I missed my newsletter deadline last week.
Not by a few hours. By days. And honestly, it bothered me not just because I let you down, but more because I knew exactly why it happened; I didn’t have the right systems in place to ensure this newsletter ships no matter what.
The last two weeks I’ve been traveling. Building relationships, connecting with founders, working on the business. Productive work. Important work. But travel that revealed a structural flaw I’d been ignoring: my current setup wasn’t sustainable. I got the warning flag two weeks ago. I kept moving anyway.
Then the deadline broke.
This is operational debt in real time. The systems that worked when you’re in the office every day stop working when you’re not. The processes that function when you have a margin collapse when you don’t. And here’s the part that stings– even though I teach this stuff, I still got caught.
So instead of making excuses, let’s break down what actually happened, what I’m fixing, and how you can audit your own business for the same vulnerabilities. Because if this can happen to someone whose entire business is based on helping founders avoid operational debt, it’s definitely happening in your company too.
People: The “What If I’m Not Available” Test
I had the right people in place. I write, my wife edits. I source ideas from conversations with founders in my ecosystem. On paper, the people side looked fine.
But here’s what I didn’t have: a backup plan for when those people weren’t available. What happens if my wife is traveling? What happens if I’m in back-to-back meetings for three days straight? What happens when the normal hand-offs don’t happen?
The “what if I’m not available” test is brutal but necessary. Walk through your critical workflows and ask: if the person who typically does this were to disappear for two weeks, what would break? Not “what slows down”, what actually stops?
For most founders at your stage, the answer is uncomfortable. You’re the single point of failure in three to five critical processes. Your head of sales is the only person who can close deals over $50K. Your lead developer is the only one who understands the core architecture. Your operations person is the only one who knows how client onboarding actually works.
This isn’t a talent problem. It’s a structure problem.
Here’s what I’m doing differently. I’m bringing in additional marketing support to create another layer of redundancy. Not because the current person isn’t capable, but because capable people get sick, take vacations, have emergencies, or simply need to focus elsewhere for a week.
The fix isn’t “hire more people.” The fix is building a structure that assumes interruption as the default state, not the exception.
Try This Week: Map your three most critical business processes. For each one, identify the single point of failure. If that person was unavailable for two weeks starting Monday, what’s your backup plan? If the answer is “there isn’t one,” that’s your glass bowl; the thing that will shatter and damage your business when it breaks.
Process: Batching Work So Systems Run Without You
On the process side, here’s what broke: I was operating on a just-in-time production model. Write the newsletter Sunday night, edit Monday, ship Tuesday morning. That works until Sunday night gets swallowed by airport delays, or Monday morning gets consumed by client emergencies.
Just-in-time works in manufacturing with tight controls and predictable inputs. It doesn’t work in knowledge work with variable schedules and competing priorities.
I’m switching to batch production. Six newsletter topics researched and outlined at once. Content created in clusters, not one-offs. The system runs on a buffer, not on my availability in any given week. When I’m traveling, the machine keeps running because the work was done two weeks ago.
This applies everywhere in your business. Your sales team shouldn’t be creating proposals from scratch for every deal—you should have a proposal library that gets customized, not built. Your customer success team shouldn’t be figuring out onboarding on the fly—you should have a documented playbook that gets executed, not invented. Your product team shouldn’t be debating prioritization in every sprint planning—you should have a framework that guides decisions, not endless discussions.
I’m also re-leveraging automation tools to source and research newsletter topics that my audience actually cares about. Using Gumloop to track patterns in founder questions, engagement on past editions, and emerging themes in the ecosystem. The research happens automatically. I just synthesize and write.
Here’s the pattern you’re looking for: any work you do more than twice should have a documented process. Any process you execute more than five times should have automation supporting it. And any critical output should have enough buffer that you’re not scrambling when life interrupts the schedule.
Try This Week: Identify one recurring deliverable in your business: client reports, sales proposals, product updates, or investor communications. How much lead time do you currently have between “starting work” and “deadline”? If it’s less than one week, you’re operating just-in-time and vulnerable to any disruption. Build a two-week buffer by batching the next month’s work this week.
Data: What Your Patterns Tell You Before Things Break
Looking back at my newsletter analytics, the warning signs were there. I just didn’t have a system to surface them before the crisis hit.
Engagement was highest on editions published between 8-9 AM EST on Tuesday mornings. My personal energy and writing quality were highest when I wrote Thursday-Friday and edited Monday. But my actual publishing pattern had drifted to last-minute Sunday-Monday work with Tuesday morning pushes.
The data showed I was operating outside my optimal window. I ignored it because “it was still working.” Until it wasn’t.
This is exactly what happens in your business. The data tells you things are drifting before they break. Sales cycle length is creeping up. Close rates are declining. Customer support tickets are increasing. Team velocity is slowing. Your finance team is asking for information later and later in the month-end close process.
None of these is a crisis yet. They’re leading indicators. And most founders don’t have systems to surface them until they’ve already become problems.
I’m now tracking not just engagement metrics on published editions, but also production metrics on my creation process. How much founder time goes into each edition? Where do bottlenecks occur? When do I hit my writing flow state versus when do I struggle? What topics generate the most audience questions and follow-up conversations?
The goal isn’t perfect data. It’s enough signal to see patterns before they become problems.
Try This Week: Pick one critical metric in your business: sales cycle length, support ticket volume, time-to-hire, or product deployment frequency. Pull the last six months of data. Calculate the trend line. If it’s moving in the wrong direction by more than 15%, you have a structural issue forming that hasn’t yet become a crisis. Don’t wait for it to break. Address it this week while you still have options.
Tonio’s Corner: Glass Bowls vs. Rubber Bowls
Crisis is part of life. Systems fail. People get sick. Priorities shift. Markets change. Investors ask for updates at inconvenient times. Key employees resign. Suppliers miss deadlines.
When things fail, you have two choices. You can collapse into crisis mode and make it everyone’s problem. Or you can treat it as a forcing function to build better systems so you don’t replicate the same vulnerability twice.
But here’s the distinction that actually matters: you need to know what in your business is a glass bowl versus a rubber bowl.
Glass bowls run your business. If they break, you have real damage—lost revenue, broken client relationships, team attrition, and competitive disadvantage. Your core product quality is a glass bowl. Your payroll system is a glass bowl. Your key client relationships are glass bowls.
Rubber bowls can be picked back up. If they drop, you start over, but the business keeps running. My newsletter deadline was a rubber bowl. Embarrassing, yes. Damaging to my credibility, maybe slightly. But not business-ending. I can recover. I can rebuild trust. The system keeps running.
Most founders treat everything like a glass bowl. Every deadline becomes a crisis. Every small failure feels catastrophic. They operate in constant emergency mode, meaning they never build systems that would prevent actual emergencies.
Other founders treat everything like a rubber bowl. They drop commitments casually because “we’re a startup, we move fast, things break.” But some things shouldn’t break—and when they do, the damage compounds.
Know the difference. Protect your glass bowls with redundancy, documentation, and backup plans. Be willing to drop your rubber bowls when necessary to preserve what actually matters.
My newsletter was late. That’s a rubber bowl. But the operational debt it revealed—the lack of backup systems, the just-in-time production model, the missing early warning indicators—those were glass bowls forming cracks. I’m fixing those now, before they shatter.
What’s cracking in your business that you’re ignoring because it hasn’t broken yet?
What did this bring up for you? Hit reply and let me know what systems in your business are running on hope instead of structure.