The Retrospective Of My 2021

My Year 2021 — Failing Upwards, Anti-productive Mindsets, Stability Sources, Nomadic Living & More.

Rachael Annabelle
6 min readJan 9, 2022


hello from singapore, london & new york city♥️

I don’t think I’ve ever remembered checking off specific resolutions when the year ends, even though I’m pretty confident I made a couple every New Years.

It’s a week into 2022, and I realized that I have yet to put down any concrete resolutions. I will eventually, but before that I wanted to sum up some of of the biggest things I’ve learnt and will be taking through with me into the years ahead.

For the most part, we learn from the people we surround ourselves with and through the books that we read. Sometimes, a lesson is given to us — but we don’t truly understand it’s profoundness until we’ve experienced it firsthand ourselves. Over time, you’ll come to realize that many of these lessons happen retrospectively, but it always happens eventually.

Through the entirety of 2021, I’ve experienced a lot — worked for 4 teams in Google, attended trainings for Miss Singapore Supranational, taken up a bunch of photography gigs, missed my graduation ceremony, moved to London, burnt out, fell sick, fell in and out of love, decided to work on my startup full-time, built a team, launched a product, and raised funding. It has been a hot (and very long) minute.

These lessons I share below were not part of my 2021 resolution, but were handed to me along the way. It took me months to fully understand each of them, and hopefully this summary will help you in your own journey (faster than how it helped me at least!).

1. We fail upwards

In other words — failure isn’t always a backward movement. Sometimes, failing unlocks even better opportunities we didn’t plan for.

Similar to the growth mindset, this means we should get creative about looking at the negative experiences in your life that might otherwise undo you. Find aspects of experiences and situations that made you better, and look for the things that made you push harder.

Many of my friends have asked where I’ve gathered the courage to pluck myself out of Singapore and move to a new city…



Rachael Annabelle | googler. founder photographer. creative consultant. pasta fanatic & occasional nerd.