The Winning Ticket To Financial Freedom Isn’t A Game Of Chance

Goals, Theory

For anyone not paying attention to the news, the Mega Millions lottery in the United States just topped a billion dollars and is quickly rising even higher.  You read that right — a Billion with a B.  For the meager price of a $2 ticket, some lucky person will eventually break their way onto the list of the world’s wealthiest people.  Talk about an impressive return on investment!  Of course the odds of actually winning that money are beyond astronomical, and one in 300 million is a difficult number to even comprehend. 

As an example, try looking at a single pixel in a typical 1080p HDTV.  Even with perfect vision, you may have to get really close and squint to see it.


That’s pretty darned small.  Now imagine trying to pick out that same pixel in a wall of 146 televisions.


That’s a lot of pixels, and randomly picking the right one carries roughly the same odds of you winning the lottery.  Long story short, even with the chances of smaller paydays for getting a few numbers right, you can pretty much kiss that $2 goodbye.

So with odds like that, why are lotteries so popular?  It’s really about the fantasy.  Lottery commissions have learned that massive prize numbers will shake loose a few dollars from even the most skeptical players as the fantasy of such a windfall takes over and drowns out not only our statistical reasoning but also, and more importantly, our everyday stresses.  I mean who doesn’t want to dream about life without needing to tolerate unrealistic deadlines, crazy coworkers, and mentally or physically exhausting work just to pay the bills?  A freaking billion dollars would solve a lot of problems!

Well I have a little secret to share.  You don’t need a billion dollars to purchase your happiness.  In fact, you don’t even need to leave it to chance.  Financial independence, where work is an option rather than a necessity, is a very reachable goal if you’re willing to actively pursue it.

Now I’m not going to sell it as a cult fantasy that won’t require real planning, sacrifice, and hard work on your part, as that would be no more realistic than selling the idea of winning a billion dollars.  I’m also not going to pitch a quick checklist of things guaranteed to allow you to retire in ten years as long as you follow the recipe exactly.  Everybody is different, and easy pre-packaged answers not only diminish the individual adaptability required to succeed but also encourage naturally cynical people to pick apart each point rather than think for themselves about how they might construct their own custom plan based on their unique situation and strengths.  The first step to independence of any type is to reject fate and embrace individual agency.

So without knowing the details of your life, what on earth can I possibly offer to help you escape the rat race?

First, a bit of encouragement.  Because Portfolio Charts is very intentionally not about me, you may not know that I reached financial independence in my late 30’s.  In fact, this site is the direct result of the extra time that freedom afforded me.  Perhaps one day I’ll give a more detailed accounting of how I got here, but for today’s purposes the important point is that while I’ve certainly been blessed in many ways, miraculous financial windfalls are not one of them.  The rest of the details are actually irrelevant — you and I are different people and no two paths are exactly the same, which means you don’t have access to the same opportunities I did nor I to yours.  Just know that I’m living proof that financial independence is not some marketing scam and that it is well within reach for normal people.  And it’s also worth noting that when I speak on this topic I come from the perspective of direct real-world experience with my own skin in the game.  We’re in this together.

One thing I’ve learned over the years is that attaining and maintaining financial independence requires a designer’s mindset.  Every person has their own unique set of goals, constraints, strengths, and weaknesses, and constructing a robust life system to passively support your financial needs and personal happiness while adapting to whatever curve balls life throws at you is an ongoing design process of continuous improvement.   But designers are only as good as the potential solutions they’re exposed to and the tools at their disposal, and the least I can do is to offer a few recommendations for places to start.

So for the same price as a handful of lottery tickets, here are a few far more productive things I would recommend redirecting that money towards to open your mind to the attainable financial independence well within your reach.  Unlike the lottery buzz that will quickly fade as soon as the numbers are announced and you toss your ticket in the garbage, these can permanently change your life for the better.

First, a few books.  I’ve provided links to Amazon, but you can just as well use the $2 from that un-purchased lottery ticket to buy a bus fare to the local library.

How I Found Freedom In An Unfree World — Harry Browne’s libertarian opus is more about mindset than money and it forever shaped the way I think about individual liberty and personal empowerment.  If you’ve ever felt trapped by circumstance or victimized by factors outside of your control, this book is just the motivator you need to break through the negative conditioning and take control of your own life.

Work Less Live More: The Way to Semi-Retirement — Bob Clyatt’s creative mix of real-life stories and insightful financial spreadsheet advice had a major positive impact on my personal relationship with work and money, and his perspectives influence me to this day.  In a saturated market for retirement advice geared towards burned-out people where “work” is often a four letter word, I also appreciate his unique perspective about not simply walking away from work but renegotiating the arrangement on your own sustainable terms.

Early Retirement Extreme: A Philosophical and Practical Guide to Financial Independence — If there’s one person who has most influenced my financial life outside of investing, it’s Jacob Fisker.  The thing that distinguishes his perspective from most early retirement thinkers is his view of independence from the money-based economy and not simply through it.  His focus on personal skills and robust systems of mutually-reinforcing goals rather than simply solving every problem with money is exactly the type of mindset that can help people of all economic backgrounds achieve financial freedom.

Once you’ve got the foundation down and are looking for more specific investing advice, consider spending another $2 on your favorite cup of coffee and sitting down for an afternoon of reading here on Portfolio Charts.  Retirement finance is very important to me personally and is therefore one of my specialties, and I believe I bring a unique perspective to the table that you’re unlikely to find elsewhere in the mainstream investing universe or even in some of the books I just recommended.  Here are a few places I’d start:

How Safe Withdrawal Rates Work — While safe withdrawal rates are not a new concept, I’ve found that many people promoting the 4% rule really have no idea how it was calculated or how it works.  As a result, a lot of the portfolio advice geared towards the early retirement community is surprisingly shortsighted while many detractors similarly base their opposition on provably false assumptions.  Read this brief article, and even without a math major you’ll already be way ahead of the curve when it comes to planning your retirement portfolio.

Your Ideal Route To Financial Independence May Be Off The Beaten Path — This was my initial post about the Financial Independence calculator, and it not only speaks to the mechanics of how it works but also explains how to visualize complex concepts like retirement date uncertainty.  Perhaps most importantly, it illustrates how your savings rate is arguably both far more powerful than even the best investing strategy and also far more in your control than fickle markets.

Retirement Income — I’ve written quite a bit on this topic over the years, and unless you’ve followed along from the beginning you may have missed some important points.  This is a collection of all of my posts on retirement as well as several important outside resources to help expand your knowledge base.  Don’t just quit your job blind to the research that will back your plan.  Know your stuff, and you’ll truly be free from financial worry and can focus on the life in front of you.

While none of the above resources will give you all the answers, they all played important roles in arming me with the tools I needed to succeed.  They also may not be enough to address your own personal challenges, and further research and good old-fashioned determination may be required on your part to sort it out.  But there’s one thing I can guarantee — spending your time actively working towards your own well-considered personal financial independence plan will DRASTICALLY increase your chances of achieving it over throwing your money away on a lottery ticket.

In fact, I wager your odds of success are also markedly better than trying to blindly follow the footsteps of your favorite retirement guru.  They may be wonderful inspiration, but everyone is different and only you are ultimately responsible for your success.  Circling back to the TV pixel math example, I intentionally picked the reference image as a kid watching a TV instead of the display itself.  Which picture best describes your own approach to bettering yourself?  And which would you prefer for your own child?


Stop turning over control of your destiny on this earth either to luck of the draw or to the drive-thru solutions of strangers who are nothing like you.  Take charge.  Arm yourself with the knowledge required to succeed.  Make informed choices.  Experiment.  Be yourself.  And live the life you want to live.

It may not necessarily work out the way you want, but by taking control you’ll always be able to make the best of the hand you’re dealt.  Financial independence is all about personal empowerment.  Stop hoping and start living!