The “Next Level” Trap

You’re Winning. So Why Do You Feel Empty?

Let me introduce you to Ted.

Ted is the guy who did everything by the book. He worked his ass off for a decade, climbed the corporate ladder, bought the house, the car, and the Instagrammable vacations. And for a while, it felt great.

Until one day, it didn’t.

He woke up, stared at the ceiling, and thought: Why do I feel nothing?

So he did what every high achiever does in a crisis:

• Maybe I just need to hit the next level.

• Maybe if I work harder, the feeling will come.

• Maybe if I make more money, I’ll finally be happy.

Spoiler: It never came.

Because Ted wasn’t chasing his definition of success. He was chasing someone else’s.

Sound familiar?

It does to me because I was Ted. And maybe you are too, or on your way there.

This is the Next Level Trap: the lie that says the next milestone will fix everything. But it never does.

Today, we’re unpacking why success stops feeling satisfying and how to build a system that makes fulfillment inevitable.

Why Success Stops Feeling Satisfying

1. You Always Move the Goalpost

Remember when you were broke and thought, If I could just make $100K, I’d be set?

Then you hit it. And immediately thought, Okay, but now I need $200K. Then I’ll feel secure.

Then $500K. Then $1M. Then private jet money.

At what point does it stop?

It doesn’t. Because if you never define "enough," you’ll never get off the treadmill.

2. You’re Addicted to the Chase, Not the Destination

The process of achieving a goal is always more exciting than reaching it.

I have a friend who hops jobs like a corporate Indiana Jones. Every time he lands the next gig, I start a 12-month timer.

Not because the work changes. Not because the company sucks.

But because he doesn’t actually want the job, he wants the chase.

3. You’ve Been Sold Someone Else’s Definition of Success

A lot of people spend their entire lives climbing a ladder they didn’t even set up.

Ask yourself:

• How much of what you’re chasing is actually what you want?

• Not what your parents wanted.

• Not what society tells you is “successful.”

• Not what looks good on LinkedIn.

But what actually lights you up inside?

If you stripped away all expectations, what would success look like for you?

How to Escape the "Next Level" Trap

1. Define What "Enough" Looks Like (Use This Simple Math Trick)

If you never define "enough," you will never feel successful.

Here’s an easy way to calculate it: The 4% Rule.

Take your annual expenses and multiply by 25.

That’s roughly how much you need to retire, assuming you withdraw 4% per year and your investments outpace inflation.

Example:

• If you need $100,000/year to live comfortably

• $100,000 × 25 = $2.5 million needed to retire.

This assumes:

• Your money is invested in a balanced portfolio.

• You withdraw 4% per year.

• Your investments keep growing at 5-7% annually, even after inflation.

Once you know your number, you can stop mindlessly chasing more.

2. Stop Waiting for "Future You" to Be Happy

If your happiness is always "one milestone away," you’re never going to reach it.

Instead, ask yourself three questions:

1. What would make me excited to wake up tomorrow?

2. How can I enjoy my work more right now?

3. If I didn’t have to prove anything to anyone, what would I choose?

For me, the answer was writing.

So I built my mornings around it. Now, I have this newsletter, a podcast, and my first novel, The Architect, goes to the editor June 1.

What would your answer be?

3. Redefine Winning on Your Terms

Most people only track success by money or status.

But what if you tracked success by:

• Time spent doing what energizes you

• How much freedom you have over your schedule

• How often you feel excited about your work

I have a friend who LOVES pickleball (it’s basically his entire personality now). But he also runs sales for a fast-growing startup.

So he redesigned his day:

• 5:00 AM: Work on admin

• 8:00-10:00 AM: Play pickleball

• 11:00 AM - 6:00 PM: Office hours

• 6:30-7:30 PM: Pickleball training

• 8:00 PM: Video games & wind down

He’s making more money than ever and living his best life.

Because when you build a life around what energizes you, everything gets better.

Your Challenge: Escape the Trap This Week

1. Define your "enough." Figure out your actual number.

2. Find happiness in the now. What’s one way you can enjoy the process more today?

3. Redefine your scoreboard. Track success by what actually matters, not just money.

Hit reply & tell me: What’s one "success goal" you’re questioning right now?

Let’s make this real.

Until next time,
Ned

P.S. Know someone chasing "more" but still feeling empty? Forward this email. They’ll thank you later… I’ll thank you immediately.