I rented out a cupcake shop for my birthday...

Not a bar.
Not a restaurant.
A cupcake shop. 🧁

But not just any cupcakes shop, it was Kara's Cupcakes in San Francisco...

To this day, as a self-proclaimed cupcake connoisseur that's eaten thousands of cupcakes, I still consider these the best cupcakes I've ever had.

I was 33 years old and the only adult to ever do this. #NoRagrets

The staff thought it was hilarious, especially since my entire group was personal trainers. Mostly fit men who made their living teaching people how to get in shape.

We each crushed 3-4 cupcakes, creating a sugar high that had us more giddy than schoolgirls until the inevitable crash left us all wanting a nap.

We made cupcakes, took photos, and I even got to work behind the counter. At the time, it was one of the best days of my life.

I didn't realize it then, but that party was a cry for help.

Fast forward six or seven years...

I'm still going to cupcake shops. But now it's Sprinkles. And I'm going a lot.

95 times in a single year and I have the receipt to prove it.

Addiction, or obsession for "healthy" addictions as achievers like to call it, definitely runs in my family and I'm a prime example.

I had the highest tier in the Red Velvet Club. In retrospect, it's kind of like having reserved seating on the short bus.

Not an honor you want bestowed on you, but at the time it made me feel like royalty with skip-the-line access and a free dozen on my birthday.

I spent hundreds of dollars on sugar. Even my weekends were planned around getting my cupcake fix.

I wasn't just a customer. I was THE customer.

Then I started reading The Daily Stoic by Ryan Holiday. Journaling. And one question kept haunting me:

Do you own your things, or do your things own you?

I looked at my cupcake ritual and realized the tail was wagging the dog.

So I quit for 30 days.
Just to prove I was still in control.

That turned into an entire year.

Here's exactly how I did it, and how you can use the same framework to quit whatever's controlling you.

When the Habit Owns You

Everyone has their "cupcake."

Maybe it's alcohol. Two or three drinks every night without thinking about it.

(My favorite vices now, although much more in control, are Goldeneye Pinot & Rabbit Hole Dareringer bourbon with a single cube. 🤌🏻)

For you, maybe it's late-night snacking. The kitchen calls at 10 PM and you answer like a well-trained dog.

Maybe it's fast food. Drive-through three times a week because it's "convenient."

Hell, maybe it's Quest bars. Even "healthy" habits can own you if you can't go a day without them.

The thing itself isn't the problem. The problem is agency. Control. Identity.

For me, the cost was adding up:

• ~40 minutes per trip, every time
• Working my entire weekend around a cupcake run (because I'm a well-adjusted adult 😉)
• 15 minutes of pleasure → hours of feeling terrible
• Sugar crashes, bloating, inflammation
• Nasal congestion, poor sleep, low energy
• Mental bandwidth and quiet guilt

I'd start to question myself, but I was in denial. I'm fit. I'm healthy. It's not a problem.

Then I'd go back the next weekend.

I'd even get angry if I couldn't arrange my day around this weekly ritual. If we were traveling, I'd find time during the week instead.

Like a functioning alcoholic, but with frosting instead of booze.

Here's the thing: to the outside world, it looked fine. Even cool. I glorified it the way everyone does with their "cheat days" on social media.

Tim Ferriss talks about eating a dozen cupcakes at a friend's birthday like it's a flex. People say, "I wish I could do that."

And in a weird way, that became part of the obsession: the fact that I could get away with it while others couldn’t.

Except I wasn’t getting away with it anymore. The dragon under the bed had grown into a monster. 🐉

When you spend more time thinking about, planning for, and recovering from a habit than you do enjoying it, the math doesn't work.

I needed to take control back.

Here's the exact 4-step framework I used.

The 4-Step Framework For Breaking Any Bad Habit

Step 1: Make the Habit Difficult to Execute

You need to inject friction into the habit loop. Not the kind of injection that gets you banned from sports, the kind that saves you from yourself. 😜

Every habit has three parts: cue, routine, reward.

For me:

1. Cue: Seeing the Sprinkles app or driving past the plaza
2. Routine: Order → pickup → eat
3. Reward: Sugar + dopamine

I attacked the cue and the routine:

• Deleted the app
• Blocked the website
• Changed my driving routes

I didn't make it impossible. Just inconvenient enough that I'd have to REALLY want it.

And here's the thing: when you have to think about it, the habit loses power. Habits thrive on autopilot. Friction kills autopilot.

(Wonder how much I'd save if I blocked Amazon on my wife's phone? 🤔 Better yet, the entire house at the network level. Putting my CS degree to good use.)

Your turn:

• Late-night snacking? Brush your teeth at 8 PM and use a K-Safe.
• Alcohol? Out of sight, out of mind or don't keep it in the house.
• Fast food? Avoid drive-throughs. Delete apps.

Remove the cue or make the routine harder. That's where the battle is won.

Step 2: Replace the Habit with a Healthier Alternative

You can't just remove. You need to substitute.

My solution: Enlightened ice cream bars, Yaso bars, So Delicious ice cream sandwiches. All around 80-100 calories. Low sugar.

The math:

• OLD: 2-4 cupcakes per week = 1,000-1,800 calories of pure fat & sugar
• NEW: 1 treat per day = 560-700 calories per week, way less sugar

I traded massive weekly sugar bombs for daily, smaller dopamine hits.

And it worked because:

• No inflammation or crashes
• No disrupted sleep
• Daily reward instead of weekly binge
• Actually sustainable

Find something that scratches 80% of the itch with 20% of the downside.

Your alternatives:

• Alcohol → Non-alcoholic beer (Athletic Brewing or Heineken Zero) or reduce consumption using a tracking app like ReFrame​
• Chips → Quest chips, air-popped popcorn​
• Fast food → Meal prep with similar flavors

Don't white-knuckle it. Replace it.

Step 3: Shift Your Identity ("I Don't" vs. "I Can't")

This is the most important step.

My mantra: "I don't eat cupcakes."

Not "I can't eat cupcakes."

This isn't semantics, it's psychology.

• "I can't" signals restriction. Something being imposed on you. Disempowering.
• "I don't" signals choice. Agency. Identity. Empowering.

Dr. Heidi Grant Halvorson from Columbia University's Motivation Science Center found that people who use "I don't" statements have significantly higher adherence rates than those who use "I can't."

One study showed the "I can't" group failed 61% of the time.

When cravings hit, I'd talk to myself in third person: "Jackson, you don't eat cupcakes. You don't eat cupcakes."

(Yes, I talk to myself in third person. This is a trick I learned from the book Chatter: The Voice in Our Head, Why It Matters, and How to Harness It.)

Reinforcing the identity over and over.

The timeline:

• Week 1-4: Required discipline and constant self-talk
• Month 2-3: Barely thought about it
• Month 4+: Zero cravings

Labor Day, over a year later, friends had Sprinkles at their house. They got them for me specifically.

I split a banana cupcake with my wife. Well, the classic married-guy 70/30 split where she 'just wants a bite' and I finish the rest.

Within minutes, I felt my insulin spike and my blood sugar surge. It felt like way too much and I resonated with the identity of being the "that's too much sugar for me" guy.

I didn't wolf it down.
I didn't want a second.
I didn't even want to finish the first.

Because I still had the identity.

Your identity statements:

• "I don't drink during the week"
• "I don't eat after 8 PM"
• "I don't do drive-throughs"

Make it your identity, not a rule.

Step 4: Ride the Wave When Cravings Hit

This technique is used for alcohol, nicotine, porn, and drug addiction. It works for any craving.

When a craving arrives:

1. Recognize it
2. Remind yourself: "This is temporary. This will pass in 10 minutes."
3. Get busy with something else (workout, walk, turn on a show, work on a project)
4. The wave peaks, then fades

My experience:

• First few weeks: Multiple waves per day. Required active management.
• Month 2-3: Waves became less frequent, less intense
• Month 4+: Waves stopped coming

Cravings are neurological. They spike and fade. If you don't feed them, they lose power.

One more thing: willpower is NOT a limited resource. Research has debunked the old "willpower is like a muscle that gets tired" theory.

Willpower is only limited if you believe it is. So no more "I don't have willpower at night" excuses.

You have agency. You make the choice.

TAKEAWAY: Your Vice Isn't the Problem. Your System Is.

I didn't quit cupcakes through willpower alone. I quit through system design.

The framework:

1. Make the habit difficult (remove cues, add friction)
2. Replace with healthier alternatives
3. Shift your identity ("I don't" not "I can't")
4. Ride the wave when cravings hit

This works for any vice. Alcohol. Late-night snacking. Fast food. Doomscrolling. Whatever owns you.

Three action steps:

1. Identify your "cupcake" - What habit is wagging you? Be honest.

2. Pick ONE step from the framework - Don't try all four at once. Start with making it difficult OR shifting your identity.

3. Commit to 30 days minimum - The first few weeks are the hardest. After that, it gets exponentially easier.

The Stoic question still applies: Do you own your habits, or do your habits own you?

You can take control back. You just need the right system.

What's your cupcake? Hit reply and let me know.