The Emotional Weight of Leadership: When to Step Up and When to Let Go

There’s something we don’t talk about enough in business: emotions. They are the unseen currents that often drive our decisions, cloud our judgment, and, in many cases, hold us back. After working with so many homegrown businesses, I’ve seen this firsthand. It’s this emotional attachment that can make or break a business, especially for CEOs who are deeply tied to their companies. But at some point, that emotional pull becomes more of a weight than a propeller, and learning when to let go is a lesson every leader needs to embrace.

For the first 20 years of my career, I worked in organizations just on the brink of massive growth. I would step in when the company was still finding its legs but on the verge of something big. I loved that phase. Watching the business grow from the inside, helping the CEO manage that transition—it’s exhilarating. But there’s always this tension. The CEO, often the founder, who’s poured their heart into the company, struggles with stepping back from the weeds and embracing a higher vision. It’s understandable, but it’s also a risk.

Let me tell you about one CEO I worked with. She was project managing everything, right down to the tiniest details. And even though she had a great team in place, she couldn’t let go. Her attachment to the day-to-day was holding the business back. I had one goal: to help her elevate herself. It took time, and it wasn’t easy—there was resistance, a lot of it—but eventually, she let go. And guess what happened? Within six months, the company was sold for tens of millions. Six months! That’s the power of stepping into your true role as a visionary.

But not all leaders are ready for that shift. Some CEOs never manage to elevate themselves. Instead, they cling to what they know—whether it’s fear, insecurity, or just the habit of doing it all themselves. But here’s the hard truth: If you’re doing everything, your team can’t grow. You can’t grow. Your business can’t grow. It’s like trying to row a boat in two directions. Eventually, you’re just going in circles.

As a leader, your job is to lift your team, not outshine them. Give them room to fail, to drop the ball, and to learn from it. You don’t get to hold all the reins and expect them to manage at the same level. That’s unfair and unsustainable. You might think that being involved in every detail is keeping things moving smoothly, but in reality, you’re stifling their potential. And when your team stagnates, so does your business.

I’m not saying this transition is easy. Letting go is hard. But it’s necessary. Your team can’t thrive if they’re constantly living in the shadow of your emotional attachment to the business. They need you to guide them, not micromanage them. They need you to lead from a higher level, seeing the bigger picture, thinking strategically, and focusing on business development. The more you focus on strategy, the more the business will grow.

I’ve worked with enough CEOs to know this doesn’t happen overnight. Fear and insecurity are powerful forces. But that’s why it’s important to work on yourself—outside the workplace. Find a coach, talk to a therapist, work through those personal hurdles, and then come back to the business ready to elevate, ready to lead.

Because here’s the thing: If you don’t make that leap, if you don’t step into that visionary role, you’re not just holding yourself back. You’re holding your team back, too. And ultimately, your business will never reach its full potential. The health of your team depends on you stepping up and trusting them to step in.

This is the emotional weight of leadership—knowing when to hold on and when to let go. And it’s a lesson worth learning if you want to see your business thrive.

So, what’s holding you back? Is it fear? Insecurity? If you want your business to grow, the time to elevate is now. Take that step, let go of the details, and watch as your team—and your company—reaches new heights.

Jaime Gennaro is a seasoned business consultant and coach with over 20 years of experience helping companies achieve sustainable growth and leadership success. She has held leadership roles in marketing and operational strategy across various industries, including tech startups and creative agencies. Jaime specializes in business coaching for entrepreneurs and guiding leaders in balancing personal and professional growth. She focuses on reducing burnout, achieving business clarity, and developing entrepreneurial leadership strategies for long-term success.

If you're ready to take the next step in your journey, I invite you to explore my 90-day private coaching package.