four lessons from my first job
on projects, data, mindset and choices with no clear answer
I recently switched to a new job.
Same industry. Different role.
Half a skillset I’m already fairly comfortable with and one that requires me to be more formal, regulated, and demands a level of extroversion that I’m not ordinarily used to.
Ultimately though, a change of pace that I so heartily appreciate.
Abundantly speaking, I have no qualms with my old gig.
It’s a marvelous place to work and my first big shot corpo job which was in a rather flat, amicable and casual environment in the industry I’ve always expected to fall into.
And so in this post, I’d like to highlight four of the most profound lessons (at least that come to memory) and a few microinsights (some shitpost, some serious, but all very much genuine) that I picked up from this cherished 2.5-year venture.
From the resident project manager: “You know you’ve done a good job when everyone is mildly unhappy.”
I used to believe that within a given team, the manager or team leader should be the most skilled person in the party.
And while this is occasionally true, it’s not necessarily the case.
The role of a manager is to do, but to manage — giving each individual team member the chance to shine with their unique set of skills.
This extends especially to project managers who I realise, most of the time, are not as savvy as the technical experts they work with — but instead introduce an exceptionally powerful skill to a team that usually iconically sucks at it: being organised.
A strong project manager uses leadership and thoughtful communication to create teamwork across business functions that otherwise speak different languages.
(A shit project manager stuffs your calendar with unnecessary meetings and leaves everyone more confused than before the chat started.)
And the advice in particular from my resident project manager at the time, who has now moved a technology-based product owner role — is that in the project management world, you can’t let anyone be too happy.
Because if one party is exceptionally excited about an outcome…
…it probably means another business unit is paying the price for it.
From my department head: “Data does not tell you what to do.”
I’ve always had the firm belief that the true mastermind and single point of failure for the business was my department head.
With supreme control of every line of code and data point that travels across the ETL, intricate knowledge of every product on the PDS, understanding the risks attached to every policy underwritten.
He is blessed/cursed with the unique risk of being a senior manager while being so hands-on (perhaps a bit too hands-on) — being so involved into day-to-day operations, juggling a thousand balls and ensuring none of them hit the ground.
Which is a little consistent with what Jan Kamp Justesen (CEO of Sweden’s LB Forskiring) once told me, that people in higher positions (C-suite) tend to get sacked not because of lack of skill, but failure to cover blindspots.
Despite that, or perhaps because of it, he’s very adamant in telling his extremely technical and data-driven team that the strongest resource in their toolkit isn’t analysis, but common fucking sense.
Pricing is an art, not a science.
A sentiment he echoes often.
And one that I’ve heard from other Chief Pricing/Underwriting Officers — that a common pitfall for even the most senior actuaries is to blindly accept what the models say, even if there is a very physically visible and verifiable evidence right outside the window.
When we say data-driven decision making, it does NOT mean that data is the sole driver of your decisions.
It is simply a tool that either supports or rejects your argument.
It cannot sit in the driver’s seat — it does not have the ass to do so.
That role is reserved for the human, to guide the story as they see fit.
From my recent manager: “Imagine what it would look like if you failed.”
I don’t have a lot of dissatisfaction points from my old role, but if I choose one as the headline, it’s the fact that I was a pricing analyst who barely done any pricing.
(And look, maybe I could have done something about it, but I was just operating on what the business required at the time over the last six-months: an all-rounder resource who could execute on technical/analytical requirements with a strategic/business lens alongside solid design/writing/presentation skills. This was, for that organisation, a very uncommon skillset.)
In my last few days, I expressed some of that dissatisfaction to my manager (who was new to being a manager — bless him), stating that I felt as if I hadn’t contributed much to the pricing team and that most of my work didn’t seem to resolve into anything actionable.
He pointed out a different perspective.
“Imagine what it would look like if you failed.”
And after thinking about it that way, I could kinda see it — while most of my projects didn’t pioneer anything new, they were necessary remedies to something that could otherwise collapse.
To anonymise the impact, if I had failed my last couple of projects:
~300 commercial business would lose have their protections de-risked, leaving them prone to life’s uncertainties.
Numerous households situated on the north coast of Australia would lose access to protection from natural hazards.
The executive team could under discretion for poor underwriting risk management.
It’s a more catastrophic way to think about it, but egotistically-speaking, I like being that key person risk to a certain extent.
When my projects feel unimpactful or inconsequential, it could do me some good thinking about my anti-vision where my work ends up in total disaster to remind myself why it’s so necessary to succeed.
Note: Said manager has promised that whoever takes my role will not be subject to these tangential projects to no avail and instead be, as printed on their job description, a dedicated pricing analyst.
From the finance lady across the road: “A decision is not good/bad on its own but becomes good/bad based on how much effort you put into it.”
Shortly after I announced my departure, I happened to get on call with the CFO (not about the resignation) who jokingly asked whether people were still talking to me now that they knew I was leaving.
Truth be told, there were a number of people who gave me a hard time for leaving.
(And I do appreciate the feedback — most feedback is good feedback and if you’re willing to give harsh feedback to my face, I like to think it means you care enough to do so and want what’s best for me. Though, some of it did feel overwhelming negative and weighed on my conscience like a sack of bricks.)
((And perhaps because of that negativity, as time went on, instead of feeling longing or nostalgia or appreciation towards where I had spent the last two-and-a-half years, I was kinda ready to just pack up and go.))
Most people had encouraging things to say. Some, quite frankly, didn’t.
Though, I think the most encouraging comment came from the finance lady across the road who I had struck a rather random friendship with: who introduced the idea that a decision on its own is never good or bad, never right or wrong - but that whether it becomes good/bad or right/wrong is based entirely on how much effort, faith, dedication and belief you put into it.
In other words, the grass is greener where you water it.
As long as I put a conscious effort in tending to the needs of the earth, I can excel anywhere. Regardless of role. Regardless of company. Regardless of what anyone says or thinks.
This plays into my central reason for deciding to leave.
Regardless of whichever I chose, I would most certainly find myself in a what-if situation.
What would life be like if I had taken up the new offer?
What would life be like if I had stayed at my old company?
And so I decided to move.
Not because I thought it was the better option, which we have established, cannot be true nor untrue.
But because it would likely be the option I regret less.
Both options will let me grow, diversify and learn in entirely different ways — one thing not being better or worse than the other, one thing not being more right nor wrong.
They are simply different preferences — like choosing your favorite animal, t-shirt or fruit1.
And it’s acting upon it that transforms a seed of opportunity into a blooming result.
👉 Other little tidbits:
Even the most charismatic speakers can be absolutely terrible at writing. Being a half-decent writer and sporting a typing speed higher than 80 words-per-minute is an edge that I so dearly take for granted.
The financial services industry lives and dies by the pivot table. Please learn it. It instantly puts you ahead of the curve.
The intended trajectory of my career is still entirely unclear, whether it’s managerial, technical or executive.
But I do know that I really don’t want my job to be my only source of income. I’d also prefer if it isn’t my primary source of income.
Everything you write in business must be written with your audience in mind, who are, most of the time, significantly less interested in how much analysis you’ve done than you are.
A colleague introduced to me what he calls a Black Belt Actuarial Technique - Blame Taichi; the art of intentionally not mentioning something in hopes of nobody noticing while having just enough in the back pocket to explain yourself. Which, on that note:
The strongest executives are those who can tell their superiors that they don’t currently have an answer to their question and that you’ll take an action to come back to them after a thorough investigation. There is a unique social mastery that comes with managing up, down, laterally, and cross-functionally.
fox, uniqlo u airism oversized tee in black and watermelon, btw
this was such a good read