Watch the full conversation of Let's Table That, featuring Christine Song here:
Christine Song didn’t “accidentally” end up as a founder.
She spent years in the rooms where decisions get made, working directly with founders, sitting close to boards, building executive teams from scratch, and scaling venture-backed companies at full speed. She learned what it takes to grow. She also learned what it costs when growth becomes the only metric that matters.
In a conversation that spans corporate culture, startup intensity, and the kind of ambition that quietly turns into self-erasure, Christine, now the founder of 5 to 9 Society, a private leadership community, shares the real story behind her shift from Chief People Officer to solo founder.
This is a blog about what she saw, what she survived, and what she’d do differently now.
The “Seamless” Transition No One Talks About
Christine gets asked all the time what it was like to go from CPO to founder. Her answer surprises people:
“It wasn’t that hard.”
Not because founding is easy but because her CPO roles weren’t the typical corporate “HR leader” setup. She wasn’t operating inside a huge public company with layers of approvals. She was working in founder-led environments where People leaders don’t just advise the business, they help build it.
When you work that close to the “owners,” she explains, you start operating with owner-level accountability. You think like a builder. You move like someone who’s responsible for outcomes, not just process. The biggest difference now? Being a solo founder can be lonely. There isn’t a built in team like there is at a preexisting company. Instead, it requires a deliberate effort to stay connected: networking, meeting people, diversifying your circle.
Why Corporate “Felt Like Molasses”
Christine started her career in corporate. At first, she assumed that’s just how work is: a big company, with structure, rules, and (slow and inefficient) predetermined processes, that could be better, but that you just shouldn’t ask about.
Over time, she kept hearing the same feedback:
“You don’t have to work so hard or so fast. You have three months. Don’t do it in three weeks.”
To Christine, that logic didn’t make sense. If you can move faster, why wouldn’t you? Why does speed get treated like a problem? And then there was the part that bothered her more: the culture of compliance. When she asked why a process worked a certain way, she’d get shut down with something like: don’t ask those questions.
That was the breaking point.
She describes corporate as an environment where her “soul was dying”, not because corporate is inherently bad, but because it didn’t match how she’s wired, prioritizing curiosity, momentum and ownership. So she did something simple that changed everything: She applied to a small startup.
The Startup High: Speed, Visibility, and “There’s Nowhere to Hide”
The first startup Christine joined had a team of 35 people, and that excited her; she wanted to know names, be close to the work and feel the impact. She also wanted speed, and the acceleration of startup life started right away.
In startup life, you’re not maintaining a machine. You’re building one, while it’s moving.
Within months, her company raised private equity. Growth accelerated. Acquisitions started. She was traveling constantly. And she learned more in one year than she felt she could have learned in several years in corporate.
But startup life also comes with a specific pressure corporate doesn’t:
Everyone sees you. There’s no hiding behind layers, no quiet coasting. Your decisions show up quickly. Your gaps show up quickly. Your strengths show up quickly. That visibility is intimidating and refreshing because for the first time, her work felt undeniably real.
“Stop Over-Optimizing”: The Advice That Changed How She Led
Christine is a builder by nature. She likes systems, processes, things that feel stable. But early in her startup career, her founder CEO kept steering her away from over-engineering.
His advice was blunt: Focus on building. Process will come later. Christine pushed back (because… chaos). He didn’t flinch. Sometimes, he’d throw her into hard moments without warning, like difficult employee conversations, before she felt “ready.”
And that was the real lesson underneath all that stress. You don’t have to feel fully ready before you do the hard thing. Most of the time, you become ready by doing it, one uncomfortable moment at a time, instead of waiting for the perfect script. That’s the trade you’re making in a startup. You give up some comfort, but you grow faster than you thought you could. And it forces a question most people don’t ask early enough: Is this the kind of environment where I actually thrive?
Startup vs. Corporate: The Difference No One Puts on LinkedIn
Christine doesn’t romanticize startups. She actually warns people against the glossy version.
Social media makes startup life look “sexy”, focusing on the cool logos, big launches, fast promotions and the exciting rooms.
But the truth is a little messier:
- leaders roll up their sleeves
- hard skills matter
- delegation alone won’t save you
- and the pace will expose what you’re made of (for better and worse)
One of her strongest pieces of advice is simple, but uncomfortable: don’t lose your hard skills.
Whether you’re in HR, finance, engineering, or ops, keep sharpening your craft. Don’t drift into becoming “just a manager” who delegates and reviews. In a startup, titles matter far less than capability. If you cannot roll up your sleeves and actually build, you will feel exposed fast. Pure delegation without depth becomes a liability.
And to those thinking about making the leap, she’s equally direct.
“Talk to people who have actually done it.”
Not just the ones posting wins on LinkedIn. Ask about the messy parts. Then be honest with yourself about whether that kind of chaos energizes you or drains you.
The Caveat of Being Too Valued at Work
For many employees, being too beloved sounds like a dream; however, it’s not all compliments and statues built in your honour. Christine’s burnout did not come from being overlooked or underpaid. It came from being valued. From being the one people relied on most.
In high growth environments, strong performance gets rewarded with more responsibility. When you move fast, you are given more. When you deliver well, you become the dependable one. When you say yes enough times, your plate slowly becomes the place everyone else sets their priorities too.
She was chosen for leadership programs, pulled into bigger rooms, praised by the board. Every new opportunity felt like proof that she belonged. So she kept saying yes. Yes to the extra travel. Yes to the added scope. Yes to proving she could handle it.
Until her body forced her to stop.
The wake up call was physical and undeniable. It made her realize that pushing through was no longer a sign of strength. It was a sign that something had gone too far. The lesson was simple and uncomfortable. Your plate will never be full enough. There will always be more work. The world will not slow down just because you are tired. So, she changed how she operates. She prioritizes sleep. She pays attention to physical signals. She treats recovery as part of leadership, not something you earn after everything is done. This helped her build a new and sustainable level of success.
What She Was Really Chasing (And Why It Didn’t Work)
Christine also names something most high performers don’t admit out loud: ambition can become a moving target.
At first, she was trying to prove she could go beyond “just corporate.” Then it became about titles. Then money. Then the idea of an exit, the one thing she hadn’t achieved yet. Each milestone led to another. The finish line kept moving.
But when she paused and asked what would actually change after the next win, the answer felt empty. So she chose the one thing she hadn’t done. She built something for herself.
And almost immediately, she felt lighter. The constant on call panic was gone.
Now she leads with different questions. Is everything really urgent? Is everything actually on fire? Do people do their best work in permanent adrenaline?
Her answer is no.
The Quiet Truth About Hybrid and Remote
Near the end of the conversation, she drops an “under-the-table” reality leaders often admit privately:
Many founders want five days a week in the office, not because they don’t trust people, but because they don’t have visibility.
If a founder’s “team” is mostly the executive team, they don’t see the day-to-day energy of sales, finance, product, customer success. And when they can’t see it, they can’t feel confident it’s happening. So they default to: if I see it, I’ll believe it.
Christine also says something nuanced: She doesn’t think people are generally passionate about working from home all day. Humans are wired for real connection and energy changes in-person. But she also doesn’t argue for a blanket mandate.
Her real point is: pick a model and do it well. Hybrid can work, but only if it’s designed thoughtfully (ex: same in-office days so you’re not commuting just to sit on Zoom).
What Leaders Can Take From Christine’s Story
Christine’s journey isn’t a “quit your job and become a founder” story. It’s a story about alignment, with your personality, your pace, your values, and your definition of success.
Here are the through-lines that matter:
- Speed isn’t inherently toxic, but unmanaged speed is.
- Being valued doesn’t protect you from burnout. Without constraints, it can accelerate it.
- Startups reward builders.
- Ambition without boundaries turns into overextension.
- Culture isn’t engagement survey scores. It’s what people say behind closed doors.
Most importantly: Redefining ambition isn’t lowering the bar. It’s choosing a bar that doesn’t cost your health, relationships, or life outside work.
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