Heading into Another Year

Happy New Year!

I know, I know, technically the new year started 29 days ago… but from my perspective, it has felt like a slow, sluggish start. I personally have certainly not felt that spark of fresh energy, and supercharge of hopeful motivation that people associate with a new year… in fact, quite the opposite:

Maybe this is part of growing older. Maybe it’s the barrage of alarming executive orders being passed every day in the new year… but I haven’t quite mustered up ‘new year energy’..

However, two other opportunities for “New Year” vibes popped up on my calendar in quick succession:

1. It’s Lunar New Year today! Welcome to the Year of the Snake!

   

   According to the South China Morning Post: “In many Western countries, snakes have long been associated with evil and temptation. However, in China, snakes hold a more complex and varied symbolism. They are simultaneously associated with harvest, procreation, spirituality, and good fortune, as well as cunning, evil, threat, and terror.” That last part sounds about right - see note above on recent executive orders. But let’s focus on the good: spirituality! Good fortune! If you click through the link, you can read your specific horoscope, depending on your birth year.

2. My birthday!

   

   A throwback to better times.

For me, I find birthdays tend to bring with them a sense of reflection and evaluation and sometimes even calibration. Three years ago, (on my 35th birthday), I wrote a newsletter that dug into how that feeling of calibration tended towards feeling of comparison instead.

All I Want For My Birthday

In that post (full title “All I Want for My Birthday… is what everyone else has!”), I talked about feelings of “falling behind”, and the inevitable comparison trap that turning another year older seemed to stir up.

What does this age mean? Am I “checking the boxes” for what being x age should entail?

Re-reading it this year, I wanted to re-share some snippets with you, dear readers. I think I had some helpful reflections back then that helped me navigate the comparison trap.. (good work, younger Woo!)

… AND since three full years have passed, below 2022’s post, I wanted to share three more reflections for 2025 - for good measure.

---

From 2022:

How To Manage Comparison (in a Non Hippy-Dippy Way)

I think there’s a lot of platitudes on social media about “just being grateful” or reminding yourself that “someone out there wants your life”, but I can tell you that when I’m sizing myself up vs my peers or people I started college or my professional career with, or calculating the very real dollar amount of forgone income or equity - I want to tell that Twitter life coach/astrologer candidly, to f*ck themselves.

If you prescribe “self-care” as an antidote to the comparison trap, I will literally scream.

Zoom out in your perspective: Years

If you’re comparing yourself to ‘everyone who got a fancy promotion or title this year’, as a thought exercise, go forward and backward approximately 10 years. When we’re in the busiest part of our career, we tend to be myopic and short sighted, and time has a very different feel to it. If you were to zoom out a bit and evaluate your current life or situation as 20 year old you, or 50 year old you, what would you feel?

Backward: ~20 year old you would likely be impressed at what you’ve learned, the network you’ve built, the experiences you’ve had, the places you’ve been able to go, and the people and relationships you’ve amassed.

Forward: ~ 50 year old you is likely not going to remember the exact year you made a certain title. At all. And they are certainly not going to remember the year your peers and friends made a certain title. But 50 year old you will remember the thematic decisions you made over the course of your 20s and 30s: the lateral career decision you made to spend more time with your family, the career pivot you took to focus on a mission-driven job or industry.

Zoom out in your perspective: Days. (Or even minutes.)

Over the holidays I overheard my partner tell his high school best friend that he’s in his dream job. A week later (a mere 7 days!) a recruiter reached out to him (because the tech job market in the Bay Area is insane right now) with a similar role at a high-flying startup, and suddenly, the new job was the new dream job, and the risk of disappointment was now sky high if he didn’t advance in the interview process.

Similarly, a friend and former executive turned entrepreneur called me today saying she had been approached by a search fund asking if she’d head up their new venture. Even though we had just spoken yesterday about how excited she was about starting her own mission-driven company, this new opportunity showed up and suddenly she felt doubt.

Does the following situation resonate with you?

• At 12:54pm you are carrying on with your life, feeling some kind of moderately ok about your life and decisions to date.

• At 12:55pm you read about someone’s promotion, or someone else’s company getting funded, or are approached about a new shiny opportunity and suddenly you are consumed by self-doubt and feelings of dissatisfaction and inadequacy.

You don’t even need to zoom out years to shift your perspective - go back to 12:54pm you 😊

Big Rocks vs Small Pebbles

Do you know the analogy for prioritization about Big Rocks and Small Pebbles? Your ‘jar’ or capacity can only hold so much and you can either fill the jar with Big Rocks (meaningful priorities), or Small Pebbles/Sand - less important things that if you let accumulate, will take up all the space in the jar.

Even though from time to time, year to year, you will find yourself wondering if you’re on track, or if you’re doing enough, for the most part, are your “Big Rocks” defined on your terms?

The concept below from James Clear is so excellent and nuanced when it comes to comparison:

James Clear @JamesClear

To improve, compare little things. -marketing strategies -exercise technique -writing tactics To be miserable, compare big things. -career path -marriage -net worth Comparison is the thief of joy when applied broadly, but the teacher of skills when applied narrowly.

When you compare small actionable things, and then use that comparison, you can get better, improve morale and self-esteem. If you compare broadly to to the big, thematic things in life that take time to evolve and aren’t always fully in our control, you risk being unhappy and feeling anxious.

It is truly so hard to not use birthdays as a yardstick, especially in the age of social media livestream updates on other people’s lives and career tracks. I finished the post with one final thought on managing through the comparison trap.

Instead of wistfully looking at the choices others have made - double down and affirm the choices you have made

This sounds a lot like “just be grateful!”, but it helps to really reflect on the choices (which are ultimately tradeoffs) we’ve made to date.

Back in 2022, instead of wistfully scrolling through peers’ promotions announcements (January on LinkedIn is a wild time), I tried to focus instead on the choices and inherent tradeoffs I had made.

• Staying at a smaller company for the culture and quality of life

• Choosing stability vs flashier brand

• A slower/more lateral career path vs endless climbing

Listen, FOMO is always available to us - one scroll away, depending on who you choose to compare to, but it’s incumbent upon us to choose not to open up and jump headfirst into that rabbit hole.

---

And, for 2025… 3 more birthday reflections to share with you!

1. Our ‘Big Rocks’ and big choices can change, signficantly

Three years ago, I felt very self-assured in some of my choices (including, not yet having kids, working for a smaller firm with more flexibility)… and here we are, three years later. I find myself at 38, having “re-traded” on some of those things: I am pregnant! I work for a big company!

Admittedly, I feel a bit of guilt in admitting that… Did I somehow let the comparison trap get the best of me? Am I merely a crowd-following, corporate, follower sheep?

Even though I know in my heart of hearts, that revising those choices were intentional and in support of broader and evolving goals. For example, going to work for a larger company (and trading some work/life balance) has given me a wide array of management and people situations that have only enhanced my coaching abilities.

As I read 2022’s post, it was a great reminder that even as we get older, we aren’t rigid/static human beings. There’s hopefully no point in time where we are fully set in stone.

Which brings me to reflection #2:

2. Since we’re always changing, doesn’t it feel better to think of every year as a start line instead of a finish line?

   I’ve found that as we get older, we tend to increasingly think about the concept of a ‘finish line’, or destination… have we ‘made it’ by 30? By 40? Basically taking that crappy comparison trap mindset, and turbo-charging it with an element of scarcity - the scarcity of time! BAD.

   

   I have countless examples from my clients, my friends and my colleagues that span ages and generations of starting new things as they get older. Some are intentional new endeavours - starting their own businesses, pivoting career paths, learning new hobbies and skills (marathons, horseback riding, obstacle courses!) .. and some are more evolutionary, or even involuntary: becoming parents of toddlers instead of babies, or teenagers instead of children, taking career breaks… There’s something terrifying and a tiny bit exciting about new things.. For me this year, I’m new to being 38, and will soon be new to being a parent. I truly don’t have much of an idea of how to be any of those things, but hoping I’ll enjoy it - truly terrifying and exciting all at once.

3. And finally, no matter how much older or ‘adult’ we get, we need to embrace joy and fear and risk and all the other things that tend to be associated with youth..

   Last month I wrote about the chaos of year end, and the endless list of things to do. Unsurprisingly - the holidays ended and I felt depleted, stressed and sadly like the full festive season had passed me by. NO FUN WAS HAD… but I finished most of the to-do list though, like a good adult…

   

   Oh good.

   And so with that in mind, I plan to use these other ‘new year’ dates this week as a do-over, and head into this year aiming to have more frivolous fun. Party brunch (shoutout 2015 Woo)! Cake for breakfast (and possibly dinner)! Planning a post-baby trip!

Making a List, Checking It Twice

Happy Holidays, friends!

Happiest of holidays, dear friends and subscribers!

Hopefully you’re enjoying some real downtime, that is with minimal stress - family, travel or festivity related. I’ll try to keep this month’s newsletter brief for the holiday, and by brief, I mean - somewhat in line with what the kids post on social media these days..

i.e. Designed for the attention span of a goldfish.

The theme of the newsletter: Lists!

• What’s In and What’s Out for 2025 (career edition)

• A quick exercise in listmaking from Essentialism (a philosophical theory and book by Greg McKeown) to set the tone of how I’d like to enter the new year

In case you can’t tell, I LOVE a list...

And another thing!

A list, is in fact, the name of this little newsletter. I used to love a “to-do’ list. When I’d wake up at odd hours of the night, wracked by the anxieties of all the things I hadn’t finished yet, my ‘soothe’ would be to jot down all the things I’d have to complete the next day. Ultimately, creating a never-ending to-do list (while temporarily soothing) never really brought me much joy.

The creation and naming of this newsletter was to reorient my thinking around this, and convert the “To Do” —> “To Woo!”

From this newsletter’s inaugural post:

About The To-Woo List

“ I believe our careers should feel rewarding and enjoyable, and not a just a means to an end. As twist on a monotonous “to-do” list; the “to-woo” list is comprised of things we want to chase and strive for.”

Ta-Da! A shift from focusing things I feel like I must do, to instead ask myself - what do I want to do and what will light me up?

Ok - now onto the lists themselves!

---

What’s Out and What’s In for 2025 (career edition!)

What’s Out for 2025

• Overthinking emails

• Apologizing “for the delay”

• Trying to do it all

• Overplanning

• Solving for likeability

• Dwelling on negative feedback

What’s In for 2025

• Proofreading emails - An email lays out the point, the ask, and a summary. Ensure its correct, direct and clear , but maybe don’t obsess too much over tone, word choice or over softening/qualifying language. If it’s a controversial email, people will ask to set up time to discuss live, which is a much better format anyway. Just send it.

• Thanking people “for their patience” - Instead of apologizing, thank people for their patience. It acknowledges that someone was waiting on something from you, without implying you’re “at fault” for not responding immediately to everyone. People’s timelines and priorities aren’t always your timelines and priorities.

• Doing fewer things - Trim down what you do, and do those things with focus and intention. Be ok owning the things that you didn’t do, because you chose to focus on a smaller select few. Do it intentionally and tell people upfront. You’ll be surprised how empowering this can feel!

• Planning less - I could not have fathomed the huge number of changes that came about for me in 2025 (wedding! work integration! changes! turnover! partner gets a job in a new state! .. we get pregnant! we move!) If I had known all this at the beginning of the year, I would have likely sketched out a massive decision tree blueprint of sorts… I LOVE PLANS. But I also would have stressed myself silly trying to account for a Plan A, then Plan B, then upending everything when a new development occurred or an unforeseeable change happened. Instead of planning more, I’m trusting myself more - that when faced with changes in the moment, even in the absence of a pre-anticipated plan, I’ll have the resources/instincts/knowledge to figure it out then (wish me luck…)

• Valuing attributes besides likability - here’s a short list of other traits that are just as valuable: competence, fairness, consistency, clarity, honesty.

• Focussing on feedback that matters - it’s natural to hone in on the most negative feedback we receive and gloss over the positive feedback (it’s called the negativity bias). In 2025, we’re shifting that - we’re focusing mainly on feedback from individuals we respect, from those that directly influence our paths/outcomes, and feedback that is actionable and meant to help. All other feedback can be deprioritized.

For deeper dives on some of these topics, links to past newsletters below!

• On not solving for likeability

  If Someone is Annoyed at You

• On being wrong

  Congratulations, You're Wrong!

• On boundaries and saying no

  Set, and Reset.

• On delegation

  Do I need to be good at everything?

---

Making a List, Checking it Twice

Onto List #2.. upgrading your To-Do list or a To-Woo list, or at least forcing you to layer in the question of “why?”

As a reforming people pleaser and doer, a big focus in 2025 for me (especially with a number of personal life changes on the horizon) is to prioritize and not spread myself too thin across too many things.

Perhaps you can relate: do you pride yourself on being a jack-of-all-trades, bridging things for others and picking up the ball? I came to the important realization in 2024 that as my life changes, as I progress in my career, and as the landscape changes around me; I can’t do all the things well.

Enter: Essentialism - “the disciplined pursuit of less”. It’s also “the art of discerning between external noise and your internal voice” - profound.

There’s a ton of wisdom in the book, but one tactical takeaway is the journaling exercise below. i.e. How to imbue more of this essentialism thing into one’s every day.

The exercise is comprised of three simple prompts:

1)What? —> 2)So What? —> 3)Now What?

1. What: Brain dump of all the things on my mind.. tasks ranging from hyper tactical, to philosophical

2. So What: Ask myself - Why does any of this matter? How does it serve my bigger goals and broader life?

3. Now what: With that in mind, what must I do today, and what can be deprioritized?

Here’s a real-time example:

What: 5 open work email threads, plan for a strategy session next month, planning for an offsite, 3 hiring processes, finish this newsletter, draft email coaching client referral, reschedule doctors appointment, book movers (yes, we are trying to squeeze in a move before year end), grocery order

To be honest, while initially the list can feel daunting, it helps me enormously, just to write it all down. Otherwise, it just ping-pongs around in my head all the time on repeat.

So What:

Time to ask myself “What really matters to me?”…

Some helpful questions:

• What serves my “bigger picture”? (hint: 5 emails do not a bigger picture make)

• If I were starting the day with a blank piece of paper (instead of a list of requests from others), what would I write down first? (what do I want to spend time doing?) - this part elevates the internal voice over the external noise

For me right now - the bigger picture looks like: feeling energized in the new year about coaching (To Woo, not To Do!), and ensuring a smooth transition at work before maternity leave in Q1 to set my team up for success.

Also time to ask, “What can/must I say no to?” I’m in the final trimester of pregnancy, which I guess means that on any given day at this point out, I could go into labour (CRAZY! note to kid: please don’t arrive too early). That realization has forced me to consider in a very real way, on a daily basis, IF I went into labour imminently, what would I need to drop?

Now What:

With that in mind, looking at my stream of consciousness rambling… a few things become clear to me.

• I must delegate or share responsibility. Even if in a small way, like looping someone else into an email chain, or asking someone else to take a first cut at a presentation. In doing so - I’ll actually be setting my team up for success when I ultimately do go on leave vs trying to shoulder more work myself

• Investing time in coaching will light me up, and small things will move the needle. Drafting an email that my current clients can use for referrals to potential clients is a leveraged use of time - if I spend 15 minutes on it, it can be used again and again (vs. spending 15 minutes responding to others’ emails)

It’s not easy, and of course it requires some amount of resourcing and privilege to say no and to delegate. But it also can’t be ‘impossible’ to prioritize. You know that old chestnut: “if everything is a priority, nothing is”?

I certainly won’t get from ten things to one thing on my list overnight, but I’m hoping this framework will help me (and maybe you!) in honing in on what matters most in the new year.

Til next year, friends! Thank you for reading along and happiest of holidays!

From Hateful... to Grateful?

Hello all!

Before we get into it, you should know that the original title of this post was “Attitude of Gratitude”…

…but then you should also know that I promptly cringed at how cheesy that sounded. And if I’m honest, while on a personal level, yes, of course I feel all kinds of gratitude for so many things in life… the political climate right now (and news of completely unhinged nominations to v. important government roles) doesn’t exactly leave me radiating joy on a daily basis.

BUT. ‘Tis the season!

Yes, THAT season. The season of absolutely absurd holiday content that I will shamelessly enjoy. How absurd, you ask? I believe the bottom right screenshot is from “Hot Frosty”, a movie about a hot SNOWMAN come to life to romance Lacey Chabert (aka Gretchen Wieners). Unconfirmed, but I’m betting she’s big city gal who works too much which is obviously blocking her heart from love. I will watch and report back.

Even though these movies have been infiltrating my feed since Halloween, I guess the holiday season officially starts now with American Thanksgiving tomorrow. (Reminder: I am Canadian, my true Thanksgiving will always be in October, and I will never understand marshmallows + sweet potatoes, you crazy Americans…)

EW.

So, in keeping with the season, and because I loves me a theme… in this month’s newsletter, we’re going to be dishing up a big ol’ serving of gratitude.

I get dizzy if I watch this too much.

In order to avoid the aforementioned “attitude of gratitude” cliché - we are NOT doing the newsletter equivalent of “going around the table and saying what we’re grateful for”. I thought instead, we’d chat about things that were did not immediately inspire a feeling of.. GEE, THANKS SO MUCH FOR THIS.

Things that may have originally seemed a bit challenging or uncomfortable.. and then, over time, with a bit of distance and reflection, perhaps some tiny little green shoots of gratitude, appreciation or even just new perspectives began to emerge.

For me, my coaching clients, followers of the “To-Woo” List Instagram account, a few examples came to light - things that yes, initially felt slightly more in the hateful camp than the grateful one… but reflecting back, and now being able to see some situations with more perspective, these developments turned out to be well… not so bad… and a bit of a valuable learning experience.

“Not too bad”. That is the bar this year, folks.

Important caveat before we jump into a few examples: I don’t intend for this newsletter to be inauthentically positive - that is, slapping on a glossy veneer of faux optimism over challenging experiences.

This sums up inflation in America pretty perfectly right now. There is no positive veneer. Everything is not *AWESOME* all the time.

Actually, being blindly upbeat (you know, toxically positive) ends up invalidating negative emotions and difficult experiences which ends up being more harmful to our mental health¹.

What I want to talk about here, is instead the act of acknowledging the full spectrum of complex thoughts that we feel in response to career shifts.

If we can be present, we can allow our brains to experience both unpleasant emotions, while also holding space for learnings, or less unpleasant thoughts that bubble up. And when we do that, there’s room for reflection and gratitude in some form to emerge. We’re meant to see the light (joy), but also the dark (heaviness, shock, discomfort), and all the gray in between… things like ‘neutrality’, ‘relief’ or even ‘amusement’.

Alright! Caveats communicated! Now onto some real life examples!

I asked myself, my clients, and the general “To-Woo” List community :

“What’s one surprising thing you’re grateful you experienced at work this year?”

And here’s what came back (aggregated, anonymized and paraphrased!):

---

“Working with people I don’t intrinsically feel similar to.

I could not be more different from my boss/colleagues/manager… and that can be jarring and occasionally infuriating. But I’m slowly trying to understand this person/these people, and that has actually gone pretty far to diffuse my annoyance. I remind myself, this person is simply trying their best, in alignment with their values, that might not be the same as mine, but that’s not so different from what I’m trying to do.”

It is a dream to work on a team and at a company full of people similar to you, with aligned values and styles. But chances are, as you progress in your career, as teams and companies grow and evolve, it’s close to impossible to only interact with people you love. Working with people different to you, opposite to you, or even immensely off-putting to you might end up being an everyday reality.

Finding a shred of common ground is a good start. “We’re all trying our best” is a a helpful reminder refrain - it’s safe to assume we’re all working in service of our financial goals, identities, families…whatever that may look like.

Harder yet, is finding admiration for someone’s polar opposite trait. Sometimes the traits that are the most off putting to us are the the ones that we maybe secretly wish we had more of. “Man, this person is unapologetically aggressive or self-serving… I prefer to lead by example and be behind the scenes… but there’s something intriguing about championing for oneself, and putting oneself in the spotlight.”

And hey, if you can’t dredge up the strength to be fully empathetic to people unlike you, perhaps you can at least muster up neutrality: “Welp. At least I’m NOT this person, operating in this way…”.

---

“Being completely overwhelmed.

I have never been as busy as I have this year. At first I just felt burnt out, until I reached a true breaking point and accepted the fact that I could not physically do it all, and needed to force rank everything on my plate.”

Listen, no one is grateful for burnout, or being totally overwhelmed. I’ve heard countless examples of people’s scope expanding at work this year, while their teams shrink, which initially leads to a lot of overwhelm, wondering how on earth they’ll be able to manage it all. A major revelation happens when we realize it’s a bit of a zero-sum game - if we have 1 unit of capacity, and 2 full lists of jobs and responsibilities - instead of trying to double our capacity (very close to impossible), we can instead descope the list of responsibilities.

This of course, requires clear communication and boundaries (see July’s newsletter on those!) but the being forced to prioritize gives us permission to not to do it all, which comes with a unique sense of relief.

---

“Getting layered at work.

At first it really bothered me and I felt inadequate, but having another boss has actually been valuable. I’ve observed a style of leadership different from my former manager’s, I have someone additional who champions for me, and I’m a bit shielded from the pressure of more senior ranks.”

The initial reaction to getting layered is usually one of frustration, or being offended. Suddenly, a babysitter has been inserted above you, obscuring your initially unobscured career track!

It also feels like a blatant rejection - you’re being told someone with different experience or attributes is more qualified than you, and potentially about to start telling you what to do. It’s very hard to not take these developments as a personal affront, when in reality, most of the time, decisions to layer are much more strategic than personal and related to the direction of the company vs. a bottoms-up adjudication of you. It doesn’t always work out as positively as this example above… but sometimes it can mean the chance to try on a different mentor or role model on for size! A layer of protection! An extra sounding board!

We’ll dive in more to this concept of layering in a future newsletter in the new year - when it can work well and when it doesn’t!

---

“Managing!

I’m managing a (growing) team this year, which I initially dreaded. I was an individual contributor for a number of years, and management felt like a chore. And… it has been… occasionally! But along with the challenges it comes with, there is an unparalleled feeling of fulfillment in coaching and developing others (especially when they’re great), and doing right by my team.”

Managing has its pain points for sure, and of course, mo’ complexity = mo problems (we unpacked this in last month’s newsletter). But the rewards of it can (should) come in the form of giving yourself meaningful leverage, and when you as manager can affect people’s outcomes and progressions for the better, it can come with a sense of fulfillment that is even more expansive than your own individual wins!

---

“Not getting promoted.

So - I’m not being promoted this year, and I’m not getting a raise. Of course that initially felt frustrating, but now I feel largely fine with it. A promotion would have created stress, and an element of needing to prove myself at the new level. Also, while I’ve always aimed in the past to maximize pay (perhaps blindly), there’s something comforting and sustainable about being at this level, I feel like I can do it for a long time.”

It’s human nature to continually expect year over year growth. Perhaps because we start off life with exponential ascension through grade school, then middle school, high school, and college. We’re conditioned early on to expect progression every year… and when we enter the workforce, we’re never conditioned otherwise. We just keep pursuing the next rung on the corporate ladder, and many of us don’t really pause for self reflection - we simply assume we want upward progression, and equate success with upward progression. Of course, the sky isn’t always the limit, and eventually we all must settle into some kind of upper limit or asymptote - we don’t all become the CEO of a company, after all!

As this reflection touches on, sometimes progression isn’t always better - more isn’t always more. What if the measure of success wasn’t only an increasingly higher title or increasingly more pay? What if sustainability, or simply ‘enough’ was the goal?

---

“An unplanned break.

I’m currently taking a career break, and it hasn’t exactly been the optimal time for it. It’s been stressful at times, and of course there are feelings of wondering when I’ll jump back in and what it’ll look like. But I’ve had time to pick up brand new hobbies (something I haven’t even thought about since my TEENS), and volunteer for my kid’s midday school activities… I logically know I’ll work again, though I can’t control when, but when I do, it’ll be largely the same as when I left it, but I’m getting a chance to do some unprecedented stuff in my personal life and really think about what I want to do next.”

Career breaks can be intentional, but they can also come as a surprise, or be an added source of stress when they are more unplanned, or go on for longer than planned. But realistically, given where many of us are in our career arcs, chances are high we’ll work again, in a somewhat similar capacity than when we took a break, (i.e. we’re likely not imminently being made redundant by AI).

It might be challenging to sit with the discomfort of the unknown, but channeling that time into personal endeavors is within our control, and ends up likely being more memorable and rewarding than having spent that same amount of time work.

This lovely Medium article touches on the complexity of unplanned breaks. Some nuggets of wisdom:

• You can do everything right in a role and still end up in an unplanned break

• Time off is about not only learning, but also unlearning a lot of what we take to be norms, expectations and cadence when we’ve been in the corporate world for a long time

---

And to wrap up, I leave you with a few more gratitude quick hits that try to lean more practical than trite (yes, I’m going to try to avoid… gratitude platitudes!) 😉😌

• Try tying gratitude to an already ingrained habit. Ain’t nobody got time to start a gratitude journal for 10 min each morning or night, but perhaps while you’re brushing your teeth, or in the shower - see if something (or someone!) comes to mind that you’re happy to have in your life

• Gratitude for someone can sometimes be easier to call to mind than gratitude for something

• Everything isn’t awesome all the time, but small, specific things can be kind of awesome. I’ve found that that type of gratitude is both easier to come up with, and ends up feeling deeper and more resonant than trying to drum up vague auras of #grateful/#blessed. While getting ready for work when its pitch dark out isn’t broadly all that awesome, small things like hot coffee and a few moments of quiet before everyone else is up, hearing an anachronistic pop song (Ricky Martin) in an Uber on the way to work, or a delightfully designed new water bottle (Owala, I don’t know why I enjoy this so much, but it has both a drinking and sipping/straw functionality!!) have brought my mornings some tiny bits of joy lately

• Turns out, accepting gratitude also creates some mental health warm fuzzies. So, even you don’t feel like you’re in a great place to project out a ton of gratitude right now… Please accept gratitude! My gratitude! For reading these little newsletters, for opening up these emails and taking a few minutes to zoom out of your daily work and life goings-on to jump down a little rabbit hole with me.

Happy holidays, dear readers!

---

Resources

“How to Make a Gratitude Practice That Doesn’t Feel Like Toxic Positivity” (Wondermind)

“Gratitude is Really Good For You, Here’s What the Science Says” (NY Times)

“A Hater’s Guide to Gratitude” (“A Little Thing that Helps” Substack)

1. Carolyn Rubenstein, PhD, Clinical Psychologist https://carolynrubenstein.com/

If Someone is Annoyed at You

...You might be doing it right?

Hello friends!

Welcome to this month’s edition of the newsletter. We’re at the end of October (HOW), and for many of us, I know that means we’re in the thick of year-end processes (GAH). Reviews, results, reflections…

Recurring nightmare.

Whether you’re managing a team, or evaluating only yourself, this time of year tends to bring up some deep reflection, assessment and calibration.

In last month’s newsletter, I wrote about a somewhat uncomfortable topic: being wrong (eek). “Being wrong” in a corporate setting with multiple stakeholders, or when managing a team, often simply equates to people not agreeing with you. And when people don’t agree with you, it may cause them to not identify with you… or not respect you… or even *gulp* not like you.

But.. but…

Very uncomfortable to think about, especially as we move into review season.

Your company might implement formal, structured feedback processes (360s, data collection, assessments).. or less formal feedback processes… (a drink with your boss, an envelope of cash)…

Hopefully you’re never in a situation where feedback/compensation/bonuses feel like this. Will the number be $5,000 widgets or Bankrupt? Impossible to guess!

But in many cases, feedback is tied to compensation/bonuses/potential salary adjustments. As such, this time of year invites not only self-reflection, but also feelings of measuring “worth”, which can definitely bring up some anxiety.

I know this firsthand (my own anxious ruminations, of course)… and secondhand. Last week, a direct report came to me fretting about their year end evaluation. This is someone going through a pretty transformative change with their team amidst the broader group and company evolving, with a persistent worry:

“I’ve had more challenging feedback and discontent on my team this year than in any year past. How is that going to reflect on my performance evaluation and progression?”

Welp. I too have been engaging in the same internal dialogue with myself over the course of the last few months. But when I heard this individual put this worry out there, it gave me some new insight (as third party perspective often does!):

First off, I didn’t find this particularly alarming even though this person felt very alarmed. Also:

• I didn’t immediately equate mixed feedback to mean this person was any less competent. I have years’ worth of data points in support of their performance (that doesn’t get negated overnight)

• I was proud of this person for weathering choppy waters

• This person was shouldering more responsibility for more people (and in turn, complexity), because they had initially proved themselves to be GOOD at managing. The reward for good work is… more good work

• My immediate instinct was actually:

OF COURSE this person is receiving mixed feedback. OF COURSE this person is finding it harder to manage. OF COURSE this person feels less “liked”.

Why? Three dynamics, which I describe in more detail below.

1. “Law of large numbers” - you simply have more stakeholders to manage.

2. “Hard(er) problems, with no clear answers”- as you progress, the challenges you’re encountering are new and complex.

3. “Whose agenda is this?” - with mo’ people + mo’ problems, you may lose sight of your own agenda which can sometimes be the only anchor of ‘doing the right thing’ when things are complex and subjective.

---

Law of large numbers

Sometimes (most times), managing feels like… this.

As you get more senior, your sphere of impact (the number of people you directly or directly impact) grows. This is true even in a life setting! Your partner, your kids, your parents, your friends - stakeholders galore!

When we’re earlier in our lives and careers, we can get by being solo agents. We have more flexibility, we often contribute to larger projects our outcomes, but we don’t often have overt accountability. Having stakeholders can be amazing, and rewarding.. but managing those stakeholders is hard. Managing a growing number of stakeholders is very hard. You often need a large group of people to row in the same direction, but everyone has different goals, capabilities, tolerances and attitudes, and you can’t always optimize around them all. In some cases, people want things to stay the same, some people want things to change, in most cases, people want a mix of both.

It’s easier to be “liked by everyone” when the n is small, there’s a higher probability that group of people wants the same thing. But as your sphere grows, that probability goes down dramatically. AND, solving for likeability by the most number of people may be at odds with strong leadership: Pleasing everyone is impossible, and trying to please everyone is actually ineffective. Hence the title of this post… If you’re:

• decisive (aka you’re acting with conviction in one direction but not other) or if you’re

• prioritizing (aka you’re giving more attention to one thing over another)…

…the people in camp ‘other’ might be annoyed at you - but as a leader, you’re probably doing it right.

---

Hard problems with no clear answers

Where are we going? How do we read this? This map is irrelevant. There is no map for where you’re going.

In the last newsletter we talked about growth. I said, “if you’re always right, you’re probably not growing.” In this newsletter, the takeaway is more: “if everyone loves you… you’re also probably not growing”.

Growing in your career means either the landscape is changing, or you’re taking on more, or most often - a combination of the two. That often means you’re tasked with hard problems with no precedent to lean back on. Sometimes those problems are transformational to the business and take teams and years to align (strategic direction, new products/markets), and sometimes those problems are smaller or more individualized, but cumulatively do a lot to impact culture, attitude and morale (who to promote, how to resource when the organization is expanding). The status quo might be the least disruptive to people, but it’s no longer an option given how much is changing around you.

Most problems you face at this stage simply don’t have a clear-cut solution, therefore, a lot of decisions you make as you progress in your career are going to be ambiguous, require trade-offs, and not unanimously accepted.

---

Whose agenda is this?

In the very excellent “The Courage to be Disliked”, Ichiro Kishimi and Fumitake Koga use the framework of Alfred Adler's psychological theories to explore how one can achieve happiness and fulfillment. It touches heavily on the power of self-acceptance, and avoiding the constraints of seeking approval. YES! All that in a single book!

Ok, the book doesn’t solve everything, but it does highlight the problem many of us face - we orient our lives around seeking approval from others.

In doing so, we end up first satisfying the needs of others before even stopping to consider what our own agenda is. When we lose sight of what is truly '“in our court”, and focus on fixing things for others, or delivering on someone else’s agenda, we risk getting swept up in stress and anxiety over things we can’t control, and never end up feeling all that fulfilled. Your agenda/north star isn’t to please everyone. Instead, it might instead be to please only a handful of key stakeholders whose feedback actually matters. It might be to learn enough (or earn enough) to feel rewarded, yet balanced.

Our own agenda may sometimes be the only thing that anchors us and provides reassurance that we’re doing the right things - especially in context of the first two dynamics I mentioned.

So. In a season where we’re self-reflecting, and soliciting feedback from the masses, it might help to simply start with the assumption that… you can’t possibly get it right for everyone.

• Too many people (large numbers)

• Imperfect, messy solutions (to hard, unprecedented problems)

With that in mind, all you can do is know for yourself that you’re trying your best, and prioritize your agenda.

---

In the spirit of reflection and feedback - I want to make sure I’m delivering tangible value to you, readers! Tell me (either reply to this email, or hit the button below) what career challenges or questions you have, and I can attempt to tackle (anonymously) in future editions!

---

Resources

“The Courage to be Disliked” (Amazon)

In case it’s helpful for your own self-reviews, or general review processes - here are some potentially helpful older posts here:

"I'm Not a Math Person"

In which we take a good, hard look at our strengths and weaknesses. Spoiler: there can be too much of a “good thing”.

Do I need to be good at everything?

Short answer: NO. When you know what you are good at and what you like to do, what should you do with everything else? Delegate, descope, upskill?

I'd Like to Speak to the Manager

Surprise, you’re the manager now! We unpack the initial transition from an individual contributor to a manager

---

If you found this and other posts helpful, I’d love if you’d share the “To-Woo” List!

Congratulations, You're Wrong!

Hello all,

Here’s hoping you survived the abrupt end of summer, and that you’re well underway with a transition to the steady rhythmic routine of fall.

I truly do envision this to be my fall mood board. This + rewatching Gilmore Girls episodes

Last newsletter we talked about making the ‘wrong’ choices, and I loftily claimed there to be no such thing! Our broad life choices can’t be categorized into the neat simple buckets of ‘right’ and ‘wrong’.. and doing so is simply a trick our mind uses to help alleviate our anxiety. (More specifically, these are called cognitive distortions - I wrote about this back in 2021, and you’ll find these to be a recurring theme in this newsletter. They are very common and easy to lapse into).

Breathe easy, I said in the last newsletter… there’s no such thing as “wrong”.

Me, putting the “Woo” in “Woo-Saaaaah”.

Ok, and I still wholly believe this about life paths or the long-term arc of our journeys.

BUT. It feels like recently, amidst escalating life busyness, for one reason or another (i.e. compounding complexity at work, trying to balance personal and work schedules)… I have found myself grappling more frequently with the reality of well, instances of being unequivocally wrong.

• Multiple wrongs. In keeping with the fall vibes… just a whole cornucopia of wrongs:

• The wrong call on hiring someone(s) - (i.e when to hire someone, who to hire)

• The wrong call on timing to communicate something to a team

• The wrong call on location/timing to book for a vacation (i.e. the entirety of the vacation is drowned out by monsoon season)

.. the list goes on.

And, of course, like you, anxious reader, each wrong creates in me an immediate, visceral reaction of URGH.

ACCCK. You know that feeling when you feel like you’ve been hit by a semitruck of shock and shame? That’s what being wrong feels like to me. Especially when - like this lady - you felt pretty sure initially that you were right.

Here’s a theory on why. Annie Duke¹ is a professional poker player who thinks a lot about correct and incorrect decision making, and describes below the specific asymmetry of being wrong. She references Daniel Kahneman and Amos Tversky (preeminent thought leaders on the psychology of judgement and well, being wrong).

…being wrong hurts us more than being right feels good. We know from Daniel Kahneman and Amos Tversky’s work on loss aversion, part of prospect theory (which won Kahneman the Nobel Prize in Economics in 2002), that losses in general feel about two times as bad as wins feel good. So winning $100 at blackjack feels as good to us as losing $50 feels bad to us. Because being right feels like winning and being wrong feels like losing, that means we need two favorable results for every one unfavorable result just to break even emotionally.

(Fun fact: Daniel Kahneman is my husband’s brain crush. He quotes stuff like this at me all the time… usually when I am moping and deep in an emotional spiral. He is one of those people that can rationalize exactly and quantifiably how sad one should be about certain mishaps.)

The concept described above by Duke of course, resonate hard. The ‘wrongs’ I mentioned above, feel so much more acute in my mind than the many other ‘rights’ I’ve made in recent history. Compounding the natural asymmetry of this is the persistent environment many of us find ourselves in, (especially in a work setting), where being right and wrong matter a lot.

Many of us work in tech, finance, in public companies, where a LOT of value is placed on being right:

• Tech: if you pick the right problem to solve, and the right market to address, your growth and returns can be exponential

• Finance: if you pick the right stock, or the right company to buy, and invest at the right price, you can earn literal multiples of money

• Public Companies: if you operate in a way, or deliver profit in a way that your shareholders value, your stock price reflects its appreciation immediately… and vice versa

These are models where being the most right, and being the most right most consistently pay off in an absolutely massive way (a way that is so massive that the payoff almost completely loses its relationship to human effort - does it really make sense that innovations in our lifetime make some people billionaires by happenstance?)

Being wrong on the other hand, in these environments, is almost immediately quantifiable and made publicly known (stock price dips, running out of money, writing off an investment to zero, press releases).

Oddly, even professions where arguably, being right consistently is much much much more important than in any other industry… (like oh say, providing life saving medical care) doesn’t have these crazy reward structures.

Seriously. I’m pretty sure back in 2019 you could have raised millions for an idea like.. I dunno, ‘Tinder. but for dogs”. Teachers and nurses be like WTF.

On top of the work settings we find ourselves in, we also happen to be almost constantly steeped in a social media vacuum. 1) Everyone can find fault in us out there on the internet (i.e. someone out there is always going to think we’re wrong), 2) These opinions pick up steam via the algorithm vortex and 3) Our ‘wrongs’ are forever be memorialized online (in tweet, screenshot, text, video etc). Proof of not being correct can be referenced by anyone, at any time and used as repeated ridicule.

NO WONDER BEING WRONG FEELS SO BAD.

So much urgh.

Now, I know our girl Annie, and our boys Kahneman and Tverseky gave us a neat little formula previously about exactly how to quantify being wrong. It’s 2x worse than being right… and yet, I feel like there’s an entire (unquantifiable!!) spectrum of being wrong.

The intensity of how bad it feels to be wrong varies… and I think it can be attributed to a few factors:

1. How high the stakes are

   Obviously the stakes are higher in life saving medical care than in sending an email with typos. A mistake that puts someone in danger presumably has stakes that are higher than hurting someone’s feelings.. and yet..

2. The literal stakes are also coloured by the prevalent feelings associated with being wrong.

   Regardless of where on the “actual danger” spectrum a mistake lies it’s also important to consider the environment: how others react, and/or what we let the said mistake mean about ourselves

Think of times where mistakes feel safe; the stakes are low, and the resulting feelings are generally positive and encouraging. You may be trying to create this kind of environment for your young children.

I think of mistakes I’ve made in recent travel plans with family or friends (see: rainy season, booking a tour on the wrong day). The stakes feel actually low, and the preexisting relationship and shared feelings I have with my stakeholders are overwhelmingly positive. It’s enough to feel apologetic, but not something to dwell on.

Then think of times where the stakes feel higher and feelings feel more negative or potent. This is where the feelings of shame, guilt, and general chaos tend to feel more amplified. I’ve thought about this a lot in two contexts that perhaps you can relate to…

Getting it wrong at work

As important as the actual stakes in one’s livelihood, for those of us that aren’t performing open heart surgery as part of our jobs, I’d argue the overarching culture of a work environment is as (if not more) important in shaping how the wrong feels. This branches out from the examples set at the highest leadership at a company, to each individual team/manager interaction.

How are mistakes treated? Are they shared publicly? Are they presented plainly, or with a “spin”? Are associated learnings shared? Is fallibility considered a negative or a virtue? Do people feel judged by their errors? Do they feel defined by their errors? Do people gossip about other people’s mistakes?

You can see how these elements contribute to a lack of psychological safety, a term coined by the Harvard Business School professor Amy Edmondson in 1999.²

If you feel like you have the overarching support of your manager, team, and company, you’re more likely to take risks, deliver honest feedback and admit to mistakes/errors. The company as a whole as is more likely to be innovative, and foster a stronger community.

This great piece by McKinsey outlines how as leaders and employees, we can foster more of this feeling in our workplaces.

For me, it’s been challenging and humbling to balance (coaching where concepts are more abstract and involve a lot of uncertainty and gut feelings), with a day job where being staunchly correct is such considered such a virtue.

Getting it wrong in coaching

This one feels particularly heightened for me lately - being wrong at something new, at something personal and aspirational, and most of all because the stakes feel the highest. The subject matter is so important: clients trust me with their questions, feelings and vulnerabilities.

But, as with any work or craft… coaching can’t be perfect. AND, the learnings from being “wrong” in coaching are rich. Coaching is very often rooted in instinct. Often without knowing much about the background or context details, coaching is meant to quickly synthesize or connect, reading the cues from their clients.

When I started in coaching training, I hated the idea of blurting out something wrong. I could see it now - my  client (who was just starting to build trust with me) would recoil or cringe or hate me, and the coaching relationship would be ruined. Through training and practice, and now coaching clients, it’s not quite as catastrophic, although it takes considerable self-management to not freak out when this happens, and instead use it as a learning cue. If something triggers a strong negative reaction in a client, that can reveal as much information as when something lights them up. Coaching isn’t always just rah rah rah, you got this!

Actual client testimonial. They’re the cat.

When is a wrong not valuable? I’ve had instances where I’ve ignored the signs that I’m on the wrong path when coaching a client, and pushed an agenda or thread that wasn’t resonant with a client. That’s a textbook example of poor self management of my ego, and results in a much worse coaching experience, not the initial mistake itself.

Welp. Now that we have a better understanding of why being wrong feels so acutely uncomfortable, and I personally have had time to process the urgh, and reflect on my most recent batch of wrongs, I hereby humbly offer a few final reflections on being wrong, particularly, on the wisdom of being wrong.

Yes, once we have recovered from the shame semitruck hit that accompanies being wrong… we might peel ourselves off the ground to reflect for a minute on the myriad of things we can learn from being wrong.

Being wrong can be good for us in a myriad of ways, that we tend to realize once we’ve processed it all.

• Empathy ✅

• Intentions ✅

• Humility ✅

• Self Awareness ✅

• Growth ✅

---

The Wisdom of Being Wrong

• Empathy: Being wrong gives us an understanding of our own fallibility, and in turn, the grace and empathy for others when they are wrong.

  • Managing a team requires this empathy frequently… sometimes the people we manage make the same mistakes that we made in our progression (easier to empathize with), and sometimes they make mistakes that are unfathomable to us (harder to empathize with, but still critical to try).

  It’s helpful in those cases to look past the wrong itself to understanding how something went wrong, and someone’s intentions.

• Intentions: you know how in elementary school math word problems, each question would be worth several points? You’d only get a single point for the actual final answer, but you’d get other points for showing your assumptions and ways of thinking along the way? “Showing your work” is what teachers call it… and oftentimes, even if the conclusion we come to is wrong, the path and intention behind it might be correct. Also - final outcomes are sometimes out of our control, but we can control the path of decisions we make to get there.

  • You might think you made the wrong call with a decision to abandon something - a project, or a career path. Maybe you left and then market conditions changed. The reflection and analysis process (the part that’s within your control) that led to your decision in the first place, is still infinitely valuable.

  • You might think you made the wrong call with your team - when to communicate something, when to grow the team. Yet, despite the outcome not being ideal, your intention was likely to solve for the greatest good of the team, and the sharing of your thought process and acknowledgement of where things went wrong may resonate meaningfully with your team.

In fact, the humility to share wrongs with the people you work with or lead, can result in improved culture and performance³

• Humility: admitting fallibility is a admirable trait in leaders. It sets the tone at the top, and can actually create more motivation in their teams and employees.

  • However, it’s important to consider the “right amount'“ of humility to share. There’s a balance between admitting a mistake, vs admitting all of your mistakes and shortcomings in a way that no longer inspires confidence

Another way of thinking about humility, intellectual or otherwise, is being the right size in any given situation: not too big (which is arrogance), but also not too small (which is self-deprecation).

Humility, and knowing how much to apply, of course, requires a high degree of self-awareness.

Self-Awareness: our wrongs give us a deeper knowing of ourselves. What are the biases and preconceptions we came to a situation with in the first place that led us to assume something (eventually incorrect)?

• I often come to situations assuming that “likability” is one of the most important factors which colors a lot of my decision making. There are situations where this is a correct assumption, and there are situations where this is incorrect. When I reflect on some of my wrongs lately - I gain even sharper perspective

And of course all of this is in service of our favourite concept…

Growth: If we aren’t making mistakes, and being wrong a healthy amount of the time …perhaps we’re not stretching ourselves enough to try new, uncharted things

• Being right all the time feels great. How nice would it be to be known as the person that just ‘knows everything’. But if you’re in a situation of change (professionally or personally, this is basically inevitable), we simply cannot know everything. We will make wrong turns, wrong decisions and have a few dissidents (aka haters) along the way

• Think about your performance reviews at work, both the ones you’ve received and the ones you’ve given. Has any review ever stated “And they just showed up on the job and did it perfectly?” More often than not, star performers are those that took feedback into account and grew with it.

And so, I leave you with this:

Making a mistake is one thing, letting it rob us of hope and boldness (aka NEVER moving past the urgh stage) is another, and arguably much more detrimental action than making the mistake in the first place.

---

Resources

• “Thinking in Bets: Making Smarter Decisions When You Don't Have All the Facts” Annie Duke

• The Curious Joy of Being Wrong (Scientific American)

• On the topic of fall vibes - A fun article on rewatching Gilmore Girls, focusing on show MVP, the third GG, Emily (Lainey Gossip)

• Learn more about me, and my coaching work here

• And if you know someone that would find this helpful, please pass along:

1. “Thinking in Bets: Making Smarter Decisions When You Don't Have All the Facts” (Annie Duke)

2. “What is Psychological Safety” (McKinsey)

3. “Humility Helps Leadership, Here’s How” (Forbes)