Hope + Possibilties: A Love Letter to the Future of Work

If you say you don't want to be political, it's often because the system is already working for you. For those of us who've had to fight for flexibility, access, or equity—that's never been an option.

The Privilege of Silence

When someone says, "I don't do politics," what they're really saying is that they're comfortable with the way things are. That comfort signals that their own ease matters more than the discomfort others experience under the same system. For many people—including me—that kind of silence has never been an option.

Personal Experience

When I became a parent, I had no choice but to advocate for more flexibility in my work life. The traditional nine-to-five structure simply didn't accommodate what my family needed. My husband's self-employment gave us some breathing room, but it still wasn't an ideal solution. I had to push against systems that weren't built with me—or families like mine—in mind.

The Political Nature of Advocacy

And that's the thing: standing up for what you need, especially when it's outside the norm, is inherently political. Asking for flexibility, becoming a subject matter expert, speaking out publicly—these are all political acts. Women, in particular, have historically carried the burden of caregiving, yet we've rarely been the dominant power in politics. That makes our voices not just necessary, but radical.

Historical Context

We can't forget the barriers women have faced: being denied property rights, financial independence, even basic autonomy. These aren't ancient struggles—they've shifted within living memory. Cindy Gallup often reminds us, "Women are not the status quo because women have never been the status quo." That line sticks with me, because it captures how much work still lies ahead.

My Work and Its Political Nature

The work I do today sits at the intersections of real estate, technology, policy, and community—and all of those domains are deeply political. To engage in them is to challenge entrenched systems, to question who benefits, and to advocate for something better.

Conclusion

So when someone says they'd rather not be political, what they're really saying is that the system as it stands already benefits them. My own experiences—raising a family in both Canada while working cross-border with the U.S.—have shown me again and again the importance of speaking up, not just for myself, but for those who can't. Because silence may feel safe, but it also keeps things exactly as they are.

• Choosing to be "apolitical" often means the current system is serving you well enough to remain silent.

• Advocacy for time and location flexibility is political because it challenges norms and policy.

• Caregiving is structurally undervalued yet central to how work and communities function.

• Publicly sharing your perspective—interviews, posts, speaking—is part of political participation.

• Policy shows up in daily life: schedules, pay, housing, urban planning, and technology access.

• Individual comfort can conflict with collective progress; silence sustains the status quo.

• "Standing up and asking for what you want when it's not the norm is a political act."

• "To be a caregiver is to be fundamentally political."

• "When you say you don't want to be political, it's because that system works for you."

• "Women are not the status quo because women have never been the status quo." — Cindy Gallup

• Remote work, hybrid work, and time flexibility as levers for equity.

• Historical barriers to women's financial autonomy (bank accounts, credit, lending).

• Cindy Gallup and MakeLoveNotPorn (context: women, power, and status quo).

• Corporate context: Canadian company with U.S. market dynamics and reputation considerations.

• Where does your ability to stay "apolitical" rely on comfort or existing structures?

• What flexibility would materially change your capacity to care for others and do your best work?

• What is one small public action you can take this week to align your values and voice?

• Share this episode with someone navigating caregiving and rigid work norms.

• Send your story or question about advocating for flexibility to be featured in a future episode.

• If this resonated, rate and follow Hope and Possibilities to support more conversations like this.

Caregiving, Flexible Work, Remote Work, Hybrid Work, Privilege, Gender Equity, Policy, Workplace Culture, Urban Planning, Reputation Risk, Leadership, Advocacy

🎙️ Hope and Possibilities with Nola Simon 🗓️ Episode Title: What Got You Here, Won't Get You There 🧭 Length: ~20 minutes 🎧 Listen wherever you get your podcasts

In this episode, I reflect on a concept that's been showing up in a lot of places in my life and work lately: "What got you here won't get you there."

It's a phrase I learned from Marshall Goldsmith, and it's one that keeps offering new layers of meaning the more I sit with it.

I talk about how this idea plays out in leadership — especially the shift from being an individual contributor to stepping into management or executive roles. I use parenting as a metaphor (because let's be honest, parenting and leadership have a lot in common), and I even dive into a pop culture example that might surprise you: Liam Payne from One Direction — and how his career arc illustrates what happens when our playbook doesn't evolve with us.

I also get personal about my own journey. I started my consulting business from a place of deep necessity — as a working mother trying to be more present for my daughters. But now that my girls are 18 and 20 and no longer at home, I'm finding myself in a new season. I'm reevaluating what work looks like for me now, and what I want to model going forward.

I invite you to reflect alongside me: 🌀 What's no longer working for you? 🌀 What do you need to let go of — even if it brought you success in the past?

• The theory of "What Got You Here Won't Get You There" and why it matters

• How leadership changes the skill sets that matter

• Why parenting is a powerful metaphor for management

• What Liam Payne's career taught me about reinvention

• The evolution of hybrid/remote work and how mandates affect trust

• Why I'm reconsidering my focus — and what I might do next

• The impact of AI, demographic shifts, and generational change on work

• Why clarity often comes after you take the next step

"The goal of a parent is to raise adults. So if you've raised adults, you've achieved your goal."

"You're not in control — but you are responsible. That's leadership. That's parenting. That's life."

"Sometimes what made you successful also makes you stuck."

"It's not that your past success isn't valuable — it's just not enough to carry you forward."

I'd love to hear your take. 🌿 What playbooks might be holding you back? 🌿 What do you think you'll need to drop or rethink to grow into your next chapter?

Send me a message, tag me online, or email your thoughts. Let's connect.

If this episode spoke to you, please consider sharing it with someone else who's in a season of change. And if you're enjoying the podcast, I'd love it if you'd follow, rate, or leave a review — it helps more than you know.