Reaching the point of "enough"
Chasing more is exhausting. Here's how to design a finish line you can cross with pride.
Gary Bloomer | SHAKING THE TREE #289
Let me ask you a question—a question that will probably feel like a heresy in a world chanting “more”: with billionaires and millionaires getting richer by the day, how much is enough for you?
Is it more money?
A newer car?
A bigger house or apartment?
Financial freedom?
Where is the line of “enough” and when will you know you’ve crossed it?
What if you’re already there?
We’re conditioned for the chase, for the reward, for more.
More revenue.
More followers.
More accolades.
More square footage.
If we let it, the horizon of ambition goes on forever and if we’re not careful we can keep running, lungs burning, legs screaming toward a mirage we’ll never get to.
And in falling for this ruse we’ve mistaken movement for progress, and accumulation for meaning.
This isn’t an anti-ambition manifesto. Far from it. Ambition built the bridge, wrote the symphony, and started the business.
Specific, strategic ambition is a good thing to strive toward.
But left unchecked an undefined ambition can quickly become a nonstop treadmill rather than a trail to blaze.
And in doing so, this blind ambition confuses the concepts of “what’s next” with “what matters.” The result is that the constant pursuit of “more” becomes less a sign of drive and more a symptom of a void we’re trying to outrun but can’t.
The ambition exhaustion isn’t from doing the work—no; it’s from thinking we can run the endless race. It’s the quiet dread of a game where the rules keep changing and the goalposts keep moving. It’s the anxiety of looking at a full life and feeling empty because you’ve forgotten how to measure anything worthwhile other than growth.
The most powerful decision you can make then is to design your own finish line. To define “enough.” Here’s how to draft the blueprint:
Part 1: The audit – figuring out what you’re actually chasing
Before you can define what “enough” is for you, you must untangle the thorny issue of “why.” This isn’t about goal-setting; it’s about motive-mining. It’s about being honest about what it is that’s driving you. You do this by:
Interrogating the numbers. Is that ideal revenue target more about security and status, or is it more about freedom? Is that follower or subscriber count more about influence and validation, or is it more about your vanity? Peel back the layers of this organizational onion to find the core need.
Spotting the ghosts and demons. Who are you still trying to prove yourself to (or prove wrong)? Who are you trying to impress or outrun? What shortcoming might you be overcompensating for? Be honest: much more of our relentless drive is fueled by old scripts written by others than we care to admit. It’s time to edit those scripts to suit your current story.
Running a “so that” test. For every ambition and lofty goal you have, complete the sentence: “I want [X] so that I can…” Keep going until you hit a meaningful feeling (peace, safety, pride, liberty, freedom, contentment, happiness) or a value (family time, creative freedom, community impact). That end point is your true north. Follow it.
Part 2: The blueprint – designing your “enough”
“Enough” is not a universal number, nor should it be. It’s more of a personal constellation of conditions, meanings, and values. It’s the point where the cost of “more” outweighs its benefit, both to you and to the people who matter to you most.
You find this point by:
Defining the plateaus and peaks. In nature, growth isn’t ever a constant vertical line; it’s more a series of plateaus and peaks, some of which are false in that there’s always something beyond them.
So it’s important to define your plateaus and peaks. What does the idea of “Sustainable Success” plateau look like for your health, for your key relationships, for your business, and your finances? Describe these things in vivid, sensory detail.
Setting the guardrails. Define what’s non negotiable. Unless you build serious and sensible walls around it to shape and contain it, the idea of "enough" can be something of a fragile idea.
So, it’s important to define your sacred rules: “I’ll have enough when my family no longer has to fret about the long term future.” Or: “I’ll have enough revenue when earning more would cost me my morning runs.” Or: “My team is big enough when I no longer know everyone's name.”
Shifting from “What’s next?” to “What’s now?” The finish line mentality allows you to change your primary question. Instead of perpetually planning the next conquest, you can pour your energy into deepening, mastering, enjoying, and contributing more from the place you’ve reached.
Part 3: The celebration – living on the other side of the line
Crossing a self-defined finish line is less of an ending and more a case of a liberation.
This means setting and defining:
The power of maintenance. There is profound skill and satisfaction in maintaining a well-built engine, or a thriving garden, or a healthy company, or a strong and healthy body. Sadly, our culture undervalues maintenance in favor of breakthroughs, but it’s in the realm of maintenance that we fine true and lasting grace and stewardship.
Ambition redirected. When we attain our goals and we begin to redirect our ambition the energy we once spent chasing the external “more” becomes fuel for the internal “better.” Better skills. Better relationships. Better character. Better contributions. The ambition doesn’t die; it simply matures and mellows because it’s finding more meaningful targets.
The ultimate wealth: creating sufficiency. This involves looking at what you’ve built, who you have beside you, and who you have become, and to sincerely say, “This is enough.”
This is the foundation of unshakeable peace because once attained, it makes you immune to the ceaseless frenzy to find more. Sufficiency then becomes the ultimate declaration of personal and professional sovereignty.
Your worth was never meant to be a tally on a ledger.
It’s in the integrity of your craft, the depth of your connections, the calm in your spirit, and the legacy of your character.
Design your finish line.
Build it with intention.
Cross it with pride.
And then, learn the profound, subversive joy of standing still, in the space you created, and simply being enough.
True ambition isn’t a never-ending race; it’s the wisdom to build and honor your own finish line. The exhaustion we feel comes from chasing external, shifting targets rather than pursuing inner sufficiency.
To break the cycle, you must interrogate the “why” behind your goals, design a personal and vivid definition of “enough” with non-negotiable guardrails to protect it, and finally, shift your energy from acquiring more to mastering, appreciating, and contributing from the abundant plateau you’ve reached.
This is how you trade the anxiety of the horizon for the profound peace of the present.
As always, thanks for reading.
—Gary
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Next time on Shaking the Tree: The generalist’s decade is coming!
ABOUT THE AUTHOR: Originally from the U.K., Gary Bloomer is a writer, branding advocate, marketing specialist, and an award-winning graphic designer.
His design work has been included in Creative Review (one of the UK’s largest design magazines). Since 2009, he has answered over 5,000 marketing and business questions in the Know-How Exchange of MarketingProfs.com, placing him among the top 3% of contributors. He lives in Wilmington, Delaware, USA.