May 7, 2021

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How To Be Working 100 Percent Remote by 2021

COVID-19 has changed business forever, and you can use that to your advantage.

As best-selling author and entrepreneur James Altucher explained in NYC Is Dead Forever…Here’s Why, companies are realizing that maybe they don’t need an in-person office at all. This fascinating analysis describes New York’s storied history as the business capital of the world, and how COVID-19 forced the world’s businesses to start working remotely – maybe from now on.

I’ve been working remotely as an entrepreneur for almost four years now, and I’m never going back. I want to work from home for the rest of my life.

That was always the goal. Before this, when I was wearing a suit every day for my desk job in corporate America, my dream was always to work remotely. During my final year, our company began an experimental once-a-week remote day, and it quickly became the best day of the week.

I love being at home, spending time with my family, and not pretending to work (something most workers do in the office for hours each day).

If you want to start (and stay) working from home, there are essentially two paths to working 100 percent remotely by 2021: negotiating with your current company to work entirely from home or quitting to become an at-home entrepreneur.

Here’s the best path for each one.

Don’t wait for someone else to do it. Hire yourself and start calling the shots.


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1. Negotiate Remote Work With Your Boss

Tim Denning is one of the top writers on Medium.com, and he’s started consistently earning $10,000 (even as high as $25,000) each month on the platform.

That’s not even the crazy part:

He did this while still working a full-time day job.

According to Denning, negotiating a weekly remote day was critical to start working on his side-business and developing his writing brand. Today, companies are more willing than ever to grant remote work. As COVID-19 is showing business across the world, having employees work remotely has a plethora of benefits. 

If you can help your boss see these benefits, you could start working remotely on a permanent basis.

When you pitch your boss, you have to think of it through their eyes – a strictly pragmatic, efficiency-focused approach that benefits the company. Frankly, your company has zero interest if you’d prefer to work from home. For them, it’s about what’s best for the company.

There’s a scene in Mad Men where Don Draper is lecturing his assistant Peggy Olson about her dissatisfaction at work. She wants more credit for her ideas.

“It’s your job! I give you money, you give me ideas!” Don yells at Peggy. 

“But you never say thank you!” Peggy bursts in anger. 

“That’s what the money is for!” Don counters. 

Your company doesn’t care what you prefer, they care about what you can do for them. It’s transactional, and companies will (almost) never give you what you want if it means they make less money.

During your pitch to work remotely, you must keep this in mind. Filter everything you say through it. Ask yourself questions like: 

  • How will this benefit the company? 
  • Why would they want me to work remotely? 
  • What’s in it for them?

Back when I worked in corporate America, I hired coaches and bought expensive online courses teaching me how to ask for a raise. Happily, I got most of the raises I asked for because I was able to make the company see why it’d benefit them.

It’s a tricky art form, but one that can dramatically change your life if you master it. Every time I asked for a raise, I spent at least two to three months beforehand making all my working statistics and metrics look pristine, so they could see how much more work I could do for them in the future.

If you want to convince your boss of anything, you must compile a rock-solid set of data, provable numbers, about why working 100 percent remotely would help the company. You must show them you’re far more efficient and productive at home. 

Now you need to prove it to them.

If your boss still isn’t open to the idea of you working 100 percent remotely, there’s another path to take.

2. Become an Entrepreneur and Make Money for Yourself

I could write a whole book – many books – on how to do this, and there are many excellent books already written on this topic. I’ll keep this simple. 

If you’re dead-set on working from home but your company won’t allow it, your only other option is probably to work for yourself and make money as an entrepreneur or freelancer.

Fortunately, it’s never been easier to make six-figures as an entrepreneur. If you can create a digital asset – an online course, coaching package, eBook, or a mastermind group or community – you can find your audience, sell your stuff, and make a fortune. 

Again, there’s a lot I can say here, but I’ll be brief. I’ve made most of my income through teaching other people what I know; mainly, through self-improvement. 

For me, it was easy to share what I was learning. I spent years in counseling and 12-step addiction programs, and it was easy to simply teach others the same lessons I was learning myself. I didn’t have to research it, I already knew all the content. It was what I thought about every day anyway. 

Ask yourself – what do you already know that you can help people with? What topics do you already know better than most people?

That’s your field. I promise you, there’s an audience who wants to learn from you.

For me, it was only a matter of learning how to package my knowledge in a way where people wanted to buy it. Essentially, I wrote content, got readers, told the readers about my products, and they bought it. 

Now, I make hundreds, sometimes thousands of dollars a day through my work – no boss, no commute, and I can take off all the time I want to spend time with my wife and newborn daughter.

If you’ve ever wanted to work from home for yourself, I’ll tell you right now: You don’t need millions of dollars of VC funding, a huge office space, or even any employees. I’ve been able to make tens of thousands of dollars doing all the work myself, and hiring cheap virtual assistants to handle all sorts of annoying, complicated tasks for me.

If this is the path you’re considering, but don’t quite know how to move forward, here are some great resources to keep in mind.

First, take this short five-question quiz to make sure entrepreneurship is right for you.

If you’re ready to move forward, here’s a list of all the tools you’ll need for your first year of entrepreneurship, and how much everything will cost.

Next, I’d recommend reading DotCom Secrets by Russel Brunson, which is the most important entrepreneurship book I’ve ever read and probably the best $10 I’ve ever spent in my entire life.

You can start working on this business even while you’re working your day job, just like Tim Denning and countless other entrepreneurs. That was my story, too – my wife and I were teaching English in South Korea and I managed to create a whole writing business working nights and weekends. By the end, I was making more money each day from my business than my teaching job!

In Conclusion

There are only two ways to work 100 percent remote in 2021:

Either convince your boss or learn how to make money on your own.

Each path has its own unique challenges, but in both instances, it’s never been easier to succeed.

Just a decade or two ago, both options were nearly impossible. It’s easy for veterans and professionals from older generations to claim, convincingly, that full-time remote work or entrepreneurship is impossible, a fool’s dream.

As Kyle Eschenroeder pointed out in his book The Pocket Guide to Action, “With the lowered cost of trying things, it means the value of listening to doubters is at an historic low. They don’t know what’s possible.

You’ll need lots of preparation and studying for each path. 

But it’s never been easier to succeed, whichever path you choose. If you’re like me, and the thought of commuting through traffic back to your cramped desk under the buzzing fluorescent lights at the office seems horrible to you…

Figure out your path, and spend time figuring out how to pitch your boss, or start out on your own. In this COVID-19 world, anything is possible.

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