Brian dives into what it takes to be successful in business, finances, and your career, and how that success relates to the risks you take. He covers the habits that seem to drive successful people to push the envelope, and how those are the people who are willing to take risks more often in order to accomplish their goals. He also discusses why people tend to take the easy road and settle for a life that they may only be content with.

So why is it that we, as humans, are typically risk averse and our fear makes us take the road most travelled, the easy way out, and make decisions that feel most comfortable? Margie Warrell, author of the article Take A Risk: The Odds Are better Than You Think, identifies a few similar actions that influence our behavior. Here is what she reports:

  1. We over-estimate the probability of something going wrong.
  2. We exaggerate the consequences of what might happen if it does go wrong.
  3. We under estimate our ability to handle the consequences of risk.
  4. We discount or deny the cost of inaction, and sticking with the status quo.

“Humans are wired to be risk averse” – Margie Warrell

Brian takes it a step further and outlines steps to take in order to take more risk responsibly, and how to begin understanding and conquering risk or your fear of failure. Take that first step, fine tune your priorities and try something that may be out of your comfort zone.

  1. Learn the difference between a calculated risk and a gamble.
  2. Create a plan of action and put a time-line together.
  3. Save money and resources to give your “risk seed” a chance to grow and succeed.
  4. Be prepared to pivot if necessary.
  5. Take a moment to celebrate your successes.

Brian, a huge Steve Jobs fan, took the opportunity to quote the man himself. As it turns out, Jobs seems to know a thing or two about taking risks.

“The greatest artists like Dylan, Picasso and Newton risked failure. And if we want to be great, we’ve got to risk it too.”

“Everything around you that you call life was made up by people that were no smarter than you, and you can change it, you can influence it, you can build your own things that other people can use.”

– Steve Jobs

If there was ever a poem that directly relates to a podcast topic, it is The Road Not Taken, by Robert Frost.

I shall be telling this with a sigh
Somewhere ages and ages hence:
Two roads diverged in a wood, and I –
I took the one less traveled by,
And that has made all the difference. 

– Frost

Enjoy the Show?

Where You Can Watch and Listen:

Subscribe on these platforms or wherever you listen to podcasts! Turn on notifications to keep up with our new content, including:

  • Episodes of The Money Guy Show every Friday
  • Episodes of Making a Millionaire every other Monday
  • Mini-shows every Wednesday
  • Ask Money Guy Livestreams every Tuesday
  • Tons of other fun content!
Related Content

Free Resources

Financial Order of Operations®: Maximize Your Army of Dollar Bills! Thumbnail

Free Resources

Financial Order of Operations®: Maximize Your Army of Dollar Bills!

Here are the 9 steps you’ve been waiting for Building wealth is simple when you know what to do and the order in which to...

Wealth Multiplier By Age Thumbnail

Free Resources

Wealth Multiplier By Age

If you want to set yourself up for future success, find out how much you need to save every month to become a millionaire.

Car Buying Checklist Thumbnail

Free Resources

Car Buying Checklist

Here’s how you can buy a dependable car that won’t break the bank. Our free checklist walks you through the 20/3/8 rule and strategies to...

Articles

How To Win With Money in Your 20s (and Set Yourself Up for Life) Thumbnail

Articles

How To Win With Money in Your 20s (and Set Yourself Up for Life)

The first decade of adulthood is one of the most important periods of your life. The course your life takes when you are younger can...

5 Creative Ways To Save More Money Thumbnail

Articles

5 Creative Ways To Save More Money

Whether your goal is to increase your investing rate or save more for big goals like buying a home, going on a nice vacation, or...

Are Index Funds Still Better Than Active Funds in 2025? Thumbnail

Articles

Are Index Funds Still Better Than Active Funds in 2025?

Over longer periods of time, index funds tend to outperform actively managed funds in most categories. Recently, total assets in index funds have surpassed the...

Financial FAQs

Courses & Tools

How about more sense and more money?

Check for blindspots and shift into the financial fast-lane. Join a community of like minded Financial Mutants as we accelerate our wealth building process and have fun while doing it.

Financial Order of Operations®: Maximize Your Army of Dollar Bills! Thumbnail

Free Resources

Financial Order of Operations®: Maximize Your Army of Dollar Bills!

Here are the 9 steps you’ve been waiting for Building wealth is simple when you know what to do and the order in which to...

Wealth Multiplier By Age Thumbnail

Free Resources

Wealth Multiplier By Age

If you want to set yourself up for future success, find out how much you need to save every month to become a millionaire.

Car Buying Checklist Thumbnail

Free Resources

Car Buying Checklist

Here’s how you can buy a dependable car that won’t break the bank. Our free checklist walks you through the 20/3/8 rule and strategies to...

Recent Episodes

It's like finding some change in the couch cushions.

Watch or listen every week to learn and apply financial strategies to grow your wealth and live your best life.

From DINKs to Single Income and 2 Kids Thumbnail

Episodes

From DINKs to Single Income and 2 Kids

Commission income, two kids, and a thin emergency fund - this is what the messy middle is all about. See how we help Tyler and...

How This Disney Star Lost All Of Her Money Thumbnail

Episodes

How This Disney Star Lost All Of Her Money

From a million-dollar year to $200K in debt, Disney star Christy Carlson Romano shares her wildest money mistakes and how she rebuilt from scratch in...

Don’t Make This Huge Roth Mistake Thumbnail

Episodes

Don’t Make This Huge Roth Mistake

When is a Roth conversion a mistake? We break down 5 situations, the 4 questions to ask first, and a case study saving one couple...