Stay Wealthy Retirement Newsletter

Sep 25 • 3 min read

Feeling Behind? Think Again


One of the most common questions I hear is:

“How are we doing compared to other people like us?”

It’s understandable, but here are two questions that might offer a helpful perspective on comparing ourselves to others:

  • If you were on track to reach YOUR financial goals, but “behind” your peers, would you be disappointed?
  • On the contrary, if you were not on track to reach your goals, but “ahead” of your colleagues, would that feel like success?

We know the sensible answers, yet comparison is hard to resist.

With bigger homes, nicer cars, and higher incomes on display everywhere, it’s easy to feel “behind” even when you’re doing well.

Escaping that trap takes intention.

To help, I’m sharing three practices for financial contentment in today's email to help you focus on what truly matters.

But first—did you catch this week’s podcast? 👇

7 Signs You’re Closer to Retirement Than You Think

Most people overestimate how much they need and underestimate how ready they are. In this episode, I share the 7 signs you’re closer to early retirement than you realize.

🎙️ Listen now on Apple​, ​Spotify​, or ​YouTube​.


3 Keys to Financial Contentment

When it comes to money, the line between “enough” and “not enough” often has little to do with the numbers on a statement.

It’s about perspective.

These three keys can help shift your mindset away from comparison and scarcity and toward real contentment.

🔑 Key #1: Choose the Inner Scorecard

Warren Buffett describes the ‘inner scorecard’ as measuring success by your own goals and values.

The ‘outer scorecard,’ by contrast, is about how you compare to others.”

A simple filter:

“Am I judging my financial life by the progress I’ve made toward my goals, or by how I stack up against my peers?”

If your financial plan is designed to fund the life you want today and sustain it into the future, you are succeeding.

By choosing the inner scorecard, you give yourself permission to measure progress by what’s meaningful to you and to stop chasing benchmarks that were never yours to begin with.

🔑 Key #2: Focus on the Gain, Not the Gap

Our brains are wired to see the Gap—the distance between where we are and where we want to be.

But in doing so, we often miss the Gain—the distance we’ve already covered.

Try this quick exercise:

  • Think back 10, 20, or 30 years. Where did you hope to be by now?
  • Look at your current reality. Which parts actually exceed those earlier hopes?

In my experience, many families discover they’ve created far more stability, freedom, and opportunity than they once imagined possible.

Celebrating the gain quiets the restless “not enough” voice and replaces it with gratitude and confidence.

🔑 Key #3: Balance Today With Tomorrow

Prudence is wise, but perpetual deferral is costly in its own way.

Bucket-list trips, quality time with loved ones, or modest upgrades that would meaningfully improve daily life often get postponed “until later.”

While account balances grow, experiences slip away.

As Bill Perkins writes in Die With Zero:

“The whole point of money is to have experiences.”

Yes, save and invest carefully.

But also decide what “enough” looks like for YOU.

That clarity allows you to convert money into the life you’ve worked so hard to afford (without guilt).

Bottom Line

In today's world, “being ahead” is often mistaken for “being happy.”

But when we keep our eyes on our own scorecard, take time to appreciate the progress we’ve made, and give ourselves permission to enjoy today instead of endlessly deferring for tomorrow, we step off the treadmill of comparison.

Real wealth isn’t measured against anyone else.

It’s found in having enough to live in harmony with your values, and then fully embracing that life.


📚 What I've Been Reading

  • Farewell Friends: Remembering Jonathan Clements (Jonathan Clements)
  • Is a Continuing Care Retirement Community Right for You? (Morningstar)
  • Why "Downside Protection" ETFs Don't Work Long-Term (Kitces)
  • What Happens Historically After the Fed Cuts Rates? (CFA Institute)
  • Ideas Arise Through Action (More to That)
  • Disney+ Is Now One of the Most Expensive Streaming Services (Sherwood)

Thank you for reading!

Please reply to this email with comments, questions, and/or feedback.

Stay wealthy,

Taylor Schulte, CFP®

Retirement Is More Than Just a Math Problem.

Learn how our 4-step system can help you successfully navigate this decades-long transition.



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