Failure

Advisors often say that in order to succeed when starting a business, you must expect to fail, not once, but many times and as quickly as possible. The funny part is that it’s the opposite of what I had heard as a kid, especially the “many times as possible” part.

I am fortunate to have grown up with very loving and generally supportive parents, but the idea of failure when growing up was very black and white. In general, failure wasn’t seen as an acceptable outcome. But, it was OK as long as you kept going and eventually succeeded or “tried your best”. But what did that mean? Did “I tried my best” really make failure acceptable or was it a way to sugar-coat the failure? 

My earliest memories of “failing” all revolved around school. Growing up, my parents introduced us to as many arts as possible, especially Indian arts, but not progressing in singing, for example, wasn’t seen as a failure. Not doing well in an exam or a class, however, was totally different. It all just came down to how it might impact your future career. And I mean, what kind of career could singing and dancing get you anyways? <insert eye roll emoji>

Not doing well in school or in any program that could propel my career was seen to be unacceptable. It was a “bad thing”, and as a result was how I defined failure. But more than anything, it was the actual feeling, the painful disappointment in knowing I hadn’t succeeded, that hurt the most. 

After college, this definition shifted. And so had the rules of failure. Answers seemed much easier to procure because there were more ways to get it, and there were now multiple versions of “the right answer”.

But, as if to balance the positive shift, the ways in which you could fail also increased.

Friends were failing to get the “job of their dreams” or to receive promotions or pay increases that they thought they deserved. Romantic relationships were failing or not happening at all, while new ones started with the hopes of avoiding failure.

In the early days of my career, I definitely met my share of bullying managers, but I learned more from working with them as I ever did from reading books. And when it came to romantic relationships, I eventually learned to accept that previous ones had failed, not because I hadn’t tried, but because they weren’t meant to be.  

As time went by, I was realizing that the definition of failure was much more vague than I had originally thought. It wasn’t as black as white as it seemed.

In October of 2017, I took a plunge and quit a corporate career that I had worked hard to build, to create something that helps women feel good in what they wear. But it wasn’t until January of 2019 when I realized the actual path I wanted to take, that I started to hear more frequently, “fail quickly and as many times as possible”. 

I knew what they meant. If you fail quickly you’ll have a chance to learn from your mistakes quickly and therefore iterate quickly. In this sense, failing sounds like a positive thing, and to be fair, it may have been positive in my earlier years too, but I didn’t see it that way back then. My bigger concern now was, how does it feel? Does failing when trying to build a startup actually feel positive or does it hurt just as much as it always did? And if it’s the latter, how can one really continue doing it so many times? 

I told myself that it didn’t matter. I’m in it for the long haul so will just take it as it comes, and whatever happens, it’s all a part of the process. 

In October of 2019, I was encouraged to apply for my first round of funding. I was still in the idea stage and had only just begun my prototype, but this specific type of funding was sponsored by the Hong Kong government and was meant to help startups complete and release their first prototypes. Those who knew of my work to-date were fairly confident that I wouldn’t have an issue getting it. However, those who had created a startup in the past warned me that no matter what, there was a chance that I might not get it and that it’s OK. As always, it’s just a part of the process.

My application deadline collided with our trip back home to the US which made the completion of it feel all the more chaotic. But thanks to my parents and fam who watched E while I worked (K was working too), and everyone who helped me vet my first pitch deck, I finished it. 

The dopamine rush I got from completing my first pitch deck for my startup was amazing. It was a major milestone for me and I was confident in what I had submitted. However, when talking to people about it, I kept telling them (and myself) that this is just my first one so if it works out great, and if it doesn’t, that’s OK too, I’ll just move on and keep going. And honestly, I believed it. 

In January of 2020, I still hadn’t heard back from the fund. We were in Phuket, Thailand with some of the family enjoying the last few days of our winter holidays, but I couldn’t get the fund out of my head, so I emailed them. 

I got my response: “If you haven’t received an invitation to present, then I’m afraid you weren’t selected.” My heart dropped… 

I went through the first half of the day trying to hold it all in since I didn’t want to dampen our family time, but was also thankful that my bro-in-law was there as he had gone through a few startups himself and had been guiding me. “It took Google 250 times to get their first round of funding,” he would say. “So if this round doesn’t happen, it’s ok, just keep going.”

I understood what he was saying, and even after I got my response, I still knew what he meant, but it just wasn’t resonating. It felt like failure. It was a failure. I had failed at getting my first round. 

I can go into more about the sad looks that I gave the cute elephants at the Elephant Sanctuary and the amount of tears I shed at the Phuket Marriott resort that afternoon (before taking the pic displayed above). But at the end of the day, I learned more about failure than I had planned to.

Having “tried your best” is not a sugar-coated version of failure, but an end to actually having put your all into something even if it didn’t pan out the way you’d hoped.

The truth was that even though I hadn’t gotten into the fund, it forced me to solidify my vision and push me into my prototype stage. It also made me realize that I needed to spend a little time building, learning, and iterating on my own before I tied myself to deadlines that would be monitored by others. And most importantly, it was an internal check on how badly I really wanted it. 

Failing that first time felt painful, but perhaps like other firsts, maybe the sting of failing hurts less after going through it a few times. Others I know who have been through this say that regardless, it’s worth the struggle, however, I hope to find out for myself. 


Edited by: Betty Ho