The Art of Starting Over Pt 9 – When Mommy and Daddy’s Money Isn’t Enough

Isabella grew up watching her father lose three businesses at once. To her it seemed like it happened overnight. One day they were shopping at Chanel and the next day at Forever 21 and H&M. When the real estate market collapsed he lost his property. Soon after the stock market crashed and he lost his investment clients, and then there was the clothing store he and his wife owned, fashion trends shifted so fast that Isabella’s parent’s clothing store couldn’t keep up, they lost it all.

It was like watching a storm hit from three different directions. Her mother stayed calm, her father stayed steady, but Isabella felt everything. Kids feel things even when adults don’t say much. She didn’t have all the words at the time, but she knew what fear looked like on two faces that rarely showed it. She also knew that selling a house you love isn’t something you do unless things aren’t going well. She was young, but she was aware. She remained in a private school, but it wasn’t the same level of privacy she had at her previous school.

Things were different.

What she remembers most is how quiet the house got when her parents were uncertain. She also remembered that there weren’t as many people around. No staff. The phone rang less. The weekend parties ended. The energy changed. She paid attention. She loved her dad deeply, so seeing him sit at the dining room table late into the night with papers spread everywhere made her nervous. She thought losing money meant losing everything.

She didn’t know he was already sketching out his next move. She didn’t know the man she feared was falling was actually planning his comeback. She didn’t know that he had been through harder times in his childhood. She really didn’t know what to think, and at the time her parents weren’t sharing information with her or her big brother.

It didn’t take long. She watched her parents rebuild every single thing they lost. They came back different. Stronger. Wiser. And because she watched it happen in real time, Isabella learned two things early in life: success can disappear in a moment, and success can return in a moment too. That paradox shaped everything she believed about security.

By the time she was grown, she didn’t want the emotional roller coaster of business ownership. She wanted something stable. Predictable. Something with healthcare, paid time off, and a salary that hit the same way every two weeks, but she wanted a big salary. So she became an engineer. It made sense. She was good with numbers. Logical. Calm under pressure like her dad. Detail-oriented. And she liked the prestige of being a woman in a field where most people didn’t expect her to be.

She worked for the same company for ten years. The promotions came. The money was good. Her parents were proud, but they always reminded her that she could do so much more if she wanted to. Her friends admired her. And she was grateful. But gratitude and fulfillment are not the same thing.

Crossing over into her thirties changed her. She started wanting something different. It didn’t make sense because she felt like she should just be grateful. When she realized she felt unfulfilled, she also felt guilty. She wondered if she was having an existential crisis. She laughed at herself for even saying the words out loud. “Who has a midlife crisis so young?” she said to me in session.

But what she didn’t know was this was becoming more and more common. Her dreams were getting loud. Her full potential wanted to see the light of day. Fear of failure could no longer keep her safe. She kept waking up at night with bad dreams. Those crocodile dreams were no joke. They weren’t attacking her, they were just looking at her. Yet she still felt attacked. Hidden fears. Hidden desires. Hidden emotions. She wasn’t stressed, not in the usual way. She was silent-stressed, which is the worst kind.

So she came to hypnotherapy, not because something was wrong, but because everything was “fine.” And fine feels heavy when you know you were built for something else.

We started with the Sleep Trio. She wanted rest. Real rest. She wasn’t resting during sleep. Her subconscious brain was speaking to her in her dreams. Once we got to the root cause, we got her body and brain to calm down, then moved into Control the Controllable program. She thought the uneasiness was related to work pressure. It wasn’t. The more we uncovered, the clearer it became. She wasn’t missing peace, she was missing creativity.

She started small. On weekends she opened her closet to friends who loved fashion but didn’t have the budget for the brands she bought and only wore it once or twice. Those friends bought clothes, bags, accessories. Then friends of friends came. Then her other wealthy friends started giving her what they were no longer wearing. Before she knew it, her living room looked like a boutique. She wasn’t hustling. She wasn’t chasing anything. She was just doing what she loved, and people gravitated toward it. She was having fun and she felt fulfilled.

By the time she realized she needed a location, it was time for her to take a vacation, and it was also her ten-year anniversary at the company, so she qualified for a sabbatical. Those two months were perfect timing. She worked sixteen-hour days, designing, planning, painting, inventorying, building her boutique into a real business. Not a hobby. A business. But with more safety nets than her father ever had at the beginning. She had her savings, her salary, her father’s guidance, her mother’s instincts, and a trust fund that allowed her to take risks without fear of losing everything. When it was time to go back to work, she quit.

People talk about privilege like it’s something to hide. Isabella never hides it. She tells people, “I had help. Don’t compare your path to mine. Don’t let Instagram trick you into thinking you’re behind.” She teaches realism when she posts about her life and her business. She teaches honesty, because trust fund kids always make it look so easy. Because it is easy for them, but not for everyone else. She teaches that success comes in many forms, and most people have to wait a lot longer than she did to see business growth.

She’s fulfilled now. And she knows that starting over at thirty-two wasn’t a crisis or a failure. It was her listening to her intuition the way her mother taught her. Ignoring it was keeping her up at night. 

She sleeps through the night most of the time, but she’s not waking up in fear anymore. Her routine grounds her: morning meditation and self-care before going to the store each day. She also has a night routine that helps her deactivate her brain. But most of all, she is fulfilled right now and she knows that she’s on the right path, even if it seems more risky to some.

If you’re waking up in the middle of the night with dreams that feel louder than your reality, that’s not something you should ignore. It will get louder. You don’t have to fix everything in one night, but you can get started tonight. This free resource could be exactly what you need to take control of your sleep.

Download this free sleep tool that I use with all of my clients. As simple as it is. It works. Start by making this one step toward better sleep with my free Sleep Trio. It’s three separate tracks that will guide you to sleep. 

It can help you fall asleep faster, stay asleep longer, and wake up at the right time feeling refreshed. I’ve helped more than 6,000 people restore their peace, and my goal is to help 10,000. Will you be one of them? 

The tool I created is free, easy, and could be the first step to reset your rest. You deserve to sleep and to have a life that fits who you are now. 

Click here to access it.