Letting Yourself Fail so You Can Succeed

I have failed — many times actually. Bombed my accounting 101 class. Shuttered up a Shopify drop-shipping site for dog clothes. Failed at relationships. Failed at many things.

But I try a lot — I try all the things I want to do. In some ways, I was able to develop a certain skill, which was pivoting my frame of mind when I failed; it became crafted optimism. I didn’t perceive my failings negatively— I perceived it as a time to shift and move my stance to the next part of my life.

Over a zoom call, a friend once blitzed me with questions about why I would pick up my things and just leave San Francisco and my startup job to try my hand in Singapore. I purposely left comfort behind and she couldn’t stomach that.

She grew up in China and was raising her family in San Mateo, and reiterated the fact that it was insane for me to just decide I would quit my job and do a random 3 months of travel, with so much uncertainty. Born with a work hard mentality, she said it was just the norm to follow the pattern: find a steady career (doctor, engineer, lawyer, academic), find a husband, get a good job, and grow a family.

My actions were atypical and riddled with risk bombs, but I told her I run calculated risk. I agree — there is risk in my career development, but I was never one to climb a corporate ladder and I wasn’t going to become a NASA astronaut anyways. In addition, I saved in preparation for this trip; I had personally set aside 10K just for this because I actually didn’t know when I’d return and this was me trying out a new norm.

While others define success by monetary gains, a high paying job, or a certain level of achievement, I define my own by the many risks that I take and if I was brave enough to try it.

I knew she was coming from a good place, but I was not one to be lectured or coddled; I didn’t need a mother figure, I just needed my friend. (Plus, my own mum is amazing and understands that I must spread my wings, but returns to the nest.) But as I grew older in my years, I realized my fear wasn’t of risk, it was living a life of complacency and a degenerating education. I made many risks growing up, and had been accustomed to failures and again, optimism plays a major role in this.

While others define success by monetary gains, a high paying job, or a certain level of achievement, I define my own by the many risks that I take and if I was brave enough to try it. If I didn’t try what I wanted, I was failing. Because why? I was living a life normalized by others, not the one I really wanted. I realized my actual fear was losing my own independence: being tied down to one place constantly, being controlled by a certain job or company, or suffocated by an environment I hate…that is my fear: losing my freedom to go and leave as I please.

What You Should Take Away From This

1. Take risks when you’re younger, and then pivot to make calculated risks as you grow into your years.
2. Societal norms suck — you don’t always have to follow the terms of life before you sign.

Life should be fun. I imagine myself as this sheepdog, happily running and leading a group to better things in life.

1. As you grow older, you grow into your years and wisdom. The sounds of other opinions can be drowned out by your own — follow your voice.
2. Fail, fail many times. Even more so when you’re younger. You’ll develop a thick skin, which will prove valuable when you’re hit with shit from all sides as you grow older. It just gets harder, not easier.

If You Cannot Stomach Risk, then Start Small

I get it — there’s a lot to unlearn when you are making risks; everything we’ve been taught to be afraid from school, from our parents, or the uncertainty we feed ourselves has to be unlearned. Start small with things that make you uncomfortable. You’ll come to find that these small things aren’t as scary as you perceived them to be.

Let yourself fail so you can succeed. When you fail, you are learning and that is 100x better than staying stagnant.

Emily is a US expat currently living in Singapore to learn about the tech communities growing in Asia. She has worked 4+ years in dev relations, community management, and event marketing within the tech and travel industry. Her time at OmniSci, Google and Booking.com gave her cross-functional expertise. In her free time, she runs the volunteer community initiatives for Singapore Women’s Network and CMX Hub Singapore, as well as promote and write on the importance of early investing and financial literacy at Fangfinance.

You can follow her on LinkedIn and Twitter.