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Cindilo Is a Making the Most of Midlife Passionista

After 25 years in law and academia assisting women during life transitions, such as divorce and reentering the workforce, CinDi created her own second act of writing and workshops for fellow Generation X women seeking to live their midlife with purpose and clarity through She recently published the easy-to-use weekly journal "When the Clock Strikes Midlife, It's Your Time to Shine," to inspire women to cultivate their midlife awakening with its interactive guided prompts and witty yet truthful perspective. CinDi has also started a new movement: #myfirsttimeover50, where she encourages women over 50 to try a new activity and ask the question: when was the last time you did something for the first time?

Here’s an excerpt from our interview with CinDiLo.

Passionistas: What are you most passionate about?

CinDi: I think overall it's growth. Not only growth myself, but others. Whether it's myself, my children, my loved ones, my friends, my BFFs on the internet, which I call my Cyber BFFs, and strangers. I always believe in growth and encouraging people to grow and learn about themselves in the world.

Passionistas: So, what inspired you to get into law and academia?

CinDi: I found myself, graduated high school, and I didn't have an idea in mind of what I wanted to do. I was the first person to go to college as far as my sisters and I. So long story short, I worked for a year in retail. I went to a seminar of a woman who did a little thing about being a paralegal and it really intrigued me.

I went on to become a paralegal and get my degree, which back then, in the 1990s, mid nineties, nobody had... not that nobody had paralegal degree, but it wasn't needed really. You know, all you have to do is have some experience working in a law office and they'll throw you to the trenches and teach you what they want to teach you.

So, I did that. And then of course, me being me, by the year 2000, I created a website called because, at the time, there was legislation going on in my state of what was going to happen with paralegals.

Passionistas: So, you've told us that you had a midlife crash when you were around 45. So tell us what happened and what personal changes you made during that time period.

CinDi: I was just at a point in my life where my children were probably the most active, they were and couldn't drive themselves yet anywhere. So, they were at an active stage in school and probably at some point starting to work. And my mother had just passed, I believe. And soon after that, my father became ill.

I was also working for a horrible employer, and I quit my job soon after. And when I look back the entire time from when my mom was sick, until then she passed, and my dad was sick and then he passed. That was a decade. And that was hard. I mean, it was, again, my sisters and I still talk about that and it's, again, one of those things where you turn around, and you're like, "I have no idea how I did that. I have no idea how I got through it, how I still took care of everyone."

So that's the other thing. I realized I'm taking care of everyone and not taking care of myself, which I think women do in general. And I also think at this point in life, you get to the stage where I can't do this anymore. You know, I took care of everyone all this time.

Passionistas: So, what adjustments did you make besides getting a new job and how do you today take care of yourself?

CinDi: I had to have a serious conversation with my husband, who's great and helps a lot and does a lot. But again, it was a really busy time, and he is also a glutton for punishment, like me. And he always did coaching. And he couldn't just coach. He had to be like president of the football team... of the football organization. So, we're both like that, which can be commendable, but it's typical. And you know, I also always wanted to be involved in my child's education and the community and the school things. And, you know, it was hard. I tried my best and that's all we can do.

Passionistas: You started The Midlife on Purpose planner. So, tell us what that is and why you created it.

CinDi: It’s a tool to encourage women to do different things, to think outside the box, and actually even plan what you're going to do. I'm not saying that you need to plan every moment of your life, but sometimes, and I'm still a perfect example of this, I forget to have fun and to plan things that I've been meaning to do for the past three years.

Passionistas: So, tell us about and what inspired you to start that?

CinDi: So, I was turning 50 in 2018 and I just, I don't know, I'm always sort of researching and even on social media, certain things catch my eye. And I noticed this woman wrote, I think she eventually wrote a book about it, but she did 50 things for turning 50. So that got my wheels turning, and I didn't necessarily want to do that, but I also, again, went back to something from my childhood, which is, "my name is Cindy, not Cynthia." But I have a cousin and sometimes my sisters would call me Cinderella or CinDi-lla.

A lot of people don't think of 50 as midlife or middle aged, but I think we do as Generation X or it's, I think, more of a stage than anything. So, if your children are leaving the nest, when you're 42 or they're leaving when you're 62, that's one of the times you, I think, feel that. As well as a lot of other life changes, you know, losing your parents or going through a relationship change or career change, whatever it might be. We get to that point somewhere between 40 and 60, where we have to make a shift, or we feel like whether we wanted the shift or not, something happened to kind of make that change.

Find out more about CinDiLo.

Hear CinDiLo’s full interview here.

Learn more about CinDiLo here.


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