Outlaw Finance: A Bold Mindset Shift for Mastering Money

Posted On 1 April 2025

I was trying to think of how to explain my approach to mastering money when this “Outlaw Finance” idea came to me from the sub-genre Outlaw Country of country music. Musicians like Willie Nelson, Kris Kristofferson, and Waylon Jennings are some of the more famous members of the outlaw country movement.

Let me start off by saying that this mindset is about bucking the system, not engaging in criminal behavior. The outlaw country musicians were the ones who did things their way, and did not go with Nashville’s music trends. The music was authentic, a bit less refined, and they controlled their careers – not the recording studios.

Outlaw finance is a bold approach to money, but it is not for everyone. This is for the tough people who want to have true financial independence. So much of economics and finances are based on scarcity. Outlaw Finance is based on an abundance mindset.

Financial Independence – Work for Yourself, not “The Man”

Financial independence is about more than just having enough money to do what you want. There is a mindset that goes with it. Those who relate to this lifestyle are willing to shift their mindset and take responsibility for themselves in a way that they are no longer dependent on employers or controlled by money.

Do you refuse to live paycheck-to-paycheck? Outlaws also don’t let money control them or their actions. I’m not saying that they don’t think about money, it’s just not the primary thing for them.

How do you break free from the cycle of living paycheck-to-paycheck? Having additional sources of income is very helpful. More importantly, it begins with becoming authentic with how you handle your finances so you can master money.

Authenticity in Spending & Saving – Spend on Purpose, Not Guilt

Being authentic means being yourself – being real. Figure out what you really want as well as what you don’t want in your life any longer. Money is a personal thing. The outlaw finance way is all about you deciding how you want to use your money.

Forget trying to keep up with the Joneses! There are some effective strategies for managing money like the anti-budget – save first, spend the rest. Don’t worry about following a strict budget. You do you, in a controlled way that you decide.

You should be the one who determines spending based on your values. Use the tools that work the best for you. Here are a few unconventional money tips. Money is a tool as well (and it feels great to have it!). Since you view money as a tool, you learn to master money and you don’t feel the need to hoard it.

Embracing Risks with Calculated Risks – Fortune Favors the Bold

We all know what fragile is – stuff that breaks easily. Something that is strong or not easily damaged is called robust or durable. There was no word for the opposite of fragile until Nassim Nicholas Taleb coined the word “antifragile” and wrote a book by the same name. Outlaws understand that some things become stronger when they experience damage. Think of our skin and how it forms calluses (becomes tougher) when the skin is damaged.

Smart risks separate outlaws from rule-followers. We look for opportunities where we can increase the value, such as investing in ourselves, our skills, and high-reward opportunities.

Not only do we evaluate risk vs. reward before making financial moves, we try new things in a small way so that if or when they break, we can learn from the experience without a big financial loss. It is through these experiences that we learn how to master money.

Defying Conventional Advice – Because the Old Rules Keep You Stuck“

“Go to school, get a job, and retire at 65” doesn’t work for everyone. I’m one of the people it hasn’t worked for. I got a BS degree (in both meanings of the abbreviation!) in history. I was told I need to “pay my dues” before I can expect to reap the benefits. Well, after paying my dues in multiple jobs only to be let go (for various reasons) before I even saw any benefits left me jaded.

Have you questioned advice like avoiding debt, extreme frugality, and reliance on retirement accounts in our old age? Debt is a tool which is neither good nor bad. Be it with debt or drinking, excess is where the trouble comes from.

Those who are drawn to the outlaw finance mindset are open to leveraging credit, business ownership, real estate, and unconventional investments. They are willing to do what it takes to get the job done, while staying true to their values.

Community Support & Generosity – An Outlaw Alone is Just a Rebel

Wealth isn’t just personal – it’s about building a network of support. We have come to realize that nobody is an island. When we work together, we can achieve more. We can also harness the power of mentorship, collaboration, and bartering in financial success.

Wealth is not just about us. It’s about generosity and giving time, knowledge, and money to others in a way that helps them. We have an abundant mindset and we know that there is more where that came from.

Outlaws are all for teaching others how to fish, not giving fish to others. We know that when we give to others without keeping score, we will receive from others more than we gave. As I’ve heard, we can’t out-give God.

Freedom Above All Else – Money Should Serve You, Not Control You

The goal isn’t about money – it’s living life on your own terms. When you have your finances taken care of, they can take care of you! You then are able to have the flexibility, autonomy, and adventure that you desire.

Real financial freedom is being free to do what you want, when you want, with who you want, without asking permission. We can seek advice from others (our spouse, for example) with what we are doing.

While freedom is important, freedom without money is what a homeless person has. On the other end of the spectrum is the wealthy person who is chained to their career. We want to live life our way, and on our own terms.

Summary

The Outlaw Finance mindset works for those tired of playing by traditional rules. You’re ready to do something different and in a way that works for you. Step up and join me on this financial adventure – you know you want to!

Take your first outlaw step toward financial freedom by playing Canoosa Finance’s Durability Bingo. Sign up with Canoosa Finance to get your free game board. It puts a light-hearted spin on a typically boring subject. The game gives you direction so that you can improve your financial durability this year.

I invite you to join this wild bunch of people who are tired of doing things that don’t work, or that don’t work for us. Together we can work to build up stronger individuals, communities, and countries. Come with me and let’s become unstoppable!