How to Win Financial Freedom (Even as an Underdog)

How do you predict if someone will be hoisting the financial Lombardi trophy one day?  And, what qualities do you need to win?

(originally posted February 2017, I’m reposting this to celebrate the start of football season!)

“He’s stupid.”

Adults used to say that about me to other adults.  For the first few years in school, my report card was a column of Cs and Ds.  While my teacher was teaching, I was too busy running my finger along the sham wood grain that lay over my desk to listen.   Maybe it was because I was a recent immigrant.  I dunno.  I don’t remember if I knew english or not by then.

Along with stupid, poor, and immigrant, add these: skinny, awkward, and shy.  I only had one friend, Ricky, but he soon moved away.  So I just walked around school by myself until the 3rd grade.

I was the “unrated” recruit.  The undrafted free agent.  So how did I pull off the upset?  

There are more important factors that stats can’t measure.  Here’s the best part — it has nothing to do with what’s happened to you or what you’ve done yesterday.  It has everything to do with what you do today and tomorrow.

What is Winning?

First, let me define what I mean by “winning.”  In this case, it’s financial peace.  (I’ve been told this is a Dave Ramsey term, but I don’t know how he uses it since I’ve never read anything he’s written.  Apologies if this term makes it confusing.)

Financial peace is specific to your situation.  It’s that financial goal that seems so far out of reach.  For some, it’s financial freedom.  For others, it’s paying off that debt.  

Here’s what worked for me:

4 Tips That Worked For Me (and Others)

1) Study the Game Film.  Again.  And Again. (Curiosity):

Most people get curiosity wrong.  It’s not just having a fancy for something.  That’s interest.  Everyone is interested in something, but not everyone shows curiosity.  

Curiosity is your wife rolling her eyes because you somehow divert the conversation (again) to the subject.  It’s having your friends tease you because you know the most minute details about something they find banal.  You talk, read, and think about it incessantly.

Curiosity = Interest + Obsession

Peyton Manning (2016 Super Bowl winning QB) knows that obsession:

Manning’s film study is the stuff of legend. He pores over game film and…will reach back years to draw on something he saw early in his career…and those who know him best say he remembers nearly every defense he has ever seen.

With curiosity, you’re willing to spend more time learning and experimenting, and it doesn’t feel like work. Curiosity is a natural agent for:

  • Focus*
  • Memory
  • Hard work
  • Taking action

You might say we do the same with things we’re passionate about.  Hence the advice we so often get about pursuing your passion.  I disagree.  Be curious instead.  Why?

Curiosity expands and enables many passions.  If there’s no market for your passion, your financial life will be challenging.  But, when you’re good at being curious, you can expand your passion library and find one that’s in demand or that you can monetize.  

Before I started JMC, I was searching for a business to buy.  One day, I ran a google search about online businesses.  After my kids would sleep, I’d read everything I could about online businesses into the wee hours of the morning.  After a couple of months, it wasn’t a matter of if, but when I’d jump into the scrum.  My curiosity is not so much about money — I write about it because it’s the subject that I know.  No, my curiosity is about the online business itself.

What are you curious about?  If you work in a field that matches your curiosity and strengths, you have all the ingredients you need to be successful in your career and will naturally make more money.  If no career matches, can you make a business out of it?  Blogging is one of the best ways to attract others with the same esoteric interest.  If you can build a community for and write articles that speak to them, then chances are, you’ll have an easier time building your online business.

You’re asking, “How do you become curious?”  Let me suggest another approach.

We’re all born curious, but along the way for some reason, we buried it.  Grab a shovel and dig it up.  This weekend, allow yourself to get lost in reading about something.  Think about it in all of its dimensions.  Tinker with it.

2) Elect to Defer:  

Psychologist Walter Mischel at Stanford conducted an experiment where “a child was offered a choice between one small reward provided immediately or two small rewards if they waited for…approximately 15 minutes.”  In follow-up studies, he found that children who waited longer for bigger rewards had better life outcomes.  This makes sense. If you defer going out until you’ve finished studying, chances are you’re better prepared for the test, which leads to better grades, more job opportunities, and so on.

Many of you know about this study.  But here’s an important thing you may not have known:  In his prior studies, “Walter Mischel had shown that the child’s belief that the promised delayed rewards would actually be delivered is an important determinant of the choice to delay.” 

Did you catch that?  We’re better at deferring if we know that the outcome is guaranteed.  But the most important life decisions don’t have the binary heads or tails outcome of a coin toss.  So what do you do when the outcome is opaque?  Enter grit.

3)  Play Through the Pain.  Grit it Out:  

Anyone who’s played through a season of football will tell you that pain is just a part of it.  There’s the saying, “Are you hurt or injured?  Either way, you’re going back into the game.”  (Unless you’re concussed.  Don’t mess with the brain!)  By mid-season, you’re hurt even before the game starts.  But when the whistle blows, your body forgets.  If you didn’t play through pain, then you probably didn’t play.  Get back in the game.  Grit it out.

Grit = Passion + Perseverance

Why is “grit” the word of the moment?  Along with the ability to defer, grit is what researchers say is the common denominator of success.

I haven’t read Angela Duckworth’s book, Grit, yet.  She may not have even covered this, but I think I’ve figured out why grit is so powerful.  And it comes down to…luck.   

Grit is worthless without luck.  Why even try if the outcome is always going to be the same?  The hedge fund manager / scholar Nassim Nicholas Taleb writes in The Black Swan:

The strategy for the discoverers and entrepreneurs is to rely less on top-down planning and focus on maximum tinkering and recognizing opportunities when they present themselves. So I disagree with the followers of Marx and those of Adam Smith: the reason free markets work is because they allow people to be lucky, thanks to aggressive trial and error, not by giving rewards or “incentives” for skill. The strategy is, then, to tinker as much as possible and try to collect as many Black Swan opportunities as you can.

(A Black Swan is an unpredictable event that occurs more often than you think. Here’s a related post about changing your financial luck.)

Basically, aggressively fail and learn from your mistakes until you get lucky.  You can’t do this unless you have that passion, which was enabled by your curiosity.  But let’s get real here.  Falling and failing sucks.

Most people don’t realize how much it hurts to be hit full force by someone just as big, as fast, as strong as you are who has been training to take you out.  His helmet hits your chin and you hit the ground flat.  His brawniness and anger comes at, then down upon you, like an enraged missile.  The elliptical ball jabs deep into your rib with his weight fully upon you and — oof!— your breath leaves you down, retching on the cool grass.

Life will hit you harder.  

For some of you, life’s targeting hit left you dizzied up.  Then its teammates piled on.

If you don’t get in the game, then you’ve got no chance.  If you quit after the first time you get tackled, you’ve got no chance. Unlike football, the financial game is only over when you decide to quit.  The game will go as long as you’re willing to get back up, line up, and run toward that end zone.  One of these days, life will give you busted coverage and nothing but green grass between you and the end zone.  Are you willing to keep going until that moment comes?

(Yours truly, gritting out team photo days)

4)  Believe:  

Even though I wasn’t valedictorian, I never thought I was any less smart.  Even though my teammates had more college recruiting attention, I never thought I was any less of an athlete.  I may have been stupid, but I never lacked confidence or ambition.  Why?  Because I believed a different story.  I knew that if I set my mind and body to something, I had a good chance of accomplishing it.

I struggle the most with writing this part.  I struggle because I don’t know how to get you to believe in yourself.  But I want to share something with you that I’ve never admitted to anyone outside of my wife.

I remember it all.  Every slight.  Every rejection.  That feeling of being minimized.  Sometimes it feels fresh and sharp.  I don’t run from these feelings.  I don’t place them in a corner and put a sheet over them.

Here’s what I used to do:  I’d turn the field and tackle them.  I’d hurl my body at them full force until they gave up and went home.  Not literally of course.  But I’d make myself so good that they’d have to admit they were wrong.**

Some of the most accomplished people in the world were underdogs, too.  Here’s 5-time Super Bowl winning QB Tom Brady with some revealing words:

I’ve never been the fastest guy in the world. I’ve never moved the best. I’ve never been very strong.  People have always said, ‘You can’t,’. . . You don’t forget where you came from. The scars that you have from those days are deep scars.

Here’s what his sister, Julie, says about Tom:  

He would want to keep fighting until he won.

Do you see your scars as badges? Do you believe in yourself to keep fighting? Sometimes you need to just replay the tape and see it from a different angle.


Something is telling you you’re stupid.  It could be actual words from someone or a mistake you made, financial or otherwise.  Sometimes, it can be just what you believe about yourself.

Whatever it is, it looks so big, fast, and strong.  And you see yourself as so small and weak.  You crumple easily to the ground.  You stay there.  It’s over…then a hand reaches down.

I say to you, arise.

Because he fell to far greater depths, he freed you from deadly debt.  Because he rose to greater heights, he gave you genuine freedom.

Turns out, financial peace doesn’t exist without true peace.

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*Warren Buffett and Bill Gates once each picked one word to describe their success.  It was their ability to “focus.”  I think they’re sort of right.  What was behind their focus?  Curiosity.

**I’m much more relaxed now, thank goodness.


  • Mustard Seed Money February 4, 2017 at 11:24 am

    I love this article. I feel like I can run through a wall after reading it 🙂 One of the things that I keep coming back to over and over to in life is just get back up. It’s only a matter of time before life knocks you down. It’s a matter if you have the mental fortitude to get back up each and every time. I think that’s what most successful people have and why others that are smarter and better positioned fail.

    • JT February 6, 2017 at 11:25 am

      Right on, Mustard Seed Money! Life has many options, but the critical ones come down to only 2: do you stay down or get up?

      Although I wasn’t rooting for the Patriots, they certainly showed us grit.


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