My twin girls left for their freshman year in college just about a month ago and all I keep thinking about is that I didn’t get a chance to teach them my personal finance class. I’m a personal finance and retirement coach and educator for crying out loud. Teaching is what I do. How could I possibly let my girls escape the nest without imparting this critical knowledge?

We were supposed to use the extra time they had doing remote senior year to go through my curriculum. When that didn’t work out, we planned to take some rainy days this summer and go through the class. That didn’t happen either. The end of August was here before any of us knew it. Now I feel guilty I let them down, and disappointed that I didn’t make it happen. It was the ONE thing I really wanted to do with them before they went out on their own.

Truth be told, I think it’s just a distraction from the raw emotions I’m feeling of being an empty nester, or part of that silly mom guilt we impart upon ourselves for all sorts of perceived parenting failures. Sending them off to college has been one of the hardest, emotionally challenging things I’ve done as a mom. They are my best friends and now they’re off living their own lives…without me. I deserve a distraction damnit. I guess I don’t really deserve to beat myself up over one failed attempt at a personal finance class. LOL. Afterall, shouldn’t their high school have taught them this stuff? If only.

Aside from my failed attempt at educating them on financial matters, I can’t really think of other regrets. I think I prepared them well for this next chapter in their lives. I know I told them to avoid drugs and partying (too much), and to be careful with dating and sex, and walking alone on campus and paying attention to their health (freshman 15). I reminded them to lock their dorm room door, to join clubs, to be social and soak it all in. I also reminded them that they are there to get an education and this is their job for the next four years (or more). I think they know all this. I think they are prepared. I don’t know. I hope they are prepared.

I’m only a month or so into this new empty nest thing and so far it’s actually not as bad as I thought it would be. I’ve been crying about them going off to college for about a year now (maybe longer), exacerbated by the s@%# show of a senior year they had as a result of Covid!

The actual moment of saying goodbye to them was perhaps the hardest because I knew that an amazing, fulfilling, and happy time of being a parent was over for me. I’ll probably mourn this for the rest of my life. You see, I made a choice to leave corporate America when they were born so that I could be a hands-on mom. Yes, I chose them over climbing the corporate ladder and building up a big fat 401k. I have no regrets. And I wouldn’t change a thing about the last 18 years. Except maybe teaching them my damn personal finance course!

Seriously, while I’ve made sure to have my own life and income from entrepreneurial lifestyle businesses, my kids have been the MAJOR part of my life, and by far, my greatest accomplishment. I’m one of those parents who loved parenting…everything about it (except those first few months when they would cry and I had to wake up and feed them…that was a b@#$%)! I was the parent who welcomed all their friends into my home, never really saying no to much of anything. Luckily, I have really good kids who didn’t need to hear “no” often. I was/am a hands-on mom, friend, playmate, coach, and all around “cool mom” and the parent who had a gaggle of kids for sleep overs, vacations, pool parties and Patriots games. I lived at my kid’s sporting events. I was here when they were here. My Land Cruiser SUV seated eight for a reason! Parenting was how I defined my life and one of my main contributions to this life.

I know that parenting never ends. I have a 28 year old son and three step sons in their 20s and 30s and I know for a FACT that parenting never ends…it just changes and I just need to look forward to new and different parenting experiences with the two youngest now.

I remember when my girls got their licenses, I cried that day too as they both got into their cars and headed off to school. I was happy for them because I remembered that awesome feeling of finally having the freedom to just get in your car and go. But, I was a little sad for me because I knew the Land Cruiser would never be full of kids again. The only constant in life is that it changes.

Adjusting to your changing parenting role as life marches on is really hard. I know it can be done because I’ve witnessed my mom who had four of us go through all these transitions. She’s my role model. She’s embraced every chapter of our lives with happiness, love, and excitement. She always looks forward to what’s next in our lives.

As I sit here at my desk, with a damp tissue next to my laptop, I need to take this lesson from my mom. She told me once that my job as a parent is to prepare my children for life. The fact that my girls (and my son previously) went off to college happily and confidently (and so far no home sickness) means that I must have done a good job preparing them for this next chapter. I feel good about this.

Writing this article and thinking about the concept of preparedness makes me feel confident that maybe I already gave them all the personal finance knowledge they need up to this point? Maybe I didn’t fail them or myself on this point? They witnessed 18 years of watching me manage my careers: in corporate America, as an entrepreneur, and as a retirement and personal finance educator and coach. They watched me manage a household and all the financial obligations of that household. They learned about budgeting and credit card debt and checking accounts, interest rates and retirement savings, car loan payments, investments and even how life and medical insurance works, medical bills, co-pays, and deductibles. They learned about marriage and divorce, child support payments and the cost of raising children.

Having moved a lot, they learned about buying and renting a home, mortgages, and the real estate industry. They both learned the concept of loaning money when their big brother wanted to raid their piggy bank…they charged him interest and demanded repayment. They both earned an allowance and learned how to spend their money and save it, and how to open checking and savings accounts. Once they became licensed drivers, they learned how much it costs to get a tankful of gas! Later in high school, they both worked and learned the value of hard work and the value of a dollar, learning about the huge impact of income taxes too. They both completed their own tax returns.

They’ve also learned more than they care to at 18 about retirement planning. They have often complained that all my significant other (and business partner) and I talk about is retirement planning: 401ks, Social Security, investments, income planning, long term care and tax planning. Ugh! One of the twins gave me a women’s fiction book as we headed to California to move her into SDSU, insisting that I put down the retirement planning books and read something “fun.” I tried to explain to her that learning about women and money, and how best to help women is fun to me.

All three of my children also learned a lot about being an entrepreneur. They were intimately involved in my art-tainment business. In fact, one of them named the company, Let’s Gogh Art at six years old! They all worked in the company too. They all booked and ran art events. They helped me create a video that I submitted to be on Shark Tank, and one even talked about why she wanted me to be accepted on the show! Later, the girls had an intimate view into the process I went through to create and launch Her Retirement and my software platform that makes retirement readiness easier and more reliable. They also set up more than their fair share of lemonade stands, book fairs and science fairs where I helped them calculate their costs, projected their revenues, and determined their profits. Great lessons in self-employment and business finances.

When it came time to make a college decision, they learned about how to fund college costs and make informed decisions about how much of an investment they would make in their education. They learned about the debt they would take on and how much the debt would cost them once they graduate. They learned about their potential income in their chosen field of study and how far that income will take them with college loan payments and all the other costs of living.

Jeepers. I guess when I sit down and think about it, I’ve involved them in money conversations and decisions throughout their lives. I didn’t really hold anything back. Kids are sponges and they’ll absorb whatever you teach them. I guess they probably have learned a lot from me about personal finance since they were very little. I guess I don’t need to really stress about not getting around to my personal finance class after all. I do hope I instilled in them a healthy relationship with money. I hope they understand that money is just a tool. It cannot buy happiness, but it does give you choices.

I know they are both very motivated to finish college and start a good paying career. I have pounded it into their head, as my mother did, to get an education and be able to take care of themselves. And eventually, when they find a partner, they won’t “need” him or her to provide for them…they will be self-sufficient, money smart and money confident women. Yes girls, you can know more and have more. And of course, you can be the “her” in hero.

I’m actually pretty thrilled that I’ve taken this regret off the table. And the best part of this story (i.e. the happy ending) is that I’m still Jake, Emma and Kate’s mom…for life. And I’m here to be their best friend and teacher…regardless if they need personal finance and retirement advice or just unconditional love.


My mom also taught me to find the silver linings in everything, and during Covid I kept telling the girls to find the silver linings. Here’s me practicing my own advice on the silver linings on empty nesting…

  • No more fights to referee
  • No more kid messes to pick up
  • No more tripping over shoes inside the door
  • No more worrying if they’re out too late
  • No more shutting off lights when they’re left on
  • No more arguing over who’s turn it is to empty or load the dishwasher
  • No more complaining there’s nothing to eat (this is a pretty legit complaint in our household)
  • More time for me to focus on building a business that I hope will be a legacy for my kids someday (or at least a way for me to catch up on my retirement savings) and…
  • New chapters of life to look forward to as the mother of three smart and happy kids (plus three step kids). 😊

Lynn Toomey, founder…Her Retirement

Confessions of an Almost Retired Mom was last modified: by

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