Caffeine Confidential: Empowering Women & Embracing The Obstacle Course 

I was having coffee with a good friend of mine this past Sunday (how suburban and house-wife-ish of me) and we got into a pretty intense conversation about women and society and accomplishments and achievements and fulfillment. You know, the usual… Given that she has just gone through a pretty turbulent year and I’m revving up to a similarly challenging one, we had a lot to commiserate about. Two points that she made really stuck out to me, though.


Obv this is my dog and not the friend that I had coffee with, but I do also have girl-power pep talks with my dog. She is sorta androgynous but also loves Puppaccinos. 


  1. We both have Masters degrees, professional experience with reputable organizations, valuable skill sets, and support ourselves. We are Independent Women. We are friends with other Independent Women. Yet, here we sit, nearing 30, still looked down upon for not being married, having babies, or even having a life partner. It’s taboo. It’s 110% okay for the guys we went to college with to quit their corporate consultant jobs at 27 and buy a one way flight to Malaysia. Yet, even the most wild, free, and independent women we know from college are married, starting families. Sure, they also have law degrees and well-paying jobs, but they didn’t skip that crucial family/husband portion. We haven’t checked that box yet, and that’s weird to other women. We are made to feel (sometimes intentionally, usually unintentionally) like we are inadequate or incomplete because we are choosing a different path to our own fulfilling lives. And that straight up sucks. So many of our friends don’t understand that we choose to pursue various career paths, travel, explore ourselves and this world, because they have never had to make that choice. They have never had to choose between a comfortable known and the uncomfortable unknown – so we are the weird ones.
  2. Those women that do struggle with relationship challenges and life aspirations don’t talk openly about it. If it’s any less taboo to take the path less traveled, it falls into the cliche category of “finding yourself,” and there’s rarely a positive connotation associated with that hippie bullshit. When we do hear these stories of inspiration and liberation, they’re often from a successful perspective. The whole “look at how all these successful people once failed in life but still turned out well” thing. But, who is talking about those obstacles and challenges as they’re happening? Who is talking about the struggles with their friends in an encouraging way, instead of that girl-gossip way that women roll their eyes over a bottle of wine as they muse “oh, Jessica, she’s off traipsing the globe like a hippie.” We will scroll trough Jessica’s Instagram, allowing our jealousy and fear present itself as condescending remarks about how she needs a real job or must live off her parents, without ever acknowledging that Jessica chose the unknown and embraced it. We can all choose the unknown, uncomfortable path, but it’s so much easier and acceptable to follow the societal map instead.

I bet you know where this is going. I don’t normally get deep on D:C, but it’s coming. Just as I share my plans and packing lists and how my plans explode with you, I feel like I need to share what’s in my emotional carry on, and how life plans sometimes explode in the most exciting of ways. It’s time to turn a taboo, cliche subject into an empowering conversation. Let’s chat.

PS: If you want to send me Starbucks to help me cope with my personal obstacle course, I’m always down for some gifted Grandes. Just sayin’.


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