The Pursuit of Freedom

And financial security

This morning I had a conversation with a group of salespeople.

They're transitioning from internal to external sales roles, I've been working with them over the past year. Today was our final call as a group. As we closed this journey, I wanted to understand something deeper – why they were in this role and what they truly wanted for themselves.

The words that emerged, over and over again, were "freedom" and "fullness."

The path they envisioned to attain these states? Financial security.

In addition to this group work, I individually coach a select few people. Every person I coach has crossed that threshold of creating financial security – they've established a solid foundation.

The irony doesn't escape me - nearly every one of them chased financial security as their path to freedom. Here’s a very rudimentary drawing I made on the call about this.

There's a common thread among many of the entrepreneurs and leaders I coach: backgrounds of poverty, impoverishment, limited opportunity.

They've experienced firsthand how being poor creates constant instability. Perpetual uncertainty. A pervasive feeling of restriction that narrows life's possibilities.

They set out to create the opposite reality through earning money and establishing security.

Then life played its clever trick.

As they climbed toward financial heights, they tied their sense of freedom to these external milestones. The outcome? They became trapped within the very structures they created to free themselves.

This single-minded pursuit of money – making it the primary source of meaning and the top priority above all else – can consume decades of one's life. Until eventually, you arrive at a disturbing realization: you don't know who you are anymore.

You've lost touch with what you truly want or don't want.

Then comes the pivotal moment of choice:

Do I address what has been unaddressed for so long?

Or do I continue on this path, burying these questions deeper and deeper?

The people I'm working with are choosing to address it. To create more alignment in their lives.

It was a beautiful moment this morning, speaking with these ambitious young salespeople, some just a few years into their careers, others with young families at home. To acknowledge that you can strive for both.

You can pursue financial independence by creating security in your life. This is genuinely important – I value it and see it as something worth pursuing.

But equally important is pursuing a sense of inner freedom.

This inner liberation comes through addressing the resistances you meet along life's journey. The things you fear. The tender and fragile aspects within yourself that you'd rather not face.

Instead of bypassing these elements, we actually turn toward them.

This is what the inner game is fundamentally about.

Most people pursue these elements separately. They spend their career focusing on the external – achievement, advancement, accumulation. Then, when they retire, they plan to give space to the internal journey.

From what I've witnessed, that's often too late.

It becomes increasingly difficult to develop those internal tools and skills once your career has concluded. The patterns are too deeply set. The identity too firmly established.

But when you bring these dimensions together – the external pursuit of security and the internal journey of growth – something powerful emerges.

It transforms into a space where freedom and fullness converge.

I've experienced this firsthand in my work as a speaker. There have been keynotes where I've walked off stage to applause and glowing feedback, yet internally felt terrible – empty, off, misaligned. The audience's experience was positive, but mine was painful.

The discomfort could last for hours or even days.

What was happening? It wasn't about my delivery or content. It was about my presence within myself – I had chosen against myself. I'd spoken in a way that wasn't true to me or showed up in a way that felt false. The audience couldn't see this disconnect, but I had to live with it afterward.

Then there are times when I've received less enthusiastic external feedback, yet felt deeply satisfied and aligned within myself.

And occasionally, there's that sweet spot – when I feel genuine and whole on stage, and the audience feels genuinely moved. These moments become markers for me, indicators of alignment between my inner and outer worlds.

What is this fullness?

It's the feeling that comes when all aspects of yourself are welcomed into your work. When your analytical mind, your emotional intelligence, your creativity, and yes – even your wounds and vulnerabilities – all have a place at the table.

Most of us feel depleted because we compartmentalize. We bring our strategic thinking to work but leave our intuition at home. We showcase our strengths but hide our struggles. We focus on results while neglecting relationships.

This selective expression leaves us feeling imbalanced and unfulfilled – successful in narrow domains but empty in others.

The sales call becomes more than a transaction when you bring your full humanity to it. The presentation becomes more than a pitch when it carries your authentic voice. The leadership role becomes more than a title when it embodies your values and vision.

True freedom isn't just financial independence. It's the liberation that comes from no longer fragmenting yourself – from allowing the fullness of who you are to find expression in what you do.

Most wait a lifetime to discover this integration, often too late.

And why would you ever want to retire from something that has become a canvas for your whole self?

This is the promise at the intersection of inner work and outer achievement: not just the security of having enough, but the aliveness that comes from being enough – and bringing all of that to everything you do.