Diana's Career Journey: Diving into the unknown on hope alone
Diana Castillo has been a part of the Black Wolf community for over 9 years. And over those 9 years I have become a big fan of the person she evolved into. She has always been a positive influence excited to celebrate the achievement of others. And as soon as she realized that she was capable of any of the challenges she has taken on over the last decade like realizing she could run, and realizing she could be strong, she then pushed herself in every workout, sometimes needing to be held back a bit from her own eagerness to conquer the next goal.
And that is why the last year has been so exciting and worrying.
Around a year ago Diana stepped down from her job without knowing what was next
I resigned from my position as a principal effective June 2024, without having any idea that the job market was as tough as it currently is. I turned down some positions along the way that would have brought me back to the same type of role or district, knowing I wanted a change and couldn’t go back after making the leap to find something that better fit what I needed.
This is the lifestyle stuff we should all aspire to. And the obligations in our life certainly have a say on the flexiblity with which we pursue change, but there is some level somewhere that we could refuse to compromise any longer.
It may not be a resignation. But it could be a boundary on an unhealthy relationship, or putting a potentially destructive behavior on hold for a few weeks despite the fears that it will leave us missing a piece of ourselves no matter how unhealthy that piece may be.
The confidence to leap is so incredibly admirable.
But we must know that life is often not romantic. In fact, life itself does not much care whether you find it to be fair or not. Diana closed the door on that chapter and was greeted with silence. Peaceful at first. Fear inducing soon after.
Hundreds of applications and many interviews later, including positions where I made it all the way to executive interviews only to find out the position was cancelled, I learned of a role in Talent Management where I would serve as an HR Business Partner at YES Prep, supporting principals to ensure their focus can remain on students by removing many of the stressors principals face.

She did the work to stay active in the job market, and she kept herself engaged and busy with whatever time she had outside of the job search. Those of us at the gym saw her become an incredible volunteer and supporter of the Houston Humane Society. Spending time helping at the facility, and fostering dogs herself. And as a result of her staying as patient as possible (easier said than done), she found a great place to land.
Holding out for 11 months allowed me to find a team that did everything in their power to make sure I accepted the position, a team that made me feel valued even before starting, and an amazing schedule that includes many work-from-home days to enjoy time with my newly adopted fur baby, and more holiday breaks and PTO days than ever before!
So, any parting advice for someone who may be realizing a change would be nice (or incredibly necessary)?
The right place is out there for anyone considering a change—just maybe don’t quit before you have the next opportunity lined up unless it’s absolutely necessary (it was for me)