Your Hidden Money Story

We all try to look good to others. But trying to keep up appearances can lead us to pain, stunt our growth, and create unnecessary prolonged worry.

We all want to be happy. And success sure is nice.

But it doesn’t mean we have it all figured out…all the time.

Life can be turbulent at times. Being fake or ignoring what is happening doesn’t serve us.

On the other hand, it doesn’t make sense to complain our life away, either. Who wants to be around people addicted to complaining?

But when we pretend, we limit connection, learning, and growth.

Pretending results in nothing but pain.

When we are willing to do anything to be liked, or limit expression to protect ourselves, we block growth, repeal joy, and drain energy.

To truly connect and go deep with someone, I want to know all there is to know—the good, the bad, the ugly. The story behind the person, underneath the surface. This allows me to be of service and to learn. To connect. This is where breakthroughs happen.

After a quarter of a century of consulting, I am clear that everyone is carrying around plenty of pain—and usually hiding it.

They may not talk about it, and we may not know about it. But everyone has areas in their life where everything isn’t exactly as they wish it would be (and sometimes far from it).

I’ve been there. Especially in 2023. Unwinding a partnership. Completely separating from a company I founded and sold.

I’ve been frustrated with myself, thinking I should have it all figured out. I’ve been hard on myself.

Life brings us lessons—it’s what we’re here for. We will inevitably make mistakes along the way.

And yet, I still have unrealistic expectations that I’ll make all the right decisions.

I want to be of service rather than require any support or help. But this thinking prolongs the pain and limits others’ ability to help.

How can someone else be of service if we don’t let them know what is going on so we can become better receivers?

No matter how smart you are, or how well you are doing, we never fully arrive and become enlightened.

Do we ever have EVERYTHING solved?
Do we ever stop learning and growing?
Is there a state of nirvana where anyone has it ALL figured out?

Plus, would a life without challenge bring forth as much joy, as much progress, without the duality of good and bad, up and down, happy and sad?

Have you ever read a story or watched a movie about someone who was born, lived perfectly, had no obstacles, and simply lived without the ebbs and flows of challenging times, relationships, or some form of transformation?

If so, that’s a damn boring story.

Superheroes are relatable because they have a weakness. Kryptonite for Superman.

What we don’t and won’t share becomes our kryptonite. When we dare to face our difficulties, it brings forth our power.

You are not alone.
You don’t have to be perfect.

You may be one idea or one relationship away from a new level of prosperity, from a breakthrough. It requires an honest assessment though.

Vulnerability allows us access to support, to heal, and to learn.

Even the best investors lose money sometimes.

Some of my best content and biggest shifts came from difficult experiences leading to lessons. It is one thing to understand something intellectually, but another to have emotional intelligence or make wise choices when facing bouts of scarcity.

People often get stuck because they don’t want to face the truth. We ignore intuition because it is inconvenient.

Some falsely believe positive thinking is all that is required, but it can be a delay, a block, or even a delusion preventing results.

One of the biggest areas people can gain results is by examining their relationship with money.

So, what is your hidden money story?

How do you view money?
How does money make you feel about yourself and your worth?
What does your net worth say about you and your value?

When it comes to our money story, there are layers:

  1. What we will share.
  2. What we won’t share.
  3. What we can’t share.

What we are willing and often share with the world, is a mechanism to protect our fears, insecurities, or where we judge ourselves. Maybe we are private about certain aspects, yet have an internal dialogue where there is comparison that creates jealousy and undermines our confidence.

This could have begun before we clearly remember. Maybe it was long ago. Maybe our first awareness of money.

If you think back to your childhood, when did you become aware of money?
Was it a good memory or something rooted in scarcity?
Did your family view those with money as productive value creators, lucky, or someone greedy? Did your family fight over money, feel it was complicated, run from money, hoard money, etc.?

Before our brains were fully formed, we may have solidified our perspective. We may have paradoxically hidden those moments of pain and frustration from our memory, tucked them into our subconscious, and placed an invisible ceiling on our results.

Our beliefs around money can govern our actions, add to our stress, and become an unwinnable game of sacrifice and strife. These invisible structures and models inform our behavior. If these beliefs go unchecked, if they go unexamined, our limited mindset limits our prosperity.

Effort can’t save us.
Rate of return won’t solve it.
Money in an account can never be enough.

It takes courage to examine the story we tell the world and ourselves.
Where is it serving us and where is it limiting us?
What are we afraid of?

There is what we present to the world and the conversations we have, and there are the stories we tell and keep to ourselves.

That is what we won’t share. But what we won’t share holds the key to freedom. To transformation. To healing and breakthroughs.

From 1998 to 2008, my money story was easy to share. I had blind spots that were about to be exposed. But for ten years my net worth increased, my revenues grew, and I was recognized for being young and successful.

But no matter how much I made, no matter how much net worth I gained, it was never enough.

I rarely enjoyed the growth or celebrated it. There was always someone with more. But because I was young, my success was celebrated and considered out of the ordinary.

This success came with ignorance and risk. I kept buying more and more real estate. Adding more programs and projects to my business as well.

Until 2008.

Everything changed and changed quickly. One major obstacle was the banks stopped lending money. Some of my properties had balloon payments and developments required long-term financing.

Instead of focusing on what I loved to do in my business, my attention turned to real estate.

Before 2008, I had only understood good times in real estate—appreciating assets, cheap money with easy access from the banks. But my real estate partners were overleveraged (as was I). And instead of having another year of growth, my cash flow, my net worth, and my time took a massive hit.

Ironically, 2008 was the time I felt the most stress and was given the most public recognition.
I had just launched a New York Times bestselling book on finance, Killing Sacred Cows.
My business hit the Inc. 500 list.
Accolades were up while revenues were down.

My real estate was now hemorrhaging and my cash flow was going negative.

A turning point in my money story came later that year when I was in Vancouver, about to take the stage to give a talk about finance. My finances and my confidence had taken a hit. I was navigating a completely new situation without all the answers.

Instead of trying to hold up appearances, I walked out on the stage and opened up. I shared what most people were unwilling to share. I talked about my mistakes, my struggles, my fears, and my lessons.

A bank had just called and wanted to know my plan for a fourplex with a personal guarantee and a balloon payment coming due.

I let the crowd know I scheduled time in person with the bank. I let them know how I reached out to my network to brainstorm ideas. I chose to be honest and ask for help.

What did the bank want? They wanted the full balloon payment, but I wasn’t in a position to pay cash. By asking questions, and by reaching out to experts in real estate, I devised a plan.

Being resourceful in a time of despair was the key to making it to the other side. 

Being honest about what was happening permitted other people to face their situation as well.

I shared my concern and process with the crowd. I had scheduled a meeting with key members of the bank. I pulled a journal out and shared the questions I was going to ask the bankers and the potential solutions I had thought of.

Then I asked the crowd if any of them were worried, having increased stress, or uncertain about what was going to happen to the economy (or even felt like it was in a free fall).

Hands slowly started to rise. People looked around and now had permission to raise their hands.

I paused. I gave it time for people to see what was happening.

Rather than stick to the money story I was willing to share before 2008, I chose to share that which I didn’t want to share, what most wouldn’t share…and something magical happened.

A line formed after the speech.
People shared emotional stories with me.
We hugged.
There was permission to be real.
I was able to hear them, see them, and support them in a way a normal speech could have never done. They were able to progress by sharing things they were holding onto.

I gave them a process to examine their reality and hope there was a way to face it and uncover solutions.

I realized I wasn’t alone and saw how much pain people were holding. They didn’t need some guru sharing strategies or stories of how great he was. Rather, they needed someone willing to be vulnerable.

Everyone wants connection, but it is often hard to pay the price. People want to heal, but may need permission to face something uncomfortable.

This was just the beginning. By sharing the stories that were only in my mind, by sharing what I was afraid to share, I found common threads. The common thread of humanity.

Facing reality, being resourceful, asking for help, and being willing to learn, saved me from bankruptcy. It let me into action. It changed how I coached, and the questions I asked, and it allowed me to receive support as well.

Asking for advice and taking action was a gateway to exponential learning.

When we have the courage to share, when we confront the past, we gain access to lessons and can illuminate the blind spots. By addressing what we don’t want to share, we can access new information.

When we ask better questions, we get answers. When we face the truth, when we allow for others to support us, we can access those places didn’t know were holding us back. Those places we can’t share because we otherwise would have been unaware.

We are unaware because of things we hide, things that are hidden from us, and because of past difficult experiences.

People are held back by thoughts developed long ago.

Our desire to be liked, to be right, and to be respected for our accomplishments becomes the prison that locks out our biggest transformation.

Where do you judge yourself harshly?
Do you feel you have made mistakes that have hurt your family and therefore your confidence?
Have you learned the wrong lessons from mistakes, missteps, or hardships?

Holding onto the pain, staying in judgment, and hiding from reality hold us back.

Defining ourselves by our mistakes leads to living a life of pain—the pain of regret, the pain of greed, the pain of comparison, the pain of loneliness, and the pain of scarcity.

Money is a tool that can be helpful or harmful, depending on the context, depending on our perspective.

Money is a construct that, when misunderstood, can lead to frustration and limitation.

What is your inner dialogue that you never share out loud?
Do you feel you should be further along, a better investor, luckier, or more disciplined?

After writing Killing Sacred Cows, I wondered how could I be in a place where I made the mistake of being overleveraged. It was because I had yet to fully understand and uncover the concept of Investor DNA. I had yet to explore my childhood and early formative views on money.

Painful as it was, 2008 was a gift. It led to me creating better content. It allowed me to find even more compassion for what people are going through. It created power and resilience to make it to the other side of this difficult situation.

So many gifts.

I didn’t love the wrapping, to be sure. But the gift showed up as I coached others through their difficult situations. A gift where I could help others navigate financial chaos, scarcity, and limiting beliefs.

What is your hidden money story?
What do you talk about and what do you avoid talking about when it comes to your money?
What are you afraid to share or for people to know?
What do you worry about when it comes to money?
What prevents you from growing your wealth (and yourself)?
What prevents you from feeling wealthy today?

When we think money is complicated or is merely about budgeting, this is part of our money story. These ideas are a construct and philosophy that focuses on reduction more than production.

If we don’t think we have the skills or the time to develop skills, or that investing is more about how much we can save rather than how much we produce, it prevents our best results.

Our inability or lack of willingness to talk about money can hold us back. If we don’t ask, and answer, the questions I am posing we limit our progress. Our wanting to have it all figured out, or thinking we already know, holds us back.

The appearance of wealth is different than wealth.
Wealth is a byproduct of a life well-lived.
Fear and judgment limit wealth.

Risk mitigation improves our Financial IQ and is critical for sustaining wealth.
Learning to be a better investor is key.
Investing in ourselves and examining our results are key.

Find ways to invest in yourself to accelerate learning and results.

You can start by finding money by plugging financial leaks. Save on tax, interest, and insurance for example. Differentiate expenses so you eliminate destructive ones and increase the productive ones.

Be willing to show your true self to mentors, peers, and trusted family members even when facing difficult circumstances or scarcity. This is key to progress and essential to learning.

You are not what you think others want you to be or what you think they want to see.

Change your conversations, internally and with others, and change your wealth and life.

With the courage to examine your money story, you can inspire others and you can free yourself.

Be yourself—or remain stuck chasing notoriety or presenting something other than reality. Embrace your lessons, learn from your mistakes, and solve problems.

How can you create the most value?
How can you learn from your mistakes?
What would it take for money to no longer be the reason or excuse you do or don’t do something?

To heal your relationship with money, be curious. Assess.
Keep what belongs and helps, learn from, and let go of the rest.

Not knowing all the answers is okay.
Stay curious and inquire—that can be the guide to uncover your Investor DNA.
What will you focus on and what will you let go of?

Facing your financial fears may be uncomfortable. It requires courage. But it tells the story of where to investigate and learn.

Is your money story of protection actually prevention?
What do you know and do well with?
Where do you want to grow and learn more?

You are not alone.

We all have circumstances and experiences that shape our perspective and can limit results.
Let go of what no longer serves you.
Shine the light on your hidden money story to rewrite the story.
Heal.
And experience prosperity.

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