4 min read

Your Overlooked Success 🏆

Here are three titles of bestselling books with the same problem:

  • Get Fit While You Sit
  • MONEY Master the Game
  • Relationship Goals: How to Win at Dating, Marriage, and Sex

The problem is... how do you know when you “win”?!

What exactly does it mean to “master” money and how do you know when you’re “fit”?

When do you cross the line from losing to winning, or achieve success?

If you do cross the line, and win… does that mean you’re done? Do you still need a budget or date nights or a fitness routine? 🤔

The Most Important Games Are Not Contests

Health, wealth, and relationships are crucial from the moment you’re born to the moment you die, and pretty much every moment in between.

In each case, you can’t “win” the same way you win a game of football or finish a marathon or get out of debt. The most important areas of life are each an infinite game.

In a finite game, there are clearly defined rules so you know when you’re winning or losing and when the game ends. You typically have distinct teams competing against each other, too.

In an infinite game, there are no built-in boundaries or success metrics and comparing your progress to others is a distraction because their success or failure doesn’t change yours.

We explore this concept in-depth in my accelerator program, because to build a thriving online education business you need to understand where your solution helps your customer make progress in an infinite game.

Infinite games are, by their nature, without end—but you still need to help your customers feel a sense of accomplishment so they know they’re making progress, and keep moving forward.

My favorite way to do that is with a success path, which grants people clarity by mapping out milestones worth celebrating along the way.

When you define the success path for your speciality, you shift the focus towards the next milestone rather than the daily toil or slog.

Here are two examples of success paths I’ve created for clients to use:

Your Enneagram Coach’s Master Coach Method:

  1. Coach Your First Client. Once you’ve immersed yourself in Enneagram training and completed certification, you’ll have the insight and experience you need to coach your first paid client!
  2. Pay it Back. Using our coaching framework, continue to meet with clients and pay back the full cost of your certification once you’ve coached seven clients through our six-part coaching series.
  3. Pay it Forward. Continue to coach clients to help them become their best self through a Christ-centered understanding of the Enneagram! Meet with one client per weekday to earn $25,000 per year, part time on the side.
  4. Transform Your Career. As you transform more lives through coaching, build your client base until you’re meeting with four clients per weekday to earn a six figure income from Enneagram coaching, full time!
  5. Teach it Forward. Build an online teaching business with courses, books, and other programs to leverage your Enneagram expertise as an influential teacher. Build your own seven figure school, teaching online.

Ten Oaks Real Estate’s Real Estate Roadmap

  1. Sell Your First Home. Once you’ve done this, you get your first commission payment and get to celebrate with a few thousand dollars in your pocket!
  2. Earn Your First Five Figure Month. Complete two transactions in a single month and you’ll earn more than $10,000!
  3. Earn Your First Six Figure Year. Keep up the pace, completing two transactions each month to earn more than $100,000 in a single year!
  4. Convert to Passive Income. Recruit real estate agents to build a team, and get commission on every sale they make. Recruit fifty agents to generate a six figure income every year, without selling, forever!
  5. Establish Permanent Wealth. Buy your own rental properties to create a legacy portfolio of wealth-generating assets that will outlast you.

How Milestones Fixed My Money Mindset

For most of my life, I have been obsessed with focused on achieving financial freedom.

That’s a socially appropriate way to say that I stress about earning money, spending money, and saving money. I come from a poor family, and my own mindset has typically been that whatever money I have is never enough.

Then I read Ramit Sethi’s Ladder of Freedom (a perfect example of a success path with measurable milestones in an infinite game).

Ramit has helped thousands of students built a “Rich Life” and along the way he realized that while goals are unique and personal there are five levels of financial freedom to celebrate along the way:

  1. Freedom from $3 worries. This is the ability to stop sweating the small stuff.
  2. Freedom to ask $30,000 questions. This is the ability to buy the things you love, guilt-free.
  3. Freedom from location. This is the ability to work and live wherever you want.
  4. Freedom from time limits. This is the ability to do what you want, when you want to do it.
  5. Freedom from expectations. This is the ability to completely craft your own Rich Life.

If you had asked me a week ago how my wife and I were doing on the path to “achieve” financial freedom I would have told you we are working hard but have a long way to go.

That’s because I was treating financial freedom like a finite game (even though I know better), and I knew I wasn’t done so I hadn’t “won” yet.

But with Ramit’s help, I can reflect on my day, compare it to these milestones, and realize that:

✅ I just paid $35 for a day pass at a coworking space without worry 🤷‍♂️

✅ I bought a $50K car a few days ago, guilt-free ✌️

✅ I’m writing from a rooftop in Old San Juan, Puerto Rico 🇵🇷

✅ My wife and I just spent three days exploring a Caribbean island 🏝️

✅ We are pulling our kids out of school to relocate to Puerto Rico 🤯

Wait a minute—that means we are actually doing awesome!

We’re at “Level 5” of the Ladder of Freedom?! Without Ramit’s success path, I would have no idea.

We have not maxed out Roth IRAs for a decade or built a passive income portfolio from real estate, cryptocurrency, or stocks.

We do have a few investments, three profitable businesses, and also some debt (even though we’ve "achieved" the finite game of paying off debt 100% twice).

Many things have not gone according to plan, but we have adjusted our plan as needed and we kept moving forward—without realizing that we sped past key milestones along the path to success.

Does that mean I will stop managing (or worrying about) my money now? No, but I will shift my mindset to celebrate the progress we’ve made.

When you create your own success path, you create a map for people to follow with a shared measure of success.