I remember the exact moment I hit one of my biggest career milestones.

Years of sacrifice, late nights, and relentless focus had led to this. I should have felt on top of the world. Instead, an unexpected emptiness crept in.

I brushed it off and told myself I just needed a bigger goal, a harder challenge, a higher mountain. Because isn’t that what success is ... MORE? 

We’re taught to believe that happiness is on the other side of achievement. That once we get there, we’ll finally feel enough.

But the truth? The finish line always moves.

• You get the promotion, but now you’re chasing the next title
• You hit the revenue goal, but now it’s time to double it
• You reach the milestone, but now it doesn’t feel as significant 

The high fades. The goalpost shifts. And you’re left running, always running, wondering why success still feels like not quite enough.

Psychologists call it the Hedonic Treadmill — the idea that no matter what we achieve, we quickly return to a baseline level of satisfaction. 

I’ve met CEOs, entrepreneurs, and top executives who’ve won at everything, yet feel empty inside.

Here's the truth: If you don’t define success on your terms, the world will define it for you.

We have a choice:

👉 Chase what impresses OR build what matters

👉 Optimize for status OR optimize for meaning

👉 Run on the treadmill OR step off and design a new game

Real success isn’t just about how high you climb. It’s about whether the view is worth it when you get there.

This Week's Insights:

• AI era is making traditional success markers obsolete

• Reflective questions on fulfillment, leverage, and adaptability

• Define what success means to you with ready-to-use AI prompts
  
  

TRENDS

For decades, success followed a predictable formula: work hard, accumulate achievements, and earn your rewards. But now, AI is rewriting that script.

The half-life of skills is shrinking.

A study by the World Economic Forum found that nearly 50% of all workers will need reskilling by 2025 due to automation and AI. What once took decades to master can now be learned or replaced by machines in months.

Career ladders are collapsing.

The traditional climb from junior roles to leadership is becoming obsolete as AI automates expertise. Instead of predictable progression, there's reduced need for managers and specialists. 

The value of “working harder” is diminishing.

AI can now write reports, analyze data, and make business decisions faster than most humans. In The Future of the Professions, Richard Susskind argues: “Technology is not just changing how we work. It is redefining who is needed for work at all.”

External success markers are losing meaning.

Titles, credentials, and even job security are becoming less relevant as AI-driven economies reward adaptability over stability. The old formula is being replaced by a new reality: reinvent or risk irrelevance.

The speed of change is creating a psychological toll.

McKinsey found that 64% of executives feel “trapped in an endless cycle” of reacting to disruption instead of shaping their future. The treadmill isn’t just moving faster; it’s being redesigned while we’re still running on it.

The Bottom Line:

If we focus on outdated success metrics, we risk chasing goals that AI will make irrelevant. If we redefine success on our own terms, we can create leverage, adaptability, and fulfillment.

TIPS

In Essentialism, Greg McKeown writes: “Success can be a catalyst for failure if it distracts us from what really matters.”

If AI is rewriting the rules, how do you define success on your terms? Start with these key questions:

WHAT'S TRULY MINE?

• Are you pursuing a goal because you truly want it or because it’s what you were taught to want?
• If AI changed your industry overnight, would you still be pursuing the same goal?
• If money and status weren’t factors, what work would still excite you?

Action Step: Write down three goals. Next to each, note whether it’s truly yours or an expectation you’ve adopted.

WHAT GAME AM I PLAYING?

• Are you optimizing for stability in an era where adaptability wins?
• Are you measuring success by effort and hours, when leverage now beats labor?
• Are you chasing traditional status markers while AI is redefining what’s valuable?

Action Step: Identify one outdated success metric you’re still holding onto. Replace it with a metric that aligns with today’s reality.

HOW WILL I KNOW I'VE WON?

• Is your success tied to external validation or internal fulfillment?
• Are you waiting to feel “successful” after a goal or choosing to feel it now?
• What’s a version of success you could step into today not someday?

Action Step: Define one way you can experience success today, without waiting for a future milestone.

TOOLS

Use the following prompts on any of the leading AI tools (ChatGPT, DeepSeek, Claude). 

To Define Success on Your Terms:

“Act as an executive coach. Help me reflect on my definition of success by asking deep, thought-provoking questions. Challenge me to distinguish between achievements I genuinely value and those I’ve been conditioned to pursue. Guide me in designing a success framework that aligns with my values, fulfillment, and long-term vision in an AI-driven world.”

To Build Leverage, Not Just Labor:

“Analyze my current career or business model. Identify where I am trading time for money versus creating scalable leverage. Suggest ways to increase impact, automation, or intellectual property to future-proof my success in the AI age.”

To Reverse-Engineer Your Ideal Future:

“Imagine it’s 2030, and I am living my ideal version of success. Based on current trends in AI, technology, and business, describe what my career or business looks like. Then, work backward to outline the key milestones and strategic shifts I need to make today to reach that future.”

What’s a success you once chased that didn’t give you what you expected?

Until next time...stay curious!

Cheers,
Nikki