roostervane academy
Close this search box.

7 Reasons You’re Not Making More Money

Last year, I set out on an ambitious research project. I wanted to find as many people as I could find who had doubled their income and find out how they had done it.

The resulting research was published in Time: NextAdvisor. But unfortunately, the site went under and the article disappeared.

The reason I started on the research was pretty simple. I found that there was so much crap out there about making money. So much nonsense.

And I had tried just about everything. I tried to attract wealth from the universe. I tried positive thinking and affirmations. I tried starting online businesses.

And all of these things were interesting. But none of these things were how most of the people I interviewed made more. 

So how do people actually make more? I want to show you what I learned from this process.

By the way, I’m not going to tell you that you’re not working hard enough. There’s plenty of money to be made without just working twice as hard as you are right now. Let’s get strategic.

Here’s why you’re not making more money.

Some of these are affiliate links to products we use and love. Thanks for supporting Roostervane! 

1. You’re not changing jobs enough

The thing research has shown time and time again is that people make the most money when they switch jobs.

As I interviewed people who had doubled their income, I realized this was 100% true

Apart from those who made money by starting businesses, everybody who doubled their income made more money at a point of change.

This worked in two ways:

1. Some people took a different job and made more money because of it.

2. Some people were offered other jobs, and their current boss offered them a raise in response.

The thing is, changing jobs is terrifying. I get that.

You might as well get comfortable with searching for and finding new jobs sooner rather than later. Because otherwise, it will cost you a lot.

2. You’re in the wrong industry

There are only so many skill sets in the world. And when you think about it, there are a lot of both hard and soft skills that you’ll find in every industry.

The thing is, I’ve realized that the same job skills will be rewarded very differently depending on what industry you’re in.

For the most part, I’ve used the same basic skill set that I have as I’ve worked for a nonprofit, for the government, and then for tech. But I made very different amounts of money in all those places.

When I interviewed people who doubled their income, I saw the same thing. People willing to move to industries that paid more for talent saw increases.

I’ll never forget interviewing somebody in cybersecurity who made $400,000 a year. 

Here’s how he got there. He served in the military for peanuts and went to school after on the GI Bill. After he graduated, he worked for the government. And although he was making $100,000, which seemed like an insane amount of money to him earlier, he wanted to make more. 

He realized that he couldn’t do it in government. So he switched industries and moved to the private sector.

$400k. Boom. 

3. You don’t have high-income skills

We live in a skills-driven economy. We live in a time where people aren’t usually compensated based on their degree, but based on their skill set.

You can have a college degree that cost you $100,000 and find out that you are unemployable. And you can take a coding course online that can net you $200,000 a year.

That’s the reality of the world we live in.

If you aren’t getting paid enough, it could be that your skill set isn’t worth enough.

You can teach yourself high-income skills to create more demand for what you do. You can also take on more complexity or move into leadership roles in an organization–using skills and strengths like project management, communication, or emotional intelligence.

These will make you more money.

Here at Roostervane, we swear by Skillshare – Try it for Free here

4. You don’t have an owner’s mentality

When I interviewed people who doubled their income, I was struck by how many of them have what I would call an “owners mentality.”

If they were working for somebody else, they often stepped up to the plate. They made sure that work happened and the company kept running. They became completely indispensable to their boss because of this.

One executive I interviewed started as a manager. But when he realized that the culture was totally toxic, he went to the CEO and explained that he had a plan to fix it.

He became a vice president very quickly. Not because he had the right skills or degree. But because he saw problems and took steps to fix them. 

He cared about the company as if it were his company. And was rewarded accordingly.

That’s an owner’s mentality.

5. You’re not negotiating your salary

Negotiating your salary is terrifying. I’ll never forget the sick feeling in the pit of my stomach when I forced myself to do it.

Because it feels like you are negotiating your own value. And your imposter syndrome kicks in. You feel like you’re not worth it. All that good stuff.

One woman in Silicon Valley told me something important. “Your boss is basically your consumer. They always want to get the best deal.”

And it’s true. Just like you might drive to a different store to get a better deal on something you want, your boss wants the very best deal possible on your labor.

And that’s why you need to negotiate. In many cases, they are willing to pay more. But why would they pay more if they don’t have to?

Research shows that of the people who negotiate their salary, 66% got a higher one.  That’s pretty great. 

6. You don’t have a side hustle

I don’t want to pressure you to start a side hustle if you’re not feeling it. The easiest way to make more money is probably to use the tips above to earn more on your day job.

But I’m a side hustle guy, so I have to mention this. A few of the people I interviewed did have side hustles.

They did things like consulting on the side or doing piece work to make extra money.

Since a lot of the people I interviewed had doubled their income by starting a successful business, a side hustle can be a really great way to test the water. It lets you earn more money without quitting your day job. And if it goes well, you can make it your main thing.

7. You don’t have a healthy money mindset

I don’t really believe in attracting from the universe or any of that jazz. But I do believe that a money mindset is important.

There are a lot of different limiting beliefs around money that many of us have. Most of them were formed in our childhood, long before we even realize we were getting them.

Here are a few common money blocks people have:

  • I could never earn more money
  • Wealthy people are bad
  • Making money isn’t spiritual
  • Poverty is noble
  • My income is somebody else’s fault
  • To make more I’d have to work harder

There’s no shame in these. All of us have money blocks.

The amazing thing is, once you start to get past them, you end up earning more money. Because you’re not afraid to believe you’re worth more and to ask for it.

The first time I broke $100,000 of my salary, I was sure it was a mistake. I was pretty sure they were going to figure out that I wasn’t worth it and fire me on the spot.

Over time, I realized that was I worth it. And I expanded my money barometer even higher.


I don’t know you, but chances are one of these seven reasons is the reason you’re not earning enough money.

Not a guilt thing. I’m not interested in that. But I do hope it helps you take a hard look at what you’re earning and maybe make a strategy to earn more!

Good luck!

Read More:

9 Rules of Money They Won’t Teach You in School

10 Secrets to Live a Rich Life

Top 10 Brilliant Money-Saving Tips

Read More:



Weekly articles, tips, and career advice