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Writer's pictureElise Tan Yee Ling
Nov 12, 20218 min read

What I would tell my 20s self regarding Career choices

Updated: Nov 21, 2021

I enjoy sharing with students about the Singapore startup ecosystem or demystifying about a career in startup or venture capital. After sharing the same content over and over again, I thought I would create and share a living blogpost instead of decks (which often get lost in cyberspace anyway) :)


I love how much career guidance is provided at schools these days, compared to 10 years ago. I wished I had that. To be honest, I chose Chemical Engineering for my bachelor degree in NUS (National University of Singapore) not because I like engineering or want to be an engineer. The embarrassing truth is that I flipped a career guide and chemical engineering graduates earned the highest starting pay. The other decision factor is just that I preferred studying a science degree compared to a business or liberal arts degree.


Unguided, unwise decisions often lead to non-ideal outcomes -- which explains why I ended up in a bank in my first job, instead of Exxon or Shell despite my degree. During my years in university, I figured out that I had no passion for what I was learning so it would be making another mistake to work in the petrochemical industry too.


Finding the ideal job requires knowing yourself well


It is hard, but it is important to be brutally honest and realistic with yourself to make the right career move.

I finally realise, after over thirty years of making mistakes (yes it took me this long) and going through all the pain, that I need to know myself well and be truly honest with myself the reasons for making any career move. And only I would know myself the best. Not my parents, my sibling, my friend or my partner.


Oh so often, we pick jobs for the wrong reasons-- "Oh this industry is growing and that's why I should join it." or "This pays well so therefore I should take up this job." or "My parents really want to see me become a...".


"Whoever loves money never has money enough; whoever loves wealth is never satisfied with his income." Ecclesiastes 5:10

When you make a career choice for the wrong reasons, eventually, you would most likely end up leaving the job. Because you will slowly start to 'fall out of love' with the job. And you will start to see how your gifts and talents are not fully utilised for it. Finally, you will feel a dread to go to work everyday and decide to change job. The unfortunate thing is that vicious cycle will perpetuate itself again and again until you have looked within and could discern if the job is a good match for yourself.


Knowing ourselves require looking within and it takes time

It took me a long time to embrace who I am and understand what I value, what gives my life purpose and what my non-negotiables are. I guess my extroversion, the lack of guidance, the asian culture of conformity are factors that prevented me from looking within. One of my favourite inspirational speaker Dr. Wayne Dyer illustrated that with a story of how a man lost his keys inside his dark house but he looked for them outside the house as there was light outside. It sounds funny but we usually forget to look within to figure out who we truly are. We see "successful" people and thought if we are like them, we would lead happy lives. This may work for some people but most need to recognise the unique being they are and what make another person happy may not work for them.


I also find Personality tests like MBTI helpful in knowing myself better. Do note that your profiles may change over time. I was a ENFJ, but became a ENTJ after I graduated from INSEAD in 2016. (I guess the MBA education brought out the analytical side of me.)


Start with discovering your strengths and skills


The skills you have and hone over time are what you will be paid for in a work. This could be the easiest part of the puzzle to figure out. One easy way is look at your grades and the subjects that you excel better at may give an indication of your hard skills.


In figuring out the ideal job, most of us look at just the "hard' skills and ignore the soft skills. In fact, your soft skills are just as important. I realise that I love influencing others and "selling" a product or idea and that means a role in areas such as partnership, marketing, sales and business development would suit me better.


Find out what you like or are passionate about


Apart from skills, it is also good to work in jobs that you have interests and passion in. This will tide you through difficulties you face at work.


Deliberately making time to reflect regularly and be aware of my emotions helped me create the breakthroughs I needed to better understand my likes and dislikes. I would catch myself feeling some negative emotions like anger, sadness etc when doing something and ask myself why do I feel that way. On the converse, when I feel happy and energized by a certain task or activity, I would ask myself why do I feel this way? Over time, you will start to see a clear pattern.


For me, I notice that while I can work well on tasks that involve tedious excel work, they drain me. I finally realise that I need to join a role that involve collaborating with others as this type of work makes me tick. My passion lies in helping others to access resources and create value more quickly. That's what sustained me through the past 10 years in the startup/ investment industry.


I also deliberately took on short term work and internships in startups and investment firms, some of those did not even pay, just to "experiment" if I would like working there. I worked at startups like Techsailor, All Deals Asia and the experience I gained was wonderful. I love how quickly I could make an impact at small companies and I realise that I don't like working in corporates as the bureaucracies and processes drain me.



This will take time but never give up finding your true calling or the mission you resonate with


We all need a North Star to guide us and stay on track when things get tough. But finding it is not easy but not impossible.


I love autobiographies and biographies because they help me understand how these people find their calling in life and how they find the right job and thereafter live a meaningful and fulfilling life. I love Michelle Obama's autobiography -- "Becoming".


I think I kind of figured out (but I'm still a work in progress) and shared it in my blogpost here. Don't give up trying to know yourself, it took me a few years to really understand myself and embrace the unique person I am.


In life, it is about finding the right fit, be it a job or a partner.

This sounds really cliche but people who have been there and done that would resonate with what I say. Finding a fit means that the job suit your interests, personality, capabilities and passions.


Many times in my life, I was tempted to join strategy consulting at Mckinsey and the likes, investment banking and other jobs that would earn a higher income or sound prestigious. But I know deep down that, while I would enjoy the lifestyle that comes with it, I would burn out quickly or quit soon after because I don't have the passion for that kind of work. I wouldn't enjoy my work.


I discovered the Ikigai concept recently and love it as it helps summarise what contributes to fit.


Ikigai is a Japanese concept that means your 'reason for being. ' 'Iki' in Japanese means 'life,' and 'gai' describes value or worth. Your ikigai is your life purpose or your bliss. It's what brings you joy and inspires you to get out of bed every day.



How do you know if the industry suits you?


Before I decided to join the venture capital space, I went through as many venture capitalists' profiles as I could as I wanted to see if my education qualifications and career progression would be a fit. I also talk to anyone in the industry (whom I meet through sending cold emails, linkedin messages or networking events) who is open to share their experiences with me. Before I started my MBA at INSEAD, I tried applying for internships so that I could better understand what they do at work.

I also read articles about venture online and find this book "Be smarter than your lawyer and venture capitalist" extremely useful.







If I could summarise (something I learn from my science-based education and MBA) is to

  1. Test your hypothesis

  2. Validate your assumptions

  3. Take a trial if you can

This framework can pretty much be used for making other types of decisions in life.


So, in my case, my hypothesis is that working in a venture capital firm would be a fit for my abilities, strengths, personality and passion (which is working and helping entrepreneurs to succeed).

Hence, to test my hypothesis, I checked if my career profile is similar to those of current venture capitalists. I also spoke to people in the field to get a sense of their personalities and what make they tick.


Next, I think about what my assumptions are. For example, one assumption I made is that venture capitalists work closely with entrepreneurs and help them succeed. I realise that this is an important factor as I enjoy working with people (I'm an extrovert so this energizes me too). What I realise, through speaking to people in the industry, is that it depends on the fund I join. If the fund invests early stage and into many companies (say 100 in a year) in a short time, it is less of a fit for me, as I would spend less quality time with entrepreneurs.


And finally, I tried to intern at a venture capital firm to observe if I would enjoy working full time in one. I didn't actually manage to find one so I worked in a super angel syndicate instead, called True Global Ventures. The stint brought me to Silicon Valley twice and it was such an eye-opening and exciting experience.


If you are looking to intern, check out https://www.internsg.com/

and great firms to intern at include:

  • Vertex Ventures (reach out to me if you are interested, at elise.tan (at) vertexventures (dot) com)

  • Sequoia

  • Quest ventures

  • Openspace Ventures

  • Monk’s Hill Ventures

  • Insignia ventures

  • Hustle fund

  • Syndicate like Investible

  • Angel funds like Angel central


Here're more useful reads:


1. if you are interested in starting or joining a startup



2. if you are interested in the Venture Capital sector




  • My colleague Benedict Tan at Vertex Ventures shared his first-year working experience in this medium post -- check it out!










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