Places where my failure took me

and things I learnt along the way

Vaibhav Gupta
3 min readJun 18, 2021

I’ve never been that excited for a year to end as I was for the year 2020. I think that makes the most of us. The world flipped over, we got home caged and the weirdest things which seemed too far-fetched even for imagination happened. We all had our share of bad experiences and conveniently blamed it on the year. So, when 2021 walked in, I for one, was too hopeful to see a drastic turn of events and improvements in every aspect of life. I know it doesn’t even make sense but if a year can be exceptionally bad, can’t another be exceptionally good?

Photo by Martin Magnemyr on Unsplash

Well, turned out it wasn’t, at least in the beginning. Where I was hoping for things to get better, it started becoming worse. For me, March 2021 was the month of failure. I haven’t failed in that many things in my entire life as I did in this March & April combined. Gave an entrance exam for Masters course, failed (Well not technically failed, got a decent score but not good enough to get me anywhere. So yeah, failed). Asked someone out, got rejected. Left my first job which I had for over 1.5years. Lost several freelance clients. Infact, failed to convince my parents that I’m a worthy architect to design our new home (I’m an architect by education, graduated from one of the topmost colleges in India. Also, that was going to be my first live project. Infact by that point I had worked on some 10+ iterations of design and ticked all boxes). Things were so bad that they almost hired another architect for the project. Feel me? Also, did I mention job interviews? Yeah, those weren’t any better and I failed in ‘almost’ all of them.

I have a big fear of failure. If there is something I feel I’m going to lose at, I wouldn’t even try. Infact, in a TV series, if a character is going to do something where things are going to get wrong for him/her, I can’t watch it. I’ll pause, mentally prepare myself and then resume (if at all).

So, combine all of that fear of failure with actual failure and things are bound to get intense. But this time a surprising thing happened. As a flip side to the coin, I realized I tried more things in that short duration, than I ever did before. The number of interviews I gave in March + April were more than the rest of my life. I had never tried to take up that many freelance projects simultaneously and never a construction project. So was the case with most other things I took an attempt at. Once that thought came in, the blues started fading away and I started becoming numb to that fear. At some point, my decisions were based on “what the heck, let’s give it a shot”. So, I tried other things where I was certain to fail — like applying for a position of Designer, at Microsoft

Here I am, a Product Designer at Microsoft. Also, guess who’s seeing his first architectural project turning into a reality ;) Seeing backwards, I won’t say that failing at that many things was the best thing. But I’m sure if things weren’t going so bad that I stopped caring, I wouldn’t be where I am right now. And right now, I’m Happy :)

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Vaibhav Gupta

Designer & storyteller. I write whatever I’ve learnt so far about design, development and other things I care about. https://linkedin.com/in/vaigu