Scott Oldford Site

Tag: working on the road

  • Freelance Writers: How to Take Time Off (Yes, Really!)

    Freelance Writers: How to Take Time Off (Yes, Really!)

    No doubt about it, the freelance life has some perks.

    You can work on a deck with a glass of lemonade or even put together some prose at your local museum.

    Sometimes, you can set your hours and make time for a mid-morning yoga class or make a doctor’s appointment for the middle of the day.

    But despite these perks, it’s hard to really, truly get away as a freelancer. Sure, you can work from a hammock (full disclosure: I am typing this from a hammock on my back porch right now).

    But you’re still working.

    But getting away — not just from your typical surroundings, but also from your phone or email inbox — is possible.

    Here are a few tips for taking a real vacation — or as close to one as you feel comfortable taking.

    Pick your destination with unplugging in mind

    It’s hard to ignore a blinking message light on your phone.

    What does that little green flashing light mean? Does it mean your editor hates the piece you submitted? Is a new editor excited to work with you on a time-sensitive piece?

    It could mean anything, really, and it’s tempting to succumb to temptation and check your messages, even when trying to “disconnect.”

    The surefire way to avoid this notification anxiety? Go somewhere your phone doesn’t work.

    It’s not too hard to find a campground with no cell phone service, data connection, or Wi-Fi. Even just a weekend where you’re disconnected can go a long way towards unwinding.

    Of course, it might also make you a nervous wreck who drives 30 miles for a data connection twice a day just in case. Some people find it less stressful to “unplug” somewhere they can check in once a day or so for five minutes and turn their phone off the rest of the time.

    A “disconnected” vacation doesn’t have to mean being disconnected 100 percent of the time. Trial and error is the best way to figure out what works best for you.

    Communicate ahead of time

    If you don’t normally work on the weekends, going far out of cell phone reception for one weekend isn’t likely to be something that requires advance communication with clients.

    But if you’re disconnecting for a longer period of time, it’s important to communicate when you’re going to be unreachable. And this doesn’t mean just slapping up an auto-reply on your way out the door saying you’ll be gone for the next month.

    If you’re heading away from cell phone reception for more than an afternoon or so, look at the calendar to see which clients might need to get a hold of you during the period you’ll be away.

    Are you expecting to receive edits on a piece soon? Is it a client’s busy season where they frequently send you last-minute assignments? There’s definitely a bit of guesswork involved, but it’s important to consider what might happen while you’re away.

    A lot of this depends on how long you’ll be gone for. If you’ll be gone for an afternoon, you likely don’t need to do anything at all, since you can respond to your messages in the same evening.

    But if you’ll be gone for a month, you’ll have some serious work to do ahead of time.

    Tie up loose ends

    Before you leave town, let your clients know you’ll be mostly unreachable. Be sure to do this well ahead of time. Don’t just send an email blast to every editor you’ve ever met.

    If an assignment is due soon, try to turn it in early, letting the editor know when you’ll be unreachable and that you’ll be happy to address edits before you leave or after you return.

    Likewise, if you’re expecting edits on a piece soon, let the editor know a few weeks ahead of time so you can hopefully complete any necessary editing before (or after) the trip.

    Of course, from time to time, you’ll still have to spend some time working on the road. But using this system can definitely cut down on the amount of time spent working when you’d rather be relaxing.

    Dealing with a freelance disaster

    No matter how well you prepare, the occasional freelance disaster is inevitable. What do you do if this happens while you’re disconnected?

    If you’re completely disconnected, you likely won’t know about the disaster until you return to the land of Wi-Fi and cell phones. The thought of this makes some people’s skin crawl, but others find freedom in the idea.

    Whether or not being completely disconnected works for you is something every freelancer has to figure out for themselves.

    But if you’re checking in once a day or every few days, you might just check in one day to find trouble brewing.

    The extent of such a potential disaster largely depends on your line of work. If you work as a PR consultant and your big client has a major problem and needs spin control pronto, you’ll likely have to jump into work mode for a significant length of time.

    But if it’s just a client who needs a quick copy edit? That’s easy enough to refer to a trusted freelance colleague.

    In order to minimize stress if a disaster requires you to respond to while on vacation, be sure to have what you need with you on the road. Bringing any passwords you might need and important documents on a flash drive can make responding to the situation much easier. Also consider storing important documents on the cloud for any access anywhere.

    Another great option to consider is using the buddy system.

    Use the freelance buddy system

    Working in an office comes with a built-in backup system. If you’re out of town, you can set up a voicemail message and email auto-reply saying when you’ll be gone and asking people to contact another team member with urgent needs and concerns.

    Freelancers don’t typically have these built-in systems available. But that doesn’t mean you can’t create your own. Knowing other freelancers, especially those in your field and those who write for similar clients, is invaluable.

    Take some time to get to know other freelancers and consider working out an arrangement with those whose work you trust and respect.

    Leave their information as an “in case of work emergency” contact, and work out with them ahead of time what they will do if they are contacted on behalf of one of your clients.

    Of course, you need to trust this person and everyone needs to be clear on expectations.

    But it can be a great way to get a reprieve from your phone and email while leaving any work concerns in the hands of someone you trust.

    And, of course, you can return the favor when they go on vacation.

    What do you do to prepare for an unplugged vacation?

  • 5 Important Questions to Answer Before Freelance Writing Abroad

    5 Important Questions to Answer Before Freelance Writing Abroad

    The idea of life as a digital nomad is incredibly seductive.

    As we tap away on laptops in the comfort of our living rooms, more and more independent journalists, copywriters, bloggers and editors are thinking, “Why can’t I do this abroad?”

    With the prospect of working next to a tropical sea or exploring the ancient cities of Europe — all while furthering your career — it’s no wonder people are intrigued by location-independent work.

    But there are practicalities to consider.

    Simply being a freelancer won’t necessarily facilitate enough freedom to become a digital nomad, and while travel is usually a desirable goal, committing yourself fully to globetrotting may not be the best option.

    If the convenience and ease of remote working has you thinking about traveling as you earn, here are some things you’ll have to think about before setting off as a traveling freelancer.

    1. Is your client base strong enough?

    It’s pretty likely you’ll have to look for new work while abroad, but having a few clients you can rely on —  either for steady work or referring others —will make working abroad much less of a headache.

    This lifestyle may well open up new opportunities for you, especially as there will be huge scope to widen your writing experience by providing stories to travel magazines and websites.

    But heading out entirely into the cold probably isn’t a good idea if you are trying to craft a lifestyle rather than a short holiday.

    Do you have a fairly reliable stream of income?

    Are your clients happy with your work enough that they’ll be willing to forgive any issues you encounter getting an internet connection? Will you need to increase your skills in order to create new opportunities to earn money?

    These are all questions it’s best to answer before you go, so you don’t find yourself on the other side of the world without the career you had been carefully building in your own country.

    2. Are you prepared to make sacrifices?

    We are inundated with images of perfect foreign shores. Yet, while there are amazing experiences to be had from travel, there’s nowhere in the world where you can permanently escape the realities of everyday life.

    You may spend a lot of uncomfortable days traveling  between locations, lose the sense of security of having all your things around you, have to carry as little as possible, go weeks without speaking to loved ones or have real trouble finding a suitable place to work.

    If you can make it work abroad, any transitory issues will be well worth it.

    However, if you’re the sort of person who likes their creature comforts and you don’t have the budget to make life as easy as possible, it may be worth considering working abroad on a short-term basis in order to see if it’s for you before committing.

    3. Will accommodation be an issue?

    Simply having a place to sleep that’s clean and not completely awful may be all you need if you’re only going to be  away for a short time.

    But if you plan to travel or settle abroad on a more long-term basis, good accommodation will be essential. There’s not much more likely to ruin your motivation and working habits than worries about where you’ll be staying that night, or living somewhere that depresses you.

    Renting locally may be the most sensible and economical option if you plan on staying in certain areas for months at a time. Renting locally will also give you a much more authentic experience in an area, letting you really get to know a country. If your budget is extremely tight, house-sitting gigs or couch-surfing with the locals may be a way to facilitate your wanderlust on a shoestring.

    Whatever you choose, it’s important to remember your surroundings will make up a huge part of your peace of mind; even in the most beautiful locations, staying somewhere that feels unsafe or unpleasant will have an impact on your enjoyment of this lifestyle.

    4. Do you have an emergency fund?

    Traveling on a shoestring may seem romantic (and would probably create loads of great writing material), but make sure you have the funds for any emergency that may crop up.

    Being stranded, ill or completely broke in another country doesn’t seem like so much much of an adventure when you have no idea how you’re going to get out of the situation. Traveling needn’t involve having oodles of cash, but you do want enough to ensure nothing can go seriously wrong.

    Keep some money squirreled away for emergencies only, avoiding the temptation dip into it if you ever fancy a treat.

    5. Have you got patience for paperwork?

    Unfortunately, becoming a digital nomad is one of those fun, adventurous and exciting things that involves an awful lot of incredibly boring bureaucracy.

    Whether you’re sorting out taxes, trying to get visas or tackling any number of unexpected pieces of officialdom, if this is the sort of thing that drives you mad, committing to this lifestyle might be more trouble than it’s worth.

    A few hours of mind-numbing form filling could be far from enough to put you off, but it’s important to be aware that a footloose and fancy-free lifestyle still comes with its own annoyances.

    Have you taken your own writing work abroad? What other questions would encourage writers to ask before they pack their bags?

  • Tracking Freelance Earnings: April Income Report From Nicole Dieker

    Tracking Freelance Earnings: April Income Report From Nicole Dieker

    How much freelance work do you complete while you travel? I tried to fit in a full month of work plus a trip to Alaska into April — and ended up spending every possible minute writing.

    First, let’s check in with my freelancing stats. Here are the numbers for April:

    Completed pieces: 60

    Work billed (including prorated work): $5,516.81

    Earnings received: $3,688.86

    As my career has evolved to include more projects that take longer than a month to complete, the way I approach saving and budgeting has to change as well.

    I created my $5,000/month income goal at the beginning of 2015 both because it was an achievable stretch goal for me at the time, and because it was an amount of money that covered all of my major financial needs: Living expenses, business expenses, savings, and debt repayment — with a little “Fun Money” left over.

    In April, I had to take money out of my savings account because my freelance checks didn’t cover all these financial needs. In May, I’m expecting to receive a large number of freelance checks — around $10,000, I hope — but I can’t treat those checks like spending money.

    First, I’ll continue my habit of putting a percentage of each freelance check towards taxes, savings and debt repayment. (I’m putting 22 percent towards taxes, 10 percent towards savings and 20 percent towards debt.)

    Then I’ll pay back the $1,500 I took out of my savings account in April.

    Then I’ll pay my living and business expenses.

    I should have a chunk of money left over, and although I’ll spend a little of that on fun, I’m going to save the rest for the next month I don’t get a lot of freelance checks.

    I’m used to earning about the same amount every month, give or take a few hundred bucks. Now, I’m going to need to get used to big check months and smaller check months — and budget accordingly.

    Setting aside more money for freelance taxes

    April is tax month, and although I did pretty well with my estimated taxes this year, my CPA and I still discovered I had slightly underpaid my 2015 taxes — which meant writing a check instead of getting a refund.

    What happened? Well, after talking with my CPA in 2014 about my probable tax burden, I set aside 20 percent of everything I earned in 2015 and made my four quarterly estimated tax payments. It turns out 20 percent wasn’t enough; my actual 2015 tax burden came out to 22 percent of my 2015 earnings.

    This means I’m now taking 22 percent out of every incoming paycheck and putting it into a special savings account I’ll use for estimated tax payments.

    As a reminder: I live in Washington State where there is no state income tax, so my tax burden is likely to be different from yours. If you want to estimate how much you need to set aside for taxes, my best advice is to talk to a CPA who has experience working with freelance writers.

    Also, let your CPA know if your income changes significantly during the year. Some CPAs will give you estimated tax vouchers (that is, they’ll give you pieces of paper that tell you how much to pay on each of the four quarterly estimated tax dates) based on how much you earned in the previous tax year.

    But if you get a boost or a drop in income, those vouchers may no longer accurately represent your tax burden.

    I’m not a tax adviser, but I can advise you to find a CPA. You don’t have to wait until next April, either; if you haven’t yet had a conversation with a CPA about what you expect to earn as a freelancer and what you should be prepared to set aside for taxes, make that appointment.

    It’ll be a smart business move — and CPA fees are tax-deductible!

    Checking in with my freelance workload

    In last month’s Tracking Freelance Earnings, I wrote about phasing out some of my old freelance metrics, such as per-piece earnings, and focusing on two metrics of success:

    • Did I meet my $5,000 monthly earnings goal?
    • Was my workload manageable?

    I’ve already written about my earnings, so let’s take a look at my workload.

    In March, I did pretty well in terms of manageable workload. In April, however, my workload felt unmanageable — which is to say I worked a lot of evenings and weekends, and in many cases squeezed work into every possible minute.

    I traveled to Alaska in April for Alaska Robotics’ Mini-Con and Artist Camp (and led a panel on making art and making money), and I had so much work I was literally writing articles in the 20 minutes between clearing airport security and needing to board the plane.

    Once I was on the plane, I opened my laptop and kept writing during the 15 minutes between finding my seat and the “please put away your electronic devices” announcement, and re-opened my laptop as soon as we were in the air and it was safe to continue working.

    I think April’s workload would have felt slightly more manageable if I hadn’t also had the trip to Alaska, but I also assumed that I could complete a standard “month of work” even though I was going to spend several workdays on a plane or at an event.

    The truth is, even though I can almost get a regular freelance workday out of a travel day (by writing in the 20 minutes between security and the gate, and so on), it’s twice as exhausting.

    I need to accept that if I’m going to be traveling, even for work-related reasons, I can’t also treat that time as “writing time.”

    Yes, I’m probably going to still look at a three-hour flight as a chance to get a little writing done. But I can’t be the person trying to get out as many words as possible before the flight attendants tell everyone to close their laptops.

    If I’m going to balance writing and travel, I need to find a better balance — and that’s something I’ll need to start thinking about a few months in advance, so I can continue to hit my income goals, meet my clients’ needs and take the trips that help me grow my career.

    How do you balance writing and travel? Also, do you have a CPA? Let’s talk travel and taxes in the comments.

  • Working on the Road: 4 Tips for Freelance Writing While Traveling

    Working on the Road: 4 Tips for Freelance Writing While Traveling

    As I write this, I’m at Chicago’s O’Hare International Airport waiting for the next leg of my journey out to the East Coast. As a location-independent freelancer, I always try to take full advantage of travel interludes to catch up on my work.

    Working on the road can be a tricky endeavor. It’s amazing to be able to work from anywhere with a WiFi connection, but it’s important to plan ahead to be able to enjoy work and play while traveling. Trekking through Machu Picchu is a whole lot less exciting when deadlines are weighing you down.

    No matter how location-independent you are, working from the road definitely has its share of challenges.

    Here are a few tips I’ve learned along the way to help balance work and travel.

    1. Plan before you go

    Before I leave home for a trip, I always pull a few lists together. I use old fashioned pen-and-paper, though many prefer digital to-do lists and programs such as Evernote (which still live in the cloud if you spill coffee all over your notebook).

    The first list I pull together is a list of deadlines that need to be completed while I’m away, urgent emails and phone calls I’ll have to find time to return, and other important items I can’t forget.

    I always try and get as many of these sorts of things taken care of as possible before I leave, but things have a way of coming up at the last minute.

    Whether it’s an urgent revision request for an article turned in months ago, or an email from the person you’ve been trying to track down for a month saying they have a small window of availability for an interview before they move to rural Botswana, sometimes things pop up on the road that you have to take care of.

    The second list I pull together is a list of offline tasks I can do. Generally, this involves “deep work” such as writing and non-web research, which is best done without online distractions such as pinging messages and emails — or the ever-present temptation of surfing the web. These tasks are great for airplanes. I don’t opt for expensive airline WiFi, though many freelancers swear by it.

    I find brainstorming also works very well while traveling. An infusion of newness and a disruption in one’s daily routine can allow for a lot of creativity. The change in scenery lends well to brainstorming, whether it’s mapping out an article, thinking of new articles to pitch, or adding a new twist to the novel you’re writing.

    2. Stick to a schedule

    When you are lucky enough to be able to work and play, you sure don’t want to blow it. That’s why it’s important to schedule your time and plan so you can make the most of both work and play.

    When I’m traveling, I like to do a little work first thing in the morning, and then check for any urgent emails I need to respond to in the late afternoon. Many times, I’ll be in locations with limited internet access, so I’ll check my emails whenever internet is available. It’s also important to take some time offline in order to disconnect and recharge.

    If I need to put a solid chunk of work in on a project, I’d  rather do that first thing in the morning so I have the rest of the day free to wander around and play without worrying about making a deadline. It also gives you the freedom to go explore the local nightlife without stressing about your assignment.

    But that’s just my personal preference. Some night owl writers prefer the opposite schedule. Experiment and find what works best for you.

    But be sure to stick to your scheduled times for work and play. You don’t want to fall down the rabbit hole of email and spend your trip responding to emails instead of seeing the sites of Belarus, Bangladesh or the Bahamas.

    3. Communicate with clients

    So, you’re leaving town. What do you tell your clients? Well, that depends on your work plan. Will you be scheduling a few hours for work every day and be available for routine, day-to-day inquiries? In that case, you may not need an away message at all.

    But if you’re going off the grid, be sure to set an away message on your email and voicemail so clients know why they’re not hearing back from you right away. Be sure to let them know when to expect a response. If you have a back-up contact for urgent matters, be sure to list that person’s information.

    If you’re planning on going off the grid for a significant amount of time, you should communicate this to clients well ahead of time so they can work with you to wrap up any loose ends before you head out.

    4. Back it up

    When you’re working from the road, it’s important to have dependable access to your files. I always have a few options available and I plan for different contingencies.

    Before I head out, I load important files that I’ll need onto my mini travel laptop. Then, I copy these files to a flash drive I also take with me. I figure if the laptop conks out, I can take the flash drive to a hotel business center or internet cafe with the files to get my work done if need be.

    As another layer of protection, I also have the files uploaded to my Dropbox account, so I can access them digitally if I need to. While none of these solutions is foolproof, having some redundancy in my data storage makes me feel much better when I work on the road.

    Do you spend a lot of time working while traveling? What tips and methods do you rely on?