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161 | Money Letters To My Daughter with Jackie Cummings Koski

Jackie Cummings Koski shares her story as a single mom that made FIRE a reality. She proves that there is no “one way” to achieve FI. The goal can be accomplished by people from all walks of life and Jackie offers a unique perspective of FI.

Jackie’s Story

Jackie grew up in the rural south with five siblings and a single father. Her dad worked extremely hard to provide for his large family. Although he worked seemingly constantly, the family still lived paycheck to paycheck.

So it was very, very tough growing up and the one thing that stuck in my head that I really remember is that I didn’t want to live like this when I got older. But my Dad, he is like one of the most amazing people I have ever known; to be able to pull off raising six kids, I mean he must have been able to do things and stretch a dollar like no one would imagine!

He went to work every single day. She never saw him take a sick day. Plus, he always had a second job in the mix. Although he never sat her down to explicitly talk about money, she learned through his actions. He avoided loans of any kind and worked hard to make things work for his family.

Unfortunately, her father passed away when she was a senior in high school. But she has carried the lessons of hard work and self-reliance with her throughout her journey.

Working Through College

After her father’s example of hard work, Jackie decided to tackle college with brute force. She worked 50+ hours a week throughout her college career to avoid taking on student loans. Looking back, she wishes she had been able to spend more time on her academics.

Even though I was working full-time, I was still going to school full-time, as well. So, I was juggling a lot! And I didn’t really get to participate in a lot of the academic experiences like maybe joining clubs, spending the time that I knew I needed for certain classes, and my GPA certainly would have been a lot higher.

If she could do it over, she would focus more on finding scholarships to fund her education instead of working 50+ hours a week. However, she did come out of college with very little student loan debt so it was worth it at the time.

Listen: Real Hourly Wage

FI Journey

For Jackie, the desire to learn more about personal finance started around the time of her divorce. Instead of looking at her finances as a part of a team, she realized that she would have to start managing money decisions on her own.

During the divorce process, she was forced to take a closer look at her financial situation. She found out that her husband with a similar career path had accumulated $120,000 in his retirement accounts while she only had $20,000. She still received half of his retirement funds in the settlement. But it proved to her that she needed to learn a lot about personal finance.

A lot of times some the things we do wrong, they teach us bigger lessons than the things that we do right.

Listen: Poverty, Divorce And FI By 43, Bonnie Truax

Better Investing Club

Once the divorce was finalized, she had to start reinventing herself as a single person. Part of that process was discovering her hidden interests, one of those was finances. She found an investment club through Better Investing which opened her mind to the world of investing. After three or four meetings, she officially joined the club and learned so much about investing in the stock market.

Money Letters To Her Daughter

While walking the path to FI, she picked up a lot of personal finance information along the way. She wanted to ensure that this knowledge was passed on to her daughter in an entertaining way.

Since she always loved writing, Jackie wrote a book of letters to her daughter to pass on her money knowledge in an easy format. The book, Money Letters 2 My Daughter is designed to share money lessons in a brief way.

Passing Along Her Knowledge

Jackie’s desire to share her knowledge did not stop with her daughter. She also strives to bring financial literacy to underserved populations. She works with high schoolers and college students to teach them the basics of money. Although it can be a tough age group, she loves seeing the light bulbs come on.

One of the ways she excites their interest is through $2 bills. She passes these out for insightful questions or good answers to her questions. She encourages them to save something, even if it is only this $2 bill.

When she has a short amount of time with a group, she focuses on the basics. She wants them to understand that always saving something is critical. Even if you are only able to save $2, it will add up. She typically covers credit because someone usually asks about it. Finally, she also shares the value of compounding growth which starts to get their minds thinking ahead.

Six-Figure HSA

One savings vehicle that has been especially important for Jackie is her Health Savings Account. She first came across it in 2008. Since she and her daughter were relatively healthy, she opted for a high deductible plan that is required to open her HSA.

Before Jackie opened her HSA, she did some research. The three things that stood out to Jackie included:

  • The money can roll over from year to year.
  • You can invest the fund and just let it grow.
  • It was an obtainable number to max out.

After deciding this was a good option for her family, she decided to max it out. One post that really helped her understand the importance of this account was by the Mad Fientist.

Of course, she considers herself lucky that she is able to allow the HSA to grow without pulling out too much for medical expenses. She tracks her expenses with an email system that eliminates the need to hold onto paper receipts. Although the IRS isn’t clear on their tracking of expenses, she always makes sure to get a receipt that says the bill has been paid in full.

Once she turns 65, she will be able to pull out this money even if it is not a qualified medical expense after paying taxes.

Jackie will be joining the show in a future episode to talk more about HSAs as a useful retirement vehicle.

Related: The Triple Tax Benefits Of The HSA

FIRE Letter

After 20 years in corporate America, she had reached FI and was ready to move on to her next chapter. However, she wanted her departure from the company to be a positive experience for everyone. So she wrote a heartfelt letter that represented her feelings towards the company. It was an inspiring and uplifting letter that thanked her boss for his support on her journey.

How To Connect

You can connect with Jackie on her site, Money Letters 2. Also, she is speaking at an upcoming conference, EconoMe. Make sure to check it out if you are in the Cincinnati, Ohio area.

The Hot Seat

Favorite Blog, Podcast, or Book: The Memo: 5 Rules for Your Economic Liberation by John Hope Byrant

An Inflection Point: After college, she accepted a job 900 miles away at Walmart in Arkansas. Her brother helped her to pack the yellow Ryder truck provided by her company. As she was driving, she knew it was going to change her world. That was the first step to moving into a new economic reality as a grown-up.

Favorite Life Hack: The 529 plan has been an instrumental tool for her. At first, she had saved money into a 529 to fund her daughter’s education. However, her daughter decided to go to community college so there weren’t too many expenses. Jackie has been able to stretch the money out in a variety of ways including sharing the funds with three of her nieces and funding part of her own MS degree.

Biggest Financial Mistake: As a struggling college kid, she decided to buy a new car with a payment of $326/month. She quickly realized she couldn’t afford it. She went to the bank to figure out the loan refinance but couldn’t refinance because she owed more than it was worth. It was an awful feeling and she plans to never buy a new car again.

The advice you would give your younger self: She would approach her undergraduate career differently. Instead of focusing on minimum wage jobs, she would spend more time on her school work and aim for scholarship funding.

Bonus! What purchase have you made over the last 12 months that has brought the most value to your life? A Ring Doorbell

Related Articles

New to FI? Be sure to check out Episode 100: Welcome To The FI Community!


Choose FI has partnered with CardRatings for our coverage of credit card products. Choose FI and CardRatings may receive a commission from card issuers. Opinions, reviews, analyses & recommendations are the author’s alone, and have not been reviewed, endorsed or approved by any of these entities. American Express is a ChooseFI advertiser. Disclosures.
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