Imposter syndrome was first identified by US psychologists Pauline Clance and Suzanne Imes in 1978, who originally termed the condition as “imposter phenomenon”. The condition is known to be experienced by high-profile individuals, including former US First Lady Michelle Obama.
Without further ado, read what Jenny, Jennifer, and Lily have to say:
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1. Have you ever battled with imposter syndrome? If so, how did you manage it and what advice would you give to founders going through the same thing?
Jenny: The short answer is no. I have not battled with imposter syndrome. An imposter is a person who pretends to be someone else. I never wanted to become anybody, and neither do I ever think of myself as somebody else.
For me, life is a journey full of adventures. Adventures come with challenges. Do I ever feel inadequate and anxious along the way? Of course. Feeling anxious is human. Sometimes you need that anxiety to produce great work. Rather than agonising over it, I just get on with the work and figure it out. Maybe that’s just my character.
As for founders, self-assurance is a distinguishing trait of great founders. The startup journey can be incredibly lonely and they need that “can-do” spirit to power through. Founders or entrepreneurs usually belong to the glass-half-full camp. A more common syndrome we see among founders is actually overconfidence, especially when things are going great and it’s easy to get blindsided by short-term success.
Jennifer: I don’t know if I can say that I’ve experienced imposter’s syndrome in the traditional sense. That said, I have certainly been in so many situations where I felt like I had to quickly learn things I’ve never done before. In these situations, I had to climb a steep learning curve exceedingly fast in order to get the job done well – all without the experience I needed.
This first happened early on in my career, when I worked in executive search. As a junior person, I was calling senior executives to try to convince them to join venture-backed startups. Credibility was incredibly important for this role, and this could only be achieved by really studying the technologies of multiple companies and what they did.
I remember trying to find a CFO for a company whose competitive advantage was using a monocrystalline vs. polycrystalline solar cell to build solar panels – this required technical knowledge that I didn’t have in order for me to speak credibly. I was really working outside of my comfort zone and it was tough!
When faced with situations like this, it’s really a matter of stepping into them – you don’t have to be afraid of not knowing. But then you have to think of the next step: do ample research to address your knowledge gaps. You don’t have to do so much research until you become an expert. Just learn enough to be able to deliver what needs to be done. Be resourceful and creative when you need to!
Lily: I was especially affected by imposter syndrome when I was younger. But as an adult, and especially after I started working, I gradually learned to overcome this problem by walking the path of self-acceptance and continuous learning.
A lot of this growth has to do with the nature of startups. Startups are perpetually in an ongoing process of managing uncertainty, their success dependent on multifarious factors. The founder’s background and motivation aside, good startups also have to be mindful of their cultures, talents, and systems. To push beyond ‘good’ to become ‘great’, startups need to have foresight and be highly responsive.
With all these demands thrown at startups, it’s necessary for them to form the right teams that help both founders and their teams to grow. Driving this back to myself, I strive to focus on my personal growth to ensure that I am the best version of myself at all times. Healthy competition with your peers is fine, but I never allow this to dictate the trajectory of my life.
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2. What is the best advice you’ve received, and in what context or situation was it given?
Jenny: When I was an engineering student at Cornell, I took some MBA classes for fun. One of the classes I took was entrepreneurship taught by the late Professor David J. BenDaniel. The professor had a doctorate in engineering from MIT before he became a venture capitalist. He brought in founders and investors for us, and that was my first exposure to the VC world. I later became a teaching assistant for his class, and part of my job was to review student assignments, in this case, business plans. I immediately knew this was what I wanted to do, so I asked the professor where I should start. His answer turned out to be a life-changing one.
He said, “To be a good VC, you need to understand how enterprises and organizations are built. Go work at least five years and learn all the ins and outs of venture building before investing.” This is the best advice I’ve ever received. That’s why I took the advice, came back to Singapore and worked on aircraft for five years.
Jennifer: My father always told me that regardless of what I do in my career – no matter the role, level, or title – I must always add value every single day. A deceptively simple piece of advice, but I’ve always kept it close to me all my life.
Another piece of advice I have comes from a former VP of engineering at Facebook (now Meta). While working on a project with him, I presented a solution which I had spent much time pouring my heart and soul into.
He quietly read my proposal before telling me, “This is good. Now 10x it.”
Outside of wanting to throw my hands up, I realised that his mindset was right. I had to adopt a 10x mentality and push beyond my boundaries. Those few words of his really transformed the way I approached what I built and delivered.
Lily: The choices you make matter so much more than the effort you put in. Drawing from my own personal experience, my attempts to lose weight in 2010 repeatedly failed – I could only go as far as one month before giving up!
It was not until my friend recommended her personal trainer to me in 2015 that things really changed for me. Upon learning my situation, this trainer set three ground rules: One, don’t question his decisions. Two, strictly follow his diet and exercise plans. Three, don’t fuss over the weighing scale in the first three months.
I confess that I didn’t entirely follow his advice at first. While I dutifully followed the diet and exercise plans, I made the mistake of weighing myself – seeing that I hadn’t lost any weight frustrated me a lot! But as it turned out, the purpose of the initial plans was to lay the foundations for a sustainable, long-lasting weight-loss routine. Three months later, I began to lose an average of 1kg a week when my trainer began adding aerobic exercises to my routine.
At the six-month mark, I successfully brought my weight and BMI down to my ideal numbers. Seven years on, I have been able to keep my weight and body fat at healthy maintenance levels. I have my trainer to thank for not just helping me to lose weight, but also to incorporate healthy diet and exercise habits into my lifestyle.
From this experience, it’s clear that choosing the best specialist is vital to the success of any given project. But what you do after appointing the talent is just as important. You need to believe in their advice and even empower them. When faced with temporary setbacks, you have to block out the noise to stay focused on the results.
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3. When did you experience your biggest setback, and how did you handle it?
Jenny: In 2001, after working at ST Aerospace for five years and an MBA, I was finally ready to launch the VC career I had always wanted. The summer before graduating, I had already done two internships in Silicon Valley, one with a startup, the other with a venture fund. I was 29 then and so ready to start. Then the biggest market crash in history happened, first the internet bubble burst, and then 911. Everybody thought the internet and the startups were gone, hence there was no point in being a venture capitalist. I didn’t get a VC job in Silicon Valley. That was when all VC jobs started in Silicon Valley.
I had three choices. Going back to Singapore and being groomed as a leader of ST Aerospace, joining my husband who was already in Silicon Valley and settling for an engineering job, or moving to Hong Kong for Morgan Stanley to look at Asia. It was a tough call as they implied dramatically different lifestyles. The first two options were both in my comfort zone and I could have had a stable life amidst the turmoil the world was going through. I thought through the options and chose what was closest to the vision I had for myself, moving to Hong Kong. It was the riskiest decision back then but thinking back now the least risky one as Asia soon became the hotbed for startups.
Jennifer: While I was working at a company early in my career, I found out that a male colleague of the same level and qualifications was earning two times my salary. It was a shocking moment and a reality check about pay inequity in the market. I have no issue with different levels of compensation for individual employees, so long as it’s fair. But what I experienced really crossed a boundary for me. To me, the salary discrepancy spoke volumes of what the company valued, and it just wasn’t a place where I wanted to continue working. And so I began to plan my exit.
That experience not only taught me about pay inequity, but also about fairness in the workplace. Today, I encourage founders to create a compensation philosophy early on in the company’s growth to establish a fair system and approach.
Of course, there are a lot of great companies and founders who work for pay equity, but there are still many others who don’t.
Lily: Last year, I was diagnosed with breast cancer. Upon receiving the diagnosis, I felt my whole world crumbling around me. I fell into despair as I was overwhelmed by all the unknowns that started to crop up. Could I beat cancer? Would I survive this? How did I get cancer? Why me?
I quickly realised that it wasn’t helpful to allow my frenzied emotions to get the better of me and lose control of my life. I had to start treatment as soon as possible if I wanted to stand a chance of beating cancer.
And so one week after the diagnosis, my husband and I began actively seeking out hospitals and specialists. I also started to dive into medical papers that detailed everything from the initial prognosis with the attending physician to the surgery. I eventually underwent surgery that was a resounding success, with my DNA tests indicating a very low risk of recurrence.
After having beaten cancer, I find that I am grateful to be alive now more than ever. I remember the fear and despair so vividly, but I feel that they underwrite the greater appreciation that I have for life today.
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4. If you could send a message to your younger self, what would it be?
Jenny: I would tell the younger me to resist the “halo effect” and stick to my own conviction. When you’re young, it’s very easy for the more established ones to tell you that they know better and you should listen. I’m sure young investors can relate to this. You have done rigorous homework, and your gut tells you that this is going to be a winning bet. Then the most established partner at your firm came along and told you all kinds of reasons you were wrong. You start to doubt yourself. Was I wrong? Maybe I missed something that’s beyond my understanding? He or she was the guy who made that famous deal after all.
After two decades of investing, I’ve come to realise that the quality of an investment decision has nothing to do with age or title. If you know the sector and the founder well enough, you should stick to your own judgement and follow your heart. Don’t listen to the established ones. Don’t listen to me.
Jennifer: The first piece of advice I would give my younger self is to look for great mentors. There are so many experienced people out there who are willing to guide those who are less experienced. And I think this can be so incredibly powerful in terms of advice, contacts, and feedback. Having good mentors helps you to grow – this was something that wasn’t obvious to me early on in my career.
If you want to build your career in marketing, sales, engineering or any other discipline, there are plenty of ways to find fantastic people to network with. It’s as simple as writing them an email to get on a Zoom meeting or to meet them for coffee and start to develop a relationship. Start by drawing up a list of people whom you think do really well in a particular function or sector. Or they could simply be great leaders. Whatever your reasons are, it’s good to start early and form your own style of professional interactions.
Another piece of advice is to always work for people whom you admire and respect. This seems obvious, but it’s especially important early on in your career. Your earliest managers and leaders are very important in shaping who you are during your formative years.
This is something that will continue to remain important even as you progress through your career. Eventually, there’ll come a point where you will also provide value to the people you work with. This is what I call reverse mentorship, where everyone gets to learn from each other regardless of position.
Lily: I’ll keep this short and simple: simply follow your heart in all that you do. For example, choose a college major you really love! This will give you the chance to do something that you’re genuinely interested in when you graduate and start working – work won’t feel like a drag when you enjoy doing it.
