A few years after they were married, my dad got a new job in Kolkata (then Calcutta), and left Delhi in a rush—my mom was to follow a few weeks later with my brother (three) and me (still in her tummy). I try and imagine how she might have felt to leave every familiar face, neighborhood, and even her language, for an unknown city. Back then, with frightfully expensive long-distance phone calls, not to mention air travel fares, moving from Delhi to Calcutta pretty much implied isolation from the rest of your family (except for an annual trip home). What might my mother, seven months pregnant and alone except for a teenage nephew to accompany her, have been thinking as she undertook the 24-hour train journey fraught with uncertainty?

Fast-forward 9 years and I remember my mom waving a teary goodbye to friends and neighbours crowded on the railway platform, who had come to see us off as we boarded the train back to Delhi. These were the people who had helped her settle in Kolkata, taught her (a vegetarian!) how to make a macher jhol (“fish gravy”) any Bengali would be proud of, and adopted her as one of their own. She still reminisces about the good ol’ Calcutta days and how there are no warmer people, nor a more welcoming set, anywhere else.

Once in a while, we can look back to times when life forced an unwelcome decision on us that led to unexpected, yet serendipitous adventures. But how about when we do have an option? Do we exercise the choice to break free and begin afresh? Here’s my take on five questions you might find yourself contemplating as you think about making the leap to new pastures.

Photo by Surbhee Grover

Should I, shouldn’t I? A question that haunts everyone contemplating change. If things are decently comfortable, should I really be looking to make a drastic change? In answering this question, I’ve found it best to look inward. Social norms and consequences only provide distractions. The one thing that helps provide me clarity, is asking myself a different question: “If I didn’t do it, would I regret it?” That’s my litmus test. And if honestly answered, the writing is (in all CAPS) on the wall.

Is it too late already…? I do believe that if we deleted the phrase “I’m running out of time to…” from our vocabulary, so much more would be possible. Expiry dates on ambition, finding love, having a relationship, learning a new hobby…are overrated. Where youth brings naiveté, age brings experience. But, (much) more importantly, apart from things that have a biological time limit (e.g. having a baby – although look at how science has negotiated even that for womankind!), no one but you should get to decide when is right (for you). 

How do I battle the demons of the past? Doing anything in a huff is rarely a good reason, nor is it a good foundation, for your next step. Quitting something does not automatically put it behind you; it just re-classifies the past under a different folder called “unfinished business”. So when you do look in the rear-view mirror, which is inevitable every once in a while, it should be to analyse and learn, not to torture yourself with “what-ifs”. You also cannot let it define you. You have to deal with it (forgive, forget, use it as fuel), before you can truly focus on your future.

Where do I begin? A clean slate is exciting, but it can just as easily be terrifying, not least because there are so many variables. As Professor Iyengar (author of The Art of Choosing) highlighted in her study, too much choice can be paralysing. The trick is to narrow them down to a manageable number, and remind yourself that the beginning does not have to be perfect. There will be ample opportunities to rewrite the story. After all, even the original version of Pretty Woman was a dark drama that explored the themes of prostitution more harshly. Thankfully the movie was re-conceived and we, the audience, got to enjoy a happier ending.

Where will it all lead, and what if it all goes terribly wrong? This one too, is also best tackled by asking yourself a different question: “What’s the worst that could happen?” If you can deal with that, then keep your vision, follow it with all your heart and might, and see where it leads you. The destination might ultimately be very different from what you had envisioned. After all, even YouTube originally started out as a video-based dating service. You can pivot as more insights and learning become available. Put aside your worry about “the end” and focus your energy on getting started.

Because in the beginning, everything is possible.

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  • Surbhee Grover


    Steel & Graffiti Inc.

    Surbhee is a strategy consultant, entrepreneur and storyteller based in New York. She provides growth strategy & innovation advice to leading consumer companies and has partnered with clients across Asia, North America and Europe (e.g. Philips, De Beers, LVMH, Four Seasons, National Restaurant Association, Clorox). She also works closely with start-ups in the consumer space. An avid traveler, explorer, and rainbow chaser, she likes to capture moments and craft stories. Her writing and photos have appeared in Forbes India and HT Brunch.