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How I Convinced my Employer to Let Me Work Remotely from Medellin, Colombia

Hey guys,

So today I am going to share how I convinced my employer to let me work remotely from Medellin, Colombia for 4 months…

During which was definitely a life changing experience 🙂

Medallo, papi!!

Alrighty, so how did I do it?

In short,

  1. Worked my ass off for 3 1/2 years building a pipeline and reputation for myself
  2. Became one of the top performers
  3. Built up trust with my employer
  4. Created leverage
  5. Made the ask
  6. Was willing to walk

Alright, so I’ll break down each of these.

1. Worked my ass off for 3 1/2 years building a pipeline and reputation for myself

So this should seem like common sense…

And it’s certainly not the sexiest ‘secret’ you were looking for…

But at the end of the day it comes down to hard work, and putting in the reps and paying the price necessary.

There are no short-cuts, as cliche as it sounds…

I grinded my ass off for 2 1/2 years straight just building a solid pipeline, until I really got my footing closing deals on a consistent basis.

It takes dedication and commitment, make no mistake about it.

During that time, I stayed dedicated.

I mean, in the first year, I basically counted and made sure I made at least 30 dials per day…

These were targeted dials, not the “smile-n-dial” kind if you know what I mean…

Anyways, I am thoroughly convinced that it was this part – the hard work & dedication – and really allowed my trip to Colombia to happen.

If I didn’t put in the work, none of that would have happened.

Let me be loud and clear about that…

You must plant seeds and sow crop before you can reap the harvest.

Also, during this time…

Because I stayed consistent & dedicated, I started building up a reputation for myself and my work ethic.

This is invaluable as your perception of someone who gets the job done and is not afraid to do the work will surely make you stand out amongst your peers.

2) Become one of the top performers

After about 2 years of going at it…

Not only learning B2B solution sales… but also learning how to sell to procurement

I started hitting my stride at that company.

It really “clicked” after I had the chance to attend a Procurement conference, where I got to meet some of my prospects…

I got to see what these people were like in real life…

As opposed to just “this person I was talking to” on the other side of the phone…

Since I had never met a “procurement” professional in my life before.

Anyways, eventually I started hitting my stride and went from the youngest rep hired there to consistently performing in the top 10% of the company

(We had about 50 sales reps around that time)

This really did two things for me… the first one is that I…

3) Built up trust with my employer

So by going from a young hire that was really green… to being a top performer…

This built up a lot of trust with my employer!

If you’ve read any of my other posts, you’ll know how important I believe trust is in sales!

They could see that,

“Hey, this kid came in not knowing much…

And outperformed a lot of other people with ‘more experience,’…

We gotta keep him!”

(At least I imagine they said something like that…)

Not bragging here at all…. But just saying how by doing that…

I really built up trust with my employer,

Because they could see that I was getting the work done!

Where as most of the people (~80% of reps) were not able to hit quota…

I was exceeding quota…

There’s a saying in sales, “Revenue curls all ills”

And it sure does a lot for the rep if they’re hitting their numbers….

The other thing it did for me was…

4) Created leverage

Because the type of sale was fairly difficult… (Selling to procurement professionals)

The number of reps who performing consistently was fairly small.

About 20% of the reps brought in about 80% of the revenue.

This made the consistent performers incredibly valuable to the company.

You see,

Because the type of sale was so niche and difficult to train for…

It made the top performers extra valuable to the company. They weren’t easily replaced…

Like workers at a McDonalds restaurant….

(Nothing against working at McDonalds… just an example)

This created leverage for myself.

Once you make yourself a “need to have” for your company,

You’ve created leverage for yourself.

Your company “cannot lose you.”

That is a good spot to be in.

Seth Godin calls these people “Linchpins.”

Once you’ve built up a reputation for yourself, through HARD WORK…

built up trust between you & your employer…

And created leverage for yourself…

NOW is the time to make the ask.

5. Make the Ask

You’ve made yourself indispensable and valuable as ever,

Your trust level to your employer is at an all time high…

And you’ve made it so that they CAN’T lose you…

Now you go in for the ask….

You state clearly, and confidently (because you’ve put in THE WORK!!) exactly what you want…

For me, it was being able to work remotely as I explore possibly living in Colombia long-term.

To be fair, I was working for an awesome employer…

The folks there were outstanding, and the managers were awesome that they let me work abroad like that.

I think I was the first if not one of a few people they ever let do something like that…

And that was super cool of them…

Anyways,

Once you make the ask, just make sure that you’re clear and concise with it.

Be clear on what you’re asking for.

The reason why they let me go out there for 4 months was because they wanted to give me some time to figure out if I wanted to stay out there long term.

They said, “Hey, if you want to stay there longer than 4 months, then you’re going to have to find your own thing and we’re going to have to part ways…”

“But if you want to come back to LA and keep working for us, you’re welcome to do that.”

I thought that they were awesome for doing that.

This case study is kinda like a page taken from Tim Ferris’ The 4-Hour Workweek.

Lastly, this following point is important…

6. Be willing to walk

Make it known… whether directly or indirectly…

That you’re willing to walk if what you want is not a possibility.

If you’ve done all the steps correctly leading up to this one…

You should have a solid chance of getting a “yes”

Now, I don’t mean be a pouty little brat…

What I mean is,

If you’ve really put in the work, and made yourself indispensible…

And doing this thing is something that you truly want to do or is passionate about?

You want to really consider how you can walk away and go do the thing that you really want to do…

I hate to sound cheesy, but at the end of the day…

You only get so many days to live…

And life is too short to not go after things you are passionate about.

Again, I’m not saying be irresponsible here.

What I’m trying to convey was that, my mindset had already been made up.

This was something I was going to do with or without my employer…

I simply made it known that, when I really want to do something…

I’m just going to go do it!!!

So I was being authentic and real here.

Don’t say this just to say this, but it has to be true!

All I’m saying is that if this is something that you are genuinely passionate about, and would regret if you later looked back at life and would have regretted it…

Then I highly suggest you do some thinking,

And figure out how you can go about doing that thing….

Because the last thing you want in life are regrets of any kind!

I actually recently made a blog post on this, based off a book I read…

Top 5 Regrets of the Dying.

It summarizes the top regrets people have on their deathbeds… (I actually made a post about this)

And guess what the #1 regret most people had was?

“I wish I’d had the courage to live a life true to myself, not the life others expected of me”

Like holy shit guys….

This is profound.

I know you have heard this concept and probably think you understand it…

But every time I take a moment to realize this… it hits me hard.

Everytime.

And I think to myself, “Like you mean the NUMBER 1 regret most people had on their deathbeds was that they wish they were just able to be themselves more and live a life fitting to them??? Holy SHIT!!!!!!”

That’s literally what goes through my mind.

So I guess, what I’m trying to say is that….

Whether your’e trying to live the life of your dreams in Medellin, Colombia…like me…

Museo de Castilo en Medellin, que hermoso

 

Or you’d like to see the Northern Lights, and explore living like a digital nomad in Europe…

Whatever you want to do….

You can do that by leveraging a skill set, and becoming indispensable at it

In this case, for me, it was sales.

So add huge amounts of value to your organization, and over time, make yourself indispensible

And when you find yourself working/living abroad… write me an email ([email protected]) to let me know how this post impacted you 🙂