Farewell Chicago


My mind seeks to define it, my body craves to touch it, my heart yearns to feel it.

Being unable to succeed in any of these facets as of late –

We are all hurting a little inside.

If I get it all down on paper, it’s no longer inside of me.

So in my effort to begin facing these emotions, I have written this post.

To discover,

how Home could mean something unexpected

and being Home-less (physically, emotionally, spiritually) could even be delightful

I keep returning to this.

Home is … a place where something flourishes.

I’ve been trying to understand why I’ve felt captivated to take this journey leaving behind by all definitions a very successful and incredible life in Chicago.

Irrespective of going abroad, I knew it was time to say goodbye to this fantastic city and all the luxuries and friends that I have been spoiled to be surrounded by.

I want to say thank you for making Chicago a place where I flourished these past 8 years.

Without your love, I wouldn’t be the confident, strong, fearless, and scrutinizing woman that I am today.

The type of woman that lives life with a magnifying glass, ticking clock, and hand grenade.

The type of woman that decides on a whim to give up everything that made up Home in her little-big mind because the music kept playing louder and louder –

to the tune of

Otis Redding – Cigarettes & Coffee,

“It’s early in the morning
About a quarter till three
I’m sittin’ here talkin’ with my baby
Over cigarettes and coffee, now
And to tell you that
Darling I’ve been so satisfied
Honey since I met you
Baby since I met you, ooh”

but the lyrics began fading into the sad, slow melody

“And whole my heart cries out
Love at last I’ve found you, ooh now
And honey won’t you let me
Just be my whole life around you…”

and one day, she didn’t hear a love song back.

March to the beat of your own heart – drummer girl.

Find a new way to flourish and home will follow.

Farewell, my old flame – may you rest in sweet peace.



Hello Remote Year


Hello Remote Year,

Darling, I cannot wait to meet you in person. I’ve heard so many fantastic things about you. Us – this adventure we are about to embark on will be once we can tell for generations to our kids and their kids. Grandma was like Dora the Explorer and traveled all around the world! As adorable and strikingly accurate as that likely will be, I’d prefer to referred to with the mystique of Carmen San Diego if you please.

I still can’t get over how we met. Driving to a Black Violin concert in the Chicago Burbs on a Sunday with Madam Katz. She inquired about how I was liking my recent transition at work. I told her I love my new role – as a Consultant de Salesforce – but hated how I never traveled to far away kingdoms anymore.

“You should consider Remote Year – look into it.”

Marvelous. Why not turn my biggest complaint about my job into my greatest asset?

So I applied for your services and waited with bated breath.

Well technically, I stalked you.

So fondly, I remember. Your first communication you sent me – an autoresponder email saying an admissions advisor would review my initial inquiry and send an invite to apply and interview if I qualified.


Eye spy with my little eye…that you are collecting my information in Salesforce. Maybe, I can convince you to choose me as one of the lucky 75 people out of 300K inquiries if I say I can help you streamline your recruitment, admissions, service, and reporting processes on the platform.

Will I hear back from you again? How do I catch your attention?

The next day you send me a newsletter from your Welcome Campaign – The Remote Life.


I inspect the email further (literally) and discover that you use MailChimp to send out your marketing communications – makes sense, you are a startup my darling and MailChimp is less feature rich, but less expensive generally. If I were you, I would be using lead scoring to track and score my every move – my email opens, my reads, my link clicks etc. You don’t want to admit your watching me too, but you have over 10K new inquiries a day and only 5 admissions officers (from my LinkedIn research), and you need some automated way to prioritize your leads. I make sure to read every email you send me and click every link on every email. It’s a long shot, but darling I need you see me above all the other stars in the universe.

8 days later an admissions advisor reaches out to me to invite me to apply and set up an interview.

The application is 5 questions long – what you would expect if you were serious about pursuing a long-term relationship with someone.

  1. What do you do for a living?
  2. What is your experience with remote work?
  3. What do you want to get out of the experience?
  4. Why Remote Year?
  5. Another typical question – my memory escapes me

I use Calendly to search for an open time for me to speak to my interviewer. She is currently in Phnom Penh, Cambodia. The only open slots are 6 am and 11 pm – welcome to time zone differences. I’m much more stunning under moonlight (i.e. I don’t do mornings) so I choose the later time slot.

So long story short – I knew you would pick me. Here’s the thing about interviews that most people ignore –

People DESPERATELY want to say yes. You just have to give them a reason to.

I am framing my story around your needs. As an admissions advisor, you have a certain quota that you are responsible for filling, and you are likely incentivized monetarily to recruit people that will retain with the program. You interview 12 people a day based on a written application that gives you some indication of fit, but the in-person interview can make or break a candidate in 5 minutes. You literally scan over the online application 2 mins before the interview and barely read it (something you accidentally admit) – looking more for indications of tremendous intent to purchase or red flags. In a good week, you spend 30 hours interviewing and have 8 applicants that are conditionally accepted and in the end only 1 that ends up depositing for the program. It’s called a Funnel and Conversion Rates. That’s usually how these things work.

All you want is to find someone like me. I am your ideal candidate.

  • I have been with my company for 4 years and have deep trust and support with the leadership of my practice. They know I will do great work and be focused wherever I am located.
  • I have extensive experience being on the road. I understand what it’s like living out of a suitcase and being around other people all the time.
  • I make a very steady income so my risk of attrition is much lower.
  • My lease is up at the end of January and you happen to have a program starting February.
  • I’m decently funny and entertaining. If you were stranded in an airport with me for 3 days, we could make a fun game out of raiding the bars for wine and whiskey and rationing it appropriately.

And sure enough – 7 days later – you get down on one knee and say Meina –

“Will you accept my conditional offer of acceptance into Remote Year Kublai?”

“Ugh what does conditional mean? (Love is not conditional!)”

“You’ll need King Huron’s approval.” That is a tale for our next letter.

In the mean time, I relish our engagement and dream about our honeymoon schedule:

February – Kuala Lumpur, Malaysia
March – Ho Chi Minh City, Vietnam
April – Phnom Penh, Cambodia
May – Bangkok, Thailand
June – Belgrade, Serbia
July – Lisbon, Portugal
August – Prague, Czech Republic
September – Sofia, Bulgaria
October – Buenos Aires, Argentina
November – Córdoba, Argentina
December – Santiago, Chile
Jan – Lima, Peru





Fire & Freedom – A Preface to Hello Remote Year

I woke up at 4 am to a burning fire outside my apartment, and I’m not speaking metaphorically about “the end of an era”, but literally to a huge mass of flames burning 10 ft from my window.

I had fallen asleep abruptly – in a swim suit top and bottoms – which I had ordered in preparation for my year long trip abroad with Remote Year starting in early February.

“How awkward, I’m going to die in a swimsuit before I get to do this trip. Hmm I should probably put on clothing…or call the police…or just call the front desk in case the fire department is already on it’s way. Man, I’m a goner if our building goes up in flames in Kuala Lumpur.” – the insane ramblings of a sane person in the wee hours of the morning.

I call the front desk, and Terrence begins to laugh –

“Oh they are filming a movie and the fire department is already here and everything.”

I perched outside my window and watched the flames grow until finally the fire department began to extinguish them. The flames fought back and continued to spread. I had faith that the fire department had the situation under control; however, mesmerized I couldn’t fall asleep until I was assured that the fire was truly dead.

In the morning, I am informed that the fire was not staged, but a freak accident.

The Universe speaks in strange ways.

“Today is the day you are are going to make me face music that I am leaving this life I’ve built in Chicago – all the places and people. The memories can come, but it’s time for me to go? Did you really need to set a movie trailer on fire to tell me that?”

When your wrong, the Universe isn’t afraid to speak up and let you know you f***ed up.

I paid a visit to the Chicago Art Institute for the FIRST time today to cross it off my Chicago Bucket List with two friends.

While eyeing a Magritte painting which provoked the question, “Why two noses?,” I get a text from someone I had being seeing for 4 months. I told him I was leaving 2 months in, but we continued to see each other in a no strings attached kind of way. After all, how does one start something serious when they know the end is in sight?

He says that he isn’t going to say goodbye to me because “I should know that he’s met someone else.”

“Why two noses? Why not two faces? Isn’t that more appropriate? Why do I care? I’m leaving and everything else is irrelevant.”

Sigh. Ending things in a Surrealist exhibit at an art museum is a little overwhelming.

My friend consoled me.

“Let’s go to the tiny rooms. It’s my favorite spot in the museum, and it will cheer you up.”

Turns out – Wes Anderson is a huge fan of the tiny rooms, and he also happens to be the favorite director of he-who-cannot-be-named. I feel sick to my stomach.

We leave to go to a bar and just talk… drink…digest…cool down and come back to reality.

We were always incompatible. I knew it from day one, but I ignored it.

Universe –

“You lit a trailer on fire today to tell me that I’ve been playing with fire all along. That I’ve been lighting matches for fun, mesmerized watching embers flicker ignite and recede, over and over, and it’s time to call it quits before I get burned. It’s a stretch, but point taken.”

I believe strongly in the interconnected nature of physical and spiritual coincidences that are in fact more related than we care to admit; as well as, the flow of destruction and creation in the Universe. With the death of one life ushers in room for another.

My heart is ready for a new adventure – RemoteYear – here I come 🙂 .