Draft chapter from the forthcoming “Income Operating System” book…
Somewhere along the way - especially in the USA! - we got addicted to the idea of GET RICH AND CHANGE THE WORLD!! Used to be people wanted to be a millionaire. Now that’s chump change. Gotta be a billionaire or die trying, right?
Let’s see how many of these sound like second nature to you:
Make a dent in the universe. Become the best! Build a billion-dollar business. Start a movement. Shoot for the stars. Go big or go home. No pain no gain. Change the world or don’t bother…
It’s the gospel of ambition that’s been preached by famous entrepreneurs, investors, startup accelerators, TED Talks, and now homegrown influencers (both real and fake).
American culture’s always idolised money and acommplishments, but it’s been turbocharged by the internet - and AI will take it again to an even higher level. Somewhere the lie that “bigger’s always better” infected the culture. Bigger house! Wait - more houses! Bigger car! Bigger meals! Supersize me! Be louder! More traveled! Famouser, richer, taller, muscle-y-er (yes I just made up some words in there).
And every dream had to be world-sized or it wasn’t worth dreaming.
(Meanwhile - is anyone surprised that anxiety, loneliness and depression are on the rise? “Compare and despair” among other things is getting turbo-charged too.)
There’s even a term for it: BHAG- Big Hairy Audacious Goal. Popularized by the business classic “Built to Last”, a BHAG was supposed to be a unifying, energizing force - a bold vision that brings people together to do something extraordinary.
And for a few people, sure - it works. Some people and teams thrive on moonshots. A few companies do need bold, clear rallying cries. Go for it!
But for most of us?
Screw the BHAG.
It’s become so default - so embedded in the wallpaper of “success thinking” - that we don’t even question it anymore. The assumption is: if you’re not aiming for something massive, you’re not aiming high enough.
That’s bullshit.
You don’t need to change the world.
You just need to change a life. Or - speaking of small goals - just edit one.
That’s what actually matters.
What if, instead of trying to become the best in the world, you just tried to become ‘better’?
What if your version of success isn’t actually building a unicorn, but reclaiming your sanity?
In 2007, after leaving Salesforce.com, my plan was to go back to the Silicon Valley way… start a company, raise money, be a CEO etc etc. But… I spent some quiet time in China that summer, in ridiculous heat. And I realized something.
I didn’t want to raise money. I didn’t want to be a CEO. I didn’t want to start a tech company. And I didn’t want to live in Silicon Valley.
I realized I wanted to make as much money as I wanted, doing something I loved. Now, I had no idea what that was. But I set out to figure it out (still working on it, but I’m much farther along!)
What if the boldest, bravest, most rebellious thing you could do right now was to pick a small, reasonable, maybe even embarrassing goal - and finish it?
The Quiet Rebellion of Not Going Big
There’s a kind of humility in saying, “I don’t need to be a global icon. I just want to work X hours a week at something fulfilling, creative or challenging - and make [$xx] a month so I can [support my parents| spend time with my family | travel | play music | build an epic anime collection | etc.”
That’s not playing small, that’s playing honest. Well, assuming you’re being honest with yourself. That’s the trick :) Can you tell the difference between a goal that ‘feels easy’ because you’re scared to challenge yourself? Like getting into a law career because both your parents were lawyers? And one that is small, but still challenging because it’s yours - like admitting to a first person that you actually don’t like law or want to be a lawyer?
Because - back to big goals - most people chasing big goals aren’t doing it from clarity or joy. They’re doing it out of cultural programming. They saw a TEDx talk, followed a business guru, or started comparing themselves to someone on LinkedIn with a yacht in their profile pic. It sound cool!
And without realizing it, they absorbed a goal that was never theirs to begin with.
But here’s a test. Ask yourself:
“If no one else knew what I was doing, would I still want to do it?”
If the answer is yes - you’re probably on the right track.
If the answer is no - then maybe you’re building a goal for someone else’s approval, not your own.
The Case for Embarrassing Goals
Let me introduce a radical idea: embarrassing goals.
An embarrassing goal is the kind of goal you’re almost ashamed to admit - because it feels so much smaller than what you’re “supposed” to want.
Like:
I just want to get one freelance client this month.
I’ve always wanted to work as a [job people will say is weird or socially frowned up].
I want to be able to talk to my friends or family about a career or life change that I’m holding back on.
I want to earn enough to stop using my credit card for groceries.
I want to take weekends off without guilt.
I want to make my first $10 selling something I created.
(Or maybe it actually is an embarrassing sexual or socially shamed goal! Ha!)
These might not make headlines. But they make lives better.
And here’s the wild thing: when you start honoring these small, true goals, they tend to lead to bigger things anyway - but on your terms. Because you’re moving from alignment, not ambition.
Be Big for You
I’m not anti-growth.
I’m not saying you should never go big.
But I am saying: only go big if it’s worth going big for you.
For some people, running a tiny, boring business that pays well is the ultimate win.
For others, it might be a big stage or a big impact. Great. But make sure it’s your dream. Not society’s. Not your coach’s. Not your dad’s. Not mine.
Let’s normalize starting small.
Let’s glorify tiny progress.
Let’s celebrate not needing to be epic all the time.
The world doesn’t need more people trying to be superheroes.
It needs more people who are willing to do their own thing - not their friends’ things, society’s things, AI’s or their parents’ things.
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Amen brother! I have an acupuncturist(I know..woo woo) that has always cautioned me about "supposed to" and "should". Here are some thoughts that support your wonderful post. he
There’s a quiet trap built into the words “supposed to” and “should.” On the surface, they sound like guidance — like directional signs intended to keep us aligned. But dig a little deeper, and they often reveal themselves as chains. Heavy ones.
"I should be further along."
"I’m supposed to do it this way."
"They should know better."
"We’re supposed to act like this."
These phrases are rarely rooted in truth. They’re usually rooted in expectations, projections, or inherited scripts that no longer serve us. They quietly demand compliance without offering clarity. They pressure us into comparison, conformity, or guilt, without examining whether the direction actually fits our context, values, or goals.
"Should" often masquerades as wisdom, but it’s really just judgment with a better outfit.
When we blindly follow the “supposed to” path, we risk:
Prioritizing others’ standards over our own principles
Chasing approval instead of progress
Letting fear of deviation override authentic creativity and innovation
This doesn’t mean we discard discipline, norms, or accountability — but rather that we interrogate them. Ask: Does this “should” align with who I am, where I’m going, and what actually matters right now?
Progress isn’t about doing what you’re “supposed to.” It’s about doing what’s true, useful, and deliberate — even if that looks different from the well-worn path.
So next time you catch yourself saying “should” or “supposed to,” pause. Challenge it. Replace it with a more honest question:
What’s actually right for me — here, now, with what I know and what I value?
That’s where real alignment — and real growth — begins.
Excellent stuff Aaron!