Working On vs Working In
Every founder faces the same puzzle every morning: Should they write code or hire developers? Close deals or build sales systems? Fix customer problems or create processes so problems don't happen? The business needs them to work in it right now. But it also needs them to work on it for tomorrow. Getting this balance wrong kills more startups than competition does.
The Daily Reality No One Talks About
Working in the business means doing the actual work—writing code, talking to customers, shipping products. Working on the business means building systems, hiring people, creating processes. Both feel productive. Both are productive. But they're completely different types of work.
Most founders default to working in the business. It feels more real. There's immediate feedback. A feature ships. A customer is happy. A problem gets solved. The progress is visible.
Working on the business feels abstract. Writing a hiring process doesn't feel as satisfying as closing a deal. Creating documentation seems less important than fixing bugs. Building culture appears less urgent than building features.
But here's what happens: founders who only work in the business become the ceiling. The company can't grow beyond their personal capacity to do work. They're not building a company—they're creating a job for themselves.
Why Choosing What to Work On Is So Hard
Every task seems important because, honestly, most of them are. The product needs to be better. Customers need support. The team needs leadership. Investors need updates. Everything is on fire and everything needs attention.
The temptation is to do a little of everything. An hour on product, an hour on hiring, an hour on sales. But context switching kills productivity. By the time someone gets deep into one type of work, it's time to switch to another.
There's also the comfort trap. Engineers want to keep coding. Salespeople want to keep selling. It's what they know. It's what they're good at. But if the business needs systems more than code, or operations more than sales, staying comfortable means staying stuck.
When Hands-On Work Makes Sense
Sometimes being in the weeds is exactly right. When quality is slipping, founders need to see it firsthand. When customers are unhappy, founders need to hear it directly. When the product is breaking, founders need to understand why.
This isn't micromanagement—it's information gathering. The details teach what the reports can't. The customer conversation reveals what the survey misses. The code review shows what the metrics hide.
Early-stage companies especially need founders in the business. With five people, there's no one else to do the work. With ten people, founders often still need to fill gaps. The business needs builders more than managers.
But there's a trap here. Founders get addicted to being needed. Every problem comes to them. Every decision waits for them. They become the bottleneck they were trying to avoid.
When Building Systems Matters More
At some point, doing the work becomes less valuable than enabling others to do the work. This shift is hard because it feels like stepping back when the instinct is to push forward.
Building systems means creating repeatability. Instead of answering every customer email, create templates and guidelines so others can answer them. Instead of making every product decision, establish principles that guide decisions. Instead of closing every deal, build a sales process others can follow.
This work is slower at first. Training someone takes longer than doing it yourself. Writing documentation feels pointless when you could just fix the problem. Creating process seems like bureaucracy when you could just ship.
But systems compound. The first customer service rep takes weeks to train. The second takes days. The tenth takes hours. Eventually, great customer service happens without founder involvement.
The Calendar Never Lies
A founder's calendar shows their real priorities. Back-to-back customer calls means they're stuck in sales. All-day coding sessions means they're avoiding leadership. Endless meetings means they're probably doing neither type of work effectively.
The ideal calendar has blocks for both. Maybe mornings are for strategic work—planning, hiring, system building. Afternoons for tactical work—product reviews, customer calls, problem-solving. Or maybe it's different days for different types of work.
Without intentional scheduling, the urgent always wins. The customer complaint gets answered. The bug gets fixed. The investor gets updated. Meanwhile, the important but non-urgent work—building culture, creating systems, developing strategy—never happens.
Signs the Balance Is Off
When founders only work in the business: Every vacation becomes a crisis. Every sick day creates backlog. Growth stalls because there aren't enough hours in their day. The team can't make decisions without them. They're exhausted but the business isn't progressing.
When founders only work on the business: Quality drops because no one who cares deeply is watching. Strategy becomes disconnected from reality. The team feels abandoned. Plans multiply but nothing ships. They have a perfect org chart but a failing product.
The sweet spot is being involved enough to understand but not so involved that nothing happens without you.
The Evolution Is Messy
The balance changes constantly. A product crisis might require a founder to code for a week straight. A hiring push might mean doing nothing but interviews. A fundraise might consume months of strategic work.
This isn't failure—it's adaptation. The business needs different things at different times. The skill is recognizing what it needs now, not following a rigid formula.
Some days the business needs a founder who ships code. Other days it needs a founder who ships org charts. Most days it needs both, in different proportions.
A Framework That Actually Helps
Instead of complex rules, try this simple question: "What happens if I don't do this?"
If the answer is "someone else does it slightly worse," then delegate and move on. If the answer is "no one can do it" or "the business fails," then do it yourself.
This creates natural priorities:
- Setting vision? Only founders can do that.
- Processing invoices? Anyone can learn that.
- Defining culture? That's founder territory.
- Managing social media? Definitely delegatable.
- First big customer deal? Probably needs the founder.
- Fiftieth similar deal? Sales team can handle it.
The Daily Choice
Every morning brings the same decision. Spend the day in the engine room making things work, or in the bridge charting the course? Both matter. Neither is sufficient alone.
The answer changes based on what's breaking, what's working, and what's needed next. There's no permanent solution, only today's best guess based on the current situation.
Some founders create structure to help. Maybe they dedicate certain hours to strategic work when their energy is highest. Maybe they batch similar activities to reduce context switching. Maybe they alternate between deep work days and meeting days.
Making It Work
The founders who succeed don't find perfect balance—they find workable rhythms. They know when to dive deep and when to stay high-level. They sense when the business needs their hands versus when it needs their head.
This isn't about following someone else's playbook. It's about developing an instinct for what the business needs from its founder today. Sometimes that's code. Sometimes that's culture. Sometimes it's customer calls. Sometimes it's strategic planning.
The magic isn't in getting it right every day. It's in adjusting quickly when the balance is off. It's in recognizing when working harder in the business won't solve what working on the business could fix.
Both types of work matter. The business needs someone building it and someone building the thing that builds it. When you're the founder, you're both people. The trick is knowing which one to be when.