We were tired. That was the truth behind the spreadsheets, the backlog, the whispered “we need help” at 1:00 a.m. when a bug slipped through again and a client sent another email asking why their dashboard didn’t load. There’s a kind of fatigue that builds not just from the work itself, but from the weight of carrying too many roles in your head. Sales, product, onboarding, finance, investor updates, customer support—it’s not that each piece was impossible. It was that everything stacked, silently and without ceremony, until even the smallest task felt like another leak you were plugging with your bare hands.
That’s where we were when we made our first hire. Not from strategy. Not from systems readiness. From exhaustion.
We thought we were doing the right thing. We had just crossed a modest revenue milestone. We had three active clients and two more in the pipeline. Our tiny team—just the two of us, founders trying to hold it together—had survived product pivots and long beta feedback loops. Hiring someone felt like a graduation of sorts. We imagined onboarding a sharp, driven person who would pick up the pieces we kept dropping and magically give us time back.
What we didn’t say aloud, but quietly believed, was this: If we hired well, our lives would get easier. That belief was the beginning of our mistake.
We hired a generalist. Smart, curious, eager. Came recommended by a friend who worked in venture. She had energy, potential, and the kind of “I’ll figure it out” attitude we’d once admired in ourselves. On her first day, we gave her a Notion board that was barely functional. On day three, she was in customer calls with no prep. By the second week, we could feel it—something wasn’t clicking.
She wasn’t failing. We were.
Every time she made a small mistake, we found ourselves reviewing her work, doubling back on decisions, rewriting things we thought she would handle. We couldn’t understand why things weren’t just… working. After all, we’d hired the help we needed. Wasn’t that supposed to relieve the pressure?
But instead of feeling relieved, we felt more anxious. Instead of freeing us up, her presence slowed us down. We kept saying, “She’s not proactive enough,” or “Maybe she’s not the right fit.” But the truth was harsher: we hadn’t built anything for her to step into. No clear outcomes, no role boundaries, no systems to support her contribution. Just a swirling set of expectations and tasks that lived in our heads and Slack threads. She wasn’t guessing because she was incompetent. She was guessing because we hadn’t made anything visible.
The turning point came in week four. After another frustrating back-and-forth on a client deck, she asked for a one-on-one. I thought she wanted feedback. Instead, she asked a single, honest question: “Do you want me to own something—or just help you feel less overwhelmed?” I had no answer. Because I hadn’t thought that far. Because we hadn’t admitted the real reason we hired.
That moment stayed with me. It reframed the entire experience. We hadn’t hired to solve a scoped, structural problem. We’d hired from emotion. From overload. From the desperate hope that a good hire would fix the feelings we didn’t have time to face.
What followed wasn’t magical. It was slow, uncomfortable repair work. We sat down—not with her, but with ourselves. We asked what we were trying to solve. Not in terms of job titles or startup lingo, but in plain terms. What work needed to happen each week to deliver on our promise to clients? Where did it currently live? Who owned it? How repeatable was it?
It was humbling. We realized most of the work wasn’t designed for delegation. It relied on context, nuance, relationships, and decisions we’d never documented. We hadn’t built a company. We’d built ourselves into a wall of responsibilities, and hiring someone just handed them a blindfold and told them to find the door.
Eventually, we redefined the role—not as “ops,” but as a structured set of outcomes tied to customer onboarding and support response time. We created a Monday check-in rhythm. We assigned ownership by deliverable, not by task. She knew what success looked like. She knew where her judgment was expected. We gave her permission to push back—and she did. Within two months, she was shipping faster than us.
But we had to earn that. And most founders don’t. They hire too early, too vaguely, and too optimistically. They confuse the pain of being stretched thin with the clarity of needing someone else. The two are not the same.
Hiring is not a signal of growth. It’s a test of readiness. It asks whether you’ve clarified the work, built systems that allow others to contribute, and emotionally detached from needing to be at the center of every decision.
When we coach early-stage founders now, especially in Southeast Asia where the pressure to “build a team” often overrides the need for lean systems, I tell them this story. Not because it’s unique, but because it’s common. We all think we’ll be the exception—that our gut feel and founder instinct will carry us through. That smart people figure it out. But even smart people drown in messy systems and unspoken expectations.
What founders need to ask before they hire isn’t “Can I afford it?” or “What’s the job title?” The question is deeper: What is the work that needs to happen? Is it repeatable? Does it require judgment or just execution? Would I trust this person to say no to me if I was wrong about what mattered?
If the answers are fuzzy, don’t hire. If you’re not ready to hand off outcomes, not just tasks, don’t hire. If your biggest motivation is exhaustion, don’t hire. Fix your system. Audit your time. Say no to work that doesn’t compound. Automate what can be automated. Outsource what doesn’t need internal care. Then, and only then, bring someone in to own what remains.
Because hiring isn’t leverage until it’s structured. Until then, it’s liability.
Looking back, I don’t regret the hire. I regret our lack of clarity. We were lucky—she was patient, curious, and eventually thrived. But many early hires don’t. They churn, quietly. They become expensive line items with low ROI. And founders blame them for not “getting it,” when the truth is, we never built it for them to get in the first place.
We need to talk more honestly about this. Not just in accelerator panels or glossy founder posts, but in the quiet moments of doubt when you’re staring at an empty Asana board and wondering why your new hire isn’t “moving fast.”
Maybe they are. Maybe you just haven’t built the map yet.
If I could go back to that moment—before the job post, before the interviews, before the chaos—I’d sit down and draw the system. I’d name the work. I’d label what needed to happen, by when, and what good looked like. I’d ask myself if I could leave for two weeks and trust someone to carry that part forward. If not, I’d delay. I’d refine. I’d respect the hire enough not to hand them fog and hope they find the shore.
Growth is not a headcount. It’s clarity. And your first hire isn’t a solution. It’s a mirror. Whatever you haven’t fixed, they’ll feel. Whatever you haven’t defined, they’ll trip over. Whatever you haven’t let go of, they’ll orbit around until you burn them out—or yourself.
So to grow or not to grow?
The answer lives in your systems. Not your inbox. Not your bank account. Not your pitch deck. If the system is ready to receive help, growth through hiring can be beautiful. If not, it’s just another version of stuck—only now you’re dragging someone else into it. Be honest. Be specific. And when you hire, hire for ownership. Not for relief. Because if you build it right, they’ll give you more than time. They’ll give you back the space to lead.
And that, more than anything else, is what your business needs.
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