Why Founders Need to Tackle the Hardest Obstacles First

In the fast-paced world of startups, focusing on quick wins, feel-good moments, and easy tasks is tempting. But as your business grows, this mindset will hold you back. Astro Teller, the so-called “Captain of Moonshots” at X (formerly Google X), hit the nail on the head in this article with his metaphor of “teaching a monkey to recite Shakespeare.” The hardest part of any challenge is often avoided, and instead, we waste time building a pedestal for the monkey to stand on, celebrating progress that isn’t real.

It’s an approach that kills innovation and stifles true growth. And if you, as a founder, allow your team to avoid tackling real challenges head-on, you’re setting your company up for long-term failure.

I think of this like a higher level to Brian Tracy’s Eat That Frog, a time-management principle that stresses the importance of addressing the most challenging, impactful task first thing in the day—your “frog.” If you can “eat the frog” early on, the rest of the day feels easier, and your focus stays on what truly moves the needle. Tracy’s advice is crystal clear: Stop avoiding the hard stuff. In a scale up if you’re not confronting your biggest challenges, you’re just delaying your success.

In this post, we’ll explore why focusing on bottlenecks—not easy wins—drives meaningful progress, how embracing constraints leads to creativity, and why following a strategic framework like the Strategy-Bottleneck-Aspiration triad can make the difference between floundering in complexity and scaling efficiently.

Avoiding the Hard Stuff is a Trap

Whenever I speak to founders of rapidly growing startups, I notice the same trap: they’re spending too much time solving low-hanging fruit. They get stuck in a cycle of picking off easy tasks, thinking it’s progress. It’s not. The problem is simple—just like Teller’s metaphor, you’re spending your resources building a pedestal while ignoring the tough work that will truly move the needle.

This concept is backed by research from Maryam Kouchaki at Northwestern University’s Kellogg School of Management, which shows that people under pressure naturally gravitate toward easier tasks. It feels like progress, but in reality, it’s a distraction from addressing the real obstacles.

Think about your own leadership—how many times have you or your team chosen to tackle the easy wins because it feels more manageable? How often do you spend time on simple but non-essential tasks because they provide a temporary sense of control and progress?

In the study, doctors in a high-stress emergency room setting often chose less complex cases to manage their fatigue and workload. However, doctors who consistently took on the harder cases improved their skills and created greater value for the hospital over time. This is a powerful analogy for startup founders. If you keep choosing the “simple cases,” your growth and skills will stagnate.

The Strategy-Bottleneck-Aspiration Triad: A Formula for Growth

Peter Compo’s Strategy-Bottleneck-Aspiration (SBA) triad is a powerful tool for business leaders who want to drive real progress. The idea is simple but profound:

1. Aspiration – Define the future state or goal you want to achieve.
2. Bottleneck – Identify the primary constraint or obstacle preventing you from reaching that aspiration.
3. Strategy – Develop a focused strategy that addresses that bottleneck.

This framework forces you to confront the toughest challenges first. As Compo puts it, “If everything matters, then nothing matters.” Identifying and focusing on the bottleneck prevents yourself and your team from getting lost in the weeds. You ensure that every decision is oriented toward solving the most critical problems rather than just creating a false sense of progress.

For founders, the key takeaway is that you need to be ruthless about where your attention goes. Strategy shouldn’t be about everything; it should be about the bottlenecks. Mark Twain once said that if the first thing you do each morning is to eat a live frog, you can go through the day with the satisfaction of knowing that it is probably the worst thing that is going to happen to you all day long.

Rules and Constraints Drive Innovation

At first glance, rules and constraints may seem like they stifle creativity. But in reality, they are often the enablers of it. Richard Rumelt likens strategy rules to guardrails on a highway—they direct and constrain action without fully defining its content. These rules provide enough structure to ensure teams remain focused on what truly matters while allowing enough flexibility for innovation to happen within that framework.

Peter Compo calls this the “Parker Principle,” borrowing from the famous jazz musician Charlie Parker, who said, “Learn your horn. Learn the changes. Then forget them and just wail.” This is crucial advice for any growing company. Once you internalise the key strategic rules—your guiding constraints—you can give your team the freedom to innovate within them.

A perfect historical example of this is Henry Ford. His bottleneck was a lack of standardisation in automobile manufacturing. Ford’s strategy focused on eliminating this constraint, and his guiding rule was simple: “Never sacrifice throughput or cost for style or options.” By sticking to this guardrail, he revolutionised the industry with the assembly line, transforming car production and making the Model T a global success.

Breaking Through Bottlenecks: A Founder’s Challenge

For founders, breaking through bottlenecks requires discipline, focus, and a clear strategy. You need to ask yourself:

• What is the biggest obstacle standing between your company and its aspirations?
• Is your team spending too much time on easy wins, or are they tackling the real challenges head-on?
• Have you created the right constraints to guide innovation while preventing distractions?

It’s easy to get lost in the everyday busyness of running a fast-growing startup. However, the founders who succeed are those who can consistently focus on overcoming their most significant bottlenecks.

Constraints as Catalysts for Creativity

While many view constraints as roadblocks, they are often the key to unlocking innovation. Artists, musicians, and, yes, entrepreneurs all know this to be true. When there are no constraints, everything seems like a good idea, and focus is lost. But when there are clear limitations, we are forced to solve problems in new and creative ways.

As Henri Matisse famously said, “There is nothing more difficult for a truly creative painter than to paint a rose because before he can do so he has to first forget all the roses that were ever painted before.” The same applies to business leaders. Constraints force teams to focus on what truly matters; from this focus, real innovation is born.

So, What’s Your Monkey?

As a founder, your job isn’t to avoid challenges but to embrace them. Forget about building the pedestal—your focus should be on training the monkey. That’s where the real progress is made. Tackling the hardest problem first, busting the bottleneck, and focusing your strategy around overcoming constraints is what will separate your company from the competition.

Think of your monkey as the hardest, most impactful task on your to-do list — the thing that, if done, will significantly move your business forward. For founders, it’s about tackling those bottlenecks head-on. If you spend your time avoiding training your monkey and instead focus on easier tasks, you’re fooling yourself into thinking you’re making progress. Training your monkey means taking on the biggest challenge first because, to circle back to Brian Tracy, “if you do that early, the rest will be easier.”

If you want to build a company that doesn’t just grow but scales, you need to start by identifying your biggest challenges, embracing them, and designing a strategy that gets everyone focused on solving them.