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The incredible power of a creative side hustle – and why you need one today

(Bear with me. This first part may sound like boasting but it’s the opposite—I’m using myself as an example precisely because of how average I am.)

I graduated from B-School in 2002 with middling grades. No one would’ve cast a vote for me as “most likely to succeed” in the yearbook. Yet since graduation, I’ve done pretty well at my corporate gig. I started as an Assistant Brand Manager at Procter & Gamble in India, moved up quickly, then shifted to the Boston Consulting Group and later became a Senior Director at Kraft and then the Chief Marketing Officer for one of New York’s fastest growing start-ups.

During this time, I’ve also taken three full years off to write my novels, backpack, and learn yoga and meditation. Basically, pursuits of the spirit that have nothing to do with work. Or don’t they?
I’m convinced that I’ve done well at my career because of my writing and the related, time off, not inspite of it. As I explain below, writing has helped me grow in ways that’s transformed my approach to work. That’s why I think everyone should have a creative side hustle. All self-help books talk about “following your dreams” and “pursuing your passions” and tend to belittle corporate careers. I disagree. It’s not about the nature of your work. It’s about who you can become through your work. If you can fully express your spirit in Procter & Gamble, for example, then why should you feel compelled to make yet another unnecessary app in your garage unless you really want to, of course? Instead, fill the vacuum with a creative side hustle that expands your spirit so you bring your full self to your work—and every part of your life.

First off though, a creative side hustle is not a hobby. It is a creative project with a measurable, tangible, high-stakes outcome. If writing is your hustle, for instance, you should strive to get a top publishing deal and become a #1 bestseller. Or be a musician trying to cut their own album, an artist aiming to get their own gallery showing, set a lofty, almost unattainable goal for the side hustle because if you don’t have that goal, you won’t push yourself to that spiritual breaking point where the caterpillar becomes a butterfly. And since this is your side hustle and not your main hustle, you’re not striving for money or security but an emotional transcendence where there’s no “man”, no system to appease, just you stretching the boundaries of what you thought you were capable of—and then stretching it some more. Why is this so incredibly effective? Here are a few things my creative side hustle has taught me that’s impacted my corporate gigs positively:

  1. You learn how to operate in extreme ambiguity

    Try selling good ideas to people—a book that means something, a breakout music album, a personal development package that truly works—and watch them run away from you. People would rather buy Lays chips and Oreo cookies and numb themselves in front of a screen watching football or playing World of Warcraft than be shaken out of their comfort zone with a new thought. That’s why as a creative side hustler, you learn to adapt. Constantly. I was very sure about Johnny Gone Down’s success, for instance. I’d written the book during one of the darkest phases of my life when my mother was dying from cancer and I was making one rash decision after another in my personal life. Johnny was written straight from the heart and helped me make sense of my own seemingly self-destructive choices. HarperCollins loved the book. They priced it at the magical Rs. 99 price point in India and distributed it everywhere from Tier 3 cities to Reliance Fresh. I hired a PR agency. A movie star launched the book. We were all riding high after Keep off the Grass’s success. And we sat back and waited for the sales to explode. Except they didn’t. The book barely sold out its first print run of 50,000 copies. Years later, Johnny’s cult-like following has never translated into huge sales. Because no one knows what it truly takes to sell an idea. So you try a new approach each time, constantly course-correcting and tweaking, until one day you get it right. Maybe. Now, I’m trying a completely different model to launch The Yoga of Max’s Discontent in the US in Spring 2016, focusing heavily on a bottom-up grassroots drive. And I’ll fail again and try a new thing again. Everything about the creative hustle is ambiguous. From staring at a blank page to selling your art, it makes the relative ambiguity of work a cakewalk in comparison. The same year I was trying to sell Johnny, I was turning around a declining beverage brand for Kraft in the US. Everything about the latter was rational, almost easy in comparison to the helplessness I felt when I just couldn’t get Johnny Gone Down to rise.

  2. You’re always a beginner

    Have you ever been rejected sixty times on just one project? Your heart contracts, your stomach tightens, your wife’s face falls, you feel like a failure in front of your kids, your world crashes around you with each rejection, yet you keep improving, keep giving it the best you have—and you get rejected once again. Sixty times in a row. That’s what happened with The Yoga of Max’s Discontent before Random House eventually bought the worldwide rights. Imagine how quickly your pride and your sense of certainty dissolves when that happens. And isn’t that a truly wonderful thing? Because you’ll never be the guy at work who struts around with pride because he knows everything about financial derivatives in the petroleum industry or marketing detergents to low tier consumers or whatever. You turn into someone who knows nothing, who’s always learning, who’s obsessed with improving, who’s a mentor to people who are struggling, because you know that every time you are 100% confident about your stuff, you’ll be rejected again.

  3. You become more grateful for your job

    I’ve gotten three book advances and two movie deals in my seven-year-old writing career. On paper, this is impressive. But here’s how the money bleeds in:

    • A book advance is paid 1/3rd at the time of signing a deal, 1/3rd when final manuscript is approved, and 1/3rd on final publication. Nothing in this timeline is under your control. Getting a top book deal is hard enough but it may take months from getting an offer to actually signing a book contract as there’s back-and-forth on every contract term between your agent and the publisher’s lawyer. At some point, you’ll be screaming silently: who cares about 0.75% points on the audio rights of the hypothetical audio book when at this rate, your paper book itself is never going to see the light of the day? But it’s outside your control like everything else. Once you sign the deal, it may take more than a year of editing and re-editing for the manuscript to be approved and then, the release date is heavily dependent on other books. The whole cycle took two years for The Yoga of Max’s Discontent after getting a book deal. Your timing could be quicker. Or slower. The point is it’s heavily unpredictable.
    • If book money is unpredictable, don’t even get me started on movie deals. I got $15k for Keep off the Grass and $150k for Johnny Gone Down. It could have been the reverse. Or more. Or less. No one has a clue about the intrinsic value of “the property”, contracts are all structured differently, and <10% of books that are optioned ever get green-lit for production. Try planning your kids’ organic whole milk boxes around the payout.

    Now, compare this to a job. You work, sometimes a lot, sometimes a little, sometimes well, sometimes not, but you always get a salary at the end of two weeks. Not 1/3rd of it after someone approves your work after one hundred iterations. Will you really sit about complaining about how your boss doesn’t understand you then in the Friday happy hour paid for by the company? Or how you had to work one weekend when your brother’s friend’s cousin was getting married? Your perspective shifts. You become the rare, happy employee who understands the value of a steady paycheck because you’ve seen the other side.

  4. You’re the only rat in your race

    I’ve seen happy, healthy careers destroyed over the obsession of who got promoted when in whose class—“I’m the fastest to become manager in my class so I’m going to stay”, “He became partner before me so I’m going to leave” etc. All these concepts dissolve when you have a creative side hustle. I’ve taken three full years off from my career, for instance, so I don’t even know which class I belong to, how young or old I am versus my peers, who reached where from school etc. All I know is that I have to do a hell of a job each day when I work because a couple of years later, I’ll be either begging for a sabbatical to write a book or quitting and having to find another job after I’m done with my book. So I’ve to be exceptional at my work. Truly excellent. That’s the only way people will look past my unconventional, zig-zag resume. It’s massively simplifying. There’s no past, no future planning, no competition, no looking left or right, you’re running your own race. Your sense of accomplishment comes from doing great work versus any external marker of success and that makes for a pretty good employee.

  5. Your potential increases boundlessly

    This is by far the biggest one. When you set yourself on fire in the pursuit of creative excellence, your spirit expands. In leaps. The creative well is unquenchable. You keep filling it constantly to draw from it—with new experiences, new travel, new people, with life in all its glory and wretchedness. Sometimes I can’t believe how much I’m changing. Three years ago when we embarked on our sabbatical, I couldn’t wait to backpack through Eastern Europe. Now, my stomach knots at the thought of seeing another cathedral or going on a vacation.  I want to meditate. I want to become silent. I want to dissolve myself and become nothing. And tomorrow, I’ll change again. I can see that effect at work. I want to learn. I want to do new things. I want to destroy every sense that I know anything at all. I want to challenge myself until I break, all of it for no material return, just because my spirit demands that of me now. We need every kind in the world but something tells me that you can’t create the future of corporations by watching football and playing the World of Warcraft. The world is changing too fast for that. You, the creative side hustler, have a chance to change the world though. Just start your hustle now.

And if writing is your chosen side hustle, don’t forget to sign up for my writing course and publishing course here.


I cover everything from idea to outline to writing structures to writing psychology and discipline and querying techniques to getting a top literary agent in the material. This is the first time I’ve offered a video course and the response has been delightful. Signing up is free!