I’m guilty of this more times than I can count—and I’ve seen countless other entrepreneurs fall into the same trap. You find something that works in your business—whether it’s a marketing channel, product, customer type, or sales strategy—and instead of doubling down, your first instinct is to go searching for the next thing. The next marketing channel. The next product. The next customer segment. The next sales strategy.
Entrepreneurs, myself included, love solving problems. And when something is finally working, it doesn’t feel like a problem anymore. That’s exactly when it’s best to allocate your time and resources to figuring out how to double down. Unfortunately, most entrepreneurs—driven by the itch to solve the “next problem”—see the challenge as finding the next big thing, not scaling the thing right in front of them.
One analogy I use often is drilling for oil. Imagine you’re not an entrepreneur, but an oil explorer. You’ve spent months—even years—drilling test wells all over the place. Finally, you strike oil. Success! But here’s the irony: the natural inclination for most entrepreneurs, myself included, is to immediately start scouting for the next drilling site.
That might make sense if you’re Shell (most recent market cap: $214.73 billion USD) and have virtually unlimited resources. Shell can drill one well and simultaneously look for the next one. But here’s the truth: you’re not Shell. You don’t have their resources. Chances are, you’re operating with limited—sometimes very limited—resources, which means they have to be deployed with precision.
Think of yourself as a cash-strapped oil explorer, not Shell. The rational move isn’t to chase the next oil patch—it’s to drill, baby, drill on the one you’ve already found. Max it out. Spend 24/7 extracting as much as possible from that well until it’s bone dry. Only when it’s completely tapped—which might take years, even decades—should you move on to the next site.
Yet in business, as soon as something starts working—a marketing channel, product, customer type, or sales strategy—we often abandon it and chase the next big score. The smarter move, especially when resources are scarce, is to double or triple down on what’s already working. Squeeze every drop out of that channel, product, customer type, or sales strategy before spending resources on the next thing.
When something starts working, it’s almost impossible to rewire the natural inclination of an entrepreneur to go solve the “next problem.” That’s why you have to constantly remind yourself: the best use of your time and capital isn’t solving for “what could work next”—it’s solving for “how do we double down on what’s already working?”
Here’s the catch: doubling down is boring. Entrepreneurs—myself included—like solving problems. The bigger the problem, the more exciting it feels. I’ve seen it over and over: when I tell entrepreneurs to double down on what’s working, their shoulders slump like I just told them their dog died. It doesn’t feel like a “real problem” to solve.
If that’s your reaction, you’re probably a little psycho—the exact kind of entrepreneur who needs this advice most. And if that’s you, here’s your challenge: don’t just double what’s working. 10X it. Make the problem, “How do we scale this thing tenfold?” That’s a meaty enough challenge for even the most restless, problem-obsessed founder.
And if you’re the type who finds 2X daunting, you may actually benefit from the book _[10X Is Easier Than 2X]()_. While the truly psycho entrepreneurs might need professional help, the book argues that thinking in 10X increments is often easier than 2X. Why? Because 2X improvements are incremental—you can usually get there by tweaking the existing system. But 10X forces you to think outside the system. It pushes you to break constraints, question assumptions, and reimagine how your business, your thinking, and even your industry actually work.
## **Hypothetical Examples**
### **Marketing**
After years of throwing money at every marketing channel known to man, you finally notice your YouTube videos are driving a significant number of leads. It’s working. Most entrepreneurs at this point try to solve the wrong problem—“What’s the next channel as good as, or better than, YouTube?” That’s not the right problem. The problem you should be solving is: how do we double down on YouTube? If you’re producing two videos a month, how can you produce four? If your thumbnails are good, how can they be world-class? If your videos are good, how can they be excellent? And if doubling down isn’t enough for you, how do you 10X it? For example, how can you produce twenty videos a month, not just two?
### **Product**
After years of searching for product–market fit, your wiz-bang spatula is finally getting traction. Customers love it. Most entrepreneurs at this point jump to the next problem: “What’s the next product for our kitchen collection that will be as good—or better—than the spatula?” Wrong problem. The right question is: how do we double down on the spatula? If you’re currently selling $200,000 worth, how can you sell $400,000? And if that doesn’t scratch your entrepreneurial itch, how do you 10X it? What would it take to sell $2,000,000 worth of spatulas instead of $200,000?
### **Sales**
You’ve tried everything to move product, and you’re starting to realize cold calling works. Most entrepreneurs now go hunting for the next sales strategy. Wrong move. The right problem is: how do we double down on cold calling? If your salespeople are making 100 calls a day, can they make 200? If not, can you hire twice as many salespeople? Can you improve scripts for better conversions, install software to speed up dialing, or record calls and use AI to optimize the process? And if doubling down isn’t enough, how do you 10X? Instead of two salespeople making cold calls, how do you get twenty salespeople calling by next week?
### **Customer**
You’ve been selling your water bottles to every segment under the sun. Sales have been “okay.” But then you notice teenage girls are buying like crazy—and they’re turning into superfans. At this point, most entrepreneurs go straight to the wrong problem: “What’s the next customer segment? Maybe teenage boys?” Wrong. The real problem to solve is: how do we double down on teenage girls? If you’ve sold 10,000 water bottles to that segment, how do you sell 20,000? And if that’s not enough, how do you 10X? What would it take to sell 100,000 instead of 10,000?
This last example highlights the most common pushback I hear when I tell entrepreneurs to “drill baby drill.” The reaction is usually: “We’ve extracted all we can from this market.” Looking back at the water bottle example, the founder might say they’ve already tapped out teenage girls—it’s saturated, done.
Any good business coach or advisor would call BS. That’s just the entrepreneur’s brain spinning a story to justify their urge to chase the next shiny object. If teenage girls are buying your product and you’ve sold 10,000 units, you haven’t tapped the market—you’ve barely scratched it.
According to ChatGPT, there are about 21 million teenage girls (ages 13–19) in the U.S. Selling 10,000 bottles means you’ve reached just 0.048% of them. Round that down, and you’ve hit basically 0%. And yet entrepreneurs convince themselves they’ve tapped out the market. That’s how crazy the entrepreneurial mind can be—always itching for the next challenge, even when sitting on an ocean of opportunity.
Here’s the truth: when you get to 20–30% market share, then we can talk about expansion. That’s 4–6 million teenage girls—not the 10,000 you’ve sold to so far. Until then, stop pretending you’ve tapped out the market. You haven’t. Drill deeper.
## **Two Actionable Steps**
**1) Look Back**
Think about what has worked well in the past. Did you fully capitalize on that opportunity, or is there still oil left in that well? If there’s more potential, go back and extract it. Stop wasting time and money chasing the next big score when the last one still has untapped value.
**2) Look Ahead**
Understand that your natural tendency as an entrepreneur is to chase new opportunities. When you hit something that works, resist the urge to move on too quickly. Keep drilling—don’t stop until you’ve squeezed every bit of value out of it. This is where a good coach or advisor can help cut through the story you’re telling yourself—that the well is dry—when in reality, it’s barely even tapped.
So before you shift your focus to something new, push your current strategy as far as it can possibly go. Recognize that your instinct will always be to seek the next shiny thing, but the real growth comes from removing roadblocks and doubling down on what’s already working. Experimentation is fine, but scaling success is what actually drives results.
In short: do more of what’s working before you look for what’s next. Drill, baby, drill.
Thanks for reading Student of the Game! Subscribe for free to receive new posts and support my work.
Subscribe