Inc. Magazine
Financial success doesn’t always bring peace. Many leaders find that money stirs guilt, fear, or a deep sense of unworthiness rooted in old beliefs. These emotions silently shape how they lead, often trading empathy for control. True leadership begins by asking hard questions, confronting personal money stories, and redefining self-worth beyond wealth.
How Your Relationship With Money Shapes Your Leadership
Author: Jerry Colonna
A recent conversation with a client brought to light a common theme I see with entrepreneurs and leaders. My client had finally (after years of walking the line between solvency and struggle) gained some financial freedom. She could use her new liquidity to buy lavish gifts for her loved ones or help a family member in need. She could even use some of it to purchase items she had wanted for a long time.
Instead of rejoicing in that freedom, however, my client found that having money stirred up unresolved feelings of confusion. She felt undeserving of her value and hard work, and she wasn’t sure she could spend it. The emotions that money can evoke are not uncommon, and anxiety frequently rises to the surface.
The unconscious emotions connected to money
In Reboot: Leadership and the Art of Growing Up, I wrote about how my story with money was shaped by my grandfather’s lemon drops and how money is never really about money. It’s about safety and security and knowing that you can fix a problem at any time because you have it. It’s about having enough and more than enough.
Such unconscious beliefs, which I often liken to software subroutines that lie at the heart of all operations, quietly shape our decisions. They whisper, “You can’t have that,” “You’d better hoard while you can,” “You’re only valuable if you earn,” or “You’re not allowed to have what you want.”
How your ‘money story’ impacts your leadership style
The deeply rooted yearning to have more than enough, to be better and gain more value can become a relentless force that impacts your life and leadership style. It’s easy to become obsessively focused on output and numbers while forgetting about the people you work with. It’s also easy to sacrifice empathy to chase the illusion of safety and worthiness that money cannot bring.
But there is a way to reconcile money and the feeling of never having enough. There is a way to end the cycle of guilt and stop living in extremes. You do have the ability to step back and reshape your relationship with what you deserve. It does come with doing the hard work—with radical self-inquiry.
How to change your relationship with money
Ask yourself these questions:
- What do I really want? If you answer honestly, I will bet it’s not wealth. You may want to make money as an entrepreneur, but there are likely a few other things you want to feel as well. Safe, capable, worthy, important, secure, and independent are all common themes.
- What do I feel when I think about money? You may feel anxious, worried, scared, or fearful. Are these feelings being driven by another force? What is feeding these thoughts?
- How are those feelings driving the way you lead? Are you leading with empathy? Do you tend to micromanage in an attempt to control all outcomes?
- What do you deserve? What do you believe you’re allowed to have?
Asking the hard questions never brings comfort, but growth isn’t born from comfort. It’s about becoming whole. It’s about rewriting the stories we inherited and those we didn’t choose to write ourselves. Maybe you, like me, grew up in a household that never seemed to have enough and that cultivated a never-ending fear of running out of what’s necessary to live. Or maybe you walked the financially unstable tightrope for so long that holding onto everything you now have is the only way to breathe.
Your relationship with money has the power to shape the leader you become. But true leadership begins when you confront those emotions, honor them, and consciously choose a different path—one that may have once felt uncomfortable, but now reveals itself as the most aligned and courageous way forward.
True transformation begins when you face the parts of yourself longing to feel safe, loved, secure, and worthy and choose, in spite of fear, to lead with clarity and conviction.
Credits: TCA, LLC.