Category: Travel

How to Have a Hard Conversation When You’re Remote

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Hopefully you have a job (remote or not!) that you enjoy most of the time, find fulfillment in, and interact with engaging and supportive colleagues. But even the most satisfied professionals have bad days and are faced with difficult situations.

But what happens when a bad day or difficult situation goes beyond a one time occurrence? Maybe a colleague continually undercuts your ideas or intentionally leaves you out of conversations, your management team is not providing the support and runway you need to grow, or perhaps a direct report is challenging you in inappropriate ways.

While it can be intimidating, when a problem arises in the working world you must face it head on. But factor in the distance of working remotely or from a different office and it can be even more difficult.

So how do you handle this? Here are 6 tips to have a difficult conversation when you’re not in the office.

1. Have a live conversation

Intonation and inflection matter so avoid email or IM. Give the person and the situation the courtesy it deserves and have a conversation. One challenge of not being in the office is not being able to simply pop by someone’s desk or office. If you need to connect with someone who has a challenging schedule send a short email indicating you’d like to discuss a specific topic, succinctly say what that topic is, and grab time on that person’s calendar.

2. Come prepared

Clear, concise thoughts are much more powerful than spouting out grievances. Spend time detailing what the situation and problem at hand is; have short examples that you can cite if pressed. Then spend time thinking about what you believe the remedy should be. Especially if you’re going to an executive with an issue one of the first questions she is likely to you is how it can be fixed. You don’t have to have the full solution but you don’t want to fumble over your words here.

3. Remember your EQ

Along with being prepared for the conversation, your thoughts on how something can improve, and setting up the best environment possible for the discussion, don’t forget to bring your EQ or emotional intelligence. EQ is most certainly one of the professional buzzwords of the day but it’s for good reason: it matters. There are loads of different definitions out there, but one way I like to think about it particularly in terms of a difficult conversation is being a full person. When you have to face conflict, especially if there’s an added barrier like different offices or a remote worker, keep in mind that we’re all people. This person who has been seemingly actively keeping you out of a project might have some very real fears about his job security, heightened by the new baby he just had. You certainly don’t want to look past issues, but it’s important to aim to see the full picture, especially when you’re not experiencing the “full picture” of the office each day.

4. Get clear on your expectations

Before any big conversation (work meeting, personal chat, you name it!) you should have an idea of what you’re looking for as a result. You can’t control what the answer or other person’s point of view will be, but you can have an idea of what you will discuss and come to resolution on. Additionally you can have an idea of what you would like in your ideal situation. It’s important to have an understanding and idea of this going into a challenging conversation, especially one you’re driving.

5. Ask for feedback

You’re not perfect. Having a difficult situation to should remind you of the fact that no one is perfect. Talking about something unideal is a great time to learn more about how you can grow and improve as a professional. Plus asking for feedback will demonstrate to your counterpart that you’re

6. If it’s a really sensitive matter and you can, travel.

Some things–when possible–are best done in person. If you’re dealing with a highly sensitive subject, or need to involve upper management, or simply need to be able to look someone in the eye during a conversation do it in person if you can. Trust your gut and if you feel it’s necessary–and it’s possible with your work setup–make the trip.


How have you handled a difficult situation when not being in the office?

5 Reasons Why You Must Take Time Off As A Remote Worker

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One of the biggest perks of working from home is that by being able to work from anywhere you can work, well, anywhere, including while traveling. While this is a great feature of being remote (that I clearly take advantage of) it doesn’t mean that the work from home employee does not need a true vacation.

I just got back from an 18-day trip out west. You may be thinking “18 days!!???!!” That’s right, 18 days. For a good part of it I worked from coffee shops and homes of my friends in the northwest US, but for an equally big part of it I was on PTO.

Some remote workers may see it as a waste of PTO since they don’t have to take time to get away. I support working through travel (read more here) but sometimes you need a true break. A friend of mine who also works remotely recently told me he hasn’t taken PTO in over a year. A year without vacation. He seemed proud of this but in my opinion, unless you are a small business owner whose company will literally stop and crumble to the ground in your absence (which is a different problem), not taking time off is doing it wrong. Here are 5 reasons why you MUST take vacation time, even when your time away is time away from a home office:

1. Your vacation days = your $$. We hear a lot about unused vacation days. (Side-note: one of my favorite ads is the MasterCard ad “One More Day” in which kids are shocked that their parents not using all their vacation days.) On top of the fact that vacation is earned, the full picture is that vacation days are part of your compensation if you are a salaried employee. Think about vacation as money: breakdown your salary into what it would be on an hourly basis. For each hour (or 8 hours, for one workday) you don’t use that is money you are throwing away. When you work without taking your paid time off you are lessening your paycheck.

2. Without you taking it your PTO just sits there, or worse disappears! Yes, some PTO rolls over and some companies have a policy of paying you out for unused days when you leave (though check your terms on both of these items) but unless you are about to resign or are planning on rolling days for a big trip, your unused time literally sits, proverbially, “there” and oftentimes if you don’t use it, it will be taken away from you. Use it or lose it, literally.

3. Rest is essential. No one, not even my small business-owning, midnight oil burning, rock-star of a father, can go without rest and true time off. It’s not good for the mind, body, or soul; which all have direct impacts on your performance at work. Even if you are your own boss you still need rest.

4. Time off helps you re-center and re-prioritize. Down-time helps you clear your head and recharge within your personal life. Beyond its head-clearing effect, it can actually help you improve at work. There have been many times I’ve returned from a trips and seen a certain problem in an entirely new light. Taking the time to get out of your own headspace and day-to-day world, seeing fantastic new places, and experiencing the greatness in life resets you. Once seemingly unsolvable issues become easily fixed, or if not easily fixed then manageable.

5. Sometimes you just need to take the time off to enjoy a trip. Sure you can work from coffee shops from different places while traveling (again, I do this ALL the time) but sometimes you need the time to do things like drive from Idaho to Montana to Wyoming, back to Idaho, then back to Wyoming, then to Colorado in a week. Or hike and bike or camp or ski or surf and sail or hit the tiki bar. Sometimes you just want to not feel obligated to check your email. THIS IS ALL OKAY. YOU HAVE VACATION DAYS SO YOU CAN DO ALL THESE THINGS ON A RANDOM TUESDAY DURING ANY MONTH OF THE YEAR. BEING ABLE TO WORK REMOTELY DOES NOT TAKE THIS AWAY FROM YOU.

Don’t believe me and my use of caps lock? Maybe some of the killer things I’ve been doing on my vacation in the pictures below and on my Instagram will help convince you:


Food trucks in Portland, OR


Multnomah Falls near Portland, OR


View of Puget Sound from the Cascades Train en route to Seattle


Obligatory picture of the Seattle skyline from Kerry Park in Queen Anne


Obligatory picture of the Public Market


Obligatory picture of the Seattle skyline from the ferry to West Seattle (clearly did lots of obligatory Seattle things)

**Note: My PTO started after leaving Seattle


#selfiefail at Lava Lake a little south of Bozeman, MT


Antique sheepherder’s wagon in Belgrade, MT


Covered wagon again because it was just too cool


Old Faithful in Yellowstone National Park


Scenic views of Yellowstone


The Grand Tetons


Tetons again


The Working Girl From Home–from the Grand Tetons–on vacation


View of the Tetons from my Idaho Airbnb


Sunset over Idaho farmland, taken in front of my Idaho Airbnb


Sitting next to a huge potato in Driggs, Idaho


Rented a bike at the Tetons


View of Jenny Lake from Inspiration Point


Panoramic of Jenny Lake as I hiked back down from Inspiration Point


The Working Girl From Home, on a bike in front of the Tetons


Bison spotting


New Denver bud

Feeling guilty for taking vacation is common for remote employees and traditional employees alike. What have you done to get over it? Have you gotten over it? Did something finally convince you to take your PTO? Share in the comments below!

When You Can Work From Anywhere, Here’s How to Do It Well

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One of the great perks of being a remote worker is that you can work from anywhere. I have a work space in my home in Atlanta but I often work from my desk in my childhood bedroom when I visit my parents, or from a kitchen table when I visit friends, or from random coffee shops or even airports while in transit. It’s a huge perk for me but like everything else with this work from home life, it’s about give and take.

Last week (and a bit of the week before) I was traveling. I flew up to Boston, worked from my cousin’s place for a day and a half so that I was able to drive to my grandmother’s in Vermont Friday after work, then I headed to New Hampshire on Sunday to spend Mother’s Day with my other grandmother and family. After that I flew to Kentucky to work from my company HQ for a week.

It’s a perk that I personally value tremendously but it can be exhausting and not without its challenges (like scrambling in the dark to get the wifi to work before your hosts wake up since you are working on a different time zone!) Even with its challenges I am quite aware of the fact that my job is affording me this great benefit so I refuse to let my location choices negatively impact my performance. So how do I do that?

When I travel like this I ask myself what my priorities are. For me it often includes a range of items from seeing family and friends, exploring new areas, eating good (but healthy) food, exercising, writing blog posts (hi!), connecting with clients on my side business, giving myself some quiet time, oh, and of course excelling at my day job since again, they are enabling me to work like this. Like everything else in life it comes down to choices.

On the recent trip I described above, along with my full-time job my top priority was to see my family. That meant that I didn’t get to exercise as much as I normally would at home, I wasn’t able to prepare (or choose) my own meals, and I wasn’t able to blog for a week (sorry!) And that’s okay, because that’s the give and take of being able to be location agnostic.

People often envy what a WFH set up allows, and I certainly see where that comes from. But what they don’t always anticipate is that with it comes responsibility and the need to really ask yourself what a particular trip, or even day, is going to be about. It’s important for my to keep myself in check regarding so my work doesn’t sacrifice for the sake of the flexibility it affords me.

How do you take advantage of, and balance, your flexibility? Have you ever worked from a friend or family member’s home? What challenges and benefits has a remote set up afforded you and how do you manage it?