Rant + Ramble

Planning Getaways as an Act of Self-Compassion

Escapism in New York City is my love language

Sierra J. McKissick
6 min readJun 1, 2023


I was never a fan of Sex in the City, but now that I am in my 30s, over-romanticizing little things has become essential to maintaining my mental health. Whether getting dressed while dancing to a Lennon Stella song, enjoying a glass of wine, or eating dessert first, I intentionally search for ways to make my daily life more enjoyable.

But, let me be clear in saying I, like most people, still manage to have at least one bite-size crisis per day — typically work-related.

Day trip to New York City in 2017

As a founder, I work around the clock to meet deadlines and keep my brands visible. In truth, my commitment to improving community health has created unhealthy routines of overworking myself. Often to prove that my professional choices have allowed me to live on my terms and be flexible with my commitments.

A better version of me who does not swear at the thought of forgetting to check tasks off my to-do list would also admit that I live between the tension of being burned out and on the verge of a breakthrough. Fortunately, I have a great mom and friends who challenge me to get outside my head, and this time, I listened to the gentle warning to ‘take a day off.’


Instead of being swallowed by work, I headed from New Jersey to New York City for a day trip with one of my favorite friends. New York is one of my favorite cities. Although I would be a terrible New Yorker, I have always believed I had a special connection with the city.

When I turned 25, I treated myself to a weekend in the Big Apple — it was my first time visiting, and I chose to explore luxury. I spent a pretty penny booking a fancy hotel in Manhattan and making reservations at popular lounges for tourists and socialites. I was young and wanted to splurge. Since my only expectation was crafted from movies like West Side Story, Coming to America, and Breakfast at Tiffany’s, my expectations were heavily flawed. After accepting being an introvert in loud chaos, I realized how much I loved the city’s on-the-go energy and the endless opportunities it offered everyday people living their lives.

I returned to the city three years after my first visit to receive a timely reminder that life is still full of endless possibilities. I spent the entire day sightseeing, eating good food, and laughing with friends. It was perfect! It felt like the best version of normal. By the night's end, I started considering moving to the city and building a career. I was quickly selling myself on the narrative “If you can make it in New York, you can make it anywhere” and ignored anything that did not align with my newfound dream.

But was I ready to pack up and move? Again?

Feeling dissatisfied with your life, relationship, or career is normal and could signify feeling disconnected or unsatisfied.

Most people experience seasons where they feel their professional career has hit a plateau. Sometimes, these seasons occur more than once. It is natural to want to change your pace and environment and even desire a different life. Occupational trends highlight Millennials are more likely to have had three or four careers between their 20s and 40s. Although change is a beautiful process that could help us advance in our purpose, sometimes we foolishly throw the baby out with the bath water.

Root & Bone Restaurant in New York City

Although moving to New York City would have been an unexpected dream come true, instead of jumping ship, I embraced the stage of creating a new phase in my life and career where I was — in New Jersey. And it was rough.


One day, I liked how things were going, and the next, I was completely overwhelmed and frustrated with every aspect of my life and work. Although I managed to discover a way forward, I still struggle with the thought of abandoning my current path for something more exciting. I secretly want to throw the baby out with the bath water. Feeling dissatisfied with your life, relationship, or career is normal and could signify feeling disconnected or unsatisfied. Reflecting on your experiences and working to uncover or name the real problem is essential to finding a way forward without creating chaos in your life — or throwing away everything good.

The best way to end premature endings is to take your time.

Things will go wrong. In my experience, when I am dissatisfied or frustrated, I am easily irritable or prone to making silly mistakes. People are designed to pursue pleasure, which can make us quick to cut off or walk away from anything that does not ‘feel good’ or yield immediate results that benefit us. Determining how long you should stay and fight for something is difficult when it does not seem to work. Although there is no formula to know when to throw in the towel, if it probably leads to codependence and other unhealthy behaviors or violence, it is likely something you need to release.

“Every woman should know when to try harder and when to walk away.” — Maya Angelou

Have you ever let go before you gave something a fair shake? I have.


The best way to avoid premature endings is to take your time. Although grace has become a cliche when used in plots of manipulation instead of compassion, grace is truly the key to understanding timing. Being gracious with yourself and others allows you to hone your intuition and determine what you need when needed. Especially when things do not feel good or are going wrong, grace invites us to explore areas where we can show more compassion for the seen and unseen forces at play and accept our flaws. Likewise, grace also holds us accountable. When we show or extend grace to ourselves or another, it is a declaration that an [in]attempt did not meet the expectation and a call to action for humility, acceptance, and change. Grace is not a quick fix but a stalemate that challenges you to ask, “How did I get here gently?” “Is this what I need?” and “What do I do next?”

I realized uprooting my life every time I feel restless is not the answer. But, inviting myself on an adventure or exploration allows me to reboot my sensibilities and intuition. Traveling creates distance from my typical schedule, allowing me time to reconnect with my vision for my life and consider alternative ways of seeing and accomplishing familiar tasks. It allows me to be kind to myself and get a bird’s eye view of my work in the best way possible. As important as my career is, timelines and goals are only helpful when they remain realistic.

Visiting New York continues to give me hope, but more importantly, it gives me a different perspective. I may never live in New York. But, I am determined to continue searching for the endless possibilities right in front of me every day and give them time to develop.

A few of my favorite cities are New Orleans, Charleston, and, of course, my longtime favorite, Nashville. Let me know some of your favorite cities to escape.



Sierra J. McKissick

I’m a writer and educator. I write about behavioral and spiritual health choices and inclusive creative strategies. @iamsierrajecre