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Why Aren't We Talking About It?
Conversations about the messy, uncomfortable and very human bits of life.

30 July 2026

The last real taboo is money

People will tell you about their marriage before they'll tell you what they earn.

By Carly Osman-Holme · 7 min read

We are conditioned to think that success is a straight line toward a bigger title and a higher salary. I spent years in that machine, convinced that if I just reached the next rung, I would finally be happy. Gilly, who was a high-flying fashion director, told me she spent her whole career chasing validation through the things she owned, the dresses she wore, and the size of her paycheck. She had it all, but beneath the surface, she was crumbling with crippling daily anxiety and the feeling that she was going to be sacked every single day.

Money is the one thing we refuse to be honest about, yet it is the primary reason we stay in jobs that make us miserable. We treat it as a survival mechanism that builds walls around us, keeping us trapped in what Gilly calls a self-made prison. We stay because of the mortgage or the fear of what others will think, but we don't talk about the heavy emotional tax we pay for that financial security.

The price of the paycheck

When I was made redundant at 38, it broke me. Even though I hated the job and cried every morning, losing that financial anchor felt like a personal failure. I see now that it was actually an awakening. I had to go inward to figure out what actually brought me joy, because I hadn't lived in joy for a very long time. I was just gliding through life on a speed travelator without absorbing anything around me.

Gilly shared a similar struggle. She reached a point where she was a fraction of the woman she thought she was, chanting to find the strength just to walk into the office. She eventually realized that the dresses and the salary were just parts of her ego self. What she actually needed was peace, beauty, and connection. When we peel back the layers of our material lives, we often find we need far less than we were told to want.

Society has trapped us into putting these walls around ourselves. Most people will choose to stay and say they accept an unhappy life because of the fear of money. But at some point, the calling to be yourself becomes bigger than the fear of the bank balance.

Breaking the social script

It isn't just about the money in our bank accounts; it is about the social currency we use to buy our way into being 'fun'. We have deeply entangled drinking with celebration. Whether it is a promotion, a birthday, or just the weekend, the expectation is that you have a drink in your hand. When you stop, people treat it like a loss. Helen, who founded a community for sober dating, told me that people assume you have lost your edge if you aren't drinking.

We use alcohol as liquid courage to mask our insecurities, especially when it comes to intimacy and confidence. Helen pointed out how terrifying it is to get naked sober for the first time after years of using a few glasses of wine to feel like a Victoria's Secret model. We use these crutches because we are afraid to own our real, wobbly, human selves. But once you take the crutch away, you realize you aren't losing anything. You are gaining clarity and the ability to actually remember your life.

  • Listen to your intuition when it gives you a quiet nudge rather than waiting for a loud shout.
  • Start journaling or creating a vision for the life you actually want, not the one you were told to have.
  • Practice self-love by finding three concrete things you like about yourself every day.
  • Recognize that energy attracts energy; staying in a job you hate just brings more frustration.

A new definition of success

Success used to mean getting a new Porsche or a massive bonus. Now, for Gilly, it is the moment a woman stands taller in a bra that fits her properly. For me, it is the ripples created when we talk about things like grief and redundancy, making others feel less lonely. We have one wild and precious life, and we have a duty to make it count rather than wasting it worrying about what people think.

If you are standing on the edge of a pivot, know that the transition won't be instant. It took Gilly six years to go from a concept to a business. But once you make the mindset shift and decide that there is a better life waiting, the doors start to open. You have to be willing to walk away from the old version of success to find something that actually feels like freedom.

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