Working from Home is Not for the Faint of Heart

When I tell people what I do, and that I work from home, far too often I hear, “I wish I worked from home and could do whatever I want…”

Well, today I’m here to set you straight.

Working from home demands a vast amount of dedication and self-discipline. It isn’t the cakewalk that you’ve made it out to be in your mind. When you work from home, you live where you work. How many of you would like to live at your desk or in your office (literally, not figuratively)?

Aside: I wrote moste of this while in the thick of freelancing and as a form of therapeutic recreation. It really helped me put a handle on how I was working and helped me take control of my life in a way that has had dramatically positive effect for myself and those around me. Here’s hoping it helps you, too.

Work Habits

On many occasions, friends and family have quipped about my habits of working in my PJs or sleeping in til almost noon. What they don’t realize is that it’s usually because I worked until 4am the night before and likely resumed working immediately after waking.

But, there’s no commute.

And therefore, nothing stopping me from being at the office at any hour of the day.

At least you can set your own hours!

True, and I’m very grateful for that when I need to cut out for an hour or a full day for various errands. Most often, though, it just means I’m working all hours of the day every day of the week. Once again, there is nothing to stop me.

But you can work anywhere! You could take a vacation any time!

Except, if I’m on vacation it means I’m not working, which means there is no active income entering our bank account. To counteract that, the simple solution is to work on the way to/from or during the vacation. Does that sound like a vacation to you?

Working from home sounds pretty awful, why do you do it?

Because I can set my own hours, work in my PJs, sleep til noon, work from anywhere AND there’s no commute. Plus, I pretty much get to do whatever I want. Haven’t you been reading the headings?

If I can be serious for a moment, working from home obviously has both benefits and detriments. Setting your own hours is only wise if you have the discipline to stop working and the ability to find value in resting and leisure activities. If you miss that, you miss everything.

(Pro-tip: you might want to read that last bit again.)

It took me four and a half years to realize that taking a break was not only relaxing, but paramount to a successful, healthy work life.

Discipline for the Uninhibited

If you’re like me, discipline is a word that makes you a bit uneasy. It means structure, routines, order, strictness, boring stagnant misery. Well, that’s how I used to feel anyway. Discipline is actually an integral part of complete, unrestricted freedom. No, really… just check out some of these examples.

Finding Freedom in Routines

As boring as it seems, a strong routine is actually the fastest way to a fun, relaxing lifestyle.  Creating a routine for yourself is one of the most important steps you can take towards freedom. Sure it’s foolish to try to schedule “fun” into a weekly calendar, but it’s more foolish to believe you’ll have time for fun if you don’t schedule a definitive end time to your work.

Here’s a brief example of my typical daily routine:

  • Awake
  • Breakfast
  • Shower
  • Personal Reading
  • Field Emails (1hr or less)
  • Get stuff done
  • Lunch
  • Field Emails (round 2, 1hr or less)
  • Get stuff done
  • Quit work, switch to personal projects/relaxation
  • Dinner
  • Personal work/relaxation
  • Bed

Respecting Your Time (Avoid Time Sink)

The biggest destructive force to a good schedule and routine is time sink.

The quality of your free time and your work are intimately connected. If you guard your free time and keep it sacred, totally devoid of any work, you’ll find that you will be more productive and less distracted while you work. Similarly, if you keep your work time entirely focused and free of interruptions you’ll find that you can work fewer hours and commit more time to hobbies and rest.

If you don’t respect the boundaries between work and leisure you’ll quickly find yourself discontent with the work you complete and unsatisfied by the quality of your down-time.

Take it from a guy who knows first-hand: when you refuse to rest you will actively seek, and feel justified in, taking distraction-filled breaks throughout the day. Later, when you feel compelled to rest you won’t be able to because you’ll have this nagging feeling that you didn’t get enough done and you need to accomplish just one more thing. Which leads me to my next point…

Manage Your Expectations (The reason you’re dissatisfied)

The leading cause of unhappiness isn’t poor circumstances or unfortunate events, it’s a mismanagement of expectations.

Consider all the times you’ve felt unfulfilled in your work, or like you had an overwhelming number of items left on your to-do list at the end of the day. Also consider all the times the new (phone|computer|movie|whatever) left you wanting. Is it because your job is overwhelming? Is it because those products/events were overhyped or under-delivered? Or, is it because you set an unrealistic expectation of how much you could do in a day, how long a project would take, or how incredible the shiny new thing truthfully is?

Leading a satisfied and fulfilled life is deeply rooted in managing your expectations properly. When you set realistic expectations for yourself, and others, you’ll soon find that your job is better than you realize, there will always be more days to get work done, and that how you’re living today – right now – is vastly more important than how much better your life can be in some unspecific time in the future.

Do the hokey pokey and turn yourself around…

That’s what it’s all about, folks. Discipline, dedication and healthy expectations. If you have those three things, you can change the world. Or, at the very least, you can work from home in your pajamas and not go horribly wrong.

Dropbox is the Best

Continuing in the vein of apps that have “drop” in their name, I give you: Dropbox. (Seriously, you haven’t heard of this already?)

Dropbox is a super-slick service that keeps all of your files synced across whatever computers you use, as well as making them accessible via their website, and iPhone app…so long as they’re in the Dropbox folder. Already impressed? Thought so. But wait, there’s still more!

Completely Free (or crazy-inexpensive)

No need to bury the lead on this one, Dropbox costs $0 forever. If you feel extremely limited by your paltry 2GB of online storage (and who wouldn’t, am I right?) you have plenty of options to upgrade your account and increase your capacity. Wait, scratch that, two options. Really though, aren’t you sick of choices? Paid accounts are $10/mo for 50GB or $20/mo for 100GB. Alternatively, you can sell-out your friends at 250mb a piece to get a maximum of 5GB 10GB of free storage. It’s a pretty swank deal.

Automatic Backups and Versioning

Never worry about overwriting or deleting a file again. Dropbox has an excellent memory and remembers every single file you’ve ever introduced, and at every single stage of that file’s life (especially its awkward teen years). Granted, for free accounts the history only goes back 30 days, but if you haven’t noticed a file missing after that long then you apparently weren’t very close.

Public Folder

Need to shoot someone a really big file? Just drop it in the public folder of your Dropbox (Oh, I just got the name. Clever!) and you’re good to go. Share it with as many people as you like, or just one. They’ve even taken the hard parts out of it and given you a contextual menu to grab the public link. Once it’s in place, all you need to do is Right Click > Dropbox > Copy Public Link. The link to the file is placed on your clipboard and ready for sharing with whomever you deem fit.

Shared Folders

Speaking of sharing, are you collaborating with friends? Dropbox has you covered. I mean, if they also have a Dropbox account, that is. Just share the folder with however many users you please and they’ll have full access to whatever files you add, and vise versa. Afraid of them deleting a file or overwriting hours of meticulous work? Don’t be. The automagical backup and versioning mechanism has you covered (you read about that part, right?).

Have a falling out? No problem, just un-share the folder. Dropbox even gives you an option of revoking access to all the files (you know, if it was really serious breakup).

The End.

If you’re still not convinced, send me five bucks and I’ll give you my honest opinion. If you are convinced, go get it, and tell them I sent you!*


*Note: You don’t actually have to tell them I sent you. They’ve probably never heard of me, though I am one of their biggest fans. As such, the links contained herein are not affiliate links, so you can trust I’m really giving you my honest opinion. Now, seriously, go download Dropbox already! And, when you’re done, come back and tell me what you think!

Droplr is for Winners

Droplr is a great tool that immediately made it to the top of my all-time favorites list. I’ve struggled for years to find a means to quickly share previews (i.e. screen grabs) of a project with other collaborators, co-workers, clients and friends. Droplr fits the bill perfectly, and does so much more!

Check out these crazy-awesome features it boasts (pulled straight from their site):

File Sharing

Droplr is the fastest way to share files from your Mac on the internet. Period.

Image Sharing (Screenshots!)

Whether you want to link to an image or embed one somewhere, Droplr makes sharing images on the web easy. Grab a screenshot, put it on droplr, share the link with whoever needs to see it.

Notes & Code

Need to share a text note? Or how about a code snippet? They’ll even syntax highlight it for you.

Keyboard support

Don’t like the mouse/trackpad & dragging and dropping? Droplr has full keyboard shortcut support.

Twitter integration.

They love Twitter. And if you do too, you know it’s one of the best ways to share.


Droplr is completely free to use with ad-supported content. Don’t worry, they’re really pretty ads. Promise.

My Favorite Part…

My personal favorite part of the app is the built-in shortcuts. It’s no secret that I love shortcuts, so it should be no surprise that this feature would appeal to me so much. But, dang, these guys got it right. If I want to share a section of my screen, I only have to press Shift+Alt+4 (which is methodically similar to Apple’s own screen capture shortcut, Shift+Cmd+4) and draw a selection. As soon as I release the mouse, blammo, the screenshot is pushed to Droplr’s server and a shortlink is copied to my clipboard, ready to paste wherever I’d like.

Equally good is Droplr’s ability to share files, notes, code snippets and more.

It’s awesome, light-weight, unobtrusive, and completely free. If you’ve made it this far into the article and haven’t already installed it, what’s wrong with you? Seriously, download it already!

Why I Use Twitter

Not everyone likes twitter, but I do. I love it.

Twitter is an often misunderstood – and therefore an often disliked and under-appreciated – web service. I think the greatest contributing factor to Twitter’s perceived short-comings is that people have pigeonholed it into fulfilling a specific task or view it as a one-way medium, shadowed by the misleading guise of Facebook.

It’s 2012, why is this relevant?

This post was originally drafted in 2010, but I’m still regularly asked, “why do you use twitter?” by people I see in real life. So, if you’re one of those persons, I wrote this for you.

Isn’t Twitter Just Facebook Updates?

In a sense, yes. Except, Twitter actually predates Facebook’s status updates and news feed by several years. Plus, every major feature added to the Facebook’s news feed since it’s release was inspired by, or lifted directly from, Twitter. Fact.

But, regardless of the similarities in their feature set, Twitter and Facebook serve two entirely different purposes in my life, and each one serves it’s purpose better.

Twitter Makes a Great News Source

Every single one of the most important breaking stories from the last year (the past several years now) was first reported via twitter. Oftentimes Twitter broke the news hours before any major media outlet was ready to report and, in many cases, was even cited as a source by the other media outlet.

Content is curated specifically to my interests

Unlike Facebook, where the news I’m seeing is a random assortment of what people are doing, thinking, liking, installing, viewing, etc. my Twitter stream is a highly curated list filled with topics that fuel my creativity and quench my thirst for knowledge. Of course, there are still the rogue tweets about what sandwich someone is eating and the occasional mundane update, but these are certainly the exception and not the standard in my feed.

It’s easy to track specific topics and events on Twitter

This goes hand in hand with my previous two points. It’s incredibly easy to follow all conversations surrounding a specific topic, event or news story given the way twitter is optimized for searching and real-time updates. The standardized adoption of hashtags (e.g. #this) over the past two years has made this task even easier.

Twitter helps me stay current in my field

I follow a number of well-known and established web developers, designers and photographers. I also follow a number of influential readers who share lots of great articles, Thanks to their proclivity for tweeting cool/useful resources I’m able to stay ahead of the curve on many trends and techniques.

Twitter helps me keep up with friends

Alright, so this is an area where I will concede to say Facebook is doing things better, but only if you’re using it right. If your friend list is a simply mass of random people, and you haven’t taken any time to group them in any way that is meaningful to you, you’re back to a useless mess of content.

With Twitter I’m able to catch updates from friends that would never make it to their blog (if they even have a blog) and catch some unique/temporal news that might never make it to Facebook either (I have to be honest, even if it does make it to Facebook, I won’t be there to read it).

Twitter is Focused*

One of my favorite aspects of Twitter is how focused it forces me (and others) to be in my word choice. Updates must be pared down and revised for maximum impact, and tweet volume must be considered as well so as to not dilute the likelihood that someone will actually read my tweets. As many have pointed out already, limiting oneself to 140 characters is a great way to get to the core of a message and determine what’s really important.

*Yes, you can always argue that people are sharing junk via twitter, but you can also make that argument across most other mediums as well… Facebook, texting, phone conversations, chit-chat during lunch. My point here is that twitter, moreso than other mediums, forces the user to focus on what they’re saying.

Twitter is a great promotion tool

Lastly, from a strictly business point of view, I’ve found that Twitter is absolutely indispensable for finding exciting work/hungry employees, or promoting a new business, product or service. As a freelancer I was able to secure a number of projects via Twitter, as an employer I was able to find a number of reliable workers. And, as a producer, I’m able to connect directly with users interested in my products and services.

Enough from me, though. Why do you use twitter? Or, perhaps, why don’t you?