How Discomfort & Dissatisfaction led to my perfect career

Ending up in #ProductManagement

Swapna M
10 min readMay 17, 2023

As a recent immigrant to the US, and having traversed multiple geographies in the past (India, Singapore, Dubai, Canada, even Malaysia for sometime) both in personal and professional capacities, I’ve held various product positions from startups to large corporations, leading enterprise and commercial products in the eCommerce, Fintech, Data, Enterprise Search & Consumer Storage domains, and have scaled a startup from 0 to 1 in 2016 as the Head of Product. More recently, I straddle a unique role encompassing product partnerships and development that impacts 1B+ search volume annually across the company. Prior to this, I led OEM partnerships for OneDrive that served 50M+ users worldwide.

However, my career hasn’t been linear in any way. In this non-linear journey, I’ve had many nasty pitfalls and learnings, disillusions, epiphanies and realizations, doubts and feelings of discomfort, which have made way for better and more authentic experiences in my career. Hence today I want to demystify the myths surrounding a ‘perfect’ career, and in the process provide a few tools & strategies that you can use to manifest that imperfect, yet perfect career for you.

Career Myths

#1 I need to find the right career from the get-go (right out of college!)

What is a “right” career anyway? Even if you’ve trained for a particular skill in school and university, there’re so many other complementary things you’ll need to learn and re-learn in order to find the perfect career.

Your strengths and your interests are going to evolve as you move through life — things that you were passionate about at one point may not have that allure over you 5 years down the line.

So don’t limit yourself in the fallacy of getting into the right career immediately after college or school. Explore some more, dabble in different domains and skills before you zone in to your interests.

#2 My salary increments should be linear/upward throughout my career.

An upwardly mobile salary should be expected and is required as you grow in your role, expertise and experience. However, sometimes consciously taking a pay-cut whilst changing professions or to land a role that is super interesting yet challenging to you is not the end of the world.

The salary will catch up, and will grow exponentially than before if you can follow your instincts, are curious to learn and have a go-getter attitude.

#3 Changing professions is a job gone wrong; is failure.

If the current job doesn’t excite you, trying to change professions /jobs shouldn’t be perceived as failure, but more of a directionally good pivot to rejuvenate your career. I’ve transitioned from a software engineer to a consultant to a marketeer to a product manager (when I didn’t know what product management was back then). I did it flamboyantly without thinking of it as a change of profession, rather an experience that’ll add to my resume.

#4 I need to course-correct my career asap!

Sometimes periods of chaos, confusion and boredom are necessary for you to reflect on the kind of career you’d eventually want. My career hasn’t been the most thought-through, however I’ve taken opportunities at various points in my career to reflect and take the time needed for me to get my mojo back. You never know what inspiration might strike you to course-correct at the right time.

#5 Being loyal to one company would provide me credibility.

This is an age-old adage that does not hold true anymore. Gone are the days when people spent their entire careers in a single company or a handful of companies. It’s a reality that people move, or companies and macro economic conditions (read : workforce reduction, layoffs etc.) make employees move. Plus, today’s Gen Z is not someone to sit still and wait — they want to change the status quo and disrupt the world.

#6 I should not be interviewing elsewhere when my manager trusts me so much.

I’ve had managers who themselves keep interviewing, just for the sake of it. And in fact I’ve heard of one manager who actively told their reports to explore opportunities outside if the they’re dissatisfied or want to keep themselves tuned to the active job market. There’s no rule that says you can only interview when you’re dissatisfied at your current role, or when the going gets tough in your existing situation. Take your manager into confidence, and even without you’ve all the right in the world to keep looking if you so will. And if your manager supports it, then that’s a sign of a great leader.

#7 I should not join a company only to leave it a week later.

This might be controversial, but don’t leave a chance unexplored just because you know there’s a better offer coming your way in the near future. That offer might not pan out, and as they say — a bird in hand is worth two in the bush.

#8 My college/university degree will dictate my career.

Maybe this is an old school notion and not sure if it persists anymore, but reiterating this just for my own sake — an university/college degree does not dictate the rest of your career. I’ve seen physicians get into product management, musicians become data scientists, bankers turned software engineers.

#9 Job referrals are a sure shot way of procuring a job.

Sometimes you just need a foot in the door, and you start contacting everyone you know who can refer you to a role in their team/company. Whilst this might prove to be a starting point, without the necessary confidence, skillset and experience, it’s not guaranteed that you’ll definitely land that opportunity (unless the person who referred you vouches for and evangelizes you in their team/company). Job referrals can be great, but I’ve found all my roles and competing job offers without referrals.

#10 Applying in bulk/volume to all jobs is not the right strategy.

Everyone has a different strategy to job search, depending on their circumstances, experience, profile and industry. I’ve used a combination of referrals, targeted search and bulk search on my career, and each of them have proved fruitful in their own right depending on my circumstances. As a new graduate, referrals sometimes might not pan out due to your inexperience. In that case, applying in volume might work for you. Similarly in later stages of your career, targeted search will work well since you already have experience under your belt. Whilst changing professions, a referral might be the best strategy. So it all depends.

#11 I’ll have to take a lower paying job if I move to a new country.

Employers stress on a “country-specific” job experience for some reason — maybe they want to make sure you’ll be able to fit culturally and understand the professional norms of that country. However, if you bring in a certain set of expertise and experience from another region/country, expecting lower pay while starting over in a new geography is again a faulty premise.

#12 I need to match all the requirements to qualify for a job.

This is faulty direction, and better that you eliminate this rule from your thoughts asap. You might spend a lot of time reading, re-reading a job description, trying to compare if you meet all criteria for a job. But then guess what? While you’re doubting yourself, somebody less with less experience, and an imperfect fit for the job has taken the cake and ate it too (got the offer!).

#13 All advice is good advice.

I received some advice after I immigrated to Canada to choose a job opportunity with a brand-name company and go the corporate route, even if that meant that I’d be paid less in the process. Fortunately in that scenario, I had a choice between two offers, and against the traditional advice, I went the startup route and joined as the Head of Product at a fledgling company. It was harder for sure, but it allowed me to learn the ropes of building a business from the ground up, instead of me being just a small cog in the wheel at a large corporation.

Potential ways to approach your career

  1. Always pay attention to what’s getting your attention — Being in-tuned and conscious to your needs and interests will lead to you making intentional choices about your career. If you think you’re reading up a lot about, let’s say, chatGPT, or are following up on the news about OpenAI, and are curious to explore a project of your own around LLMs, then maybe you need to explore this path further and become attentive towards it. I’ve landed my major roles/opportunities by intuitively paying attention to what’s getting my attention (e.g. consumer software or ML/AI) and “manifesting” it in my career. Other times, when the role didn’t evoke an enthusiastic response from me (how much ever I tried!), I needed to get out of that situation quickly (fail fast) in order to direct my energies into the roles that I’d be more passionate about.
  2. Curiosity bags the cat! —If nothing in particular is catching your attention today, keep exploring (go wide) with various roles and opportunities. Be curious about new trends and topics you’re less familiar with, try to get a gist of what they’re all about and feel free to explore some of them to their logical end. I was curious about blockchain tech for sometime — I read up about it, attended various events/conferences, spoke to industry professionals, even tried to build some thought-leadership around it. However I also realized at some point that maybe it’s not my cup of tea, and left it to pursue other things that were grappling for my attention. Sometimes curiosity is all you need to sift through the noise, explore multiple things quickly, and stick to the ones that you inherently feel excited about.
  3. The art of Zen & Spontaneity — There is a concept known as Wu-Wei in Chinese philosophy, that means a state of perfect ease, or effortless action. In other words, if we apply spontaneity to our actions and interactions with others, we can live effectively and with ease. The mind will be dynamic, spontaneous and unselfconscious. With your own career, in addition to exploring and being attentive to your interests, sometimes you just need to go with the flow and dive in spontaneously. You may not know what lies on the other side, but be open to explore and dynamically change directions by letting your unconscious thoughts guide your actions. In choosing between a role in a behemoth organization and a role at a startup, I intuitively went with the startup not self-consciously and strategically calculating at the time about my future prospects. But I let my unconscious mind and gut-feel guide me, since I knew it’ll be advantageous for me in some way, which became clear years later.
  4. Disrupting the status-quo — Sometimes, you may want to do something completely different, to achieve certain objectives or sometimes without rhyme or reason. Or it may be so that you’re too comfortable in a role, and just want to do something out of the ordinary to disrupt the status quo. Whatever the reason, if it feels the right thing to do, go ahead and do it! In some occasions in my career, when some project or work-stream is proving to be challenging, I’ve turned the situation around either by changing the narrative, the way I look at the situation, the way I approach my stakeholders, or sometimes I created a new role for myself (out of the ordinary that my stakeholders weren’t expecting) that encompassed the existing work-stream itself, reducing the noise that the original project was unnecessarily causing. I call it Flipping the Table, if the table is not set to your liking.

Manifesting the perfect career

Once you feel you’ve stuck a note in the right zone,

  1. Go deep — once you’ve identified and zoned into an area of interest, ideally you should dig deeper to see what other aspects you find more appealing to keep an evolving interest in the subject. Try to read more around the specific topic, as well as other peripheral areas that might align to the core subject, develop subject matter expertise around it, learn more and teach others.
  2. Build connections / network — You’ll go farther if you’ve people around you with the same passion for your subject of interest. Hence building connections and networking in your work area provides you more insight into how others are approaching the same challenges and carving out their career path.
  3. Have activities outside of your work — playing around with your passions outside your work helps in keeping the zest for all areas of your life, and gives you that much needed inspiration when the occasional existential crisis strikes. Be it outdoor activities, painting, hiking, cycling, writing, traveling, and everything else in between, each and every fruitful activity will make you richer in experience and help you stay inspired for your perfect role/career.
  4. Develop skills that are applicable in the wide industry — My parents, who are in the sixth decade of their lives, immigrated to Canada in 2023. And even at this age, my father is searching for employment opportunities, not only in the industry he’s familiar with, but also newer industries where his transferable skills can be of value. Plus, in today’s macroeconomic conditions, you need to be spry and lean/agile to be able to shift strategies and pivot to new problem spaces as need be. Hence skills that stand the test of time help in those transitions — software, sales, marketing et all.
  5. Have a confidant — Be honest about your career aspirations with a couple of people you trust. As they say, sometimes just putting it out in the universe helps you manifest that opportunity. It can be your friend, a mentor, your well-wisher, a trusted professional acquaintance — whoever you choose, make sure they’re willing to listen and provide some thoughtful inputs and grounded feedback to your goals. They might also be acute listeners who can provide guidance or empathy to your journey.

Final Thoughts

“If you don’t like how the table is set, turn over the table.” — House of Cards

This has been my motto for sometime now. When things are going your way, you can continue enhancing that path for yourself; but when the going gets tough, be confident enough to flip the script and control the narrative of your life.