I went back pretty much immediately. I didn’t realize, but people had tried to tell me that it was more about feeling lost in parenthood than about being stressed that my company would burn down. A real factor is that I was fortunate the company was already six or seven years old by the time my first child was born. That made a big difference.
In the early years, I don’t know that I could have just walked away from it. But in the later years, I had an amazing leadership team that did their jobs better than I could. Knowing that gives me a lot of confidence. There are still aspects where I think I can contribute more, but those are optional now. We have people who ensure the packages go out, who talk to our customers every day, and so on. From a business perspective, I’m not in the thick of it, which gives me huge latitude.
Still, I went back to work very early after my first child was born because I thought, “This is what I do, and that thing over there is not what I do.”
NICOLE
That part is scary and hard.
AMBIKA SINGH
Exactly! I didn’t know how to handle that. So I had a less-than-ideal maternity leave the first time. The second time, I actually left the country.
We Airbnb’d our house and went to Australia. It was winter in Seattle, which was a negative experience for a sun seeker like me. I was trapped inside with a screaming baby. So, for baby number two, we Airbnb’d the house. Everything in my life tends to be a little over the top. I had a baby, and two weeks later, we packed up our entire house. Two weeks after that, we moved to Australia. But it was great for me because I was in the wrong time zone, which forced me to let go. The team did amazing. We had an incredible quarter, and I got to spend some quality time with my kids.
NICOLE
That’s awesome! I love how you solved the problem by leaving the country. It’s easier than staying because if you’re here, you’d still be in your routines and want to check emails and all that stuff, right?
AMBIKA SINGH
For a non-entrepreneur, they probably thought it was insane. But all my entrepreneur friends were like, “Oh yeah, do that! You have to do that! If you’re not going to do that, why are you even pretending to take leave?”
NICOLE
Right? It’s like you’re just going to work from home instead of going to the office!
AMBIKA SINGH
Exactly! It was really effective. I literally couldn’t do anything else.
NICOLE
So you were stuck in Australia, raising your kids there.
AMBIKA SINGH
Yes! You’re totally right. These are the absurd realities that I live in. My inability to exercise any self-control requires me to move to the furthest place from Seattle.
NICOLE
You really went polar opposite to go to Australia! That’s awesome. I love that. You have a lot of freedom as an entrepreneur, which allows you to make choices like that.
AMBIKA SINGH
Exactly! I just did it and thought, “I’ll be back when my maternity leave is over.”
NICOLE
That’s amazing! Now, I’m curious—how many years have you had Armoire?
AMBIKA SINGH
So, Armoire is nine and a half years old. She will be 10 this June.
NICOLE
Oh my gosh! That’s right! When this episode comes out, it will be the 10th anniversary of Armoire. That’s amazing! Looking back, what do you feel about the journey?
AMBIKA SINGH
Wait, sorry, I’m one year off. She will be 10 next year, in 2026.
NICOLE
Same question still applies. What would you say to your past self starting this company nine years ago? Did you ever visualize it being where it is now?
AMBIKA SINGH
I’m sure a lot of entrepreneurs say this, especially those like me who came from a generation of consumer companies focused on growth at all costs. We were venture-backed and came out of MIT’s accelerator, so my spreadsheet now looks absolutely absurd with my more experienced eyes.
NICOLE
Like you could ever have hit those numbers!
AMBIKA SINGH
Exactly! But I thought it would be gigantic. I didn’t really know what that meant or how to achieve it. Now, I feel strongly that we are adding something positive to our members’ lives. It felt then and still feels like, “How do we get this into more people’s hands and create great outcomes for our customers and the planet?” I just didn’t have a good sense of how relatively slow growth could be. I hesitate to say slow because it’s all relative to your frame of reference and what people tell you.
NICOLE
Right.
AMBIKA SINGH
Looking back, it’s clear that great companies don’t grow to a billion dollars overnight. It takes them 10, 20, 30, or even 40 years. Those are the real time frames: five years for one milestone, ten years for another, and fifteen years for yet another. I was caught up in the mindset that every quarter we’d make a massive leap and double our growth. It doesn’t work that way.
NICOLE
I find that really interesting about entrepreneurship too. I’m in the online space, and you are as well, but we have different kinds of businesses. I’m almost seven years into my business, and it has grown much slower than I originally thought. I know so much more now, and I enjoy it in a way that I didn’t in the first couple of years when I felt like a mess. I didn’t understand the business at all.
I recognize that while some people have had exponential growth years, that’s not the case every year. I see people I admire having maybe two exponential years out of ten. It’s not like every year is a huge success. So, you realize that slow and steady wins the race. If you love what you do and are passionate about your mission, that’s what keeps you going rather than the pressure to be massive.
AMBIKA SINGH
Right. From a financing perspective, I think it’s not very positive to raise a bunch of money upfront because you don’t give yourself a chance to grow in a slow and steady way. I raised a significant amount of venture capital in the beginning, and now we have a line of credit and are moving toward a more formal banking relationship. It’s not to say we haven’t had incredible backing that has helped us get this far. It’s just a different way of building a business compared to how you’ve built yours.
NICOLE
Yeah, mine is just me. I’ve been funding it myself and investing as I go. It’s a different kind of business than what you’re doing, which involves warehouses and a huge volume of inventory.
AMBIKA SINGH
Exactly.
NICOLE
I remember when I saw you speak recently, you mentioned that one of the biggest challenges for you in running a business has been going back to ask for money repeatedly. Can you speak more about that? What is it like, especially as a woman and a woman of color in an industry like fashion that probably doesn’t see a lot of VC investment? How have you seen things shift, or how have you shifted as you’ve navigated that?
AMBIKA SINGH
In the early days, we came out of MIT’s accelerator, which provided some initial funding that carried us through the first year. After that, I started talking to anyone and everyone who would listen, in Boston, Seattle, and everywhere in between. I quickly learned that this wasn’t a problem that a lot of men understood. In broad generalizations, it seemed to be more understandable by women.
I recognized early on that I would face challenges not only as a woman of color CEO but also because my business model was different. I often encountered blank stares when explaining it. Even now, I still get questions like, “If you find a shirt you like, why don’t you just get more of that shirt? Why do you want a different shirt?”
NICOLE
That’s such a question! But I guess that’s something a guy would ask.
AMBIKA SINGH
Exactly! They literally can’t understand why you would want to take that risk. I’ve had in-depth conversations where they say, “You have to get ready and out the door in the morning. Why would you want something you haven’t worn before?” It’s hard to explain that perspective because it’s so different from mine.
NICOLE
I could have 15 white shirts, and they can all be different, right? Because it’s fun, and they all look different!
AMBIKA SINGH
Exactly! I knew it would be tough. I wasn’t going to fit the mold of what they had seen before, and my business certainly wouldn’t match their expectations. One area where I found success was that for a time, 50% of the money on our cap table came from women, which is almost unheard of. Many of those investors were non-professional, starting as my customers who wanted to see the business succeed.
I had my first “aha” moment when a customer told me, “This is changing my life. Can I invest in this?” At that time, I had weeks of cash left, so I had a problem. She asked, “What do we do?” We reasoned that she could become my investor. We began exploring options, and I realized that while there are barriers to entry for regular people in the investing world, there are also ways to participate.
For women looking to get involved without going on an entrepreneurial journey themselves, this is how companies like mine survive. You can embark on an entrepreneurial journey with someone who will be a grateful recipient of your capital and yield outsized returns. Female CEOs tend to be more successful on average than their male counterparts, and businesses targeting women in areas with a lot of white space are likely to succeed because there’s an unrecognized demand. Nobody knew you wanted four different white shirts; they thought you just wanted one.
NICOLE
I use Armoire, and as a consumer, I think it’s so convenient and easy. I started using it for events because every time I bought an event dress, I wore it twice and then never again. Those dresses are higher-end investments, so I thought, “Why not borrow it for the same price and try on a bunch?” There’s something so fun about receiving a package with clothes to try on. If I don’t like some of them, I just send them back, and it’s amazing.
I had a friend with a last-minute event, and I said, “You should really rent because it’ll be so much easier. You won’t have to keep that dress.” That’s how I started, and I still enjoy using it for various reasons. From a consumer perspective, I appreciate not having to buy so many clothes. I can just have some new items and send them back, which is fun. But I can see how someone who isn’t into fashion might think it doesn’t make sense. Most of us are aware of the impact of fashion and buying clothes, and we’re trying to reduce our consumerism. It’s all for the price of one pair of jeans, so it’s a no-brainer.
AMBIKA SINGH
Absolutely. One of my goals is to lobby for the true cost of trash to be internalized at both the consumer and business levels. If we did that, I believe it would dramatically change our behavior.
Younger consumers often say, “But I can get this three-dollar item from Shein that looks almost like this.” Sure, you can, but then you throw it in the trash without considering the environmental cost of that action.
I have this vision of everyone paying for their trash in a way that reflects its true cost.
NICOLE
That’s a fascinating perspective.
AMBIKA SINGH
Exactly! When it comes to food packaging, I don’t think about the fact that my food delivery will fill up my entire trash can because someone else deals with it.
NICOLE
It’s so true! I completely agree. We need to reduce our consumption, and it takes a lot of thoughtfulness because everything is designed to make it easy for us to consume. Sometimes, I try to add friction to my consumption habits. I’ll unsubscribe from services to make it harder for myself to buy things I don’t need.
AMBIKA SINGH
Totally. But it’s interesting that we’re all making these values-based decisions. I think we both are. There are true economic costs that we’re not internalizing because we’ve pushed those off to the third world, where people are holding our garbage, or even to poorer communities in our own country. That’s where all the garbage goes—out of sight, out of mind.
NICOLE
Totally. What would you say now, though? You’re almost at 10 years in. Do you feel clear about this being your path, or do you see it as what you’re doing for now and really love your company? Or is it something else entirely?
AMBIKA SINGH
I still feel like she’s a young adult. She still needs some help. I don’t feel like I’ve made it yet, but I am starting to see that she’s on her way. To make that more real, the financial situation is still tenuous. I need to turn some dials to ensure that it becomes a solid, long-term investment.
A key issue is that we’re not yet paying market salaries across the employee base. I need to figure out how to make more money so I can do right by my employees. My goal is to be a better-than-average paymaster. I think Netflix has done a great job of this: they pay better than everyone else and have high expectations. I would love to achieve that because right now, it feels like just a high-expectation environment.
NICOLE
But you guys just won an award for the best workplace!
AMBIKA SINGH
We did! This might be the thing I’m most proud of from an external validation perspective. It was a surprise to me, too. Even though I’m proud of the millions of dollars in revenue we’ve generated and the thousands of lives we’ve touched, this felt different. I really want people to know.
NICOLE
Well, tell everyone what you won!
AMBIKA SINGH
We received the Workplace of the Year award, given to a company that has created a great place to work. It’s voted on by the community, hopefully by your employees, but also by the surrounding community. I heard that about 20,000 people voted this year. I didn’t realize it was that big, which made it feel a bit like a popularity contest. Still, it shows that people are aware of something positive about Armoire, and that felt so important to me. I hope we leave behind a legacy of doing something for the planet, adding great value to our customers, and creating a workplace where our employees feel valued.
NICOLE
That’s amazing! And it’s from Geek Wire, which is a big deal. You didn’t expect to win, right? You went to the event thinking you wouldn’t be the one to receive it.
AMBIKA SINGH
Honestly, I was unprepared. I didn’t think there was any chance we’d win, especially since there were very big names in our competitive set. I was honored just to be nominated. I thought, “I’ll just have a couple of glasses of wine and leave it at that.” Then, suddenly, I had to talk!
I said something like, “This last 30 seconds has been very clarifying for me. If at the end, the thing I’m most proud of is whether I added value to the lives of the people closest to me, then this award is telling me that I have.”
NICOLE
You know, as you talk about that, I’m envisioning the pathway we all have in terms of worth and value. It’s not like you felt worthy of that award before it showed up. In that moment, you had to step up and say, “Okay, we get to receive this award.” How do you view that journey for yourself? Being a CEO of a company like this must push you to do that frequently.
AMBIKA SINGH
That’s a great question. If I rephrase it, it’s about how I can avoid being so shocked when we receive an award. How do I know we’re great before that?
NICOLE
Exactly! It’s like you’re pushed into greatness. You have to acknowledge that you’re better than you’ve been giving yourself credit for. What do you do in those moments?
AMBIKA SINGH
I’ve been sitting with the fact that I’m pretty hard on myself. I remind myself that even if all the ducks aren’t in a row, a very important duck seems to be in the right place. I should give myself a break and recognize that something that matters to me has come true. So, I’m approaching it from a perspective of building confidence and reassurance.
NICOLE
I love what you’re sharing because many women I work with struggle with confidence and visibility. You’re in a very visible role as a CEO, and they often ask how you do it. I tell them there are tips and tricks, but sometimes, it’s about pushing yourself into situations where you don’t know how to succeed that helps you learn.
AMBIKA SINGH
Absolutely!
NICOLE
Now, you’re the one who won the Workplace of the Year award. That’s you adopting that identity for yourself!
AMBIKA SINGH
The downside is that I give myself a lot of negative self-talk, and I’m sure some of your clients do too. We need to find a way to acknowledge the positive signals and give them back to ourselves in a productive and real way. I see a difference in managing women versus managing men. With many of the women who work for me, my job is often to remind them of all the great things they’ve accomplished and the positive impact they’ve made. I know they’ve already been hard on themselves before our one-on-one meetings.
On the other hand, I don’t always get that same energy from men, where it’s more about accountability. I hesitate with some of these things. A mentor once told me that you can’t have your personality one way and expect to lose all the downsides.
If you’re gritty and resilient, you can’t beat yourself up for not being easy on yourself. We should work on being kinder to ourselves. But we also need to accept that the yin and yang coexist.
Another personality trait I have is that I take on a lot of responsibility. I believe everything can be solved, which is a great professional trait, but it can also be painful. I’d like to take on fewer things, but recognizing that taking on less will also reduce the upside is part of my journey. I’m trying to find balance, as Eastern philosophy teaches us about the dichotomies of positive and negative, good and bad. That’s where we find balance and peace.
NICOLE
I love how you explained that. It’s important for people to hear because, as you said, we’re often hard on ourselves for traits that can be very positive. We have to learn to temper those qualities. I think of hard work as one of those traits. It’s great, but it shouldn’t come at the expense of everything else. How do we harness that effectively?
I’m also a fast action taker, which has its pros and cons. Sometimes I dive into things without thinking them through, and then I have to scale back. But that’s also what makes me successful in many areas. We all have those traits, right?
AMBIKA SINGH
That’s such a good example. If you weren’t that person, maybe you’d be more thoughtful before starting something, but you’d lose that part of yourself that’s really great. The challenge is finding a way to temper those traits to a sustainable level that energizes you.
NICOLE
Exactly! I love your examples. Being gritty is wonderful, but when life throws hard challenges at you, you have to be resilient in ways you might not want to be. It’s about developing different parts of ourselves, and I appreciate how you articulated that balance of yin and yang.
NICOLE
Well, this is such a delight! I love talking to you because you have such an interesting perspective. What you’ve built is so cool and powerful. I also want to say that I love being a customer of Armoire; it’s so fun for me! I really enjoy seeing what you guys are doing all the time, especially in Seattle, with all the events and encouraging community engagement. It’s amazing and so fun.
AMBIKA SINGH
Thank you! It’s been incredible to see the community come together. I feel very grateful to be a part of it.
NICOLE
So good! Are you ready for a few fast action questions? They’re really easy but fun. Okay, what is the last thing you watched on television?
AMBIKA SINGH
The Last of Us.
NICOLE
Was it good?
AMBIKA SINGH
It’s a bit too close to home for me. Do you know what the show is about? It’s about humans surviving a plague and what happens afterward. I wouldn’t say I’m loving it; it’s quite dark.
NICOLE
Have you read Station 11? It’s similar to that.
AMBIKA SINGH
Yes! That book was so good, but I felt a bit down after reading it because it’s so dark.
NICOLE
Did you watch the show?
AMBIKA SINGH
No, I didn’t watch the show, but I think they did an incredible job. The actors are amazing across the board. I still think about it.
NICOLE
I would turn the page and think, “I don’t know what’s going to happen,” which was stressful but also so good.
AMBIKA SINGH
Exactly!
NICOLE
Okay, what is on your nightstand?
AMBIKA SINGH
This is funny—I can picture it right now. There are two Paw Patrol action figures that came in this morning and a pair of sunglasses. One kid was wearing the sunglasses and carrying the Paw Patrol figures. They’re still down there! There’s also a book called The Second 50, which is fascinating. The main takeaway is that we’re only one or two generations into people predictively living past the age of 50, so it’s not strange that we don’t know what to do in our older age—nobody knows what to do. It’s a really peace-giving perspective for anyone feeling lost about the second half of life.
NICOLE
That sounds cool! I’d love to read a book like that.
AMBIKA SINGH
And the last thing is a brochure from a travel company—that’s my version of daydreaming.
NICOLE
Daydreaming of what’s next! You could go anywhere, just like you did before.
AMBIKA SINGH
Absolutely!
NICOLE
Awesome! Next question: when was the last time you tried something new, and what was it?
AMBIKA SINGH
That’s a great question! I’ve been doing some cooking, which is unusual for me since I live with a master chef who has been feeding me for years. My dad is also a master chef, so I’ve been spoiled! Now, with my kids, I’m learning to cook a little. We made scones the other day, and I enjoyed it, but they were less impressed. Only I ended up eating the scones at the end! Then we made a mango granola parfait that had much more sugar and was probably more interesting.
NICOLE
I love it! Cooking is such a fun exploration.
AMBIKA SINGH
It really is!
NICOLE
Okay, last one: what are your top three most used emojis?
AMBIKA SINGH
Oh, that’s so funny! I love these questions. I use the teary-eyed emoji a lot, which represents a grateful thank you for me. I cry often—both positive and negative tears—so it feels emblematic of my emotional state. Then I use the prayer hands emoji for similar reasons. Finally, I really like the cartwheeling lady emoji.
NICOLE
Oh yes, she’s really fun!
AMBIKA SINGH
I find myself cartwheeling five times a day!
NICOLE
Cartwheeling! I love hearing about people’s emojis. Someone once told me about the face melting emoji, and I didn’t even realize it was an option. Now I like to use it a lot.
AMBIKA SINGH
That’s a great one!
NICOLE
It’s very expressive! I knew about the cartwheeling emoji but didn’t use it much until now. It adds such a pop of energy and fun!
AMBIKA SINGH
Definitely! Try getting it into your rotation. What are your top three emojis right now?
NICOLE
I know my three! I definitely always use the laughing emoji. I go through phases with others, but I often use the glitter sparkle emoji a lot.
AMBIKA SINGH
I like that one!
NICOLE
Glitter sparkles! I also rotate through different hearts for different purposes—like the beating heart or the double swirl hearts. But I’m a frequent emoji searcher, so I don’t stick to just three. I’m always rotating.
AMBIKA SINGH
I love it!
NICOLE
Yeah, it’s fun to explore.
AMBIKA SINGH
I’m going to steal that! It’s such a good icebreaker.
NICOLE
Absolutely! Asking about top three emojis gets people thinking, and you learn a lot about how their brain works.
AMBIKA SINGH
So cool!
NICOLE
Thank you so much for coming on, Ambika! We’ll link everything for Armoire below so everyone can check it out. I highly recommend it; it’s a fun way to liven up your wardrobe and feel good about it. This has been such a powerful conversation, so thank you!
AMBIKA SINGH
Thank you for making this happen! It was a blast—definitely the best part of my day. I loved it!
NICOLE
Thank you! And thank you all for tuning into today’s episode. Before you go, if you’re a high-achieving woman who wants to uncover your biggest blind spots preventing fast, intuitive decisions, I’ve got a 72-second assessment for you. Make sure to DM me “close quiz” on Instagram. We appreciate every note we receive about how the podcast is making a difference in your life. Until next time, I’m Nicole Tsong, and this is the School of Self-Worth.
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