Stardate S03E99

Sean K. Gabriel
Captain’s Log: Supplemental
8 min readJul 3, 2023


These notes are perhaps overdue by half a year. Much has happened and I’ve had a lot on my mind since. Time to share.

At the lovely Carmelo in Lyon, December 2022. This Sean had no clue how 2023 would play out

Normally we start these with a look back at the season’s weeknotes — 36 weeks of blogging prior to my hiatus. But I’ll also add a fresh take now that I’m back in the arena:

The metagame

More and more, I find the hardest part of writing isn’t to write, but to start — especially when you’ve been out of it for a while. Best remedy then is to not stop in the first place 🙃 yet looking back on 2022, I had to contend with starts and stops for February’s move back to London, May’s India trip, and family happenings in August, October and November.

Whenever I slip from a weekly cadence, monthly seems to be the next best thing. Any longer and memories fade (as I can now see with my struggle to recall January’s learnings in E01). And with 6 months off before E99, I’m super grateful to have a record of my working weeks to review. Being on a sabbatical properly cleared out my work memory — without these to go back to, a year’s worth of learnings would’ve been fuzzy at best.

So I feel like there’s a clear case for a new season of weeknotes once work resumes. But I also want to keep the format fresh, and feel ready to move past the ‘prompts’ structure into a more deliberate practice. Not just recounting what I learned here, but using it to sharpen my opinions on the world of work. (And sometimes being wrong. And being okay with that.)

Other ideas I’m mulling are hansei, decision journaling, CAMP scoring and leaving myself with more questions than answers over the weeks.

Oh, and less self-filtering. It worked wonders for Letters.

The arcs

February 27–March 13, road warrior: 😲😏🤞. Crisscrossed London daily for client workshops. Conflicted about my increased load of sales duties. Reminded that winning isn’t always the goal.

March 20–April 11, testing and learning: 😼😤😙😝. Kicked off PM hiring and dove back into product strategy. Relearned why good territories are anchored in a user journey. Explored innovation belief chains, gave away Legos, and absorbed career learnings.

April 25–May 15, staying curious: 😊✌️🤩😃. Studied delays in our management work. Reflected on community growth and career growth. Enjoyed some refreshingly simple takes on 0–1 strategy (i.e. get big with one hard-to-copy advantage).

June 7–20, the stall: 🙂🤨🙈. Jumped too soon into work, before the lagging indicators caught up. Felt the pull of organizational gravity.

June 28–July 10, bracing for impact: 🫣🥵😬. Got bulldozed, chased, and interviewed. Questioned expertise, failings, and what we deserve. Remembered to think in spectra and be clear where I stand.

July 17–August 11, the altMBA: 🤩🫠🌻🚀. Arguably the best professional development experience of my career. Studied the power of disagreement, framing, sonder, shipping, and a generous posture. All of which helped me go deeper on strategic thinking in a new talk.

August 17–September 6, wave function collapse: 😵‍💫🧘😫🤒. Looked for a new rhythm in the face of running bench teams, hiring, calibrations, and target accounts. Overstretched myself and ran afoul of the iron triangle as my world pulled back into sharp perspective.

September 12–29, the lower right quadrant: 😑😋😪. How many roles was I hiring for again? Between meeting all the PMs and DLs, BDDs and community managers, tried to keep my head above water by looking back at my future goals and pushing to follow up better.

October 17–November 7, facing my saboteurs: 🎢😞💩🙏. A bad time for seminars but a great time for PQ. Did my best to remain clear-eyed about the changes unfolding across the business, studying the paths of our peers, but still reeling from each goodbye.

November 15–December 21, the aftershock: 😮‍💨🤔🤗😉. Grappled with how and what to share, while taking stock of my professional identity. Accepted my unfinished business and shipped a last hurrah for the discipline. Tried to focus on the opportunities ahead.

The nuggets

  • Don’t forget why you want to win. It shouldn’t just be at the expense of others.
  • It’s not always prudent to dismiss what you don’t agree with. Rather, put it aside and revisit it after a time. It might strike you differently when your own perspective is different as well.
  • You shouldn’t have to guess about a leader’s motives. Ideally, they’re stated upfront, and are consistent with their actions.
  • You’ll always get greater returns maximizing value than minimizing waste. So, lead with value over efficiency.
  • Raise objections early. The longer you wait to challenge directly, the harder it gets.
  • Can losing your cool be funny? Try to laugh at a frustrating situation, and you might be able funnel that frustration into constructive humor.
  • What do you believe is succeeding purely due to your own skills? And is it really so?
  • Titles only tell you so much. Don’t fall for the status trap.
  • Don’t let your current company’s lens blind you to the wider world. If it doubt, do the research.
  • Summarizing complex work succinctly is an art, but really valuable when done right.
  • Managers are always products of their own experience.
  • Leading means opening oneself to being publicly judged for mistakes. Scary, but necessary.
  • To orient where you’re headed in your career, try to (S)CAMP rate it. Even better to share it in a highly trusted circle where you can be vulnerable.
  • Product roadmaps map intended outcomes over time, whereas delivery roadmaps map intended outputs over time.
  • Roadmaps are fundamentally a tool to communicate intent, and not a strategy tool. It’s therefore important that they always travel with the context of the strategy they are executing.
  • Feeling like an impostor could mean that you’re growing, stretching, and trying new things.
  • One way to move up the strategy ladder is to transition from problem owner to problem picker.
  • A leading indicator of organizational fit is whether they’re precious about the specific phrasing of a job title you’ve had, rather than building an understanding of the responsibilities and remit you had there.
  • What makes for meaningful diversity depends on the context. A leader’s role is to identify and shape this context.
  • Whereas diversity speaks to the composition of the group, inclusivity can be framed as a good process for combining group judgments to minimize bias.
  • Don’t fall for the trap of cutting the individual underperformer from a team. Instead consider the strongest composition of the remaining members.
  • Every weakness is a strength in the right context. And vice versa.
  • Give vulnerability to get vulnerability. Our sense of belonging can never be greater than our level of self-acceptance.
  • Changing your mind in response to new information isn’t a bad thing at all. It’s a sign of intelligence.
  • You don’t need another framework. Start with what you believe. Then others will show up, for themselves, because they share those beliefs.
  • Stop trying to change peoples’ minds. Instead, try to frame the situation in such a way that their beliefs will lead them to that conclusion on their own.
  • All the great ideas in the world will never inspire, or impact, or make change, if they never leave your own mind.
  • When stuck on a big decision, try to de-emotionalize your decision making process. And don’t let a bad outcome convince you you made the wrong bet.
  • It’s all been done before. So don’t worry about being the first with an idea — it’s almost certainly a mirage.
  • Agreement is not a prerequisite for growth.
  • Don’t toe the indifferent middle. Always pick an edge.
  • Not all ideas are worth scaling. As scale tends to create bureaucracy and bloatware, you need an excellent starting point for scale to be worth the effort.
  • Want to combat indifference and average thinking? Start by naming an undeniable shift.
  • You can always be transparent about not being able to talk about something.
  • You’ve done “enough” discovery when you’ve de-risked the odds of an expensive failure according to your risk appetite.
  • Whether you call it strategy or principles, it should help you say ‘no’ to doing the “wrong” things.
  • Check for a rising tide before you decide your boat is lifting the fastest.
  • Be the guide to the entire market. But you need a compelling narrative to back it up.
  • There’s a difference between judgment and discernment, of oneself, others and the circumstances around us.
  • Systems with subsystems need to be managed together. Else you risk process becoming the product.
  • You don’t need to beat market leaders at their own game. Change the game, pivot the worldview. Be different.
  • Delivery problems are always downstream of product problems.
  • Think critically when an outlook is handed to you by those in charge. What success metrics would you trust?
  • Mario Kart got it right with Ghost Mode — your best benchmark today is the you of yesterday.
  • Meet unwelcome surprises with playful energy. You might find a way of changing your mind.


Timing is everything in our careers. And while the end of 2022 threw me for a loop, it’s led to a rejuvenating 2023 I couldn’t have foreseen. I got to explore New Zealand & Australia’s east coast, reconnected with people I admire, and am enjoying a newfound freedom to daily life back home. A year’s worth of travel packed into three months:

This Sean would’ve told the earlier one: it’ll work out for the best!

Knowing this is how things would pan out, should I have leapt sooner? I’m not convinced that would’ve been the best move. The last couple years have been full-on, ‘adulting’ years when I zoom all the way out, yet I was able to draw on support and still grow as a professional, and a maker. Letters might still be just an idea had I not met the Rubies in July. The trip down under might never have happened had my last project carried on.

The shadow of hustle culture is hard to shake, though, especially when it seems like everyone is moving ahead except for you. I have self-doubts left to confront as I look ahead to where I want to be, and who I want to become. So I’ll leave my future self with a few suggestions:

  • Check you’re living your values based on how you spend your time
  • Spend more time with people whose rhythms complement yours
  • Seek mentorship for the road ahead, from those with not just lived experience but a common context
  • Take those first 90 days with intention when they come

Let’s leave it there for today, and I’ll finish the sabbatical story for you in a future season. Till then 🤙



Sean K. Gabriel
Captain’s Log: Supplemental

Aloha (🤙。◕‿‿◕。)🤙 big on team building & lean product dev. Author @ Thinking aloud with #weeknotes. Works best when caffeinated ☕️