How I Convinced My Boss To Let Me Work From Home

I have a confession to make.

The reason why you are reading this because of a Chainsmokers concert.

During my junior year of undergrad, I interned at a top startup accelerator company.

One afternoon as I was about to commute 90 minutes home from the internship, my friend Alex called me.

He asked if I wanted to go to a Chainsmokers concert that night. I debated. At the time, he was a good friend, but not a great friend.

Plus, I had to be up at 5 AM the next morning to entertain a guest speaker for breakfast, not to mention the late-night 90-minute drive home.

But, for some unknown reason, I decided to forgo a night of reading Tim Ferriss’s Tools of Titans and joined him.

The concert was not only incredible but also a tipping point in our friendship. And at the end of the night, I decided to invite Alex to join the breakfast the next morning with the guest speaker and myself.

Looking back now that breakfast was a turning point in our career paths.

How so?

Well, the guest speaker ended up becoming my first mentor. And Alex impressed him so much that he earned himself a job that allowed him to work from home.

A few months after that breakfast, I started studying abroad in Sweden. Meanwhile, Alex was working from home and traveling throughout Europe.

During this time, we met up in several countries, and I witnessed the lifestyle of working from home.

I’ll be honest. I couldn’t believe what I was seeing.

How can he do whatever he wants (e.g., explore the city all day) and then work at night? Or work in the morning and then go out at night, having fun and making new friends.

Doesn’t he need to be working from 9 – 5? Or be working US business hours? How does his boss trust him to do this if he can’t see him in an office?

For some reason, I couldn’t wrap my head around it.

How is this happening?

It seemed a bit like magic at the time, and I quickly became envious.

Envious of the ability to work from wherever and whenever.

More specifically, the freedom of time and mobility. Along with all the opportunities that became possible with it.

Returning home from my study abroad, I had four months to find a job before I graduated.

While peers talked about what company they wanted to work for, how much money they wanted to make, and the different interviews they had lined up.

All I could think about was Alex. And how he was able to work from home and his freedom.

Luckily I was able to get a work from home job at a yacht charter company because of the accelerator company I interned at.

That job allowed me to:

  • Work from home in a Miami luxury high-rise (work views below).
  • Travel around Europe (dog sled in Norway, island hop in Croatia).
  • Visit family & friends around the US.
  • And much more…

Life was incredible!

I had the same freedom and control of my lifestyle, just as Alex did. And it was all because I was able to work from home.

Then one day, without warning, my entire life came crashing down.

It started with a call from WeWork. They told me that my boss had rented an office.

I couldn’t believe what I heard, so I immediately called my boss.

I’ll never forget our conversation. My boss said, “We will all be more effective working together in an office. That’s what other companies do, and we should do it too.

At the time, I didn’t know what to say. I was speechless. I just thought there’s no point in arguing with him since he was the one who signed my paychecks. 

So I just accepted it.

As a result, I had to start making 1-hour commutes back and forth from my Miami high-rise to what I now like to call the “cube-farm”.

I probably don’t have to tell you, BUT…

If being stuck in bumper-to-bumper traffic, with people cutting each other off and honking and swearing at each other, doesn’t get you excited to go to work, I don’t know what will.

For me, the traffic was PURE HELL.

Not only did it affect my mood, but I was losing 2-hours each day.

That’s 8.3% (2 hours) of my day taken away from sleeping, exercising, spending time with friends & family, learning a new hobby or language. Heck, even having more time to do more work.

And the WORST part, my freedom being taken away from me. Simply put, I was no longer in control of my day.

Instead, I had to leave for the office at 7 AM and wouldn’t get home until after 6 PM. Plus, the commute took a lot of energy out of me.

After surviving for six weeks on the cube farm, I finally had enough. I needed to go back to working from home. So I decided to make a list of ideas on how to do this.

Here’s what I came up with:

  • Quit my job and start an online business
  • Find a work from home job

Building an online business sounded like a ton of work and would take several months to replace my income. So I decided to try finding a work from home job. 

After several cover letters and applications later, I had zero success.

I quickly learned that there are not many work from home jobs, and the available ones are incredibly competitive because of the freedom aspect.

Discouraged from failure, I turned to my mentor and asked for a reference at the work from home company he worked for. Upon receiving my email, he called me to ask for more details about why I wanted to leave my current job.

He thought I loved my job.

After hearing my 10-minute rant of why my world was ending because I could no longer work from home, he wisely stated.

“You know, ‘Undo’ commands aren’t just on keyboards…”

And then it hit me! My big “aha” moment.

If I could work from home before, why can’t I convince my boss to let me go back to working from home?

My mind started racing with excitement – the potential of escaping the cube farm and getting my freedom back.

This breakthrough led me to start researching and reading everything I could get my hands on about working from home (case studies, industry reports, Reddit / Facebook communities, etc.).

The evidence I found was overwhelming.

Not only is it beneficial to work from home as an employee, BUT it’s more beneficial for companies to have their employees work from home compared to in-office employees.

Say what?!

Yes, there are several company benefits, such as:

  • Saving time and money
  • Increased employee productivity
  • Improved employee recruitment and retention
  • More employee empowerment
  • Better work/life balance

With all this new information, I created a visual presentation to share my findings. After having a friend look it over, I sent it to my boss.

In the email message (with the presentation attached), I told him I’d like to work from home again so I could not have to go into the office, be able to travel again, and enjoy my high-rise views.

I’m not joking when I say this, but he replied with just the word “NO”.

A big fat N-O. All caps. Nothing else. My heart sank when I saw the reply.

I felt defeated. What am I going to do now…

There’s no way I’m going to convince him after that. I guess I’m just going to have to suffer and lose 2 hours each day in traffic, and that’s just the way it is.

I don’t feel proud to admit it, but I gave up again.

Dejected, I went back to applying for work from home jobs. Including ones with significantly less pay and that I was overqualified for. I also tried brainstorming new online business ideas, but nothing seemed promising.

Once again, I had ZERO success.

I even got rejected by the company my VP mentor worked at, even with his reference.

He called me to tell me the news. Our conversation soon transitioned, and I began to explain to him about my failed attempt to convince my boss to work from home.

He listened patiently and told me that the presentation sounded promising, but said my approach needed work.

This was my second “aha” moment.

I realized that all I cared about was why I wanted to work from home. Not why the company should want me to work from home.

With this new mindset, I gathered enough courage to give it a second attempt.

This time using a whole NEW approach. A company first approach.

Rather than telling him I wanted to work from home, I told him I wanted to discuss my future at the company. More specifically, how I can help the company grow more and be a more effective employee.

I sent my boss a meeting invite, and I had a shot.

I spent the next few nights tweaking the presentation, focusing on highlighting benefits to the company, surfacing common fears & objections, sharing case studies from other work from home companies, and much more.

And then came the big day!

I won’t dive too much into the presentation itself because you’ll see all the SECRETS soon enough.

But the presentation lasted about 15 minutes, followed by about 30 minutes of my boss asking me questions and sharing his concerns.

To be honest, I was not prepared for his questions, and it showed.

Still on the fence, my boss decided to bring in our HR team member to poke holes in my plan to work from home. After having another 30 minutes of Q&A, we finished the conversation without a final decision.

At the time, I thought leaving that conversation without a final decision was the worst thing that could have happened.

But truth be told, it was one of the best things that could have happened because it allowed me to follow up.

In my follow up email, I was able to list all the concerns my boss had, and solutions to these concerns.

Soon after, my boss called me into his office to discuss my follow up email. After walking through my proposed solutions to his remaining concerns, he said I could go back to working from home.

But if I was traveling, I needed to share my tentative travel plans, so he had clear expectations on time zones and overlapping working hours.

Nonetheless, I had gained back my freedom! Success!

All of the weight on my shoulders had been removed, and I felt free again.

This feeling was followed by a rush of energy and excitement that led me to conquer the world again.

And that’s precisely what I did!

Fast forward 1-year since then, and I’ve been able to:

  • Travel the entire world visiting 25+ countries.
  • Upgrade my standard of living from my Miami lifestyle.
  • Save over $10k legally by avoiding US taxes.
  • Spend more quality time with family and friends, and make new friends all around the world.
  • Focus more time on my health and go from 25%+ to 13% body fat.
  • Learn to salsa dance, Muay Thai fight, speak Spanish, and so much more.

Sam in Thailand
Sam in Cozumel
Sam in Mexico

Now, I don’t share all these things to show off or brag, actually the opposite.

Instead, to encourage you and help you envision a potential lifestyle, you will unlock once you can work from home.

And to be clear, you don’t have to work from home and travel. Even if it’s spending more time with family, having more time for yourself, or being more flexible throughout your day.

That freedom is priceless.

If it’s not apparent already, I whole-heartedly believe that working from home is the best way to work on this planet.

Because I know first hand, your life will drastically improve when you are too.

And like me, if you’ve failed before at trying to convince your boss to work from home. Or you haven’t had success at starting an online business. Or haven’t been able to find a work from home job. 

I want you to know it’s NOT YOUR FAULT.

You just didn’t have the right framework, tools, and scripts to succeed.

But NOW you do! And this is why you are here.

You’re here because you want to be free! And if that’s what you want, you’re in the right place.

All that’s left is to do is to get this free step-by-step book to convince your boss to let you work from home

If you do that, you’ll be free.

And yes, even with these proven frameworks and scripts, there might be fear still creeping in your mind, “Can I really do this?” And I want you to know that that’s completely normal.

It shows you care about having your freedom and wanting to work from home. Otherwise, you wouldn’t be reading this.

You’re already 50% on your way to working from home because you’re showing up and reading this book.

And I care about you and your success in working from home, so much that you have my direct access to me 24/7/365 at [email protected].

Yes, I’ll personally reply if you message me.

I’m here to help you convince your boss to work from home and overcome any unreasonable objections or NOs they might throw your way.

I can’t wait to see and hear all about your successes once you are free.

Submit a Resource

Resource submissions will be reviewed in 24 - 48 hours. Please contact [email protected] for any additional questions.