The Home Office

A Survival Guide to Working From Home

Published in

Startup Lessons Learned

7 min readJan 22, 2014

Whether you're a stubble-bearded/legged, freelance creative or a Ponsi scheme hack, Working From Home (WFH) is a big part of the job. At first the concept might seem romantic – you've got time to make your own pour-over coffee, your loyal dog is curled around your feet as you sit at your desk, and best of all, there's no need to keep your fingers poised over alt-tab as you sneakily update your facebook status at 10am on a Monday.

As an experienced work-at-homer though, I can attest that those romantic notions shrivel and die in a pit of unproductive despair as social media claws at your business dreams and 9 to 5 slowly becomes noon to midnight. WFH is about survival.

Set the Alarm

It might not seem like it, but routine is especially helpful to the creative (and/or productive) process. I recently met a very successful author who is currently ¾ of the way through his latest novel. His hours are INSANE, but they are routine (2am to 10am) and they meet his needs perfectly. He has tamed his creative process like a boss – which makes it his, rather than the property of his muse.

Personally I function better on the 9 to 5. I'm focused and sharp when I need to be and it ensures that I'm socially available when the bulk of my friends are. I also take weekends like a healthy individual should – no-one in their right mind would willingly accept employment that was more than 5 days a week and on-call 365 days a year.

Learning to work when it's work-time and to play when it's play-time helps with the most difficult part of WFH, which is “discipline”.

Put on a Tie

It's casual Friday EVERY DAY at home, homie! Doubleyew-Eff-AYCH!

No, it's not. You're at your home work-station to work. Nothing in a work-week feels better than churning out a productive day and feeling like a pro at the end. You CAN'T feel like a pro if you're in your underwear – it's not possible.

Get up, take a shower, get dressed in a fashion suitable to your career and be the image of a useful employee. If you want to wear pajamas all day, go be homeless.

Commute

WTF, if you WFH, you don't have to commute?! That's 50% of the reason we do this, right?!

A percentage of my work is out-of-home and typically that means a 1.5 hour commute through San Francisco rush-hour traffic. Rough.

However, that 1.5 hour block has taught me something. I'm much more efficient (and creative, and energetic, and engaged) at my job if there's a transition period between home and work. I love that 1.5 hours, I can listen to NPR, chat with my ride-share buddies and even read a book (well I could if there were reasonable public transportation along my route...). It takes a lot of the pressure out of the day and allows me some personal time that I would otherwise only get on weekends.

I'm not suggesting that you drive your car around the block for an hour before work, but do give yourself some time between getting dressed and starting work. I like to sit down with a cup of coffee and read a book. This is your time, after which you belong to your job.

Climb the Ladder

One of the grandest discoveries of WFH is that you are, to some measure, self-employed. You are the boss. The discovery that quickly follows is that the structure of regular employment really did a lot for you and suddenly you can't tell which direction is up with your career.

You not only have your own workload to deal with, you also have to do your own taxes, come up with ideas and implement them all on your own...you even have to manage marketing campaigns (we all have to advertise if we're self-employed). If you're constantly clambering over tasks that distract from your main workload it's hard to advance.

So dump it like a truck. If you don't have time or skills to manage these outlying tasks find someone who does and dump it all over them (there are plenty of other WFHers out there that specialize in the stuff you suck at). If you're lucky, you might find a friend or intern who can do it for free/cheap. Expect that you'll end up paying though, and that it’s just part of the process. Start by outsourcing your taxes (ain't nobody got time for that). If you can afford to feed yourself, there’s a good chance you can afford a CPA to do your year-end taxes. With a schedule cleared of decentralized tasks you can start reaching for the next level with your work.

Be Your Own Worst Boss Ever

“Now” cried Max, “let the wild rumpus start!”
— Where the Wild Things Are

Wrong, child in your cute little pajamas, you need to start conducting yourself as though you have a conniving, grown-up, overbearing, metrics-oriented, drill sergeant of a boss. They are monitoring your internet traffic! They are watching over your shoulder! They are telling you to tie your laces and straighten that damn tie!

It's wonderful to not have to report to anyone and to have the freedom to troll the internet for hours taking coffee breaks whenever you want and eating all the office doughnuts in one sitting. But no-one is paying you to be a slouch – you're paying yourself to be productive, so be productive. Wasted hours do not a rent-payment make.

Cut yourself just a little slack though, it's awfully hard to stay laser focused for an 8 hour block without anyone around you setting an example. Try working in 90 minute blocks. Set an alarm and don't allow yourself to do anything outside of your task for that period. When the alarm goes off you can take your bathroom break, have a glass of water and assess where you're at in your day.

Visit the Water Fountain

It is miserably lonely at home alone. It is so nothing at all like the MacCaulay Culkin movie promised it would be...

With no one to talk to you may start to feel like your closest point of social contact is updating your facebook status or neurotically checking your inbox every 8 minutes. Obviously, doing so would make you a useless self-employee, but don't feel so bad, we're social creatures and there are healthier ways to get our social tummies rubbed. On that gap between a scheduled 90 minute productivity block give your grandmother a call, she'd love to hear from you.

Be human about your social needs. “Likes” don't stimulate like real conversation does.

Take Lunch

You have to eat.

It undoubtedly seems like no-matter what you do you're swamped with tasks and there's just no time for a lunch break. You're lucky to eat at your desk, and yet regular employees (those fools with their over-bearing bosses) always set time aside just to eat – 5 days a week in fact.

Breaking up your day by taking a lunch break (out of the house if you can afford it) resets your drive and motivation to get work done. You come back refreshed and full of healthy calories that your brain and body can metabolize into dollar bills. If you leave your brain on all day it burns out. Consider this your screen-saver moment.

Go Home

I live in San Francisco so I can barely afford rent on the best of months. This translates to renting a one-bedroom with my wife and being very very organized so as not to have our lives constantly spilling out of the limited closet space. We both WFH, and we both sleep in this home, so finding a dedicated office space requires some creativity. This is our 3rd permutation of the WFH one-bedroom solution and this time we nailed it. Our living room has a super comfy futon and so is the official bedroom now, and more importantly, the “bedroom” is completely office space.

Everything office lives in the office and at the end of the day we close the door on all of it. We call this “going home”. One of the biggest challenges with being self-employed (and WFH) is learning how to turn the work off at the end of the day. After a super productive day I love nothing more than “commuting” home from the office to my cute apartment with plush furniture, no computer screens and a cold beer waiting for me in the fridge.

The work day is over – go live the life you've been paying for all day.