Paper plans: The Intersection Where Life Meets Tough Career Choices

Written by
Pranav Manie

I often wonder why my mother chose to stay back in Bhubaneswar and not move permanently to greener pastures. A career move that would have guaranteed a fast-track to being an executive in her function in her industry.

I was probably 11 or 12 when I was told that this happened a few years ago. I had zero idea how career decisions worked, or what a career even was. It must have been one doozy call to make, because as an early professional myself in the internet age, I began to value mobility a lot. And I also believe money brings happiness. I imagined myself in a career that would have necessitated moving at breakneck speed.

But I’m far from being supersonic. There are various reasons, both deliberate and non, for this. But I don’t really want to go into either. I’ve honestly never used a framework to decide next career moves, but the fear of others having storyboarded theirs gets into me.

Can careers be storyboarded?

David K Liu at Google asks a few questions as guiding principles for career moves. The first is, “Ask yourself what your hero would do in the same situation”. There’s a reason Michael Jordan once said that “there’s a weight to being Michael Jordan”. You love him, but you’re not sure you want to be him. And even the greatest to ever lace it up decided to put a complete break on his career because of severe burnout and be with his family. 

In that same piece, Liu asks “what would you feel if your rival did this”. I don’t think that envy or jealousy has led to anything good for anyone. Larry Bird didn’t want to beat Magic Johnson, he wanted to beat the world.

Tough career decisions are not as simple as a one-size-fits-all framework where the only rule is hustling. Career decisions are often a function of privilege, and it obviously takes a level of self-awareness to realise that. Something that a one-size-fits-all always misses. I ask Leesha Agarwal, founder of sustainable clothing label Adah, if she could tell me her emotional state when trying to make a tough decision. Her first answer acknowledged how important privileges played a role in her life. She began her label right out of college, bootstrapped, with some financial help from family. Without certain cushions, she would likely not have taken the risks she has.

It’s also a function of how smart you play them. Apoorva Govind calculates that at age 30, if you stick to a toxic job (for whatever reason), you’re wasting 3.3% of your career, and that number increases exponentially as you age. By this logic, she calculated that she wasted 24% of her career so far. Of course, this is purely a percentage of net worth.

It’s hard to separate emotions from purely rational thinking when you’re pressed to make a life-changing decision. And that kind of decision often feels like the difference between a beautiful paradise you’d imagined for yourself, or a disgusting regret you want to bury deep – even if you were likely choosing between 2 very closely-rated offers.

Going with the flow.

For Leesha (27), this emotional state really boils down to accepting the hand you got and playing your cards right. She looks forward to two main feelings: a) the acceptance of it all, and b) the excitement of starting something new. She had to accept that scaling her own venture likely meant that she would lose the reason why she started Adah – to really build sustainable wardrobes. So she decided to take a backseat. She was also able to move on to leading growth at an early-stage startup. No matter how many sheets she could use to write her pros and cons, she will never know until she takes that leap of faith.

However, those sheets to write your pros and cons might be necessary. Ramaa Muthukumaran, a knowledge management professional at a non-profit, restarted her career in her 40s after years of being a housewife. She believes in being as informed as possible. She sought support wherever she could – cold DMing people she had zero degrees of connection with, using the powers of the internet, not hesitating to ask people the simplest questions. She’s a firm believer in being vulnerable with people when it comes to doubts.

Navigating that emotional state of mind requires you to know what your priorities in life are. For Khush Dembla (21), dropping his hard-earned admit to a finance degree at Columbia, or quitting his high-paying management consulting job was a function of this. “I don’t want to be tied to something that doesn’t allow me to do other things, or enjoy the finer things of life and keep my company”. Even as the stereotype of being a finance professional demands that he work overnight on projects, Khush doesn’t want that for himself.

While it’s hard to separate emotions from logic in tough situations, paradoxically, emotions also govern the frameworks you want to employ. For Arpit Saxena (in his 30s), AVP at State Street, the risk-reward ratio in a switch / jump was all that mattered in the beginning. If you’re betting x, you might want at least 4x within a certain period of time. However, his definition of risks and rewards changed as he got more experienced. “What is the % increase over my last role” is not the only metric to value rewards by. By his 3rd job, a private equity stint, health and family had become factors he needed to account for. He's shifting much of the focus of his life on his football-loving baby, and taking the pace of professional life slower than before. 

Each of these 4 people have one more thing in common: either from the start or over time, they have come to realise that work should not dominate their life.

Ramaa says bluntly, “If you want to do well in your career, have a second one for sure.” She has a travel blog website on the side that she’s trying to scale up. Leesha believes that work can never give you all the happiness in life. At some point in her life, she’s faced the fear that if she has nothing to do, she’ll just end up throwing herself in work which will likely have a monetary outcome. “When you work for someone else and make that 100% your purpose, it’ll bite you back later”, she says. Arpit believes that sustaining a work-heavy lifestyle for 2 decades is unhealthy.

Ambition does not stay linear. It also keeps changing. 

They have also realised that ambition doesn’t always have to be linear or convex. It can go up, down, sideways, in circles, gradually or suddenly, or even flat. We are yet to be comfortable with this idea. Ambition can often be blinding, and we don’t often pause to think (until it’s too late) that we could just let it stand still for a little while. This thoughtful LinkedIn post is reflective of changing attitudes where people are willing to trade in their bonuses for more personal time with loved ones. For once, this generation is valuing time almost as much as money. It’s why Ramaa decided to restart her career, even if she was seemingly starting from scratch as compared to other younger people. Or why someone like Khush was okay with leaving a high-paying job with no immediate backup. 

For example, the most well-known positive non-linear career accelerator is the MBA – with it comes thinking about ROI and debt, but also in terms of what you decide to give up for those 2 years of the education. Interestingly, Leesha and Khush don’t see a lot of value in the degree, especially when running a business is more execution than anything. But this thinking also involves looking at money as something you don’t need an MBA to achieve whenever you want.

Even the MSc + MBA holder in Ramaa believes in perpetual learning. If she enters a degree, she’s in it primarily for the learning and not the money. “How many engineers know how to innovate?” While that may also be a function of the sad state of India’s formal engineering education, as a teacher in the past, Ramaa believes in education for its own sake, which is why she's also pursuing an MA in education along with her job. For everything else, there’s always a newsletter by Morgan Housel.

The myriad ways in which market forces influence our ambitions are interesting. We’re expected to do an MBA during a recession. Does ambition only have to be just getting a lot of money at any cost? We lose a long-term view of what the “unoptimized life” could look like, as Paul Millerd discusses here. A life that’s guided by curiosity, and not greatly affected by market forces – because you work for yourself.

People are quickly catching up to the idea that your career needs to be long-term first, fast-paced second. You don’t have to be a consultant at 24 and a venture investor at 26, you can find your way around. One of the reasons why NBA star Derrick Rose got injured the way he did is because of his extremely explosive offensive style of play. While he was regarded as a generational talent when he first played, he was never the same post-injury.

Always a company of one. 

This doesn’t necessarily mean you have to think that your life swings in binaries of having a job / not having a job, or opening a business / not opening a business. It could just be work as you see it, that you need to do from time to time to earn enough money to live the life you want. You could do it as part of a firm, or not. Even with a small sample of 56 companies, the UK’s 4-day work week pilot had impressive results – with 92% companies wanting to continue the program, and 30% declaring the 4-day work week permanent for employees.

For the ultimate goal in the professional world to be self-actualisation (instead of being the best and biggest), factors like time, bandwidth, and purpose will hold much more weightage in your life than today – and the CTC’s importance will go down. And the legitimization of career options that don’t have to involve full-time working will only advance the same. It’s probably not easy to recession-proof your life, but it’s an important prerogative to invest in yourself, and not the work you do to earn a living.

I don’t ask my mother questions about herself very often, and I should. But I guess this is one of the instances where I’ve already understood what she’s been trying to tell me for as long as I’ve existed.


Pranav Manie is the author of Hot Chips, a monthly deep dive at the intersection of culture and numbers

Work-life conversations that question the status quo.
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Work-life conversations that question the status quo.
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