Most of us want some version of financial freedom and security. The ability to spend our time the way we would like, on what we would like and with whom we would like. Freedom to have options for ourselves and our kids. Or maybe we have a whole different definition of financial freedom altogether.

But whatever it is, whether we want the opportunity to travel, work if we choose or all the benefits that come with financial success, it is very easy to drop off the proverbial financial wagon and have the wagon run over you. One small mistake, forgetting a payment, buying the wrong house at the wrong time, or even one or two bad unavoidable events can demolish everything we have worked so hard for to achieve. So we need to be proactive in safeguarding ourselves against the seven major obstacles that can derail our success.

So what are the major obstacles that can stop us from achieving our financial goals and how can we be proactive in safeguarding ourselves against the seven major obstacles that can derail our success?

Undisciplined spending

Spending beyond your income or spending impulsively on high price objects/activities is the most common that people talk about and is a major impediment to financial success.

⦁ How do you fix it? Get honest about what matters to you. Think about what you would like your money to do for you. What you most enjoy and what would make you happy spending your money on. And be completely honest. If you enjoy going on nice vacations, then a goal for your money might be to have a nice expensive vacation with your family. There is nothing wrong with that, it’s your goal – your purpose for working and making money!

So when you are thinking about an undisciplined aka unplanned expense – like buying expensive shoes – think about if the purchase is in line with your goals i.e. if it’s something you really want and if it will help you reach your goal. If the purchase won’t, then don’t do it

Materialistic thinking

Large corporations are very skilled at telling you what you didn’t even know you ‘needed’.  Any preoccupation with physical items that do not go in line with your financial goals or wishes for money will completely tank any dream you have of financial security.

⦁ How do you fix it? Enjoying life and the pleasures it provides is great, but going overboard and spending all you have on things will let you end up with things and no money. If the items are not in line with your goals, then you’ll be miserable that you spent your hard-earned money on things that don’t align with your goals.

Burdensome debt

Debt can be an unavoidable, maybe even a necessary part of life. And controlled calculated debt can be better than using cash, but burdensome debt which compounds with high-interest rates year after year sucks your finances and not to mention your soul.

⦁ How do you fix it? The best way to counteract burdensome debt is to determine what is your current debt level is and how you will address it. So gather up all the information you have on your debt. You can put it all in a spreadsheet. List the creditor, how much you owe, the interest rate, due date, and minimum payment. Once you know the full damage you can make some plans and decide on your course of action.
i. File for bankruptcy
ii. Pay the debt
– If you only have a couple lenders  you can try to lower the interest rates on each
– If you have a lot of cards, or you can’t get your rates lowered, then consolidate and just pay one bill (I personally LOVE for consolidations – private student loans, credit card debt, etc).
– Transfer credit card debt to 0% intro card/offer
– Set up the debt to get automatic payment and then let it ride


They say the only thing that is for certain in life is change, death, and taxes. While you can’t avoid paying taxes (or at least you shouldn’t), there is no honor in paying more than is required. The goal is to get a very small return or no return each tax season. That means you got all your money throughout the year and paid Uncle Sam his fair due as well.

⦁ How do you fix it? Make sure you take advantage of all the tax deductions and credits you can. FSA, child tax credit, earned income tax credit, head of household– there are many deductions available, and a lot more if you own a home and do itemized deduction.

Tip1: If you are worried about owing money to the IRS, you can set your w4 to take more out in the first half of the year, then take out your correct amount for the remainder of the year. That makes you less likely to owe money, and also not give Uncle Sam an interest-free loan for the year.

Tip2: Use a tax calculating tool – like or to determine if itemizing is a better way to save for free.  Even if you are using an accountant, it can be helpful to see your results for yourself, so you can ask your account thoughtful questions. Tip3: Before filing, always compare married filing separately to married filing jointly to see which has a better return.

Tip3: Before filing, always compare married filing separately to married filing jointly to see which has a better return.


This is the silent killer of wealth and purchasing power. While you are saving your hard-earned money in your bank account, with interest rates being kept artificially low you are earning way less than the inflation rate. Your $100 savings deposit is worth $100.10 but your purchasing power after 2% inflation is only $98.

⦁ How do you fix it?  There isn’t much that we can really do about inflation. We can save a little more to account for it – so save 102 dollars instead of 100 to keep purchasing power the same, or we can invest more in the stock market which can yield higher returns, but also has the risk of losses, or you can invest in inflation-protected treasury bills (TIPS) which protect against inflation but can also lead to losses in inflation is lower than expected.

Poorly structured investment portfolios

Having an investment portfolio can be a great tool towards financial success, however, undiversified, inappropriate risk levels or investments with heavy fees can all produce the opposite effect or erode any earnings potential.

⦁ How do you fix it? A portfolio is better than no portfolio doesn’t cut it. You need to be aware of the fees associated with your portfolio, be comfortable with the diversification and be honest on your risk level you are appropriate with. I know it’s annoying and can be confusing, but let’s grit through it and take some time to dig up a copy of your prospectus for your investments and see how it’s all structured. If you aren’t sure where to start, look at low-cost index funds – that’s what Warren Buffet recommends and is a great way to get you started and even finish with. Sure there are some instances like a company managed 401k, where you don’t have much choice since it’s that or no company match. If you don’t want to self-manage you can always use the advice of a financial advisor. Just

Unforeseen financially devastating events

Sickness with a high medical expense, divorce, job loss, disability, lawsuits can all wreak havoc on your finances.

⦁ How do you fix it? We can’t protect ourselves against everything because anything can happen. It helps to have at least the deductible for our home/rental insurance, and our car insurance saved in our emergency fund, and an extra 500 if we can. It also helps to have an exit strategy a plan in case things go south. Move-in with your parents, cash out your 401k, get a second job as an uber driver, etc for example.

So get busy now

These issues are, or at least can be, major issues obstacles to achieving our dreams of financial freedom. While we can’t prevent some of them from happening, we can make preparations to avoid the pitfalls of quite a number of them.

This article couldn’t cover all the details and ways to mitigate or avoid obstacles, but it gives you somewhere to start.

If you already see where you are falling into a pitfall, then make the choice to start working on getting out of it.

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