Welcome to the "To-Woo" List
Welcome to the "To-Woo" List
New newsletter, who dis?
Hi! I’m Janice Woo, and welcome to the “To-Woo” List. Is the name a cheesy pun on my very fun-to-say last name? Yes.
The “To-Woo” List is also a weekly newsletter with some thoughts on jobs and how we relate to them, general job problem-solving and career fulfillment. The name is also meant as a play on a “To-Do” List. I know some days my job consists of getting through an endless list of tasks - whereas I want to spend more time thinking about careers as the things we want to “woo”: skills we want to build, relationships we want to establish and changes we want to make.
This is the product of my (over)thinking about career satisfaction, accumulated over a decade of job seeking, job optimizing and job creating. I have been so energized by informally helping people make career decisions that align with their values, that I want to explore doing so in a more formal way. It’s very much a work-in-progress, but I want to build a repository of content to attract ideas and like-minded people into my orbit.
What gives me the right?
You’re probably wondering if the internet really needs another newsletter filled with self-help advice/daily affirmations in muted pastel colours. TBH, I wondered the same thing, which is why it took me a while to get started. But having had hundreds of informal career conversations with colleagues, peers, mentees/mentors and friends, I realized that I was starting to develop an affinity for facilitating career thoughts, and was building a wealth of insight. I am so fortunate to have awesome people in my network, mainly women in mid-level to senior roles in demanding jobs and industries spanning energy, banking, venture capital, tech and startups and I’m honoured that they trust me enough to talk about their deepest career dreams and fears.
As for the formal intro, LinkedIn will tell you in broad strokes I’m a career finance professional. I’ve spent time in financial institutions large (Goldman Sachs then J.P. Morgan) and small (8 person fintech startup then 80 person fintech startup). I’ve been at operating companies, and am now in VC. I’ve overseen capital markets, operations, business development, and as a one-time Chief of Staff , everything else you can think of.
What can you expect here?
This issue of the newsletter is mainly an intro of and to this list, but every week going forward, the newsletter will contain:
Musings: thoughts from my own experience that have shaped my career journey
Conversations: a real-time question or topic from my network. We’ll cover things like compensation dynamics, workplace politics, career switching and so much more . My approach is to examine issues first as logically as possible, and then dive deep into the emotions associated with it
Resources/links: interesting links, posts, podcasts, miscellaneous things from the actual experts :)
Tell me about you: I am a naïve baby deer when it comes to creating content, so the more ideas and feedback you give me, the faster I’ll learn and iterate into something you find valuable
Musings
Some of my personal philosophies on career
Once, when I was in a period of soul-searching and career optimizing, someone told me (somewhat defeatedly), “You’re never going to find a perfect job. It’s called work for a reason”, implying that careers were meant to be a grind. Yes, jobs have their day-to-day ups and downs, but I believe we aren’t meant to feel stuck, overwhelmed or frustrated in our careers for any extended period of time. It is worth our attention and energy to make that shift: shifting our mindset, shifting our expectations, or even fully shifting our role/company.
Social media tells us that in order to attain career euphoria, the path is easy…
*eye roll*. Assuming you don’t have a source of unlimited wealth, career optimizing also needs to consider that elusive “passion” in the context of:
Career satisfaction is a mix of passion + pragmatism. While taking that awesome early startup job sounds amazing, if you’re also considering starting a family in the next year, comprehensive health benefits might be a non-negotiable. Oprah said it best: It’s not that you can’t “have it all”, but you may not be able to have it all at the same time. (By the way, social media reinforces the belief that we need to have it all right now, instantly and immediately. *another eye roll*)
Conversations
For this first version of the newsletter, I’ll kick off with something a bit different to better introduce myself. This “conversation” is really an internal monologue I frequently have with myself …(who can relate?)
In some ways, my career path seems pretty linear (all finance roles: investment banking, sales and trading, fintech startup, VC). In truth, I’ve worked across industries (energy, consumer, fintech, healthcare), in different cities (Calgary, New York, San Francisco), and of different types (corporate, asset manager, startup). I can’t tell you the number of times a recruiter has given me the feedback: “You have an interesting resume but it’s way too unfocused.”
Feedback like that has certainly created an insecurity in me that wearing so many different hats would count against me, and that I wouldn’t ever gain true expertise in anything. But switching careers and companies a few times afforded me the opportunity to self-reflect and identify the things that I really enjoyed and did well at naturally.
“Range, How Generalists Triumph In a Specialized World” by David Epstein is a phenomenal book that touts the value of trying different roles in order to find things that are well-matched to us. It helped alleviate a lot of my insecurities, and there countless valuable concepts discussed, but one that I found particularly interesting was the concept of “habits of mind”:
“Everyone needs habits of mind that allow them to dance across disciplines.”
For me, I found that my ‘habits of mind’ are industry and job agnostic. These are things I naturally do well at in all my jobs, and even socially, with friends. Some themes that have kept arising through my career:
People-centric decision making: while advising the company president on long term strategy vs. advising a junior associate on a compensation negotiation may seem different on the surface, I found their decisions were both anchored in the same feelings of risk tolerance, reputation, credibility and alignment with the company. Likewise, when speaking with girlfriends about goal-planning, it didn’t matter if their day job was COO or Full-Time Parent, their doubts were often shaped by the same things: feelings of inadequacy and fear of the unknown.
Translating and reframing: my actual day job involves a lot of translating concepts and numbers between teams and stakeholders. To do that job right, I need to summarize often-complex minutia into a story arc, and even more importantly, actively listen to investor’s questions to determine their goals and concerns. The many career paths I’ve considered have all held this common theme - how can I ask questions a different way, summarize salient points, present the story a certain way, to shape the outcome for an organization, a team or a person.
Expertise can be something very specific (a proficiency with a program, for example, like SQL, Java), but it can also be something ambiguous and almost impossible to summarize on a typical job description. Part of our ongoing learning is to assess what uniquely are are for us, and to seek opportunities that require those habits.
Resources/Links
“Range: How Generalists Triumph in a Specialized World” by David Epstein, the book flips the well-known script for success of specialization and repetition. A super compelling case for breadth of experience, and a reminder that it’s never too late to start exploring an interest or vocation
“How to Maximize Serendipity” by David Perell. Perell is a writing teacher and podcast host who believes that writing is networking, and that content creation will lead people and opportunities to you. You need a destination for people to find you, a “serendipity vehicle”, which was the framework for this newsletter
Cool ladies doing cool things: Leyna Bloom is the first transgender woman of colour to appear in the Sports Illustrated swimsuit issue
Tell Me About You!
What are other pieces of advices (like “Just follow your passion!”) have you received in your career that seem impractical?
What are your “habits of mind”? The unique way your brain processes new concepts, the way you run projects and teams, the common threads that are woven through your professional and personal life?
What content or topics would you like to see discussed on The To Woo List?