The first time I took a real vacation, I came back convinced my company didn’t need me. And I mean that in the best possible way.
At the time, I was three years into running my second venture. Things were stable on the surface. Revenue was predictable, the team was functioning, and I was working longer hours than ever before. I told myself that I couldn't step away—not yet. That the next stage of growth was “just around the corner.” That the team still needed my approvals, my presence, my involvement.
But underneath that veneer of control, I was slowly burning through my sharpness. Decisions took longer. My leadership felt foggier. I was reactive when I used to be steady. It wasn't obvious to anyone else. But it was starting to leak. In how I responded to late-night Slack messages. In how easily I snapped when a launch timeline slipped. In the quiet sense that I was losing altitude without realizing it.
A founder friend forced my hand. She called me out—gently but firmly. “You’re managing, not leading. You’re running on habit, not intention.” I fought her on it. I argued that things would fall apart if I left. That the timing wasn’t right. That there was too much on the line. She didn’t back down. She booked a getaway for both of us. No laptops. No calls. No excuses. Just seven days in Langkawi, off-grid enough to make escape feel real.
That trip changed how I think about downtime. Not as an indulgence, but as a lever for operational clarity and personal restoration. And since then, I’ve told every founder I mentor the same thing: if you’re telling yourself you can’t take a break, you probably need one more than ever.
The mythology of the ever-present founder is strong, especially in Southeast Asia. Many of us grew up watching our parents hustle relentlessly. We carry that ethic into our startups. We see rest as the reward, not the requirement. And when our businesses begin to grow, we double down. We show up more, stay longer, reply faster. We convince ourselves that being irreplaceable is the goal. But the best founders I’ve seen aren’t the ones who are everywhere. They’re the ones who design companies that survive their absence.
When I finally stepped away, the cracks in our systems showed up almost immediately. A client issue that no one owned. A finance workflow I’d kept in my head. A team member who over-relied on my daily check-ins. But those weren’t signs that I was essential. They were signs that we were fragile. My constant presence had become a crutch. Removing it didn’t cause the weakness. It revealed it.
Coming back was humbling. Not because everything went wrong—some things did, most didn’t—but because I realized how much my team had grown in the space I gave them. Leaders stepped up. Processes evolved. And most importantly, I saw my own blind spots more clearly. I wasn’t just tired. I was carrying too much because I hadn’t taught the team how to carry it with me.
That’s the hidden truth most founders miss: taking a vacation is one of the best operational audits you’ll ever get. It shows you where trust hasn’t been built. Where ownership isn’t clear. Where your systems depend on your presence instead of functioning through process and culture. It’s not about rest versus work. It’s about interdependence versus bottleneck.
Since then, I’ve made founder vacations a mandatory topic in every early-stage coaching session I run. I ask blunt questions: What would break if you left for two weeks? Who would notice first? What systems would grind to a halt? The answers are always revealing. Some founders laugh it off—until I push harder. Others get defensive. “I’m not burned out.” “I’ll rest after fundraising.” “My team’s not ready.” But that’s the trap. We convince ourselves that the business depends on us, when in reality, it’s often being constrained by us.
The resistance is real, especially in cultures that still associate time off with weakness. In Malaysia, Singapore, and Saudi Arabia, I’ve seen founders skip holidays even when their teams are out of office. There’s a performative endurance that creeps in. As if the ability to keep showing up is proof of commitment. But building something sustainable means you have to model sustainability. If you don’t rest, your team doesn’t think they’re allowed to either. And when that fatigue compounds, it doesn’t just hit morale. It hits creativity, communication, and decision quality.
Some of the worst hiring and product decisions I ever made were in periods when I hadn’t stepped back. I said yes to things that didn’t align, just to move faster. I kept staff I should have transitioned out, because I didn’t have the perspective to see their misfit clearly. I greenlit a roadmap that looked good in a deck but broke in execution—all because I didn’t take a beat to recalibrate.
We talk a lot about founder resilience, but not enough about how rest fuels that resilience. It’s not just about sleep or spa days or switching off Slack. It’s about building internal spaciousness—room to think, to zoom out, to feel again. When you’ve been in constant output mode, even silence can feel uncomfortable. But it’s in that silence that insight starts to return.
One founder I coached in Riyadh resisted time off for over two years. His startup was growing, investors were happy, but he was brittle. Sharp in meetings, cold in one-on-ones, impatient with partners. His team didn’t say it out loud—but they were starting to disengage. I challenged him to take a proper break, no partial logins, no “just checking in” WhatsApps. He finally relented—ten days in Spain, no Wi-Fi for half of it.
When he came back, something shifted. He started asking better questions. He delegated differently. He held space in meetings instead of rushing through them. His team noticed. So did his board. The company didn’t magically transform overnight, but it moved with a different rhythm. One that wasn’t just founder-driven, but founder-anchored.
That’s the difference. A founder who’s always “on” becomes a bottleneck. A founder who knows when to step back becomes a multiplier.
If you’re reading this and still resisting the idea of taking a break, ask yourself this: what would happen if you disappeared for ten days? What would that reveal about your business? Your team? Yourself? If the answer terrifies you, that’s not a reason to avoid it. That’s a reason to start preparing for it.
You don’t have to go to Bali. You don’t have to turn it into a retreat. You don’t have to make it content for LinkedIn. But you do have to make it intentional. The kind of break that actually resets you. That lets your nervous system unclench. That reminds you who you are outside your pitch deck and your burn rate.
Because here’s the truth I wish someone had told me sooner: the founder your company needs next quarter is not the over-functioning version of you. It’s the one who came back different. Clearer. Calmer. Recentered.
Vacations aren’t just about rest. They’re about recalibration. They force you to confront where you’ve been compensating instead of delegating. Where you’ve been avoiding instead of deciding. Where you’ve been surviving instead of leading. That clarity is worth more than another sprint. And often, it’s what makes the next sprint possible.
So if you’re still treating rest like a luxury, stop. It’s part of the job. A real one. Not an optional perk. Not a reward for hitting milestones. A job requirement—just like reviewing financials, hiring a lead engineer, or fixing your churn problem.
Your future self—the one who makes better hires, builds a healthier team, sees around corners—that version of you is waiting on the other side of your first real break.
Go meet them.
And then bring that clarity back with you. Your business will thank you. And more importantly, so will you.
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