Freelancing on the Road: Can it be Done?
I’ve been weighing attending an important conference later this year, a trip which will require that I leave my home office, get in my car, go to the airport and catch a flight. I don’t get out all that much, but when I do I’m likely to travel clear across the country, being away from home for several days to a week at the most.
Hitting The Road

Heading out of town for a conference can be very refreshing and professionally rewarding. Preparing well in advance can ease the stress while you're freelancing on the road.
Because I only make these kinds of trips 2-3 times each year, I look forward to getting away and doing something different. I like my home office, love my family, yet I usually come back from these types of conferences refreshed and bursting with creative flair. Importantly, I can thrive on those productive fumes for the next few months.
What I dread, however, is trying to maintain my other work while I skip town. Sure, planning in advance knocks out some projects, while others must still be managed while I’m gone. I’m a sole proprietor which means I have to do everything myself, but if I plan well in advance I can minimize my work while away from home so that I can enjoy the conference.
Getting Prepared Now
How do you handle road trips? I’ve come up with five tried and true methods to help me work better, faster and smarter while I’m away, including doing the following as I prepare to leave or while I’m on the road:
Write Ahead – My writing schedule requires that I write daily for some clients which means that I have to plan well in advance to have those jobs out of the way before I leave. On occasion, I’ll write on Saturday mornings which is generally a no-no for someone who values his work/family time separation. If my wife is on board with this plan, then I’m free to write, but if a family responsibility comes up I’ll have to double up my writing in the evening or in the early hours of the morning. I’ve written 7-10 days in advance before, successfully scheduling my blog posts to appear at designated times.
Bring the Laptop – Obviously, if you own a laptop you bring it with you wherever you go. The day before I leave I make sure that all of my files are backed up to my external drive (or off-site with Carbonite), complete my virus scanning, and place a battery back up and extension cord in my carrying case. I never check my laptop – I claim it as my carry on bag – and I don’t let it out of my site. Ever.
Carry a DVR – I own a tiny Olympus digital voice recorder (DVR) which I bring with me to conferences. With fresh batteries included and a back up set on hand just in case, my little DVR comes in handy when I’m listening to a long speech or needing to confirm a quote. Still, I routinely jot down notes on paper and compare everything in my hotel room or in the conference’s press room.
Plan for Emergencies – One trip I took two years ago nearly turned into a nightmare when my email connection fizzled in my hotel room. I had to pack up all of my stuff, head down to the hotel lobby and purchase wi-fi access for the evening. Even then, the connection wasn’t that fast which meant that surfacing the ‘net took longer than expected. I finally finished up my work around 3 a.m., which meant I had just four hours of sleep before the next big meeting at 8 a.m. Next time, I’ll stay in the press room to finish my work, where the internet connection is fast and reliable.
Email, Cell Phone, Contact Information – No, I don’t own a Blackberry nor do I own an iPhone. What’s wrong with me? Well, I have a family to support – luxuries can wait. Before I head out, I answer all of my email messages, but I don’t indicate that I’m away from the office. I do recharge my cell phone and I bring my recharging cord with me. I also update all of my phone contact information and, just in case I lose the phone, I jot down key numbers and keep them in my wallet.
Less Stress
If I keep these five things in mind, then I’m less stressed while away from home and I actually enjoy the conference. I may still have to handle a few client tasks while on the road, but I keep these to a minimum. My time away is usually on my dime which means that I don’t have the luxury of going on the road knowing my work is covered back in the office or my trip paid by a client.
Photo Credit: Ronald Schuster
See Also — Should You Schedule Your Blog Posts?

By LD Jackson, September 29, 2009 @ 8:55 pm
I can’t imagine doing this for a living, Matt. I get stressed enough as it is. It would be even worse if my income depended on my writing.
.-= LD Jackson´s last blog ..President Obama’s Afghanistan =-.
By Matthew C. Keegan, September 30, 2009 @ 4:43 am
Larry, sometimes it gets crazy! Since writing this article, I decided not to attend this particular conference which is being held in Las Vegas in early November. I have too many irons in the fire, I don’t want to absorb the expense, and I’d rather finish the year in a calm mood.
You’re right — writing can be stressing especially when deadlines loom. But, I love what I do!
By LD Jackson, September 30, 2009 @ 6:32 am
@Matthew C. Keegan
As crazy as it sounds, I love doing this too. Even though I do not do it for a living, it is still enjoyable to put my thoughts down on “paper”, as it were.
.-= LD Jackson´s last blog ..Tsunami in the Samoas =-.
By Matthew C. Keegan, September 30, 2009 @ 7:27 am
@LD Jackson
Agreed! Whether done full time or as a sideline hobby, blogging can be tremendously enjoyable. Ten years ago I would never had considered as much, but these days writing online is where its at.
By Mechanic Mark, September 30, 2009 @ 6:36 pm
Las Vegas sounds exciting(never been there). But you seem to have good reasons for passing on the trip. I like you am a 1 man band. Can’t wait till the day I can add a trusted employee that I can leave things with.
.-= Mechanic Mark´s last blog ..Automotive Heating Problems =-.
By Matthew C. Keegan, September 30, 2009 @ 7:43 pm
It is the SEMA show, Mark. Yes, I would love to go but money is an issue at the moment. If I can travel on someone’s dime, then I’ll do it. But, at this time it won’t be a free ride. I’ve passed through Las Vegas, but haven’t gone to the city yet.
By john, September 30, 2009 @ 9:58 pm
I’ve been following your blogs for a while now and this is honestly one of the best I’ve read. Its a simple and organised blog. Thank you for sharing this with us.
By Matthew C. Keegan, October 1, 2009 @ 7:58 am
Thanks, John. I like to speak plainly to people without getting too complicated on what steps they need to take to improve their work.
I’ll leave the fancy prose to the booksmiths and editorial set.
By Sydney, October 2, 2009 @ 9:58 am
I always prefer working in the comfort of my home…maybe its because I don’t have a over load of work…But thanks for your tips..will surely follow it when necessary.
By Eric H. Doss, October 2, 2009 @ 3:01 pm
Matthew,
Maybe you should start a series based on reader’s worst “Disaster While Freelancing From The Road” stories. I have had some hairy times with internet connections, dead hard drives, forgotten pieces of kit, etc.
Hate to hear that you’re not heading to the conference in LV, I’ve found that if you can’t justify the trip for business, you should just chalk it up to mental health and go, finances allowing… Getting out of the office/house is an essential part of making the freelance/work from home thing work.
Eric
.-= Eric H. Doss´s last blog ..Now With DoFollow Comments =-.
By Matthew C. Keegan, October 2, 2009 @ 3:06 pm
Thank you for your comment, Erich.
I’ll consider your suggestion for a disaster series, but fortunately I haven’t had that…yet.
I would love to get away, but it is the financial thing that is stopping me at the moment. This year has been the most challenging I’ve had since I started working for myself in 2002. Work is coming in, but several clients have cut back too. Thus, I need to conserve the cash and find some other mental health releases along the way.