Earlier this week, a website that I like to frequent; Art of Manliness, published an article entitled How Millennials Can Overcome Their 6 Biggest Financial Challenges. As a first wave Millennial who has struggled with personal finances, I was able to relate to each and every one of the 6 big financial challenges outlined. I’m going to share with you how I have been able to overcome some of these challenges one by one.


Challenge #1: Millennials are financially illiterate.

Personal Management merit badge didn’t quite cut it I guess. Although I worked all through high school, I never developed any kind of appreciation for the money I earned and thus no regard for what and how much I spent. I got the money and then I spent the money. If I had some sort of bill, I would turn the money over to my parents who would then take care of it. I never saw the bill, I never learned how to read them nor see any cause and effect. A good example of this is when I got into a car accident that was my fault in high school. I paid for the deductible out of my savings, but these were savings that I had accumulated over the years through gifts from family for events like First Communion and such. I never saw the money and I never saw were it went. There was no pain in the loss and I never learned.

I paid for my car insurance, but again this was through my parents. I was their dependent and on their policy. I just turned my money over to them. I never saw what my liability limits were, what my deductibles were, nor the costs associated with each.

I didn’t know anything about insurance, bills, credit cards, interest, banking, mortgages nor investments when I had graduated college.


I never learned anything about these topics until 2007 when I started working for Enterprise Rent-a-Car. It was here that I not only learned a great deal about customer service and management, but also the very real consequences of auto insurance.

This was a great start, but there was still a huge gap and I was still making compounding financial mistakes that came to a head when my insurance agency didn’t pan out. Around this same time two other things happened. I was talking to a family friend who was one generation ahead of me and outwardly successful. I was bemoaning living pay check to paycheck despite what I thought was middle class income. His reply, “Oh, you’ll always be living pay check to pay check. At different points some cheddar will come along but you will have to use that for something and it will keep going forward like this.” Around the same time I was gifted Total Money Makeover by Dave Ramsey. To break it down to it’s simplest idea, Total Money Makeover was about how freedom from debt = freedom and that there aren’t any tricks to achieve it. I decided to follow Total Money Makeover’s view and began my autodidactic education. I began listening to audio books on Audible which is a great service I’ve now used for two years. I would batch books on similar topics that would flow into other subjects. I started with books about the 2008 Financial Crisis such as; The Big Short by Michael LewisMeltdown by Thomas E. Woods, and Too Big to Fail by Andrew Ross Sorkin. These turned into books about personal responsibility like Awaken the Giant by Tony Robbins and Extreme Ownership by Jocko Willink. These eventually became books on personal financial growth like The Millionaire Next Door by Thomas J. Stanley and Rich Dad, Poor Dad by Robert Kiyosaki.

I now try to consume a book every two weeks and made it part of my 2017 New Year’s Resolutions.

Challenge #2: Millennials are financially fragile.

This almost goes without saying. Postponing house and car repairs was the norm. When you are pay check to pay check there is already no wiggle room. Throw in an unplanned expense whether it be medical or an auto deductible and you have to seriously dip into a line of credit. This compounds because now you will have a larger interest payment when you were already pay check to pay check. When my agency closed we had nothing to fall back on. We didn’t have a savings and we had a minimal amount that we could borrow from our 401ks.


Budget, pay down debt, grind, and repeat. It’s hard to anticipate when sh#t will hit the fan. I had known for some time that my agency wouldn’t be my future, but didn’t do anything to prepare for it other than cursory job searching. When the sh#t did hit the fan it hit hard. I didn’t receive my last commission immediately due to a dispute which left us in a hole for that week’s bills. I sold the gold I owned as well as some cards from my collection of Magic the Gathering I had built over 15 years. I started driving for Uber as well. I called and talked to someone from the bank that had my mortgage and worked out a deal with them too.

We made it through that period and we are probably better for it. Once we did, we immediately saved some money for that “oh Sh#t!” fund. This seems to be an underappreciated step in the Debt Snowball as many people would rather pay off credit card debt with it.In practical terms that doesn’t work for two reasons. First, if some sort of crisis occurs, you have to use the credit card again. The dependence on the credit card still exists and it affects your spending. Two, there is a certain amount of discipline to building up $1,000 in savings and having it sit, untouched. Similar to a moth escaping its cocoon, this strength becomes the base with which you pay off the rest of your debt.

Challenge #3: Millennials are burdened with student loan debt.

My wife and I were fortunate when we went to West Virginia University. I was fortunate in that my parents could afford my undergraduate tuition. My wife was fortunate in that the state had just instituted a scholarship program to which she was more than qualified. We both worked and had most of our housing paid for since we were both Resident Assistants for multiple years and worked during the Summer. After 4 years we both graduated and my wife went on to physical therapy school and I went into the workforce so we weren’t burdened too much by the $70,000 we had in student loan debt…wait $70,000? Where in the f@ck did that come from!


The student debt crisis is a complete absurdity and will hit it’s breaking point, but that is another article for another day. We did not prioritize our student loan debt. We took Dave Ramsey’s approach and paid off our smaller debt first which has made our remaining student loan debt more digestible. The biggest takeaway that I found is that you have to pay attention when changing your pay schedule. If you switch to a lower payment schedule, you have to be aware that you are likely only paying interest rather than principal + interest. Just being aware of that can save you tens of thousands in interest.

Challenge #4: Millennials’ wages are stagnant.

Yup they sure are. No use in whining about it. The days when an employer would indiscriminately give 5-10% salary increases are gone.


View yourself as a brand or commodity. Treat your work experience as such to that you are able to market to your current employers and future employers. Constantly up date your Linkedin profile and resume. Develop your “story” that you can talk about in interviews. Grow new skills, pay attention to trends, and contribute in meetings. Make yourself indispensable so that when the time comes, you will have leverage when asking for a raise. Yes, that is something you will have to do. Sitting and waiting around for your boss to offer you a raise will not happen.

Alternatively you can create your own job or position. Take note of any area in which your current employer is lacking. Use that information to create a business proposal and formally offer it to the right person. Make sure it identifies why it is in the business’s best interest and why you are the person to lead it. Even if they don’t take you up on the offer, you will be remembered.

Challenge #5: Rising rents eat up a burdensome amount of Millennials’ income.

We bought our house in 2009. The housing market didn’t have a huge correction in our area nor for our price range. After 8 years, we barely have equity that we could use on a new down payment. We also have to house my mother-in-law. Luckily we have her in an apartment owned by family who charges less than market value. Still, two cable bills, two energy bills, etc, eats into our budget.


#4 on my New Year’s Resolutions is to buy a house. We fixed our credit so our interest rate will go down by more than a point. We are also only looking at houses that can house our mother-in-law while also maintaining our sanity. This will allow us to consolidate some of our monthly expenditures and use budget leftovers to pay down the remainder of our student loans and eventually speed up our mortgage payoff which will hopefully be 15 years.

I think in general my generation just has to scale down. Premature affluence is a killer and seeing only the good stuff people are buying on social media promulgates the notion. What people aren’t seeing on Instagram or Facebook is either the hard smart work that goes into these purchases or the repercussions when some one is buying outside of what they can afford long term.

Challenge #6: Fewer and fewer millennials are becoming full-time entrepreneurs.  

I tried it before and didn’t pan out. I had neither the temperament nor discipline. My business plan was weak and I didn’t set up the structure to follow through with it. There are a lot of excuses we can’t be entrepreneurs most obvious are #1-#5 on this very list. There is definitely a mindset that we need to play it safe and that the famous Millennial success stories like Mark Zuckerberg are aberrations.


Late Gen X’ers and Millennials are the ones creating a new gig economy. From Uber, to AirBnb,  Ebay and Etsy, the door is wide open for us to be entrepreneurs. I’m also not done being an entrepreneur. I refuse to sit idly as my idea book fills up with business ideas that I never act upon. So I started this site. I fully intend to make money off this site and wish to be completely transparent about it. That is why there is a disclaimer at the top of this post. The links that lead to Amazon throughout my posts (like this); those earn me commission if you buy anything on Amazon within 24 hours of clicking on my link; even if it isn’t the item listed.

Carry it with me everywhere.

This is actually one area that I think Millennials have an advantage on older generations. Our prime is going to be filled with a changing of the guard. Does anyone think cable television will look anything like it does now in 15 years? Those adapted to Netflix, Hulu, and SlingTV know the answer. Will we buy cars from dealerships? The answer lies with Tesla. Hell, even money itself is changing with the block-chain technology existing behind Bitcoin.

We may have to endure a few years of being uncomfortable; realizing those $60,000 jobs we thought we’d have right out of college with our Bachelor of Arts degrees will never come to fruition, but we will adapt.

Author: David Matthews

I started this site as a way of discussing what I’ve learned about the relationship between personal finances and physical fitness. What I have learned allowed me to lose 50lbs and improve my credit score 150 points in the same year and become a happier person.

Husband. Father. West Virginia University Grad. Licensed Insurance and Financial Professional. Sports fan (Philadelphia, WVU, and Manchester City). I’m also a huge nerd (like Magic: The Gathering huge)

Published by David Matthews

I started this site as a way of discussing what I've learned about the relationship between personal finances and physical fitness. What I have learned allowed me to lose 50lbs and improve my credit score 150 points in the same year and become a happier person. Husband. Father. West Virginia University Grad. Licensed Insurance and Financial Professional. Sports fan (Philadelphia, WVU, and Manchester City). I'm also a huge nerd (like Magic: The Gathering huge)

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  1. Interesting blog as always, David, but I must disagree with you on one point. The absolute worst debt you can carry is credit card debt. You’re paying usurer’s fees of 22% or more, while the savings you accumulate are earning 1% or 2%. It’s crazy math, so even if you feel a psychological boost by having a savings account, it’s mathematically a bad move. If you have a new crisis to meet, you’re better off paying the credit card debt first since you can always try to take out an emergency loan and it’s sure to be less than your credit card interest. And needless to say, when the balance is finally paid off, never never ever carry a balance again. The credit card companies are thieves and should not be able to charge such ridiculous fees. They really take advantage of people who usually aren’t even fully aware of what is happening to them. They just pay the monthly fee, which, unbeknown to most people, also includes interest on the new things they buy from the date of purchase, even though they haven’t even received a bill for it.

    We order a lot of things on Amazon. I’ll have to figure out how & where to click to give you the commission.

    1. Credit card is the worst debt but its not as unique to Millennials as student loan debt, that is why it isn’t specified.

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