When Everyone Else Tells You How to Sleep… And You’re Still Lying Awake

Your life can look calm on the outside, while your brain is holding an emergency meeting at 12:39am.

That’s what was happening to Jessy.

Jessy is in her late 40s and lives in Boca. She had just done something incredibly brave. She left a job with a boss who was mean, controlling, and frankly… narcissistic. For years she had worked for other people, even though she was wildly talented and always dreamed of opening her own business.

Now she finally did it. She had clarity, connections, and supportive friends. And she also had a very quiet fear that no one else could see.

“What if this doesn’t work? What if I can’t pay my mortgage? What if I’m doing this all alone?”

During the day, she held it together. At night, her brain did not. That’s when the anxious thoughts took over.

Not because she was weak. Not because she was broken. But because her nervous system didn’t feel safe yet. And when your nervous system doesn’t feel safe, it refuses to power down.

Tool #1: Schedule Your Worry (Yes, On Purpose)

Here’s what we didn’t do. We didn’t tell her to “just relax.” We didn’t say, “Think positive.” We definitely didn’t say, “Imagine roses and chocolate.”

Instead, we gave her fear the time and respect it actually needed. We created a daily “worry time.” Ten to fifteen minutes. Same time every evening. This is a commitment to your mind: you are allowed to think, analyze, and process, but only during this dedicated window. Your worries have their time and place, and that’s it. When the time is up, you physically and mentally put them away.

Here’s the key idea: we are going to worry no matter what. We are human. Our brains need to process and work through the worry. Scheduling worry time is giving permission for that process. And when that time is up, we can put it away and rest, knowing our mind has had its turn to process the day.

She sat down with a notebook and wrote out every anxious thought. The business fears. The money fears. The what-if-this-fails fears. Then she folded the paper, put it into a box, and said out loud:

“I’ve done my best for today. This worry isn’t serving me right now. I’m handing it over to G-d. We can deal with this tomorrow.”

It wasn’t spiritual bypassing. It wasn’t denial. It was containment. Her brain finally got the message: “You are allowed to think. Just not at midnight.” Within days, her nights started to soften. Not perfect. Not magical. But quieter, less frantic, and more human.

When Help Makes Sleep Worse

Around this time, Jessy’s sweet neighbor started having breakfast dates with her. This neighbor is very into health. She tracks everything. Steps. Water. Protein. Macros. Mood. Life.

Naturally, she also tracks her sleep. Down to the minute. Which stage she was in. How long she dreamed. How much deep sleep she got.

And every morning… her app gives her a grade. A good night. Or a bad one.

She suggested Jessy use it. What a disaster.

Now Jessy knew exactly how many minutes she was awake, exactly when she woke up, and exactly how “bad” her sleep was. Suddenly, bedtime became a performance. She wasn’t resting. She was bracing.

There’s even a name for this: orthosomnia. The obsession with getting perfect sleep. And the cruel irony? The harder you try to control sleep, the more it runs away from you.

Tool #2: Take a Break From Sleep Data (And Ask a Bigger Question)

Instead of asking, “How many hours did I get?” try asking something deeper and way more useful: “Is this tool helping me move toward a better way of life… or pulling me further away from it?” This question shifts your attention from numbers to experience. It’s no longer about checking, judging, or measuring, but about noticing patterns and how you feel physically and emotionally after a night of rest.

Notice I didn’t even say sleep. Because this isn’t just about your nights. It’s about your relationship with control, safety, and self-trust. If your tracker makes you more anxious, more obsessed, more rigid, or more afraid of bedtime, then it’s not a health tool anymore. It’s a stress machine with good branding.

Try a gentle experiment. Seven days. No checking sleep stats. No REM numbers. No deep sleep charts. Just notice your energy, your mood, your patience, and your clarity. At the end of the week, ask yourself: “Do I feel more alive… or more monitored?” That answer will tell you everything and give you insight into whether these tools are supporting your well-being or fueling anxiety.

If your brain turns into a project manager at bedtime, you’re not broken. You’re overwhelmed. And your nervous system is trying to protect you.

Sometimes all it needs is a place to put the worries and permission to stop being measured.

Hydration matters more than most people realize. I learned this the hard way during my own son’s wedding. Read more here:

The Simple Sleep Trick I Forgot During My Son’s Wedding

If you want help stepping out of the sleep-pressure loop and rebuilding trust in your body again, you can book a free 30-minute call here:

https://calendly.com/chevymermelstein/30min

No pressure. Just a real conversation.