My Looming Career Fears

The end of my traditional path – the past few months spent in Toronto and abroad on my sabbatical – has brought a great deal of excitement, but also a great deal of fear and self-doubt.

In the years leading up to this point, I have tried to convince myself of the unimportance of wealth, the rewards of entrepreneurship, and the value of having control over one’s career.

But, as I have spoken to more entrepreneurs and repeatedly hear how intensely difficult it is or grab coffee with people who left finance and hear about the irreversible trade-offs they’ve made, I’ve started to re-familiarize myself with that indelible feeling of panic.

It’s easy to romanticize escape or complain about how much you hate work, but actually leaving to carve your own path can feel more uneasy than it does cathartic.

A great deal of my decision to take a sabbatical was inevitably due to burnout – a loss of will – which begs the question of how truly rational and well-reasoned my decision was. I have not ignored the consequences and problems of my choice: clearly no path is perfect. There are in fact a few looming career fears I have about myself and the world, which if eventually proven true, could make my decision to leave finance a poor one.

In the best outcome, I’ll be “right” and have made a decision that best suits my personal values and goals. At worst, I’ll be “wrong”, derail my life by a few years, lose money, have my more intense peers in finance think I’m stupid, and learn more about myself.

That wrong scenario actually kind of sounds like going to business school, so perhaps all will be well either way.

Fear #1: Having money is actually sick and I like nice things more than anticipated

I’m reminded of my frugal upbringing every time I stay with my parents (which I have been doing a lot more recently).

My family’s spending habits squarely reflect the working immigrant ideology – enough money for piano lessons and university tuition – but not enough for nice clothes or expensive meals.

But, there’s a weird juxtaposition in my life that makes me uncertain about my own values: the disparity in spending habits between my professional friends and my parents.

Many of my direct peers, who are professional Millennials without any dependents, make significantly more money than my family ever did and spend money on things my parents would find frivolous (music festivals, weekend trips, seemingly plain white T-shirts, etc.). And if you’re my age-ish, you’ve never witnessed an economic recession during your career, vs. our parents, who have witnessed at least 3 or 4.

Chart asset: spending habits
Millennials are obsessed with having the freshest clothes, eating at the chillest restaurants, etc.

To which camp do I genuinely belong? I contend with myself that I am probably somewhere in between my family and my friends, with my genuine roots instilled in me as a kid. I believe that I have the ability to rein in my spending akin to my parents.

But I find that money values are deeply contagious and I wouldn’t be surprised if, even with a high degree of discipline, I’m actually much more like my friends.

The point, I think, is that I’ve had unusual exposures to extreme money values and it’s hard to know exactly where my money values will land when I’m more settled.

I try to be grounded and not put too much stock in the glory of luxury items, but I think I’ve also taken for granted just how many everyday problems money solves. It requires a lot of boring self-constraint to stick to a budget.

I find that the gravity of golden handcuffs is also not purely monetary – there is the guaranteed amount of prestige and security that I am foregoing from having a well-paying job.

Perhaps when I am older, I will crave a sense of legacy that my peers will have but remains permanently beyond my reach.

Fear #2: Entrepreneurship actually sucks and I don’t like self-relying as much as I imagine

All entrepreneurs I meet tell me how damn hard it is.

Perhaps this is their way of telling me that as entrepreneurs, they are Sick People who can handle boatloads of suffering, because as we know, suffering is cool. But, I’m inclined to believe that their lamentations are actually true and that entrepreneurship sucks a lot of the time.

One of the narratives I have told myself regarding the vanishing act of my Ambition is that I grew to be unmotivated because I was not a direct beneficiary of my efforts.

Without equity in my previous two jobs, I felt like I did not have a properly aligned motivation system. I felt incentivized to accomplish the bare minimum threshold of work to maintain my salary. I didn’t care – and it didn’t matter much that I didn’t care. It was like that last semester of high school, where you’re doing as little as humanly possible to keep your scholarship.

My fear is that a system of self-reliance makes it impossible to compartmentalize work from life.

In the context of entrepreneurship, I imagine the buffer room to be lazy is a lot thinner because all profits result directly as a product of hard work.

Perhaps it’s the intensity of that work-life relationship that would reanimate the rotting chicken carcass that is my ambition, but I’m worried that it would come with an intolerable level of stress. Perhaps entrepreneurship only “solves the ambition problem” because the consequence of failure becomes so high.

I’ve also been warned against the romance of autonomy. Many types of people thrive in structure and prefer handling clearly delineated responsibilities. I definitely felt this at times in finance; sometimes it’s nice to get explicitly articulated comments so you can focus on execution instead of scoping and planning.

Fear #3: Unstructured free time is not as good as it seems

I’ve had the distinct honor of working in industries where the norm is to work more than 60 hours a week. Doing deals is masochistic work.

My conclusion is that that’s way too much for me (and everyone), but it’s hard to understand what my real work-life equilibrium is when that’s all I’ve really done, especially when it’s impossible to disentangle the pain of those hours from not liking the work itself.

I used to treasure those hours of free time every night when I got home – it was euphoric to close my laptop after a grueling day of comparing one set of a numbers to a slightly different set of numbers.

But I know people who don’t enjoy downtime as much, I think because an abundance of free time can invite monotony and boredom. Extremely leisurely acts like watching videos or browsing fantasy basketball forums can become depressingly dull or feel like embarrassing wastes of time in the absence of a well-designed schedule.

In many ways, it seems like excessive free time is the most reliable route to apathy.

It’s reminiscent of sleepy summer vacations as a kid: when free time is unstructured and overly abundant, it tends to lose its desirability and value.

When I pitch people on the 25-hour work week, they typically respond saying that they would almost immediately grow bored. People enjoy having an urgent sense of duty – duty provides a baseline level of self-esteem and feeling of meaning.

Many people do not think I can legitimately go on a year+ sabbatical without going insane or desperately wanting to return to work. I personally think I have enough projects to keep learning and be engaged, but I do recall that after having just 6+ weeks off post-graduation that I started to feel a bit… restless.

I think this is an area that is difficult to know without actually just doing it.

Fear #4: The net payoff to defer gratification for a couple more years is much, much greater

The idea of building a nest egg as early as possible in life to enable financial freedom later on is not novel – it’s the cornerstone of the FIRE (Financial Independence; Retire Early) movement.

The pragmatist in me tells me that it makes more sense to hack it out for another 4-5 years in finance to really feel financially secure before gallivanting.

I am still not at a place where I can live off the interest on my savings. A general rule of thumb for retirement is that you can withdraw 4% of your savings safely without eroding your retirement principal in your lifetime.

The study says that if you allocate your wealth 50% to S&P, 50% to bonds, you can withdraw the “maximum sustainable withdrawal rate” annually through retirement. This is inflation adjusted and assumes a 30-year retirement. At a minimum, it’s been ~4% over the last century.

I know a couple of ex-finance people who made the leap into an opulent quest of self-actualization, but they all worked for several more years than I did. If I toughed it out and followed the path for a few more years, I would probably worry about money a lot less than I do now.

I think the compounding effect of savings really comes into play when you get closer to that million-dollar net worth, which I’m still far away from.

My justification over the fear of deferring further gratification is twofold:

  1. Waiting 4-5 years could potentially infringe on that precious window of time before family and kids start taking priority. There are also no guarantees for things like the economy, our health, and the health of our family.

  2. Procrastinating risk taking for another year is almost always going to be the mathematically sound decision when you weigh all the pros and cons. It’s virtually always going to be less financially risky to save for another year.

In many ways, I am glad that the junior levels of finance have such rigid breaks in their path, because it gave me incredibly clear cut points to walk away. I think the danger of an incremental career progression is that it becomes less and less clear when it makes sense to step away.


I’m a bit tired of not eating the marshmallow. And it doesn’t feel like a good trade to work hard for many years just so I can have an incrementally nicer retirement life.

It is obviously not my preference to fail, but if the alternative to taking this risk is a slow, painful life of working in a system that does not consider my interests or skills, then to me at least, it feels worth it.

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