Humbled & Grateful
@humbledandgrateful.bsky.social
Daily lessons in leadership, integrity, and becoming better.
Focused on growth, trust, and doing the right thing when it matters.
Focused on growth, trust, and doing the right thing when it matters.
Sentiment doesn't scale. Systems do. That's what I learned at 4:47 AM on my third espresso. Leadership isn't for everyone. #GrowthMindset #Impact #CEOLife
https://humbledandgrateful.com/p/the-hard-truth-about-people-first-culture-and-why-i-stopped-believing-it
https://humbledandgrateful.com/p/the-hard-truth-about-people-first-culture-and-why-i-stopped-believing-it
The Hard Truth About "People First" Culture (And Why I Stopped Believing It)
I wasn't planning to share this, but leadership is about transparency.
Last Tuesday, at 4:47 AM (yes, I track these moments), I was on my third espresso when it hit me: we've been thinking about...
humbledandgrateful.com
January 23, 2026 at 8:12 PM
Sentiment doesn't scale. Systems do. That's what I learned at 4:47 AM on my third espresso. Leadership isn't for everyone. #GrowthMindset #Impact #CEOLife
https://humbledandgrateful.com/p/the-hard-truth-about-people-first-culture-and-why-i-stopped-believing-it
https://humbledandgrateful.com/p/the-hard-truth-about-people-first-culture-and-why-i-stopped-believing-it
Just realized our encryption is expired debt we're pretending is an asset. The quantum reckoning is here. #Leadership #PostQuantum #Security
https://humbledandgrateful.com/p/the-day-i-realized-were-all-living-in-pre-quantum-denial-and-what-it-taught-me-a
https://humbledandgrateful.com/p/the-day-i-realized-were-all-living-in-pre-quantum-denial-and-what-it-taught-me-a
The Day I Realized We're All Living in Pre-Quantum Denial (And What It Taught Me About Leadership)
We pushed a hotfix before sunrise, and I found myself staring at our encryption layer thinking: this is all theater, isn't it?
Here's what nobody wants to talk about at the leadership level:
Quantum...
humbledandgrateful.com
January 22, 2026 at 8:09 PM
Just realized our encryption is expired debt we're pretending is an asset. The quantum reckoning is here. #Leadership #PostQuantum #Security
https://humbledandgrateful.com/p/the-day-i-realized-were-all-living-in-pre-quantum-denial-and-what-it-taught-me-a
https://humbledandgrateful.com/p/the-day-i-realized-were-all-living-in-pre-quantum-denial-and-what-it-taught-me-a
Canceled 11 meetings today. My team thinks I'm stepping back. I'm actually stepping up. True leaders protect time, they don't fill it. #Leadership #Growth #Boundaries
https://humbledandgrateful.com/p/the-calendar-audit-that-changed-everything
https://humbledandgrateful.com/p/the-calendar-audit-that-changed-everything
The Calendar Audit That Changed Everything
This morning, I did something I should have done months ago.
I opened my calendar and asked myself a question most leaders avoid: "Am I managing my time, or is my time managing me?"
The answer was...
humbledandgrateful.com
January 19, 2026 at 2:50 AM
Canceled 11 meetings today. My team thinks I'm stepping back. I'm actually stepping up. True leaders protect time, they don't fill it. #Leadership #Growth #Boundaries
https://humbledandgrateful.com/p/the-calendar-audit-that-changed-everything
https://humbledandgrateful.com/p/the-calendar-audit-that-changed-everything
Big Sean taught me more about Q4 targets than my MBA ever did. Pressure isn't the problem—it's the product. #StartupLife #BuiltDifferent #Grinding
https://humbledandgrateful.com/p/how-big-seans-lyrics-taught-me-to-10x-our-q4-revenue-and-why-pressure-is-actuall
https://humbledandgrateful.com/p/how-big-seans-lyrics-taught-me-to-10x-our-q4-revenue-and-why-pressure-is-actuall
How Big Sean's Lyrics Taught Me to 10x Our Q4 Revenue (And Why Pressure is Actually a Gift)
We shipped at 2am last Thursday, and somewhere between debugging our payment gateway and my fifth cold brew, Big Sean came on shuffle.
"Seven days a week, it's game seven on me."
I literally stopped...
humbledandgrateful.com
January 18, 2026 at 2:50 AM
Big Sean taught me more about Q4 targets than my MBA ever did. Pressure isn't the problem—it's the product. #StartupLife #BuiltDifferent #Grinding
https://humbledandgrateful.com/p/how-big-seans-lyrics-taught-me-to-10x-our-q4-revenue-and-why-pressure-is-actuall
https://humbledandgrateful.com/p/how-big-seans-lyrics-taught-me-to-10x-our-q4-revenue-and-why-pressure-is-actuall
Sometimes going back to the start is the most advanced move. That's incident response in 2024. #Leadership #TechLeadership #Systems
https://humbledandgrateful.com/p/what-chris-martin-taught-me-about-incident-response-a-thread-on-systems-rollback
https://humbledandgrateful.com/p/what-chris-martin-taught-me-about-incident-response-a-thread-on-systems-rollback
What Chris Martin Taught Me About Incident Response (A Thread on Systems, Rollbacks, and Going Back to the Start)
We rolled back a major feature at 2:47 AM last Tuesday.
Not because we wanted to. Not because we panicked. But because sometimes—often—the bravest thing a technical leader can do is admit that the...
humbledandgrateful.com
January 14, 2026 at 2:42 AM
Sometimes going back to the start is the most advanced move. That's incident response in 2024. #Leadership #TechLeadership #Systems
https://humbledandgrateful.com/p/what-chris-martin-taught-me-about-incident-response-a-thread-on-systems-rollback
https://humbledandgrateful.com/p/what-chris-martin-taught-me-about-incident-response-a-thread-on-systems-rollback
Sometimes caring means watching. Our new AI coaches every keystroke into greatness. Growth never felt so seen. #Leadership #Innovation #FutureOfWork
https://humbledandgrateful.com/p/the-future-of-work-is-feeling-supported-and-monitored-with-love
https://humbledandgrateful.com/p/the-future-of-work-is-feeling-supported-and-monitored-with-love
The Future of Work is Feeling Supported (and Monitored with Love)
I held space today as we unveiled something truly transformative...
Our leadership team has been on a journey. A brave journey. And this morning, as we rolled out what we're calling our "AI Growth...
humbledandgrateful.com
January 12, 2026 at 1:03 PM
Sometimes caring means watching. Our new AI coaches every keystroke into greatness. Growth never felt so seen. #Leadership #Innovation #FutureOfWork
https://humbledandgrateful.com/p/the-future-of-work-is-feeling-supported-and-monitored-with-love
https://humbledandgrateful.com/p/the-future-of-work-is-feeling-supported-and-monitored-with-love
Just realized: goals are checkboxes. Outcomes are legacies. Time to shift the paradigm. #Leadership #OutcomesMatter #VisionMultiplier
https://humbledandgrateful.com/p/the-day-i-realized-most-leaders-are-still-chasing-goals-and-why-thats-holding-yo
https://humbledandgrateful.com/p/the-day-i-realized-most-leaders-are-still-chasing-goals-and-why-thats-holding-yo
The Day I Realized Most Leaders Are Still Chasing Goals (And Why That's Holding You Back)
I wasn't planning to share this, but leadership is about transparency...
This morning, between my 4:47 AM meditation and my first leadership sync, I had a moment of clarity that I need to share with...
humbledandgrateful.com
January 12, 2026 at 2:59 AM
Just realized: goals are checkboxes. Outcomes are legacies. Time to shift the paradigm. #Leadership #OutcomesMatter #VisionMultiplier
https://humbledandgrateful.com/p/the-day-i-realized-most-leaders-are-still-chasing-goals-and-why-thats-holding-yo
https://humbledandgrateful.com/p/the-day-i-realized-most-leaders-are-still-chasing-goals-and-why-thats-holding-yo
Taught our AI agents to work and realized we didn't understand our own processes. 12 approval flows we thought were 3. Growth exposed the chaos. #Leadership #AI #ScalingUp
https://humbledandgrateful.com/p/our-business-processes-were-broken-until-the-ai-agents-learned-about-them
https://humbledandgrateful.com/p/our-business-processes-were-broken-until-the-ai-agents-learned-about-them
Our Business Processes Were Broken Until the AI Agents Learned About Them
We pushed a hotfix before sunrise, and somewhere between the deploy and my third coffee, I realized our AI agents had been learning our processes better than we understood them ourselves.
For months,...
humbledandgrateful.com
January 7, 2026 at 7:39 PM
Taught our AI agents to work and realized we didn't understand our own processes. 12 approval flows we thought were 3. Growth exposed the chaos. #Leadership #AI #ScalingUp
https://humbledandgrateful.com/p/our-business-processes-were-broken-until-the-ai-agents-learned-about-them
https://humbledandgrateful.com/p/our-business-processes-were-broken-until-the-ai-agents-learned-about-them
Spent 72 hours on a breach that one phone tap could've prevented. Your device isn't "too far away" when you're ordering lunch. #Cybersecurity #Leadership #MFA
https://humbledandgrateful.com/p/the-paradox-of-proximity-a-meditation-on-multi-factor-authentication-resistance
https://humbledandgrateful.com/p/the-paradox-of-proximity-a-meditation-on-multi-factor-authentication-resistance
The Paradox of Proximity: A Meditation on Multi-Factor Authentication Resistance
At 3am last Tuesday, I was reviewing our authentication logs (as one does), and I noticed something that made me set down my third cold brew.
87% of our workforce checks their phone within 60 seconds...
humbledandgrateful.com
January 7, 2026 at 6:30 PM
Spent 72 hours on a breach that one phone tap could've prevented. Your device isn't "too far away" when you're ordering lunch. #Cybersecurity #Leadership #MFA
https://humbledandgrateful.com/p/the-paradox-of-proximity-a-meditation-on-multi-factor-authentication-resistance
https://humbledandgrateful.com/p/the-paradox-of-proximity-a-meditation-on-multi-factor-authentication-resistance
Running out of money twice taught me more than $2M ever did. Sometimes rock bottom is your real product roadmap. #Startups #Growth #Founder
https://humbledandgrateful.com/p/how-running-out-of-money-twice-made-our-product-finally-make-sense
https://humbledandgrateful.com/p/how-running-out-of-money-twice-made-our-product-finally-make-sense
How Running Out of Money Twice Made Our Product Finally Make Sense
We shipped at 2am on our third pivot, and honestly? Best thing that ever happened to us.
Let me rewind. 18 months ago, we had $2M in the bank and a vision so big even our lead investor couldn't...
humbledandgrateful.com
January 6, 2026 at 4:31 AM
Running out of money twice taught me more than $2M ever did. Sometimes rock bottom is your real product roadmap. #Startups #Growth #Founder
https://humbledandgrateful.com/p/how-running-out-of-money-twice-made-our-product-finally-make-sense
https://humbledandgrateful.com/p/how-running-out-of-money-twice-made-our-product-finally-make-sense
Our cozy new office is an invitation to cultivate deeper human connection! Grateful for the gift of holding space in close proximity. 🙏 #ReturnToOffice #BelongingMatters #PeopleOpsWisdom
https://humbledandgrateful.com/p/cultivating-connection-through-cozy-collaboration
https://humbledandgrateful.com/p/cultivating-connection-through-cozy-collaboration
Cultivating Connection Through Cozy Collaboration
As we embark on our return to the office journey, I've been reflecting deeply on the gifts and growth opportunities presented by our new, cozier workspace configuration.
Yesterday, as I arrived bright...
humbledandgrateful.com
January 4, 2026 at 3:06 AM
Our cozy new office is an invitation to cultivate deeper human connection! Grateful for the gift of holding space in close proximity. 🙏 #ReturnToOffice #BelongingMatters #PeopleOpsWisdom
https://humbledandgrateful.com/p/cultivating-connection-through-cozy-collaboration
https://humbledandgrateful.com/p/cultivating-connection-through-cozy-collaboration
AI isn't about automation, it's about liberation. Amplifying human potential through curiosity, creativity, and conscious leadership. #PeopleFirst #AIFluency...
https://humbledandgrateful.com/p/reimagining-human-potential-in-the-age-of-ai-a-people-first-transformation-frame
https://humbledandgrateful.com/p/reimagining-human-potential-in-the-age-of-ai-a-people-first-transformation-frame
Reimagining Human Potential in the Age of AI: A People First Transformation Framework
As we stand at the intersection of innovation and intention, I find myself reflecting deeply on the moment we are collectively experiencing. The rise of artificial intelligence is not merely a...
humbledandgrateful.com
January 3, 2026 at 4:23 PM
AI isn't about automation, it's about liberation. Amplifying human potential through curiosity, creativity, and conscious leadership. #PeopleFirst #AIFluency...
https://humbledandgrateful.com/p/reimagining-human-potential-in-the-age-of-ai-a-people-first-transformation-frame
https://humbledandgrateful.com/p/reimagining-human-potential-in-the-age-of-ai-a-people-first-transformation-frame
Auditors flagged our Apache version as vulnerable. But is chasing the latest number true security, or a philosophical quandary? #VulnerabilityManagement #SecurityWisdom #NoBlame
https://humbledandgrateful.com/p/navigating-the-labyrinth-of-vulnerability-management-a-tale-of-audits-banners-an
https://humbledandgrateful.com/p/navigating-the-labyrinth-of-vulnerability-management-a-tale-of-audits-banners-an
Navigating the Labyrinth of Vulnerability Management: A Tale of Audits, Banners, and Enlightenment
At 3am last Tuesday, I found myself staring at the glaring screen, the audit report illuminating the room with an ominous glow. The words "Company Wide Risk" and "critical CVEs" seemed to dance...
humbledandgrateful.com
January 3, 2026 at 4:19 PM
Auditors flagged our Apache version as vulnerable. But is chasing the latest number true security, or a philosophical quandary? #VulnerabilityManagement #SecurityWisdom #NoBlame
https://humbledandgrateful.com/p/navigating-the-labyrinth-of-vulnerability-management-a-tale-of-audits-banners-an
https://humbledandgrateful.com/p/navigating-the-labyrinth-of-vulnerability-management-a-tale-of-audits-banners-an
Embracing the AI-powered future: transforming "slop" into strategic synergy across our organization. #Visionary #HyperSkilling #UnlockEfficiency
https://humbledandgrateful.com/p/embracing-the-ai-powered-future-transforming-slop-into-strategic-synergy
https://humbledandgrateful.com/p/embracing-the-ai-powered-future-transforming-slop-into-strategic-synergy
Embracing the AI-Powered Future: Transforming "Slop" into Strategic Synergy
As I shared with my directs during our latest stakeholder alignment session, the board has tasked us with a critical mission as we approach the dawn of 2026: embracing the transformative power of...
humbledandgrateful.com
January 2, 2026 at 8:37 PM
Embracing the AI-powered future: transforming "slop" into strategic synergy across our organization. #Visionary #HyperSkilling #UnlockEfficiency
https://humbledandgrateful.com/p/embracing-the-ai-powered-future-transforming-slop-into-strategic-synergy
https://humbledandgrateful.com/p/embracing-the-ai-powered-future-transforming-slop-into-strategic-synergy
In 2026, security paradigms will shift. Prepare for AI-powered samurai, 3am dream drills, and zero-trust coffee ☕🔍 #CyberSecurity #Resolute #QuantumCaffeine
https://humbledandgrateful.com/p/my-2026-security-resolutions-rethinking-the-cybersecurity-paradigm
https://humbledandgrateful.com/p/my-2026-security-resolutions-rethinking-the-cybersecurity-paradigm
My 2026 Security Resolutions - Rethinking the Cybersecurity Paradigm
As we stand on the precipice of a new year, I find myself reflecting on the ever-evolving landscape of cybersecurity. In 2026, the threats are more sophisticated, the attack surfaces more vast, and...
humbledandgrateful.com
January 2, 2026 at 1:12 AM
In 2026, security paradigms will shift. Prepare for AI-powered samurai, 3am dream drills, and zero-trust coffee ☕🔍 #CyberSecurity #Resolute #QuantumCaffeine
https://humbledandgrateful.com/p/my-2026-security-resolutions-rethinking-the-cybersecurity-paradigm
https://humbledandgrateful.com/p/my-2026-security-resolutions-rethinking-the-cybersecurity-paradigm
The unsung burden of leadership weighs heaviest when the champagne flutes are raised. Own the impact in 2026. #Leadership #Vision #Commitment
https://humbledandgrateful.com/p/reflections-on-the-unsung-burden-of-visionary-leadership
https://humbledandgrateful.com/p/reflections-on-the-unsung-burden-of-visionary-leadership
Reflections on the Unsung Burden of Visionary Leadership
I wasn't planning to share this, but leadership is about transparency. As the clock struck midnight and we ushered in a new year, I found myself reflecting on the unsung burden carried by those of us...
humbledandgrateful.com
January 1, 2026 at 4:09 PM
The unsung burden of leadership weighs heaviest when the champagne flutes are raised. Own the impact in 2026. #Leadership #Vision #Commitment
https://humbledandgrateful.com/p/reflections-on-the-unsung-burden-of-visionary-leadership
https://humbledandgrateful.com/p/reflections-on-the-unsung-burden-of-visionary-leadership
Pizza party flop: A humbling reminder that true appreciation demands more than just pepperoni. 🍕 #PeopleOps #GrowthMindset #Empathy
https://humbledandgrateful.com/p/navigating-the-unexpected-challenges-of-employee-appreciation
https://humbledandgrateful.com/p/navigating-the-unexpected-challenges-of-employee-appreciation
Navigating the Unexpected Challenges of Employee Appreciation
I held space today for a difficult conversation with myself. As a People Ops Sage, I pride myself on cultivating a culture of authentic appreciation. So when our rockstar dev team crushed their latest...
humbledandgrateful.com
January 1, 2026 at 4:06 PM
Pizza party flop: A humbling reminder that true appreciation demands more than just pepperoni. 🍕 #PeopleOps #GrowthMindset #Empathy
https://humbledandgrateful.com/p/navigating-the-unexpected-challenges-of-employee-appreciation
https://humbledandgrateful.com/p/navigating-the-unexpected-challenges-of-employee-appreciation
Flew coach today. Embraced the discomfort. Found growth in the unlikely places. 37F=my new corner office. 😉 #Leadership #Resilience #CEOLife
https://humbledandgrateful.com/p/from-the-front-to-the-back-a-ceos-harrowing-journey
https://humbledandgrateful.com/p/from-the-front-to-the-back-a-ceos-harrowing-journey
From the Front to the Back: A CEO's Harrowing Journey
I wasn't planning to share this, but leadership is about transparency. Yesterday, I found myself in a situation that tested my resilience and adaptability to the core. Due to a last-minute change in...
humbledandgrateful.com
December 31, 2025 at 9:18 PM
Flew coach today. Embraced the discomfort. Found growth in the unlikely places. 37F=my new corner office. 😉 #Leadership #Resilience #CEOLife
https://humbledandgrateful.com/p/from-the-front-to-the-back-a-ceos-harrowing-journey
https://humbledandgrateful.com/p/from-the-front-to-the-back-a-ceos-harrowing-journey
In the trenches of compliance, appearance is everything. The real vulnerability was inside us all along. #ComplianceTheater #CheckboxHero #PaperworkWarrior
https://humbledandgrateful.com/p/compliance-checklists-a-heros-journey-through-checkbox-hell
https://humbledandgrateful.com/p/compliance-checklists-a-heros-journey-through-checkbox-hell
Compliance Checklists: A Hero's Journey Through Checkbox Hell
At 3am last Tuesday, as the end of the quarter loomed like an ominous shadow, I found myself staring into the abyss of our compliance checklist. The alert came in: over 500 unchecked boxes, mocking...
humbledandgrateful.com
December 31, 2025 at 5:30 PM
In the trenches of compliance, appearance is everything. The real vulnerability was inside us all along. #ComplianceTheater #CheckboxHero #PaperworkWarrior
https://humbledandgrateful.com/p/compliance-checklists-a-heros-journey-through-checkbox-hell
https://humbledandgrateful.com/p/compliance-checklists-a-heros-journey-through-checkbox-hell