Why More is Never Enough
You’ve worked hard. You’ve climbed the ladder, built your wealth, and hit financial milestones you once only dreamed about. But instead of feeling satisfied, you immediately set your sights on the next thing. A higher net worth. A bigger house. A more prestigious career move.
Sound familiar?
For high-achieving professionals, ambition is a double-edged sword. It drives success but can also create a never-ending cycle of “I’ll be happy when…”—when I hit $8 million saved, when I buy a vacation home, when I retire early. But once you reach that milestone, the goalpost moves again.
This endless chase can leave even the most successful people feeling unfulfilled. The problem isn’t with wanting more—growth is part of human nature. The problem is never pausing to recognize how far you’ve already come.
So how do you break the cycle? How do you achieve more while also appreciating what you’ve built? Let’s explore why wealth alone isn’t the answer and how redefining success can bring more fulfillment to your financial journey.
The Achievement Trap: Why Success Feels Empty Without Perspective
The Gap vs. The Gain: Why You Never Feel Like You Have Enough
Dan Sullivan, author of The Gap and The Gain, describes two ways to measure progress:
- The Gap: Comparing yourself to an idealized future that you haven’t reached yet.
- The Gain: Measuring yourself against your past self and recognizing how much you’ve already accomplished.
Most high achievers live in The Gap. No matter how much they earn or achieve, they focus on what’s still missing. They see only the distance left to go, not the ground they’ve covered.
This is why hitting financial milestones often feels underwhelming. Instead of celebrating, you immediately expand the goal. You’ve saved $5 million? Now you want $10 million. Bought your dream home? Now you want a second one.
But when you live in The Gain, you measure success differently. You recognize that today’s reality was once your goal. This shift in mindset allows you to experience more fulfillment while still striving for future success.
Why Undefined Goals Keep You Stuck in the Cycle
Another reason wealth doesn’t always bring satisfaction is goal ambiguity. If your financial plan is just “keep making more”, you’ll never feel like you’ve arrived.
Consider two different mindsets:
- Undefined Growth: “I just want to keep increasing my income and net worth.”
- Defined Goals: “I want $8M saved for retirement, two international trips per year, and financial security for my family.”
The second mindset provides clear markers of success, allowing you to celebrate when you reach them. Without specific goals, you’re chasing an undefined version of “enough” that keeps expanding.
Redefining Success: How to Feel Fulfilled While Still Growing
Step 1: Define Your Personal Version of Wealth
What does “wealth” actually mean to you? Instead of letting external comparisons dictate your financial goals, take time to define what success looks like on your own terms.
Ask yourself:
- What do I want my money to do for me?
- How do I define financial security and freedom?
- What experiences or lifestyle upgrades actually matter to me?
For some, wealth means owning multiple properties and growing investments. For others, it’s having the flexibility to travel, spend time with family, or retire early.
Clarifying your personal vision allows you to set meaningful financial milestones rather than constantly moving the goalpost.
Step 2: Track Your Financial “Gains”
During our client meetings at Truly Aligned, we always start by reviewing progress—the small wins and major milestones we’ve hit together.
This could be:
✔ Setting up a high-yield savings account for travel spending
✔ Maximizing stock option strategies to reduce taxes
✔ Drafting estate planning documents for wealth preservation
✔ Transitioning from employee to entrepreneur with financial confidence
By tracking tangible progress, our clients see how much they’ve already built—which brings confidence, motivation, and appreciation for the wealth they’ve created.
Try this for yourself: Look back at where you were financially five years ago. What have you achieved since then? Recognizing these gains helps you break free from The Gap and feel more fulfilled in your financial journey.
Step 3: Balance Future Growth with Present Enjoyment
There’s nothing wrong with wanting more, but are you also enjoying what you have now?
If your financial plan is all about the future, you might be delaying happiness indefinitely—thinking you can only enjoy life after reaching a specific number.
To counteract this, consider:
- Setting intentional spending goals—If travel is important, define an annual travel budget instead of endlessly “saving for later.”
- Allocating money for lifestyle upgrades—Instead of only focusing on net worth, consider what improvements would enhance your life today.
- Celebrating financial milestones—Take a moment to appreciate when you hit a savings target instead of immediately raising it.
True financial success isn’t just about how much you accumulate—it’s about using wealth to create a fulfilling life both now and in the future.
Final Thoughts: What is “Enough” for You?
If you constantly feel like you need more to feel secure, it might not be a financial problem—it might be a mindset shift that’s needed.
✔ Define what financial success looks like for you.
✔ Measure progress by how far you’ve come, not just how far you have left to go.
✔ Enjoy your wealth along the way instead of endlessly moving the goalpost.
At Truly Aligned, we help high-achieving professionals build wealth with clarity and purpose—so financial success doesn’t just mean more, but also enough.
Want to take control of your financial future and define what “enough” looks like for you?
Take our Wealth Archetype Quiz to see how your financial mindset is shaping your decisions—and how you can align wealth with what truly matters.
FAQs
Why do high-achievers struggle to feel satisfied with their wealth?
Many high achievers measure success by future goals rather than past progress. This creates a cycle of always chasing more without appreciating what’s already been achieved.
How do I stop constantly moving my financial goalpost?
Define clear financial goals with measurable outcomes. Instead of just “saving more,” set specific targets—like $8M for retirement or an annual travel budget.
What is The Gap and The Gain by Dan Sullivan?
It’s a book that explains how people either compare themselves to an ideal future (The Gap) or measure success by past progress (The Gain). The latter leads to greater fulfillment and motivation.
How can I balance financial growth with enjoying my wealth now?
Allocate money for both future goals and present enjoyment—whether it’s travel, lifestyle upgrades, or experiences that matter to you.
Securities offered through LPL Financial, Member FINRA/SIPC. Investment advice offered through The Wealth Consulting group, a registered investment advisor. The Wealth Consulting group, WCG Wealth Advisors and Truly Aligned, INC are separate entities from LPL Financial. The opinions voiced in this material are for general information only and are not intended to provide specific advice or recommendations for any individual. All performance referenced is historical and is no guarantee of future results.