Why Planning Less and Executing More Is Where the Real Learning (and Growth) Happens

As solopreneurs, we often find ourselves drowning in plans, strategies, and “next steps.” We research, analyze, and tweak our business ideas until we think everything is perfect. But in reality, while planning is important (at least a high level plan), it’s the execution that actually teaches us the most valuable lessons.

The truth is that no amount of planning will prepare you for the unpredictable challenges of running a business. It’s when you get out there and start doing the work that the real learning and growth happen.

Here’s why planning less and executing more can transform your business—and your mindset—as a solopreneur.

1. Plans Never Survive Contact with Reality

As much as we love the idea of having a perfectly structured business plan, the reality is that things rarely go according to plan. The market shifts, customer needs change, and new opportunities pop up when you least expect them. The more time you spend planning, the more you risk being paralyzed by the fear of making the "perfect" plan.

When you start executing, you quickly realize that the best way to learn is by adapting in real-time. The beauty of execution is that it forces you to face the reality of your ideas. It helps you identify flaws, improve strategies, and tweak your approach based on actual feedback (not assumptions).

Example:
Imagine you’ve spent weeks developing a detailed marketing strategy. You’ve planned out every post, ad, and campaign. But when you finally execute the plan, you discover that your target audience responds much better to a different style of content. This lesson wouldn’t have been learned by planning; it was only through execution that you learned what works best for your audience.

2. Failure Is the Best Teacher

In business, failure is inevitable. But that doesn’t mean it’s a bad thing. In fact, failure is one of the most valuable learning experiences you can have. The more you plan, the more you try to avoid failure by getting everything "just right." But no plan is perfect, and no business venture is without mistakes.

By executing quickly, you allow yourself to fail fast and recover faster. When you take action and make mistakes, you gain real insight into what works and what doesn’t. These lessons are far more useful than endless hours of planning. Each failure offers data that you can use to pivot, improve, and refine your approach.

Example:
Let’s say you launch a new product with high expectations. However, it doesn’t sell as well as you thought. Instead of blaming yourself, you analyze what went wrong—maybe the pricing was off, or the marketing didn’t speak to the right audience. This real-world feedback will inform your next product launch, allowing you to improve based on actual results, not theoretical plans.

3. Action Builds Momentum

Momentum is key when it comes to growing your business, and execution is what creates it. The more you take action, the more momentum you build. Planning can give you direction, but it’s the constant execution that propels you forward. When you execute more, you also start to experience the positive side effects of momentum—things start moving faster, you become more confident, and new opportunities open up.

You might spend hours researching a niche, only to find that the real market for your product is in an entirely different area. Execution gets you out there and into the market, where the real momentum begins. Action leads to progress, and progress leads to results.

Example:
If you’re a coach, you might spend months planning out your perfect program. But what you don’t know is how your audience will respond to the actual content. As you start delivering sessions, you get immediate feedback. You tweak your program based on client reactions, and before you know it, your offering has evolved into something much more valuable and effective.

4. Execution Forces You to Focus on What Matters

Planning often gets us caught up in the small details—the aesthetics of a website, the perfect product packaging, the most effective email sequence. While these things matter, they don’t move the needle in the same way that actual execution does.

When you focus on executing, you’re forced to prioritize what really matters—client relationships, generating revenue, solving problems, and creating value. It’s easy to get lost in the weeds of planning, but execution is about focusing on the bigger picture and taking the steps necessary to make progress.

Example:
As a solopreneur, you might spend weeks tweaking the perfect brand colors or obsessing over the design of your business cards. But in the meantime, you’re not actually selling your services or building client relationships. By executing more and spending less time on the details, you focus on the activities that generate real income and growth.

5. Execution Builds Confidence

Confidence is built by doing, not by overthinking. Every time you take action, you gain a little more confidence. The more you execute, the more you trust yourself and your abilities. This is essential for solopreneurs, as confidence is a key driver of success. It allows you to take risks, make decisions, and move forward, even when things are uncertain.

Planning can sometimes lead to analysis paralysis, where you feel stuck because you’re trying to anticipate every possible scenario. But once you take that first step—whether it’s launching a marketing campaign, signing a new client, or creating your first product—you’ll quickly find that you learn, adapt, and grow as you go.

Example:
When I first started my consulting business, I spent a lot of time planning my offerings, trying to perfect everything before launching. But once I started executing, things began to fall into place. The more I put myself out there—whether through client calls, content creation, or sales—my confidence grew. Each small success built on the last, and before I knew it, I had a thriving business.

Final Thoughts: The Real Learning Happens When You Execute

In the end, execution is where the real learning happens. It’s where you encounter challenges, gain insights, and build momentum. While planning is important, it’s the act of doing that leads to growth. When you execute more and plan less, you open yourself up to the valuable lessons that can only come from real-world experience.

If you’re ready to stop overthinking and start executing, I highly recommend checking out my article on the Pomodoro Effect—a simple productivity technique that can help you stay focused and execute more effectively.

Click here to read the article and start taking action today!