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Teleworking Isn’t As Easy As It Seems (How in the world do you work from anywhere?)

After a decade of working for other people, I’ve started my own business. I’m pretty excited. I’m using my skills, knowledge, abilities, and connections, and I have no one to answer to but myself. If I succeed, it’s because I worked hard. If I fail, it’s because I didn’t get the formula right. The best part is that I can work from home, I can work from my coffee shop. I can work in Virginia, in DC, at my mother’s kitchen table in New York.

Or can I?

The tricky part of working from anywhere is knowing how to do it. Anyone who works from home, whether you’re out of your home office all the time or you telework a few days a week, will recognize the challenges I’m working with.

Here are some observations from my first five months as an independent contractor and advisor with a home office. My biggest hurdles have been dealing with location, tools, surroundings, schedule. A lot of my issues I believe are just growing pains, and I’ll figure out what works best for me over the next few months.

  • Finding the right location
    Right now I’m sitting on the couch in my living room and writing, but I have both a desk in my “home office” and dining table that would probably make a more comfortable writing location. I could also leave my home and find a place to work, but will I have WiFi where I end up? Library? Coffee shop? What about the calls I have to make? Do I really want other people to hear my business conversations? Do they want to hear my business conversations? That’s kind of rude, isn’t it? And the panic that comes after the dreaded dropped call! “I’ll be in the car for an hour, let’s talk then.” Greeeeeeat idea, yeah.
  • Having the right tools
    I have my computer, some file folders, my new awesome custom notepads to give to my clients (that makes me legit, right?), and my printer. What else do I need? Internet. Cell phone. Cell phone head set? Accounting software or just an Excel spreadsheet? What if I have a face-to-face meeting? Where do I go? Meeting space is a tool. Might be a bit awkward to have a business client in my dining room. I need some promotional flyers. I need more business software. Argh! My brain is a tool. Is it in proper working order?
  • Dealing with surroundings & distractions
    I can’t get over the pile of laundry I forgot to fold last night. I know its there waiting for me in the next room. But I have some e-mails that I must return now, and I have to write up a proposal for a potential client before the end of the day. I’ve never wanted to fold laundry so badly!
    I have a pet who has gotten used to me being home during the day. She’s so excited to play with me, and she’s become so much more obedient recently…well…OK! Five minutes! We’ll hop around for five minutes and then I promise I’ll go back to work. (Literally, hop. She’s a rabbit.)
  • Creating the right schedule
    If you have the flexibility to work at any time of the day, chances are you will. I’m having a hard time knowing both when to STOP working and save some tasks for the next day, and when to stop doing whatever it is that is not proper work and start to be productive. I have no problem writing at 9 am or 9 pm. If my creative juices are flowing, I don’t want that to stop. I try to schedule several weekly informal coffee meetings with colleagues to make sure I keep on track. (“I’m meeting Chris at 10 am, so I should be done with XX by 9:30 am and then pick up with YY again at 12 pm.”) Also, I put EVERYTHING into my iCal now. I really didn’t do that before. Just tried to remember everything I had to do. Not so good.
    To add two other, tiny, little wrenches into the scheduling issue, I also have a little craft business and participate in a crafter group. I have shows and events usually two to three times a month. In addition to that, I help out at my friend’s store a few times a week. I’ve been there since before I went out on my own. They appreciate the extra hands and I like putting something else down on my calendar! I also use their location as another place to work, sometimes.

I’ll admit it, I’m a newbie when it comes to this work from anywhere business. I’m still getting my feet wet, but I understand these broad challenges now, and I’m learning to deal with them in a way that works for me.

What advice do you have for those who work from home? Have you done it? What worked? What didn’t?

(BONUS: Working from home allowed me to watch Discovery this morning from my roof deck. Here’s my full photo set.)

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Corey McCarren

Great photo’s! I manage by having separate spaces for everything. I don’t like eating at my desk. Why? Because my desk isn’t for eating, my desk is for working. The break room and benches outside are for eating, and I know when I’m there, I don’t have to think about work. If I were working from home often, I would carve out a spot that’s just for work, so when I’m there, I know it’s not appropriate to worry about the dishes I forgot to clean last night. At college, I went to the library for homework just because it was a space I could say “okay, this is for work.”

Jack Hernandez

Not everyone can work from home, and I feel that the first thing a telecommuter has to do is realistically evaluate his/her work from home capabilities. Logistically, it sounds perfect, but after considering the distractions, personal resource usage, not having access to technology, and lack of real human to human interaction, you may have second thoughts. Of course, what you do for a living is probably the most important factor.

As a graphic designer who also freelances, my home workstation is more capable than my kit at the office. But at home, I have too many distractions from my freelance projects that beg for attention to access to my favorite computer game that invariably extends my 15-minute break to a deathmatch session. I also have internal clients at my day job, and as much as I use email already, not being able to interact personally with my coworkers troubles me professionally.


A lot of it to me is your last point on schedule and state of mind.

Working from home you really have to find your own personal flow – could be working less hours or more hours (odd hours or normal). But key is finding what works for you

Additionally some of it is personality based so you have to know your strengths and weaknesses. Personally I know there is a limit for me – if I work from home more than 3 weeks in a row, I get less energized so I need to make sure I get to home base at least once a month

Debbie Hopkins

I work from home and fortunately haven’t had a problem with being sidelined by distractions, laundry, TV, etc. I set basic work hours for myself, but they are a bit flexible to accommodate for other things. No more fighting the crowds at the grocery store after work – I just go at 10am when nobody is there, and work a few minutes later that evening. If there’s a class at the gym I want to take, I’ll start work early and take my lunch break during the class time.

I don’t think telework is a good fit for everyone, but I’m much more productive at home, without an office full of people to get distracted by talking to. 🙂


I’ve worked from home once in a rare while and while I am on the road for a conference or other business related trip. At home I do not have a problem, as I live alone and it is pretty distraction free.

The main issue I find working from home or on the road is usually the connection speed I have. Some applications that I have are too slow to use through a VPN, even with 3 Mbps broadband. I have to leave the desktop in my office turned on so that I can remotely login to the machine through the VPN, which does make it better – as long as I remember to do that and that a power outage or something else doesn’t turn the machine off.

Another issue is that some of the technical support I do is almost impossible to do remotely and I need to be at the particular computer to troubleshoot it. Thankfully that is a pretty rare case.

Dorothy Ramienski Amatucci

One word: compartmentalize. When I work from home, I make sure to keep my mind on my work. Luckily, I have a home office, so I think this makes it easier, but nonetheless, I mentally prepare myself to devote a set amount of time to work … and only work. I say, “Ok, I will work from 8a – 12p … and then take an hour break for lunch”. I don’t know if this is how others do it, but I think about working from home as though I am working in an office.