Not hitting your income goal isn't just a money issue. It's a...
Tim Denning@Tim_Denning
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Aug 31, 2026
~3 min read
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1
Not hitting your income goal isn't just a money issue.
It's a psychological problem.
Here's how to fix it:
It's a psychological problem.
Here's how to fix it:
2
Working a traditional career destroys your mind.
• You take for granted how much the company logo does the sales & marketing for you
• You get used to being underpaid
• You're taught to follow instead of lead
• You learn to see black & white rules
Entrepreneurship allows you to make more money. But first you must heal your mind.
• You take for granted how much the company logo does the sales & marketing for you
• You get used to being underpaid
• You're taught to follow instead of lead
• You learn to see black & white rules
Entrepreneurship allows you to make more money. But first you must heal your mind.
3
You won't exceed your income goal with a salary
This is immature thinking. And investing in the S&P 500 will take years to make money.
By then you'll be too old to enjoy the money.
Even if you do become CEO at work, you'll have no free time and be stuck in meetings.
This is immature thinking. And investing in the S&P 500 will take years to make money.
By then you'll be too old to enjoy the money.
Even if you do become CEO at work, you'll have no free time and be stuck in meetings.
4
Building a business is a better strategy.
You sell your same skills + experience to the open market.
And you sell them to multiple customers instead of one customer (an employer).
You sell your same skills + experience to the open market.
And you sell them to multiple customers instead of one customer (an employer).
5
You will feel imposter syndrome
You will think you're not enough of an expert. But that's because you underestimate how skilled you are.
You only need to be 10 steps ahead of your prospect, not 10,000 steps.
You will think you're not enough of an expert. But that's because you underestimate how skilled you are.
You only need to be 10 steps ahead of your prospect, not 10,000 steps.
6
You see risks instead of opportunities.
This stops you from investing in yourself. It makes you spend time thinking about why it won't work.
Instead of why it will work.
This stops you from investing in yourself. It makes you spend time thinking about why it won't work.
Instead of why it will work.
7
You expect to be confident at the start
But you can't think your way to confidence. You'll become more confident when you:
• Execute
• Get results
• Have proof that it works
But you can't think your way to confidence. You'll become more confident when you:
• Execute
• Get results
• Have proof that it works
8
You're terrified of the market being saturated
But the market sucks. Most people suck at what they do, and won't be around in a year.
Saturated markets mean people are buying what you want to sell.
The bar is so incredibly low in your field.
But the market sucks. Most people suck at what they do, and won't be around in a year.
Saturated markets mean people are buying what you want to sell.
The bar is so incredibly low in your field.
9
You're immature
• You're holding onto outdated philosophies.
• You've been institutionalized.
Or you're listening to silly gurus who flash cars and don't give a damn about you.
You must grow up. None of this is complicated.
• You're holding onto outdated philosophies.
• You've been institutionalized.
Or you're listening to silly gurus who flash cars and don't give a damn about you.
You must grow up. None of this is complicated.
10
You need help
Being stuck in your head is slowing you down. And going it alone with trial and error doesn't work
Find a competent professional and pay them for help (just like you would if you had cancer).
Being stuck in your head is slowing you down. And going it alone with trial and error doesn't work
Find a competent professional and pay them for help (just like you would if you had cancer).
11
You gotta be around others doing it
Spending time with people also doing it makes the process less lonely.
Entrepreneurship is weird. Normies don't get it. So you must be around more weirdos who understand what you're building.
Or you'll drown in the opinions of employees.
Never ask an employee for advice on building a business because they don't get it.
Spending time with people also doing it makes the process less lonely.
Entrepreneurship is weird. Normies don't get it. So you must be around more weirdos who understand what you're building.
Or you'll drown in the opinions of employees.
Never ask an employee for advice on building a business because they don't get it.
12
You're undervaluing your skills.
If they've already earned you money, the business is validated.
What isn't proven is whether you can do basic sales and marketing. It's simple but not easy.
Once you master this, you'll never depend on an employer to feed your family again.
If they've already earned you money, the business is validated.
What isn't proven is whether you can do basic sales and marketing. It's simple but not easy.
Once you master this, you'll never depend on an employer to feed your family again.
13
You don't feel the pain of being underpaid enough
You know it's true. But you have no urgency to do anything. It's too comfortable to stay the same.
So you drown in "I'll start when I'm less busy"
That day never comes. Years turn into decades.
And once your best years are gone, the extra money has far less value.
You know it's true. But you have no urgency to do anything. It's too comfortable to stay the same.
So you drown in "I'll start when I'm less busy"
That day never comes. Years turn into decades.
And once your best years are gone, the extra money has far less value.
14
How you think about money determines how much money you make. It's time to start thinking like a business owner.
You have to master money to live the good life.
You have to master money to live the good life.
15
I’ve figured out how to reliably make $100K per month.
If you’re interested in learning how I made it happen, here are the details:
timdenning.com/100k-lic/
If you’re interested in learning how I made it happen, here are the details:
timdenning.com/100k-lic/