Hi all,
Welcome back! This week I’m back home in Calgary this week for long overdue catchups with friends and my parents, and in true Calgary fashion, have lived through a full 45 degree Fahrenheit swing of temperature. (I used Fahrenheit here because it sounds more dramatic - it’s only a 22 degree swing in Celsius - but let it be stated for the record that despite having lived in the US for almost a decade (!), I still fully subscribe to Celsius. Nothing is more logical than freezing temps at 0. And I don’t think we need the granularity of say, 70 vs 71 degrees Fahrenheit. You can fight me on this, I will take you on).
In this week’s newsletter, we unpack some common fallacies of ‘dream careers’, and how the idealization of the concept bears some parallels to common fallacies of dating. Thanks to spending a substantial portion of my late twenties and early thirties living in New York and San Francisco (two cities known for robust and …unique? dating pools), I’ve spent almost as much time thinking about and speaking with people about dating satisfaction as I have about career satisfaction.
I’ve noticed over the years both within myself and others, that while our generation should feel fully happy and actualized given the many many opportunities to both meet new people and explore new careers… it seems like exactly the opposite is true… and the stats support it: only 50% of people in the U.S. feel satisfied at work1 and more than half of the adult population in the U.S. is single2. For the record, I can attest to the fact that being single is great, and it’s excellent that it’s becoming way more viable (especially for women), to stay single, live alone, and focus on other parts of their lives besides romantic relationships. But studies show that another reason people are staying single for longer, is that they are “holding out for a soulmate”.
A 2018 survey asked the question of a group of Americans: “Would it better to wait for a soulmate or just settle for someone convenient?”…. I find this line of thinking completely and utterly flawed. The binary nature of the question is infuriating, and suggests that such thing as a single perfect person for everyone exists, and the alternative to waiting to meet that person is somehow settling (??!)
This type of polarized thinking is mirrored almost perfectly in career thinking. You are either holding out for your one true passion, or dream job; or you are in an ill-suited job that you should change. All of this is heavily amplified by social media, only the posts of the very highs and the very lows are shared. Couples are shown at their highest highs - getting married, having children, celebrating anniversaries (#couplegoals #bae #loveofmylife), and job accomplishments are shared at their highest highs (#dreamjob #pursueyourpassion)…
This type of thinking doesn’t leave any room for people to navigate the realistic nuances of relationships or jobs… Below I share some thoughts on other such myths, and in conversation with a friend, dissect what things we shouldn’t “settle” for, and what things might be navigable in a new and imperfect job.
*Quick digression: the source of subject line of this week’s newsletter… allow me to share my very first dating experience in NYC when I moved there in 2013. The date was a set-up by a mutual (Canadian) friend. He was pleasant enough in a buttoned-up, finance kind of way. We made small talk over work, similar tastes in music, and the annoyances of working in the US. FYI If you get two Canadian ex-pats in a conversation, the topic will almost certainly drift to comparing the merits of the TN visa vs. the H1-B visa vs. the L-1. (Fascinating stuff).
We commiserated about the struggles of first moving to the US, him having done so 5 years prior. Despite being in my late twenties and being gainfully employed (by the company that owns Chase bank, no less), I could not obtain a credit card, because credit history does not travel seamlessly cross-border - so I had the American credit history of an infant upon my arrival in the US. (Years later, I now have the credit score of a really responsible teenager, thank you for asking. Like the kind of teenager that uses her debit card, frequently checks her bank balance, and has never drank alcohol on purpose).
The rest of the date progressed well in my opinion after we dissected immigration law. We stopped ourselves at taxation considerations (didn’t want to go too crazy on the first date, you know…). We had a few more drinks and he shared fun facts about Drake early b-sides (could he BE any more Canadian?)
I’d been warned by friends that dating in NYC is notoriously flaky, so I didn’t really expect to hear from this person after the date.. but lo and behold, the next morning, an email arrived in my inbox with the extremely cryptic subject line…
“The solution to all your problems”.
I opened it to read:
“Hey, had fun last night! I thought about your credit issue, and I took the liberty of calling Amex to see if I could cosign you a card under my account, and good news, they said yes!
The only weird thing is we'd both receive joint statements. Let me know what you think.”
Listen, it’s possible that he was just the nicest Canadian ever (thereby making the nicest human being ever)… but ZOMG. Too much. Too soon.
ANYWAY, that digression was mainly to underscore that almost never is a person you’re starting to get to know, or analogously for this newsletter, a job you’ve just interviewed for, and about to start - “the solution to all your problems”. But that is hands down my favourite dating story AND email subject line I’ve ever received, and now I have a reason to share it with you all.
Musings
Raise your hand if LinkedIn posts like this make you want to scream.
What I want to know is how does someone know that they are “starting their dream job” before they’ve ever started? This kind of content that seems to proliferate LinkedIn nowadays feeds the weird and unrealistic expectation that:
a “dream job” exists
we somehow know on day one that it’s our dream job
if a job at any point is unexciting, challenging or not straightforward it’s onto the next
In many ways, it draws parallels with modern views on dating and relationships:
a soulmate exists
we know that this person is our soulmate because of a massive initial spark
if the person we’re dating shows any sign of being unexciting, not passionate, or too complex… it’s onto the next
As mentioned above, the availability of substitutes are abound - we all have tangible examples of other options. Job postings and dating profiles alike are curated and sent to our phones’ notification center daily, that make the cost of switching feel pretty low… but it doesn’t necessarily lead to satisfaction. In fact, the unrealistic expectation of holding out for perfection impedes happiness. The mere thought that perfection exists, also leads to unhappiness, if you feel like you’re not close to attaining it. So what are some more realistic frameworks to satisfaction in this lifelong journey we’re all in to make meaning of work, (and maybe also form meaningful relationships)? Let’s start by dispelling the myths first.
#1. “When you know you know”: the myth of the spark
Matching with something/someone that seems interesting is only the very beginning. Yet society, pop culture and social media) have conditioned us to think that finding your passion, or finding your soulmate is akin to being struck by lightning. Both are a sudden and earthshattering moment in time, and then you’ll be well on your way in your chosen lane/romantic pairing of choice.
But science suggests that “just knowing” is actually a much longer, drawn out (and less dramatic) process. As teenagers, we are only just starting to discover our likes and dislikes, and we cycle through a lot of different things before we enter adulthood, and even then - it’s an ongoing active process, another concept that social media doesn’t seem to do justice. Social media encourages the bypassing of the interim, meandering steps that people take to become successful or fulfilled - users/followers love an overnight success story. Angela Duckworth’s research on interest and passion reveals that what is in fact more likely the path to finding a meaningful relationship or career path is the combination of “an initial trigger of discovery, followed by subsequent encounter that retrigger your attention again and again”.
The other implication of this need for repeated encounters, is that we can’t introspect, or brainstorm our way into igniting a passion… likewise we can’t avoid dating altogether and hope that someone falls into our path.
I’m not making the claim that everyone needs to date a lot, or try on a lot of different jobs, I think the journey of discovering well-suited partners and careers can also happen within the same relationship or within the same job over time.
#2. “The be-all, end-all”: the myth of forever
Not every job is your forever job. Not every person is your forever person. Entering into something early on with those expectations puts a lot of pressure on everything and everyone (most of all ourselves), to seek perfection.
Studies show that when it comes to finding and developing our passions, what can be most beneficial is a period of autonomous exploration without expectation. Early breadth of experience helps us calibrate what we like to do, what we like to think about, what we like to talk about, our working and conflict styles. Just like it’s rarely successful to date with the explicit intention of marrying, it’s not beneficial to cut out the exploration phase in our careers. Even if job or role isn’t exactly where you want to end up in a long term career, isn’t it beneficial to spend some time in the role honing a specific skill set, or to discover what tasks and problems you enjoy solving more than others?
#3. “This doesn’t even feel like work”: the myth of ease
Rewarding careers aren’t necessarily easy-breezy. Just like a solid, fulfilling relationship isn’t conflict-free. What seems like a budding interest at the beginning, likely won’t be proven as a long-term fit until you’ve allowed yourself to settle into the experience, and navigate through not only the fun, new, exciting experiences, but also the challenges.
If you think back to the highest highs in your career and life, my guess is those highs didn’t drop into your lap after a blissful, worry-free journey. (Unless you’ve won the lottery somewhere along the way, and even in that case - taxes seem like a nightmare.. am I being too cynical?) Usually, our triumphs, and the reaffirmation that we’re with in the right relationship, or on the right career track comes after a challenge. A tough problem at work that you built a process or model to fix, a vacation gone horribly awry that you fought with your partner about to get through - the exhilarating wins, the growth and mastery of things - the best parts of any journey - come only when you’re deep into something, and have powered through a struggle.
Jobs can have the right high-level attributes: right industry, right income range, right brand - but do you like solving the problems of this job? When things get hard or stressful, is it still enjoyable? Are you around like-minded people who you enjoy solving problems with?
Likewise with a partner… it’s unlikely you will never fight. When you inevitably do - are your conflict styles complementary? Do you trigger or inflame each other?
#4. “Shiny and new”: the myth of novelty
Starting a new job believing it is your dream job means that you only think it’s your dream job based on preconceptions and superficial attributes (title, pay.. or analogously to dating, things like height, profession etc.) It’s all just so shiny and new!
It makes sense that we are excited by novelty - at the earliest onset of a new job or relationship, we have limited information, and the information we have is usually the newest and shiniest of all information.
It’s a basic human need to chase novelty, but it turns out, novelty is not only created by something new. Psychologist Paul Silvia describes it this way: “For the beginner, novelty is anything that we haven’t discovered before. For the expert, novelty is nuance”. In routines and jobs (and relationships) we’ve always been in, it may seem impossible to feel much freshness. But the deeper we go, often the more we realize how little we actually understand - there are always rabbitholes to go down. Arguably, seeing something we think we know well in a different light, is as interesting or novel to our brains as encountering something brand new.
In conclusion, the expectation of finding a dream job, or just discovering a lifelong passion one day is as flawed as ending up with our one true soulmate. The process actually probably looks like this: Go out and interact with the world, learn about jobs, meet interesting people and see what someones or somethings you have pleasant feelings about.
When you land on something that has a bit of promise, test it out in different interactions. For a career, this could look like informational interviewing people that work in a certain field that you think you might be interested in. For people, it could be joining some kind of social group with no explicit intention of dating.
If you have doubts, don’t eject from the situation. Slightly pivot instead. Is someone boring on a first dinner date? Take them to an arcade or comedy show and see if it brings out a different side of them. Does your day job seem too process-oriented? Can you take on a different project, or ask to work on a different team to see what else is going on in the company?
Use challenges as an assessment tool. When something in your professional or personal life does not go according to plan, observe how all parties react and problem solve. Is there blame? Is there encouragement? Can everyone communicate effectively?
Conversations
I leave you with this amusing conversation - I recently caught up with a friend who started a new job, and four months in, has discovered it is decidedly not rainbows and unicorns and dream job hashtags. She also happens to be actively dating, so over a few drinks, we dissected the surprises of the new job, applying the (hopefully not beaten to death) analogy of dating. Even though I just spent most of this newsletter telling you to stick with something and to not get disillusioned when a job seems imperfect, there are some things that are likely actual dealbreakers🚩
Being catfished - the interview process dazzled you, but once you start the job it is nothing like you imagined. You are working on completely different work, with a completely different team, and while that part sucks, the ickiest part is that they felt the need to mislead you in the first place
Cultural misalignment - like finding yourself on a date with a surprise antivaxxer, you find your new workplace has fundamentally different (potentially toxic) cultural attributes
One side dominates the conversation - You are rarely asked for input. The company and your managers force their opinion, their culture, their values/norms on you, but never ask about your motivation, or life outside of work. It’s like when your date across the table has spent an hour detailing their work, their family, their vision, their preferences, and is now telling you in excruciating detail about their workout and supplement regimen without ever taking a breath for you to speak
You’re always stuck with the bill - You feel shortchanged all the time - you’re paid under market, you’re under resourced in the job and the worst part is it feels unacknowledged.
What do you all think? I have a feeling this week’s post will be somewhat controversial… do you think we put too much weight in solving for perfection? Is sticking it out in a relationship or job considered settling?
Also, would LOVE to hear your worst dating stories, or new job surprise stories!
Resources/Links
Short simple read from “Designing Your Life” that affirms that fixating on the need to find a single life-defining passion is dysfunctional and anxiety-inducing (Stanford Alumni Association)
“Give it Time before deciding you hate your new job” (Harvard Business Review)
Cool ladies doing cool things: Justice Ketanji Brown Jackson has been confirmed to the US Supreme Court, making her the first Black woman to serve on the highest court in the nation. If you’ve seen the confirmation hearings, or been on Twitter at all - you know that it’s been a sh*tshow, with Republican Senators going to low lows to discredit her… but let’s not let that take away from what a momentous and amazing milestone this is. And who better to celebrate it than the cast of SNL: