Reboot: How to Manage Career Breaks and Return with Greater Success

By Issac John

'It's hard for me to say this, knowing the great feedback most of my peers had for you, but at this stage for our business in India, we just require someone who has some more entertainment marketing experience than you do. Hence, we wouldn't be taking your candidature forward for this position.'

When Issac quit his dream job of Head of Marketing at PUMA in 2015 and took a career break to study screenwriting in New York, little did he know what he had signed up for.

Over the next eighteen months, he would face over a hundred rejections from famed brands, headhunters, publishers, talent agencies and producers. After being rejected in the final interview rounds of brands like Uber, Netflix and Airbnb, he slowly and steadily clawed his way back into a mainstream career. Issac went on to lead a team of over a hundred people at Discovery, having built their direct-to-consumer OTT business in Asia-Pacific (discovery+), and has authored two books - all in a span of five years since that career break.

Over the past two years, Issac spoke to more than fifty working professionals, all of whom went through a break in their career for various reasons. Reboot is an intimate, honest and rich compendium of all those experiences, mistakes, lows and highs that people confronted with a career break go through. It shares the message that no matter the odds you are up against, a career break is always temporary, and, in many cases, it can even prove to be life-changing.

• Language: English
• Publisher: HarperBusiness
• Release date: Nov 5, 2022
• ISBN: 9789356292451

Issac John

Issac John has led large direct-to-consumer teams spanning marketing, product, design and tech functions, with stellar consumer brands such as Discovery and PUMA. A big believer in re-shaping careers, he has taken two breaks over the course of his career of sixteen years, one of which took him back to school at the New York Film Academy at the age of thirty-three. Both his breaks, while leading to short-term pain, turned out to be game-changing for his personal and professional growth. Issac is currently building his own company as an entrepreneur-in-residence with Antler India, an early stage VC firm.

Book preview

PART I: LETTING GO

Whether it’s the first step of a child who’s just learnt to walk or that of an Olympic long jumper taking his shot at glory, that first step is a moment always fraught with some degree of uncertainty and nervousness. Similarly, that first day, week or month of a break can feel either overbearing or empty. Alok Kohli, presently Senior Director, Franchise at Pepsi, woke up on the first morning of his break and called it a ‘strange experience with nothing to do’ in his TEDx IIM Rohtak talk. As someone who has taken two breaks, I found his admission quite relatable.

Sometimes, one might not get a chance to decide the exact timing of when a break hits one’s career. And at other times, especially if you decide to voluntarily take a break, you will know exactly the day after which your day-to-day routine will be a thing of the past. Either way, there are several things that you can do to settle into ‘this new journey’ when all the hours on your calendar will completely belong to you.

This change of momentum in your days can feel uneasy and throw you into a thought spiral of looking over your past. At such a crucial point of time in your career, it is hence important to take a step back and focus on the things that are within your control. Some of these aspects need some work even before your break begins. This section enumerates those and aims to set a foundation for your break to be fruitful just as you embark on it.

1

The Decision

‘I was clear I didn’t want to sweat to make money for people I’d never meet.’

When I was yet to make up my mind about taking a longer (second) sabbatical, I had a chance meeting on a flight from Delhi to Bangalore with Tushar Vashisht, a young co-passenger who identified himself as the founder and CEO of HealthifyMe, a company I hadn’t heard of. He had a fascinating tale to tell about his own career trajectory. This was in 2014, when I was still with