My last night in New York was spent with close friends. We had an incredible dinner at our favorite Italian restaurant and a bottle or two of malbec. We went from low-key emotional to full-blown sentimental.  As a parting gift, my friend gave me a book, a collection of essays entitled Goodbye to All That: Writers on Loving and Leaving New York.  

New York was a dream that came true, a hard-earned reality that I was ready to leave. While I’m confident in my decision to trade coasts, I wasn’t ready to face reality and definitely not ready to read this damn book. I placed the paperback at the very bottom of my carry-on and ignored it for a month.

I’ve visited New York twice since the day I officially moved in May, thanks to some consulting work and a friend’s wedding. I’ve been feeling a bit bi-coastal and it’s bittersweet. A part of me is drawn to city life. There’s always something to do, things to see – so many different forces that can create endless combinations of experiences.

While I miss New York, I know under its gloss and luster is a demanding, toxic energy that I needed to step away from. Some would disagree with my word selection here but after 6.5 years of being a New Yorker, I was on the cusp of becoming a jaded asshole. That’s not who I am nor who I want to be.

Now I’m sitting at a Peet’s Coffee following up on cover letters + resumes, and listening to J. Cole. Job hunting in southern California moves at a slower pace than the likes of New York or San Francisco, and I’m finally getting requests for calls and interviews.

On paper, I am an accomplished communications/advertising professional. I moved to New York to accelerate my career. I started from the bottom like Drake and focused my energy on professional growth. I challenged myself to take on more work, immersed myself in projects where I was the least knowledgeable, exchanged ideas with artists, dreamers, and entrepreneurs. In between the hustle, I built strong friendships with people who have become family to me.

As demanding as New York is, I felt like I was thriving, that I had earned my spot and this city wouldn’t dare spit me back out. Rex said something along the lines of, “I feel like we owned New York and kicked its ass.” So true, we did – because DRAKE stands for “do right and kill everything.” and we’re about that life.

Present day, I feel unimpressive. Imagine this scenario – It’s a typical Saturday night, I’m at a bar drinking Bulleit rye on the rocks when a stranger asks the ever-so-cliche, “so what do you do for a living?

Here’s my current  status;  

  • I am unemployed.
  • Not a homeowner, no apartment either [my parents are my roommates].
  • Just got my hands on a used Toyota Camry [so +1 for that].

I would come across either as an aimless millennial or pretty much a scrub who occupies her best friend’s ride trying to holler at men.

I am unconventional in that I have never lined up a job before quitting my current one. My modus operandi is to save a ton of money, travel, and then focus on finding another job. I recognize for many this isn’t an option. I don’t take it for granted

But I need the downtime in transition. It allows me to fully detach from the daily grind. I get to process and think about what I liked/disliked at my old position and where I want to be as my next step. I’ve always been introspective and as I get older, it becomes an even stronger and necessary trait of mine. The questions that I constantly think of are;

  • What dream have you not pursued?
  • Or is there such thing as a dream job?
  • What do you want for yourself within the next year?

I think about those questions above and I feel like I’m getting better at answering them. Friends who have experienced this transition, who are also driven and ambitious, have been helpful coaches. Ultimately, the struggle for me is between the desire for career growth + financial stability versus the pursuit of dreams.

If you are lucky, you have your dream job. It’s one you both enjoy and are passionate about. It provides for all the necessities in life. But there are those dreams you’ve had since you were young – ones you abandoned for the safer, more sensible route. If given a blank check, what would you really be doing? Would you launch that new startup you’ve been thinking about? Maybe spend years in the countryside of France writing your novel? Write music and spend it all on studio time?

Maybe it’s not a choice between the two but a compromise. Or maybe it’s about making a choice and committing to it 100%. I don’t know. I’ve got a couple of solid leads lined up and interviews on deck so we’ll see. I’ve also got projects in infancy that are ready to mature.

I am impatient and I’m trying to rewire myself in that respect. The uncertainty is unsettling, but it’s also pretty damn exciting. At least I know I’m committed to my truth, regardless if it’s uncomfortable and frustrating. This is just a transition, a temporary phase, a terrible interlude on an otherwise perfect album.


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Iris Portillo

Iris is a former Brooklynite who recently traded the east coast for the west. A communications professional who travels whenever possible. Appreciates compelling writing, cinematography, photography, whiskey, good puns and comedy. Music lover.

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