How To (Actually) Work From Home: Advice From Someone In The Trenches

In one of my all-time favorite books, Letters From A Stoic, Seneca, pens this:

You mustn't let this worry you as if you were having to make a great decision. There's nothing so very great about living - all your slaves and all the animals do it. What is, however, a great thing is to die in a manner which is honorable, enlightened and courageous. 

Think about how long you've been doing the same as them - food, sleep, sex, the never-ending cycle. 

And each time my eyeballs go from left to right on those four sentences, my mind races off - like a horse who's released itself from its own reigns.

After a while, my mind fatigues. That's when I drip back from the clouds and confront the humbling question that the philosopher is really wanting us to chew on:

"What am I going to do with this life?"

Sure, it comes off as cinematic. But contrary to what you see in a lot of the self-help and entrepreneurial media outlets these days, I'm suggesting this question is only for those who build seven-figure start ups, move across the globe to start orphanages, or invent the next app that fundamentally changes how we communicate.

This question is also equally valid to the people who make a modest living, live in the suburbs, and enjoy using the apps that get invented. 

The people we read about in magazines or get interviewed on podcasts account for maybe for 1% of the population - and a lot of the time, they're doing incredible work.

While they provide great stories, the one-percenters dish out top-down advice. Meaning, they've peaked their own summit and now they are turning back and sharing what worked and what didn't.

To be sure, this is valuable - and I'm by no means degrading the approach.

But for someone like me who is currently on the climb, it's hard for me to relate to someone who has several decades of experience on me or has achieved a level of influence that my mind can't even wrap around.

So, I've been wrestling with "what should I do with my life?"

After bouncing around from many non-related attempts - including bartending, tech sales, real estate, personal training and working in a seafood market filleting fish- I discovered that I like to write and I happen to land on this thing called freelancing.

However, I soon realized I would have figure out how to be the best freelancer I could be. And this quest as I've come to learn, is one that I'm not trekking alone.

Today, about 53 million people are doing freelance work. By 2020, this group will account for 50% of the American labor force.

One of the reasons why this outlet is booming is that it offers two things that we are valuing more than ever: autonomy and it highlights the quality of work instead of the quantity of hours.

The right to self-govern and the flexibility to do your best work in the time it requires instead of waiting for the clock to strike 5 to punch out is what a freelancer thrives on.

Moreover, when freelancers are given parameters to operate, but have the opportunity to create and internalize their own goals, better work is produced. 

More evidence is showing that the greatest motivation and satisfaction comes from the goals we choose for ourselves. This sets the stage up for intrinsic motivation - the desire to do something for its own sake.

And employers are starting to notice the value in this cocktail of autonomy, quality over duration of work and intrinsic motivation.

One glaring example is Bellhops - a growing start up that has established itself with an autonomous workforce:

Bellhops hires City Managers from major colleges and universities throughout the country and then contracts directly with recruited students, or "Bellhops," to execute small residential moving jobs in their city. All the Bellhops have direct access to a company-wide job board and can "grab" jobs either as the Captain or Wing-man. The Captain manages and coordinates the move with the customer and gets paid a higher wage.

Bellhops are able to execute moves year-round and have complete autonomy over their schedule, who they work with, and how much money they make.

According to co-founder, Cameron Doody, "People don't just want a job anymore; they want a fulfilling job," he says. "Fulfillment at work comes with the freedom to make decisions and own your position.  Employee empowerment breeds elevated customer service, because everyone treats their job like it's their own company."

So it's clear that whether you're a solo-freelancer or someone within an organization acting like an "intra-preneuer" that the qualities of the work have a similar ilk - autonomy, quality of work over duration of work and intrinsic motivation.

But what happens when you actually get this? What type of strategies and habits must be in place in order to thrive in this unconventional setting?

Over the last few years, I've written close to 300,000 words - most of them to fulfill my freelancing job and the rest of it aimed towards my personal stuff like the blog you're reading now.

And in the process I've had to learn how to take advantage of the very thing I wanted so badly - autonomy, focusing on the quality of work rather than working for a number of hours and being intrinsically motivated.

When I got the opportunity to write for, the door had opened up and the conditions were perfect. I had to be prolific if I wanted to be one of the best. 

What follows is a toolbox of strategies that I've crafted working remotely as a freelancer. These will help you become prolific and keep your sanity at the same time.

Writing is my thing. But it doesn't have to be your thing in order for this system to work. I've laid this out so a broad audience can use it - creatives, salesmen working from home, artists, mommy-bloggers, life coaches, painters, freelancers.

Whatever. You get the point.


Treat it like a job

You've finally landed the position or discovered what you want to pursue. And now you've got all this free time and nobody checking in on you.

Uh, oh.

This is where Netflix can dominate you.

But instead of thinking of having a wide-open day, treat your craft like you would a job. For example, if someone is a barista, they have work shifts right?

They come in, they do their work and then they clock out to head home.

You need to treat your freelancing work the same way. The advantage in your case however, is that you get to choose what you work on - contrary to the barista who must make soy lattes for 8 hours.

A good starting point is to identify when you do your best work.

When are you most on-point mentally? When are you sharp? When are you most creative?

This is different for everyone - so don't fall for the eye-rolling advice that you get from mainstream productivity blogs and podcasts which trumpet that working before the sun comes up is the best way for everyone.

It's usually just an ego-flex because they do it (and they're advice is grounded in a data-point of one).


Abide by the four hour rule

I wrote extensively on this here.

But, if you want the cliff notes version here it is: You have about 3-5 hours of deep work (averaging about four hours) in you each day. In other words, after that amount of work on your craft, quality tends to dip.

Also, this window is best executed in intervals. Research shows that 90 minutes sprint sessions are best followed by a short break. This approach of sprint-rest-sprint should equate to anywhere from 3-5 hours.

Now, don't warp this advice into thinking that you only need to work 3-5 hours per day. This time is dedicated to your art. The work. The craft.

I'll use myself as an example. My 3-5 hours is dedicated to writing. But, my days are usually 10-12 hours. I spend the rest of my time outside of my deep work sessions lifting weights, reading, researching, editing, pitching editors, and using social media.


Get dressed and shower (multiple times)

I've got no research to back this up. But, empirical data shows me that it can work.

In my early days of freelancing, I used to get up and go straight to the keyboard. My logic was that if I got to writing first thing in the morning, I could crank out a few hundred words with a clear mind.

But the only cranking I was doing were the thoughts in my head about how sloppy and groggy I felt. So I shifted my strategy to take a shower and get dressed like I was going to "the office."

This small shift did wonders. Now, when I engage in work mode, I fell like I can dominate. I look good and I feel good.

No longer am I  noticing my bed-head in the reflection of my screen and I'm not resisting the fact that my mouth taste disgusting. Instead, my brain has gotten a chance to wake up and I feel ready to do great work.

This strategy also works mid-day as well. I use it following my lifting sessions in the afternoon. However, it can also work as a mid-day reset. Ya know, the afternoon slump around 2 or 3 P.M.?

Hop in the shower and get re-dressed and it'll supercharge the rest of your day.


Don't turn into a hermit

High performance coach Brendan Burchard said this:

"To chase your dreams, you've got to get outside your house."

Well for freelancers and those doing work in a similar fashion, this presents a pickle. Most of the time we are chasing our dreams, but it happens to be that in order to do that we must be inside our homes (or coffee shop).

Meaning, we must be inside a lot to do our work. And sometimes, we go down the black hole and reveal our heads once in a while and wonder "What year is it?"

So, here is my rendition of that quote:

"To chase your dreams, don't become a hermit."

The simple strategy I use is to set an appointment to have some human interaction that isn't work related once a week. I usually set these days for Friday afternoon - it sets me up for a reward at the end of the week.

After I've pressed into my work for five days, this offers a pressure release valve for my mind. And, it puts me belly to belly with a human - instead of being glued to a screen.

This can be anything. For example, I'm going to meet up with my sister to workout today and hang out with my nephews afterwards.

In recent weeks, it's been meeting up with my brother for lunch with no agenda. But it always turns into several hours of rich conversation.

Ideas are currency to freelancers and creative people - and there is no better way to cultivate ideas than having conversations with other humans. 


Wrapping Up

"What should I do with my life?" is the question we opened with.

To answer that question it makes think of the Ford Motor company when they released the ford Model T in 1908. The people behind this movement weren't thinking, "what's next?"

They were immersed in the very thing they were involved with right then and there. 

"What's now?" is how they operated. 

And I think that's how we answer the big-hairy question of "What should I do with my life?"

For me, teaching people with my writing as freelancer is what's now for me. Similar to the humans back in 1908 pushing the automobile forward, I too, must not look to what is next when something right in front of me offers a credible answer to "What should I do with my life?"

Writing is what I'm doing with my life right now. If you happen to find yourself in a similar situation as a freelancer, you have the same opportunity.

The strategies you just learned will help you be prolific.

Press on. The world needs your work.