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I love being able to find a connection with the story of every person that we have on our podcast.  This week though, I felt a special connection to our graceful guest, Jackie Cummings Koski. Her story of being a single mother, the details she shared about the awakening that took place after her divorce and the absolute success path she’s experienced since making up her mind to change her environment resonates deeply with me.  

Not only does she share her story with empathy and honesty, but her experience gives new color and depth to this ongoing discussion about Privileged Frugality versus Choice-less Frugality.  She has experienced both on her journey towards Financial Independence.

About Jackie

Jacki Cummings Koski holds the designation of CEPF (Certified Educator in Personal Finance), she is a Financial Literacy Advocate and she is award winning author. She is known for writing the Award Winning book Money Letters to My Daughter. Jackie is very active in the House of FI community, as well as the ChooseFI community, and we are all better for her insight and thoughtful participation.  

In addition to all of the wonderful work she does for the personal finance community, Jackie is one of our only guests that has reached Financial Independence.

Jackie’s biggest issue now is her hesitation with pulling the retirement trigger!  She is having the dreaded #onemoreyear syndrome!

Jackie’s Money Story

Jackie Cummings Koski grew up in the Southeastern United States.  She was raised by a single father, as one of 6 children. Her father, a poor factory worker, knew how to stretch a dollar.  He was able to teach her how to live with dignity through mandatory frugality.

This experience of growing up impoverished lit a fire within Jackie – who vowed to make more money and to create an environment around herself filled with rich opportunity.  

Well, she did it!  She finished college, launched her career, married and had a daughter.  

Life was good, until it wasn’t, and Jackie endured a difficult, emotional divorce.  

The Impact of the Single Mom Bond

Finding ways to connect and bond with your children is priceless.  The most heartwarming thing about Jackie’s story is the depth of the bond she has with her daughter.  It was this bond that led her to writing her award winning book, Money Letters to My Daughter. In the text, Jackie educates her daughter and others about money matters that she faced, and learned from.  In the episode we speak about her daughter’s reception of the book.

The Benefits of the Health Savings Accounts

Made most famous in the FIRE community by The Mad Fientist, the Health Savings Account, or HSA is known to be THE ULTIMATE retirement savings vehicle for the “low consumer of health services”.  A person that is likely a low consumer of health services is the person that has no medical (physical and mental health) issues that require expensive, repetitive intervention.

If you are one of the low consumers of healthcare, the HSA may be for you.  If you use health care often, but can cover the costs of service out of pocket, you should still look into this awesome product.

The HSA was introduced in the early 2000’s and it is the only savings vehicle that offers a tax advantage with each contribution, a tax advantaged growth (invested contributions) AND tax free distributions (when you take the money out).  

After finding the Mad Fientist, Jackie doubled down on her contributions to her HSA, and currently has over $100,000 in tax free savings!  

Listen to the show to hear how she plans to access the money!!  

Credit Education

As a CEPF, Jackie educates others on how to check credit scores and calculate credit utilization rates, amongst other things.

Recently you read this post about filing bankruptcy, Bankruptcy is a real possibility, and managing your credit accounts and utilization rates can go a long way towards to protecting you from accruing overwhelming debt.

Money Mistakes To Learn From

So, financially independent, retiring early, what has Jackie made mistakes about when it comes to money?  Here’s the short list :

    1. Spending 30% of your gross income on a vehicle
    1. Making assumptions about financial ideas instead of checking those assumptions at the door
    1. Jackie purchased expensive new cars, but teaches us her process for buying cars now
  1. Not finding a qualified tax preparer. A provider should ask detailed questions about your situation – not making assumptions about your position. 

Jackie on the Final Questions:

    • Always save something.  This creates a habit that will serve you well for years to come
    • What is Jackie reading right now?  Audiobooks and podcasts. Her favorite podcast right now is one she just hear about Coach George Raveling, who was a bodyguard at the Martin Luther King’s I have a dream speech    

Other links in this episode:


The Mad Fientist Article on HSAs 

IRS Publication 969 Health Savings Accounts

IRS Publication 502 Medical and Dental Expenses

The Total Money Makeover

Listen to our previous episode where we spoke with Kara Perez about side hustling her way through debt!

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