Pursuing Passion and Purpose without Fearing Failure

We often hear the advice “follow your passion”. That is easier said than done when you are unsure where your strengths lie, or filled with doubt about whether you are good enough, or when you have bills to pay.


In the second weekend of the Future Women Leaders Forum (FWLF) 2021, close to 80 final-year undergraduates and fresh graduates came together to hear how to fearlessly pursue their passion. Over the full-day event, they heard from women who have carved out unique careers on how to build a resilient mindset and get over failure.

Our speakers from the second weekend of FWLF 2021. Clockwise from top left: Fiona Carney, Chief Marketing & Operations Officer, Microsoft Asia Pacific; Gwendolyn Regina, Founder, OnQuestions; Kuik Shiao-Yin, Co-founding Director, The Thought Collective; Darlene Espena, Assistant Professor of Humanities, Singapore Management University; Yolanda Lee, Founder & Chief Executive Officer, Uncommon; Yen Siow, Founder, Discovering without Borders; Clara Yee, Designer & Co-Founder, in the wild; Maya Hari, Vice President, Asia Pacific, Twitter.


Here are some key takeaways:


#1 Explore alternate career trajectories.

Careers are no longer linear. Fiona Carney, Chief Marketing & Operations Officer at Microsoft Asia Pacific, believes that the Career Mosaic is a good framework to think about your career.


Traditionally, most people start out their careers as individual contributors working on executing tasks, before they progress to managerial positions to take up leadership roles. However, times are changing.


Even at a junior position as an individual contributor, you can provide strategic perspectives traditionally done at the senior management level, or take charge to proactively shape your career for the next few years.


Career trajectories are not linear anymore, so transferability of skills is key. What do you enjoy? What gives you energy? Think about the core skills that you are building with each role and think about how to transfer that into an environment that makes sense for you, whether that is a corporate job, the gig economy, or entrepreneurship.



#2 What good questions are you not asking?

Everyone has a set of beliefs that subconsciously shape how you interact with others and react to unexpected events. Gwendolyn Regina, founder of OnQuestions, demonstrated how to question these pre-existing beliefs to broaden our horizon of what is possible and what holds us back.


“We use pre-existing beliefs… to reinforce pre-existing beliefs.”


To improve how you think, steer away from “converging” close-ended questions. Instead, ask “diverging” questions as they can expand your perspectives.

As a framework to achieve your goals, consider these guiding questions:

  1. What do you want?

  2. What do you know?

  3. What do you not know?

  4. What questions are others not asking?

  5. What assumptions must hold true?

  6. What assumptions can you disprove?

  7. How can you expand the horizon?


#3 Changing Definitions of Success


For the panelists on the Trailblazers: Defining Your Path While Redefining Success panel, the changing definitions of success gave them the courage to pursue their own path. For Clara Yee, Designer & Co-Founder, in the wild, that meant learning to see what was real and what was superficial in the creative industry. For Maya Hari, Vice President, Asia Pacific, Twitter, 10 years ago success meant climbing the corporate ladder, but now it has shifted to how she can spend her time and influence towards supporting entrepreneurs in the region to be world-class. And for Yen Siow, Founder, Discovering without Borders, it has changed from making a difference in individual lives to snowballing that impact to influence other people to make a difference in vulnerable people.



#4 Get stronger with every failure.


Many of us are uncomfortable with failure because it evokes shame, inadequacy, guilt, and

blame. However, failure is an essential part

of being human.


Kuik Shiao-Yin, Co-founding Director of The Thought Collective, advised us to sit with the feeling of failure, absorb it, know it, and fully feel the sadness and disappointment. After that, use that failure as a driver to push yourself forward by processing and making meaning out of it, so that you do not get stuck in a rut.


To process your failures and make meaning from them, Shiao-Yin introduced the Gestalt

Cycle of Experience/Change:


1. Sensation, from an external trigger that you identify with one of your five senses (For example, I see only $100 in my bank account.)


2. Awareness, where you create a story (For example, I do not have enough money so I am a failure.)


3. Emotion, from the stories I tell myself (For example, I am ashamed.)


4. Action, through identifying the story and emotion, and only acting on the sensation

(For example, I feel ashamed. Why is that? Because I feel like a failure. Why is that? Because I see that I only have $100 in my bank account.

However, while that may not be enough to sustain my livelihood, I do not have to conclude that I am a failure, and so, do not have to feel ashamed of that.

Instead, I can just tackle the issue at hand - to ensure that I can survive with the money I have. I can find immediate ways of earning money to sustain myself for the short term. This will buy me more time to find a way to earn money for the long term.)


5. Contact/Satisfaction, where I have satisfied my want or need (For example, my income increases.)


6. Withdrawal, where there is closure from letting go and making a larger meaning out of your failure


Use this framework to deconstruct the failure you experience. If you find yourself obsessing over a failure, it is likely that you are stuck in one of the stages of experience and cannot move on to complete the cycle.

#5 Overcome setbacks with the right mindset.

Shiao-Yin also shared that there are three kinds of family narratives that inculcate different mindsets into children and shape how they tackle setbacks:


Ascending narrative – life will get better Descending narrative – life is a series of disasters and bad things waiting to happen Oscillating narrative – life is a cycle of ups and downs


Children taught the oscillating narrative turn out to be the most resilient when they face setbacks.


When things look bleak, knowing that setbacks are temporary will help you retain an upbeat perspective to handle the challenges.


On the flipside, knowing that life can potentially throw a curveball when everything seems to be going well can mentally prepare you for harder times, so that you would be more ready to bounce back up.



#6 Success does not determine happiness.

On the big questions on happiness and suffering, Darlene Espena, Assistant Professor of Humanities at Singapore Management University, explained that we cannot point to any single definition of happiness and say it is the correct one because people define happiness in different ways. Most people think that success is a prerequisite to happiness. But based on current research, it’s the other way around. Happiness fuels success, and happy people are more likely to be successful. Our happiness is how the brain processes the world. According to Martin Seligman, a pioneer in positive psychology, we need more than happiness in life, and that there are five elements to a flourishing life:


1. Positive emotion. People who are more optimistic have an enhanced quality of life.


2. Engagement. Episodes in your life when time stops and you’re in a state of flow and savouring being in the zone.


3. Relationships. Maintaining good connections is a skill.


4. Meaning. Insert yourself into a purpose bigger than yourself.


5. Accomplishment. Feeling of pride and achievement. In order to get over failure, one needs to:

1. Adopt a positive perspective in life. You can look at the challenges as opportunities to learn and grow and maintain a positive attitude for the future.


2. Find activities that make you happy and do it as often as possible, make time and enjoy those moments.


3. Have good relationships as it is important in our well being. Do not take relationships for granted and find ways to connect with them.


4. Find your life’s meaning and purpose. Challenges are stressful but it’d be easier to navigate them more smoothly and make it more bearable.


5. Lastly, take time to savour accomplishments in your life. Pamper and celebrate your achievements and then continue to set your goals and something you look forward to.

#7 Let curiosity guide your path.


At the Designing Your Life Workshop, Yolanda Lee, Founder and CEO of Uncommon asked participants to reflect on their passions, motivations, and values that would then become their “ingredients” to their purpose statements. While finding these “ingredients”, some of us might be swayed by the pressure of finding one’s purpose immediately, but that can lead you down the wrong rabbit hole. Instead, let your curiosity be your compass. Reflect on what you are really interested in and what fulfils you, and take a series of tiny steps today to move towards this purpose. Build your trusted network and let them support you in getting closer to your goals.


No one has all the right answers to one’s life goals and purposes. Neither can you find success without failure. But you can ask questions that keep you on track, be piqued with curiosity to find your way in life, and always pick yourself back up after each setback.



Organising Committee: Recruitment Organising Team: Yvonne Mak, Eliza Ho, Eileen Teoh, Cheong Yu Qian, Hon Liang Yi, Sherryn Tham, Audrey Tim Min Hui, Ng Jiahui, Crystal Ong Author: Tay Mingfang Graphic: Dorothy Siok, Jamie Koh Editors: Joaquim Tan, Joey Ong, Kristin Loo


Graphic Source:https://www.enduringmind.co.uk/mindfulness-cycle-of-change/



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