How to plan for serendipity

by sana rao

22 May 2018

It would not be an exaggeration to say that I've built my career on the scaffolding of rigorous goal setting and strategic use of blinders. There was a point in high school where I switched over to this intentional way of defining what I wanted to achieve and setting out to achieve it. Akin to how companies operate I would set yearly goals that were non negotiable. Over time, I also started to use a wonderful colleague's guide to doing a life audit and every time it precipitated some major life changes and resets. I've always enjoyed this intentional way of thinking, because it is an incredibly effective way to inculcate self motivation and to make a habit out of pushing myself in ways that stretched me out of comfort zone, to a point where it has almost become second nature.

But as expected, setting non negotiable goals meant that every time I would fail at reaching a milestone I would be crushed. Surprisingly though, when I would achieve a milestone, instead of celebrating I would end up in a vacuum, not knowing what to do next. So over the past couple of years, I've found myself thinking about new ways to negotiate with the idea of progress.

This process of questioning was kickstarted by my decision to move to London. The life audit had already revealed that my heart didn't lie in Silicon Valley, and when my manager at the time presented the opportunity of moving, I surprised myself (and him) by jumping at such a big life decision so quickly. Sure I worried about the impact it would have on my career trajectory and opportunities, but this was one of the first few times I became consciously aware of what it feels like to be so radically open to a new opportunity that it means discarding the path I had set for myself almost entirely.

Depending on personality types, people either react to change by closing up or by opening up, I went through both in stages. My first year in London was incredibly hard, with no hard goals to propel myself forward, I retreated inwards. Not knowing the rules of a new culture and how to control my journey I slowly learnt to let go of the idea of control and replace it with the idea of presence. I still have a plan (the life audit still stands) but I've stopped being attached to it — which has meant that I show up and I participate, wherever I am and whoever I am with... there is nowhere else to go after all.

Almost immediately, I've noticed everything and everyone around me respond with equal measure of openness and presence. It has opened me up to experiences I would otherwise never have even noticed, people I would never have crossed paths with and places I would never have gone. I've reconnected with family, rekindled my romance with writing, found deep friendships that had been right in front of me all along, wanted to share more, wanted to listen more, wanted to see more.

Being open to and making room for serendipities this way, has changed the course of my life for the better, cleared up my line of sight and opened up my heart. It's been a long and messy process because i've had to dismantle my definition of self and how I relate to progress but it has made all the difference in how I engage with the world.

If you've found this way of thinking useful, and would like to chat about ways to help you make that journey yourself, i'm @sanarao on Twitter.

About sana rao

Work @deliveroodesign. Worked @twitter @apple. Started @postcardpoets. Always re-evaluating everything.

  • The Pastry Box Project
  • Powered by SuperYesMore
  • Privacy Policy
  • Terms Of Service

A How Bad Pretty Bad venture

back to top

An error occured

We suggest that you refresh the page. It may very well solve the problem.

If you're a developer, you may be interested in knowing that it's a Javascript error. Checking the console and letting us know what went wrong would tremendously help us improving this application!

Close this box

yoyo