The Leader’s Conundrum


Have you ever asked yourself, "Why do I bother?" It’s a question that can creep up on you, especially when you're running a business alone.

The heartache, the stress, the anxiety—all for what? I know I’ve asked myself that same question.You push through every challenge and rise to meet every new day with a mixture of hope and dread. 

There’s this internal pressure to keep going, to be resilient, to not let things fall apart. But at what cost? 

You find yourself wondering, "What’s the point of it all?"Then comes the inevitable follow-up question: "Why do I even have staff?" Even if they’re great, having staff can feel like just another layer of complexity. 

Suddenly, it’s not just about managing your workload; it’s about being responsible for their well-being, their mistakes, their expectations.

Today, I want you to ask a different question: Who are you really doing this for?

The Real Conundrum: Why Are You Here?

When you run a business alone, you shoulder the weight of every decision, every success, and every failure. The sleepless nights, the juggling of multiple roles, the sense of isolation—it can be overwhelming. But what if the issue isn't so much about the weight you carry, but rather the purpose behind it?

At the core of the leader’s conundrum is a need to reconnect with your why—the deeper reason you started this journey. 

Was it to create freedom for yourself? 

To make a difference in the lives of others? 

To build something meaningful? 

In the grind of day-to-day business operations, it’s easy to lose sight of this.

Reframing the Stress

Often, stress stems from a feeling that we’ve lost control. You manage endless tasks, solve problems that weren’t on your radar, and deal with external pressures. But if you take a step back, you’ll see that stress also comes from a disconnect between your actions and your core purpose. 

When you lose touch with that deeper purpose, everything starts to feel like an uphill battle.

What if instead of focusing on what’s going wrong, you focus on what’s driving you? 

What if you allowed your why to be the compass guiding you through challenges, rather than letting stress lead the way?

Here’s how you can start reconnecting with your core purpose:

1. Reflect on Why You Started

Take a moment to remember the early days of your business. What inspired you to start? Was it a desire for independence? A passion for a particular craft or service? A vision for changing an industry? Reconnect with that version of yourself. Even if your motivations have evolved, the essence of why you began this journey is still valid.

Reflection exercise: Write down three reasons why you started your business. Keep this visible as a reminder of your why when things get tough.

2. Reassess What Matters Most

The demands of a business can blur your focus. It’s easy to get caught up in tasks that don’t align with your core values or original goals. Spend time reassessing what truly matters to you. Is it client satisfaction? Personal growth? Financial security?

When you know what matters most, you can let go of what doesn’t. This doesn’t mean abandoning responsibility, but rather giving yourself permission to prioritize what aligns with your values.

Practical tip: Conduct a weekly review of your tasks. Are they contributing to your larger goals? If not, delegate, automate, or eliminate.

3. Shift from External Validation to Internal Fulfillment

One of the hardest parts of leading a business alone is dealing with expectations—those you place on yourself and those you think others expect of you. 

Maybe you feel the need to prove something to the outside world, whether it’s through financial success, growth, or recognition. This can be an endless cycle of stress, always chasing external validation.

Instead, focus on what fulfills you. 

What brings you joy and satisfaction in your business? 

Is it creating something valuable for your clients? 

Is it the sense of accomplishment when you solve a challenging problem? 

By shifting your attention inward, you can ease the pressure to meet external expectations.

Action step: Each week, list one small success that made you feel fulfilled. Reflect on how it aligns with your core purpose.

4. Build a Support System That Aligns with Your Vision

Even if you lead a business alone, it doesn’t mean you have to carry everything alone. Whether you have staff or not, you need a support system that reinforces your vision, rather than detracts from it. 

If your current staff or contractors are causing stress, ask yourself if they are aligned with your goals. If not, it may be time to reassess roles or find new support that resonates with your mission.

Additionally, having an accountability partner, mentor, or fellow business owner to share your experiences with can lighten the emotional load. You’re not just building a business—you’re building a life. And life needs relationships that nurture and inspire, not just employees or assistants to delegate tasks to.

Practical tip: Reach out to one trusted person in your network and have an honest conversation about your challenges and purpose. Sometimes, external perspectives can help you see your vision more clearly.

5. Redefine Success on Your Terms

The leader’s conundrum often stems from a narrow definition of success. We’re conditioned to believe that success means growth, profits, or recognition. 

But what if success is simpler than that? What if success is staying true to your vision, living by your values, or creating a sustainable work-life balance?

By redefining success on your own terms, you remove the pressure of constantly striving for more. It allows you to appreciate the journey rather than focusing solely on the destination.

Reflection: Write a new definition of success based on your personal values, not societal standards.

Let Purpose Be Your Guide

The leader’s conundrum is real, and it’s something every business owner faces at one point or another. But the solution isn’t in working harder, expanding faster, or shouldering more responsibilities. It’s in reconnecting with the very reason you started.

When you let your core purpose drive your decisions, the stress may still be there, but it won’t control you. The challenges may still arise, but you’ll navigate them with clarity. The path may be uncertain, but your why will keep you grounded.

Ask yourself: Who am I really doing this for?

And let the answer be your guide.