By Caitlin Upshaw

I grew up knowing I’d be a Broadway star, so naturally I became a lawyer.

After the 2004 election season, which was a huge blow to the LGBTQ community in particular, I knew I had to do something BIG. I went to law school with the idea that I’d practice public interest law, ideally serving low-income clients in alternative family structures and working toward social justice in Portland. As I did well in law school I found myself being shuffled into the “should” lane of law–take a big firm job, make big money, pay off loans, by fancy car, etc. Less than a year into that big firm job, I was laid off in a terrible economy, along with the only other woman in my class of new firm associates. At the time, I wasn’t angry–I was relieved.

I hated the job and the boys’ club, and a few months of unemployment was just what I needed. However, as I look back, I see the patterns that led to such a clearly gendered decision, and almost 10 years later, I finally got mad.

I’m still happy I lost that job, but I see those same sexist patterns repeat themselves in every organization I’ve been a part of. I now feel incredibly fortunate to have had the veil lifted so I can see not just sexist patterns but deep structural racism that drives virtually every decision in every white-dominant organization. I’m now an HR leader in a progressive organization that still has problems with its embedded white supremacy, a woman-led organization that still has problems with sexism. As a queer woman, I hold white privilege, education privilege, and cisgender privilege, among others, and my professional mission is clear: to use every bit of power and privilege I have to lift up and work for the advancement of women and people of color.

(To One Who Doubts the Worth of Doing Anything If You Can’t Do Everything):

You say the Little efforts that I make

will do no good: they never will prevail

to tip the hovering scale where Justice hangs in balance.

I don’t think I ever thought they would.

But I am prejudiced beyond debate

in favor of my right to choose which side

shall feel the stubborn ounces of my weight.

– bonaro w. overstreet

Caitlin Upshaw is an HR~Equity~Inclusion Director in Portland, a (former) employment lawyer, and a (current) pro bono immigration lawyer. She found her way to her own workplace happiness after years of practicing law when she made the switch to HR, with a strong focus on racial and social justice in the workplace. Caitlin’s HR passions are equity & inclusion, leadership coaching, conflict resolution, and creating humane policies that work for employees and companies. She also loves her awesome family, running, hiking, local music festivals, theatre, football, and fútbol.

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