What We Think We’re Allowed

A client recently sent me an email that stayed with me for days. She’s smart, successful, deeply thoughtful—and she’s doing the hard work of questioning long-held assumptions about all things—her work, her life, her loves. And, most relevantly, her relationship to money.

In her note, she asked for guidance about working with that which money brings up for her. And embedded within was a moment of acute self-awareness; it was that self-awareness that struck me. After years of walking a financial tightrope, she’d come into a bit of liquidity—enough to ease some burdens, help her aging mother, to buy a home, maybe even exhale. But what followed wasn’t ease; it was confusion.

On the one hand, she contemplated buying her husband a long-coveted and very expensive watch—a grand and loving gesture. On the other, she found herself ordering and returning three different beauty care tools, worried about saving a few hundred dollars, despite knowing which one worked best and would serve her every day, despite knowing what she wanted. She just didn’t know what she was allowed.

After sharing the experience, she named the deeper pattern: “I don’t think it’s some selfless generosity, more a feeling I’m not worthy of a balanced and responsible pot of wealth.”

She continued, “I seem to know only how to live frivolously or like a skinflint.”

Oh, I know this terrain. I’ve seen clients gasp in panic when their husband, out of generosity, bought them a car as an anniversary present. I remember another client secretly returning a diamond ring her husband had bought for their tenth wedding anniversary—the ring he couldn’t afford when he’d first proposed. She was convinced that keeping it would land her in the poorhouse.

And I know this terrain intimately; I’ve travelled it myself.

In Reboot, I wrote about how my own story with money was shaped by my grandfather’s lemon drops. How, as a desperately fearful child—one growing up in a household that never seemed to have enough, I would marvel at the kitchen pantry with the painted green door where Grandpa Guido had stashed a tin of lemon drops. And how that tin ever seemed to empty. And that house, with the smell of figs coming into the kitchen from the tree just off the kitchen porch, would mix with the smell of fresh ground coffee (stored in the little box under the grinder that hung on the wall, next to the portrait of Padre Pio). Those lemon drops—were sweetness, provision, and enough-ness.

What I didn’t understand until after years of therapy was how that memory had imprinted itself on me. How my hunger for “enough lemon drops” had become a relentless driver. How I equated money with safety, dignity, worthiness. How I burned myself out—nearly killed myself—chasing something money could never truly give me.

“Money was never really about money,” I wrote in Reboot: Leadership and the Art of Growing Up, “It was about safety. About not being poor. About being seen. About proving I was good 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.”, or “You’d better hoard while you can.”, or “You’re only valuable if you earn.” Or, more, “You’re not allowed to have what you want.”

As Annette Lieberman and Bernadette Dunne remind us in their wonderful book, The Money Mirror, “Even in successful adult women, the money messages of childhood—particularly those about entitlement, spending, and self-sacrifice—remain coded beneath layers of accomplishment.”

That coding can lead to wild inconsistencies: lavish gifts in one moment (usually on others), penny-pinching (especially if it involves us) in the next. Guilt trumps abundance, and a fear of losing it all haunts every moment. The sense that we’re only allowed to live in extremes—frivolous or broke, all or nothing.

If this is familiar, here’s an invitation for you. Ask yourself these questions:

What do I actually want?

And

What do I believe I’m allowed to have?

The gap between those two questions may be uncomfortable. It may stir up even bodily resistance. But this is where transformation begins.

Jacob Needleman, in Money and the Meaning of Life, writes: “The human being must learn to use money consciously, just as he must learn to think consciously, to feel consciously, to act consciously. This is part of the great task of becoming a human being.”

This “great task” isn’t just about money. It’s about becoming whole. It’s about rewriting the stories we inherited and those we didn’t choose to write ourselves. It’s about honoring the parts of us that just wanted to feel safe—and choosing, now, to lead ourselves with compassion, clarity, and courage.

And maybe, just maybe, to believe that we are allowed to have a life that’s neither overstuffed nor starving, neither feast nor famine. But enough.