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





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