This Week I'm Reflecting On:
How I got to here
For the last six months, I’ve had the opportunity to experience what few from my background obtain: a break from full-time employment. I was able to take a breather from clocking into the office everyday. For the first time in 24 years I didn’t have an employer.
It wasn’t from retirement, parental leave, or FMLA.
It was a choice because I could and I wanted to.
I wasn’t sure what to expect, how long it would last, or how I would fill my time. I thought at least I would have fun exploring the locations I found myself in and I’d have the “free” time to go anywhere.
What I didn’t expect was the realization of changes that had been quietly building for years. Shifts in where and how I want to live, the rhythm of my relationships, and the type of work I feel called to do. This season didn’t create the change, it actualized it.
So this week, as I’m stepping back into ‘professional’ socials, meetings, and consults I’m reflecting on: how I got to here.
Back in November 2024, I left my 13 year career to go on an adventure. *#2025adventure is how I labeled in my budget. It’s not cute but it is functional.
I knew I needed a few guardrails for myself if I was to take a proper break. Three seemed reasonable.
Do not apply for jobs until February 🙈
Do not take any work-ish meetings 🙉
Do not spiral out about not having a job 🙊
*3 was and still is the toughest
I also had some goals for myself during this time. Three very obtainable goals.
Try all the coffee shops you can ☕️
Be in a bookstore or library at least once a week 📚
Live by your “Non-Negotiables” 🛟
*yes this is a set up for a callback
During these drip coffee in my cup ponderings throughout my #2025adventure I thought about my future and I found myself marching in the streets, volunteering with SwingLeft and ACLU People Power, helping launch 50501 initiatives, creating a website incubator for Team FEMS, pushing independent content creators on private socials, and generally fighting for democracy in some way every single day.
Was I expecting this? Ha, no and Hell Yes.
Ha, no – because I had envisioned more naps, I wanted to be back in the Paris Summer Olympics, coconut tree brat vibes, staring at the ocean for an offensive amount of time. ☀️🥥🌴
Hell Yes – because the only reason I - as an American woman - could be in a position to go to college, join the army, have a career, a bank account, a house that I own, a passport with my maiden name, wearing pants and driving my car WAS BECAUSE SOMEONE MARCHED IN THE STREETS FOR ME. 🪧
I’m about to yap, so let me back up…
I grew up in rural Kentucky. In a large family that didn’t have horses or a trust fund. I joined the United States Army National Guard at 17 to pay for college. Waitressing at $2.13 an hour in a Bible Belt small town below the Mason-Dixon line wasn’t going to provide the funds. *Surprising since at the time I only owned a used 1994 Geo Prizm I bought with cash and it was pre-avocado toast days so what was even tempting my millennial wallet. 🤷♀️
I managed to work each day and attend school at night gaining a bachelor’s and master’s through public universities and community colleges. That access to education led to access to technology which led to my career with a Silicon Valley startup called NetBase. *They mashed up “Internet” and “Database” for the name. I thought it was cute. 🤓
Being in a career that paid me a comfortable livable wage afforded me the ability to build a savings account. Pay off student loan debt. Start a retirement account. Live alone, spend time with my friends, AND get my nails done.
This career path also provided the opportunity to travel both in “the States” and abroad. My first international trip was a solo trip to London to consult and onboard a client. Work paid for me to be there, I paid to stay the extra weekend to visit monuments I’d only seen in books. And my amazing exploration of the world continued this way for 13 years across 16 countries and 200+ major cities.
I was given admittance to our globe's largest brands and agencies, shown a subset of problems their teams were facing, and I was asked to help. I was able to pick a team, structure it for best performance, and build a value system that sustained us through the most difficult challenges.
I was able to give back to my community through guidance on boards, in time spent volunteering with local non-profits, and being an official foster mom in the state of Texas.
I paid for therapy to assist me in unraveling the past so my next responses and decisions could be clearer. I maintained connections to leadership that mentored me. I cultivated a circle of love that inspires and sustains me.
Even with all of this in my pocket, in my corner, having my back, and being a blonde woman who happens to be white, I was—and still am—fighting off the anxiety that without codified policies, the things I’ve worked for my whole life could vanish overnight. I see it happening to others. I’ve read about it in books that record our history. A constant theme reeking from the pages: humans tend to oppress humans no matter how hard they work.
To me, that means work won’t save you.
My brain is constantly humming, looping, circling the questions: Why are we living this way? What would it take to change it in a neighborhood, in a city, in a state? Who is already doing this work? How do I use the knowledge I’ve gained to engage in actions that will continue the progress?
I believe problems created by people can be solved by people. Every societal structure we have was built by humans, so it can be rebuilt by humans.
I am curious: What makes us human? Why are we constantly taking away and blocking access to what makes humans, human?
Warning: a decade plus in a fantastical career that both pays you enough to breathe and allows you to work on cutting edge technology that changes the entire landscape of society might just give you the confidence to go after really big problems.
I am from a family of farmers, homemakers, coal miners, cake bakers, mechanics, and seamstresses. We didn’t have the internet until I was 13. Everyone did their own house repairs and everyone worked a side hustle to afford Christmas gifts.
The blue collar bootstrap society made me.
The white collar tech evolution held me in a livable present.
It will be progressive politics for humanity that will provide a future for me.
Yes. I’m going all in on reimagining the status quo: running for public office and working alongside “tech for good”.
I’ll be sharing my journey in my “This Week I’m Reflecting On:” series tackling these puzzles that keep me up at night. As with coffee roasts, these reflections will range in depth and flavor: sometimes bold and heavy, sometimes light and surprising. Variety keeps us awake, curiosity brews differently by the day, and if it is gonna be on the menu, I’m ordering the flight.
I will pose a “what do we/I do with this” challenge and suggestion. My goal is to follow up on YouTube a few days after the Substack post is live to show how I’ve tackled the challenge.
This is your invitation to join me for coffee. Feel free to sip slowly and reflect on your own journey, scroll in peace, or stir the pot with your own thoughts. ☕️
#CupOfCalculatedCuriosity #ReimaginingSystems #ChangeWithCassie #StayCaffeinated
Ooooo I love this! We have a lot in common :)