Redefining Gratitude

A late night reflection on the privilege of choice.

Hopefully by now you’ve had your evening tea and settled in 🫖

There's something about Thanksgiving eve that always pulls me into reflection mode. I'm originally from Trinidad and Tobago, where Thanksgiving isn't a date on our holiday calendar. However, when I moved to the US in 2015, experiencing the air of gratitude that envelopes this week became special to me. Each year, its significance deepens, adding new layers of meaning to this cherished tradition. Maybe it's the natural tendency to take stock as the year winds down, or perhaps it's the quiet before the holiday rush.

Tonight, I'm thinking about what drives meaningful work today, especially if you’ve been an active player, coach, or even spectator in the major leagues of SaaS growth over the last decade. With 2025 on the horizon and a good amount of ambiguity entangled in its arrival (think economic pressures, the disruptive rise of generative AI, and continued layoffs to advance profitability), the space between what companies invest in and what truly inspires people to do their best work seems to be getting undeniably wide.

On one side, we see the familiar hallmarks of corporate culture: monthly all-hands, employee-of-the-month programs, and competitive benefits packages that look great on paper. On the other, I’ve heard sales and marketing leaders consistently express in strategy sessions and quiet conversations their desire to ship meaningful work without bureaucracy, set clear boundaries around after-hours Slack messages, and have candid conversations about career growth. But it's the intersection—those rare moments when a leader thoughtfully asks, "What do you actually need to do your best work?" and then acts on the answer—that transforms workplace relationships from transactional to meaningful. When teams can openly discuss project challenges, know exactly what success looks like, and trust their feedback will be heard, real innovation happens.

This disconnect isn't new. Honestly, the more things change, the more they stay the same. History proves it. In the 1880s, George Pullman built what seemed like a worker's utopia in Chicago: beautiful homes, manicured parks, theaters, and libraries for his railway employees. But there was a catch. Miss your rent (paid directly to the company), and you'd lose your job. Express the wrong views, and your family might find themselves homeless.

A decade later, Milton Hershey tried his own spin in Pennsylvania, creating a chocolate worker's paradise complete with quality housing, entertainment venues, and a proper downtown. But paradise came with strings—strict curfews, drinking bans, and managers monitoring workers' personal lives. Fast forward to today, and Elon Musk is building the town of Snailbrook in Texas, complete with a Hyperloop Plaza and company-owned amenities. Why do I drag you through a boring history lesson? To draw recognition to the fact it may be a different era with sleeker perks but there’s the same underlying playbook: make work a lifestyle so you can’t really tell the difference when you’re on or off the clock.

Yet today, we have something those workers didn’t really have back then: genuine choice (p.s. it’s only been 50 years women could open a bank account or access credit without her husband to show the contrast 😅). We can choose not just where we work, but how we work. We have the autonomy and agency to shape our careers and lives in ways unimaginable just decades ago.

Let’s be brutally honest about what choice really means.

When Amazon mandates return-to-office policies, they’re exercising their choice to lead in alignment with their growth goals. When professionals decide to stay or seek opportunities elsewhere, they’re exercising theirs to do right by their future. There’s a crucial distinction, though, between grudging acceptance of change and thoughtful adaptation. Conformity does not equal adaptability. The first leads to resignation and burnout; the second opens doors to possibilities we might not have imagined.

So tonight, as you wind down before tomorrow's festivities, consider what you're truly grateful for in your professional journey. Perhaps it’s the ability to choose projects that align with your values. Maybe it’s the freedom to work from anywhere or the opportunity to build something meaningful on your own terms. As a mom of three toddlers and someone who has experienced her fair share of toxicity in the world of technology and industrial marketing, I find that cultivating awareness and responding humbly with the privilege of choice always in mind, is what keeps me grounded. I do what’s best for my family first and foremost, knowing it will sometimes diminish my chances for winning a new project or client and that’s more than okay.

Nature of the business.

Nature of parenthood.

Both can’t always be symbiotic 😅

Whatever shape your gratitude takes, remember this: in an era of constant change, our ability to adapt and choose our path forward is one of our greatest strengths.

Wishing you a thoughtful Thanksgiving filled with good food, meaningful connections, and the quiet confidence that comes from knowing you can chart your own course, whatever tomorrow brings.

Cheers,
Chae