We ended our March column, RED & BLACK … Don't Regret Your Regrets?, with me telling Red, "I do not 'do' regrets," but our actual conversation continued as she wanted to know how that is even possible to do. Knowing that she loves lists, I decided to put one together for her.

As a bit of backstory, having loved ones die, especially untimely deaths, can have a powerful impact. That is what happened to me growing up. It made me realize that the future is not a guarantee, but merely an incentive. And that, in turn, had a direct influence on my priorities. And, how I approach life … with no regrets.


  1. If You Love Them, Let Them Know
    This is probably the most obvious, but if "postponed" can become an extremely painful regret. Since I learned this at such an early age, I have been doing it almost my entire life – and can tell you that it quickly becomes a habit. Not sure how to start? Make a list of the people you love, and either through words or actions (or both), let them know. It can be a simple call or visit (virtual counts), or an unexpected email or note. Or, a long letter. FYI, this also works for people you respect, admire, or appreciate.
  2. Maybe You Do Not Need To Work Less
    As a die-hard workaholic and someone who proclaims, "I have no life," you might think this falls under "Do as I say, not as I do." Yet, if you were to track my time, you would see I always carve out time for exercise and try my best to be there when my sister and nieces need me. Pre-COVID, I always saved Saturday evenings for dinner with dear friends. Work/life balance means finding time for the things that are most important or bring us the greatest pleasure, which is different from saying "I need to work less."
  3. Be Brave
    This is semantics. If I said, "Take risks," I would get push-back as most people are risk-averse. For me, I look at risk-reward; does the upside potential outweigh the downside risk? Over the years, I have done things that did not work out as planned. Do I wish I had not done them? No, I look at what positive things came out of the experience (many mistakes can be fixed) ... even if only lessons learned. Research shows that people's biggest regrets tend to involve things they did not do when they had the opportunity, not the things they did.
  4. Worrying Wastes Time (And Cause Wrinkles)
    Time is a precious commodity as you can make more money, but you cannot make more time. So, why waste any of it worrying about things that are beyond our control? The next time something has you worrying, decide what you can do to change the outcome. If the answer is "nothing," then think about what you need to do to prepare for the worst-case outcome. Then, shift your mindset and focus on the best-case scenario. (I know Red often thinks I am an "eternal optimist" and sometimes has a hard time reconciling that to me being pragmatic.)
  5. Emotions Are Not Created Equal
    Yes, Red is the warm and fuzzy emotional one, while I am the pragmatic one. But, sometimes, you have to learn to be less emotional. For example, everyone has been emotionally hurt at some point, yet I know of people who stay stuck in bitterness and never get past the pain. If you learn to forgive, you can replace the time spent being resentful with more positive things. Maybe even little acts of kindness (a smile, a compliment, a small gesture). No one ever lay on their deathbed and said, "I wish I had been meaner and more spiteful."
There is no point in regretting what you wish you had done differently, but nothing stops you from coming to terms with your regrets and moving forward with a clean slate.
My youngest daughter's now a freshman at college, but it seems like only yesterday that she was in the midst of the college application process. So, when Black and I recently featured "Thank You For Sharing!!!" from a College & Career Readiness Counselor about my approach to letters of recommendation, I realized it was probably worth "rerunning" for those students and parents going through the challenges of college selection. (Trust me, you'll get through it … but remember to enjoy this time as once they start college you'll miss these days.)

Well, my younger daughter, Sawyer, is a high school senior. And it's November. Which means that we're in the midst of the college application process. It's exciting. It's also very stressful. So, I thought I'd share a few tips that I've recently learned in the hope you'll find them useful. But first a disclaimer!

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Over the last month or so, I have been contacted by various people and organizations wondering how I managed to "teach" my 40+ year-old-sister about personal finance. (Yes, you can teach an old dog new tricks, especially if you are an even older dog.) It seems everyone is looking for a step-by-step guide or even lesson plans, but I realize the key to making smart financial decisions is to learn to talk to yourself. And then, if appropriate, expand the conversation to your significant other and/or family.

Upfront disclaimer: I am not a financial expert or a self-help guru. My sister had a crisis, and I did the best I could to help her. (OK, so I also turned it into a book, but that was because I thought it would make a good sitcom.) Which meant, much to her dismay, instead of giving her "answers" … I gave her questions. Lots of questions.

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People have told us they're using our sisterly banter to start conversations with others (family, friends, and even in classrooms), so Black created "Conversation Starters".


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As a mom, over the years, I've had to become familiar with various children's health issues and basic healthcare (and don't get me started on health insurance). But whenever it was something more than the common cold or flu, a stomach ache, or the usual scrapes and bruises, I felt like I was back in school. And between the terminology and trying to understand how the body works, I often felt like I needed a nursing degree. Not to mention, there's so much information on the internet, it can be overwhelming as well as confusing and sometimes scary.

Over the years, I've also had to deal with my aging parent's more serious health issues, and I've lost count of the pages of notes I've taken and questions I've asked. Or the conversations discussing risks vs. benefits that I've had with medical professionals and my sister. (I'm glad Black finds statistics "fun" and can look at them unemotionally because they give me a headache.)


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Until recently, I had never heard the term "health literacy," and when I first did, I initially thought about general literacy skills such as the ability to read and understand numbers. Skills that are essential if you are sick and need health information and services, but also impact health decisions that should be simple, like filling out forms, taking over-the-counter drugs (aspirin, cold and flu remedies, etc.), and learning about the things we should (or should not) do to live a healthier life and reduce the chances of serious illness.

But then, I thought about how anytime I had to deal with a health issue, especially ones that could potentially be serious, it was a tedious, complicated, and technical challenge. And, at the risk of sounding arrogant, I like to consider myself well-read, pragmatic, and comfortable with numbers and research documents. In other words, although it impacts some people more than others, the issue of "health literacy" affects us all. (And, that does not even address what it does to the cost of healthcare.)

THE CONVERSATION STARTERS

  • Before now, have you ever thought about "health literacy"? How would you describe it? What impact does it have on your life? How can it impact your ability to be successful in the workplace?
  • Why do health and healthcare topics seem so daunting?
  • Does health literacy only impact you when you are facing health issues? Explain your answer.
  • Have you ever had a medical situation or condition that required you to learn more about it? Where did you seek information? Did you have any problems learning about it? Explain your answers.
P.S. – You might be interested in our Conversation Starters for Financial Literacy and Digital Literacy.