Stop 4: How’s my Defense?

Offense sells tickets but Defense wins championships.– Bear Bryant

Defense is the most underrated factor for success in any arena. Every team, business organization, and financially successful person has to have defense to succeed. Your offense is what helps push you forward but the defense keeps you from falling back!

If you’re climbing the treacherous mountain towards your success vision it is important to be able to focus on making progress. Your defense allows you to maintain that singular focus. Without it for every inch you climb forward there is a shift in the gravel that causes you to slip down a few inches or even a whole foot. Once you slip on that climb two things happen:

  1. The ground you were holding on to is now weaker. This makes slipping again more likely. Every time you slip it becomes more likely that you will slip again and fall further each time.
  2. You begin to doubt your ability to pull through. Once you begin slipping you overly focus on slipping again. This derails your ability to make progress and leaves you exposed to making another mistake and slipping again.

If you’re not careful these two factors will build upon one another and your feet will be back on the ground in no time.

When you see climbers they give a great deal of thought to their defense. The goal isn’t solely to not fall off the mountain. It’s to maintain the progress they have already earned! This is where your financial defense comes in.

How’s My Defense?

Continue reading

Stop 3: Where Am I Today?


Has any one heard of Jeff Bezos? What about Warren Buffet? Bill Gates? Oprah? I could continue but this isn’t Forbes and I can only fight the money envy for so long. These people are considered by Forbes as the richest of the rich.

Of the four people I listed guess how many inherited a significant portion of their money?




These four incredibly wealthy people made their money in one lifetime and could spend the rest of that lifetime trying to spend it to limited success. But how do they judge their wealth? Is there some comedic sized money counter hidden in a secret layer that works non-stop (presumably powered by nuclear fission)? Furthermore, how is some magazine finding this out? It’s hard to imagine Warren Buffet bragging about his wealth while munching on an Egg McMuffin.


How did you get in here?


Forbes and everyone with an internet connection knows these astronomical numbers because they are not tracking their cash; they are tracking their Net Worth. By tracking their purchases of appreciating assets they can track their estimated Net Worth. Net Worth is the single most important number in your financial picture! It’s the financial scoreboard that lets you know how you’re doing. Seems important right? Than why do so few people even know their number!?!?!

Do you know yours?


Where Am I today?

Continue reading

Stop 2: How Long Do I Want to Have to Work?

Have you ever watched a commercial for prescription drugs? There are usually two kinds. The cold clinical kind that spells out all the benefits of the drug they are advertising and the other kind. I want to talk about the other kind for a second.

The other prescription drug commercial shows people before and after they take this revolutionary drug. It opens with people miserable. They’re sitting in some non-descript room staring longingly out the window wishing they could enjoy the day. Then suddenly the hard to pronounce wonder drug is introduced to them by their doctor (who definitely is not paid to recommend this branded product). All of the sudden they’re kite surfing and running with the bulls. They’re finally living the life they always dreamed of! If you haven’t seen one of these here’s an example

While I have no pills or a medical license I do want you to get to the after just like in the drug commercials. In Stop 1 we decided what that “after” looks like. Now let’s choose when we reach that magical world.

How Long Do I Want to Have to Work?

Continue reading

Stop 1: What is Success?

The first stop on your Roadmap to Success is to answer this question:

What is success?

Don’t look to the hacks over at Merriam-Webster for help here. Success has as many definitions as there are people on the planet. Every person has an idea of what success is and it is in stark contradiction to what others may consider it to be.

A reality TV star likely views fame as success but Daniel Day Lewis can barely be bothered to be recognized for his amazing acting. Success is deeply personal and until you’ve quantified what your success vision is, you’ll never reach it.

The first step in shaping your financial picture is deciding what success looks like. This is a fun step. Unlike your tweed wearing 3rd grade teacher I am asking you to daydream. I want you to close your eyes. Imagine someone you admire telling you that you’re a success.

What Does Successful You Look Like?

Continue reading

The Roadmap to a Successful Comeback

“A journey of a thousand miles starts with a single step” -Lao Tzu

Aside from providing uninteresting people with material for the captions of their Instagram photos, Lao Tzu taught any trip, regardless of distance, begins the same way. However, Lao Tzu did not provide guidance on how to take the first step.

Quotes are funny that way. They can give us a small piece of what we seek but never the full recipe. Personal finance is no different. Look at almost any mainstream personal finance article and it is rife with quotes to inspire change.

“Save 10% of your income!”

“Build a 3 month emergency fund!”

“There are hot singles in your area!”

Each of these quotes is equally useless without proper context. Surprisingly, it is the context that separates success from failure. Every piece of our financial picture is a cropped close-up of a much larger portrait. Bringing that entire image into focus at once is a daunting task. Naturally, every person becomes overwhelmed and asks the same question:

Where do I begin?

Continue reading