As an entrepreneur, have you ever been stuck on a task and just couldn’t figure out why you couldn’t push through? Maybe you’ve found yourself procrastinating on a big project or constantly feeling overwhelmed by your to-do list. Sound familiar? Well, there’s a simple yet powerful tool that can help you get to the root cause of these roadblocks: asking “Why?”
And no, I don’t mean just once. I mean asking it over and over—five times, to be exact.
In this article, we’ll dive into two critical “Whys” that every entrepreneur should understand: the 5 Whys to get to the root of any problem, and the bigger Why, which is your core purpose and motivation for doing what you do. Together, these Whys will help you clear mental roadblocks, gain clarity, and make smarter decisions. Trust me—learning how to ask “Why” will change the way you approach your business!
The 5 Whys: Your Secret Weapon for Problem-Solving
The 5 Whys method is a technique first used by Toyota to uncover the root cause of problems quickly and efficiently. Here’s how it works: when you hit a roadblock, ask yourself “Why?” five times. Each answer peels away a layer, bringing you closer to the actual cause of the problem—not just the surface-level symptoms.
Here’s a real-life example:
Imagine you’re constantly falling behind on responding to client emails, and it’s starting to affect your relationships.
1. Why am I falling behind on client emails?
“Because I feel overwhelmed by the volume of messages I get daily.”
2. Why do I feel overwhelmed by the volume of messages?
“Because I don’t have a structured approach to managing my inbox.”
3. Why haven’t I implemented a structured approach?
“Because I believe I need to respond to each email as soon as it comes in.”
4. Why do I feel like I have to respond immediately?
“Because I worry clients might think I’m not committed if I don’t reply right away.”
5. Why am I worried about clients perceiving me that way?
“Because I equate constant availability with excellent service.”
The issue isn’t just the number of emails—it’s the fear of losing client trust by not being available 24/7. This belief is causing unnecessary stress and preventing you from creating a manageable system.
Once you realize that your response time isn’t the only way to show commitment, you might find a sustainable approach, like setting specific times for email responses and letting clients know when they can expect to hear from you. This respects both your time and theirs, keeping you efficient and building stronger boundaries.
Another example:
Let’s say you keep putting off writing that blog post for your business (you know, the one you’ve been meaning to finish for weeks).
1. Why haven’t I written the blog post yet?
“Because I’ve been busy with other tasks.”
2. Why am I so busy with other tasks?
“Because I didn’t prioritize my day properly.”
3. Why didn’t I prioritize my day properly?
“Because I felt overwhelmed by how much I had to do.”
4. Why do I feel overwhelmed?
“Because I haven’t set clear boundaries for my work hours.”
5. Why haven’t I set clear boundaries?
“Because I’m afraid of missing out on opportunities if I don’t work non-stop.”
Boom! The real problem isn’t that you’re just “busy.” The root cause is that you haven’t established boundaries, leading to burnout and, ultimately, procrastination. Once you identify that, you can focus on addressing the real issue and create a sustainable solution.
Alternatively, you may realize you’re putting off the blog because it doesn’t feel urgent or connected to your main work of helping clients. This relates to the bigger Purpose or Why, which we’ll dive into next. By aligning your tasks with your deeper Why, you’ll focus your energy on what truly matters.
Why This Technique Works for Entrepreneurs
As entrepreneurs and freelancers, we’re constantly solving problems—but too often, we’re addressing symptoms rather than causes. When you ask “Why?” repeatedly, it forces you to go deeper, uncovering the real challenges blocking your progress.
For example, I used to find myself frustrated when I couldn’t push past a task (I still do sometimes…). But once I started using the 5 Whys technique, I realized that many of my blocks came from perfectionism. Identifying the root cause helped me shift my focus to building self-confidence and accepting that progress is more important than perfection.
The beauty of this method is that it’s simple, quick, and doesn’t require fancy tools. Just you, your questions, and a willingness to be honest with yourself.
The Bigger Why: Your Purpose as an Entrepreneur
Now that we’ve covered the 5 Whys for problem-solving, let’s dive into the bigger Why: your purpose. This Why is your driving force—the reason you started your business in the first place.
In his famous book “Start With Why,” Simon Sinek talks about how knowing your Why can transform your business. People don’t just buy what you do—they buy why you do it. When you’re crystal clear on your Why, it becomes easier to stay motivated, make decisions, and attract clients who resonate with your mission.
While understanding your purpose is vital, it’s equally important to ensure your goals align with that bigger Why, and that your daily tasks support those goals. It’s one thing to know your purpose—like “Save live with this medical device”—but setting clear, specific goals, such as “Get funded by end of year,” is another. If your goals don’t align with your purpose, and your daily tasks don’t support your goals, you’re likely to encounter obstacles.
When your goals are in sync with your purpose, prioritizing becomes easier. Ask yourself, “Why is this goal/task important?” If it reinforces your broader Why, it’s worth pursuing.
How Understanding Your Why Can Boost Your Productivity
Whenever you hit a block or find yourself questioning your next step, come back to your Whys. This bigger purpose or goal will help you refocus on what matters. It also gives you clarity on which tasks deserve your attention and which ones are distractions.
Let’s say you’re overwhelmed with tasks, and you’re not sure where to start. If you know your Why, you can evaluate each task based on how it aligns with your core purpose and your main goal. This makes prioritization much easier.
Combining Both Whys to Overcome Entrepreneurial Blocks
Now, imagine combining both of these Whys—the 5 Whys for problem-solving and the bigger Why as your purpose. This powerful duo helps you tackle problems with a deeper understanding and clarity.
For example, if you’re struggling to hit a business goal, start with the 5 Whys to figure out what’s really stopping you. Then, revisit your bigger Why to see if the goal you’re chasing actually aligns with your long-term purpose. If it does, great! You’ll know how to adjust your strategy. If it doesn’t, you can pivot to a more meaningful goal.
When you pair these two approaches, you can clear out the clutter and focus on what truly matters.
Practical Tips for Implementing ‘The Whys’ in Your Business
Tip 1: Ask the 5 Whys whenever you feel blocked.
Take a few minutes to dig deep into the problem instead of jumping straight to action. Write down your answers to gain clarity.
Tip 2: Revisit your Why regularly.
Whether it’s every quarter or when you’re about to make a major decision, remind yourself why you started your business. Use this as a guide to prioritize and delegate.
Tip 3: Be mindful of over-committing.
It’s tempting to take on too much, especially when we’re driven by passion. But as we discussed in my previous article on setting mindful expectations, understanding your Why helps you set more realistic goals and avoid burnout.
Conclusion: It All Comes Back to Asking Why
Asking “Why?” might seem simple, but it’s one of the most powerful tools you can use as an entrepreneur. Whether you’re tackling a problem with the 5 Whys technique or reconnecting with your bigger purpose, taking the time to reflect and assess will help you stay focused and avoid overwhelm.
It’s not about being less ambitious—it’s about working smarter. When you ask the right Whys, you’ll be able to make better decisions, prioritize more effectively, and build a business that aligns with your values and vision.
So, the next time you feel blocked or unsure of your next step, take a moment to ask yourself: “Why?” You might be surprised at what you discover!
Found this article helpful? Share it with fellow entrepreneurs/freelancer friends or drop your thoughts in the comments. Let’s support each other on this journey toward more mindful and purposeful entrepreneurship!