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..
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...
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:
“ 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
On being wrong
On boundaries and saying no
On delegation
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?
What: Brain dump of all the things on my mind.. tasks ranging from hyper tactical, to philosophical
So What: Ask myself - Why does any of this matter? How does it serve my bigger goals and broader life?
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!
