I've Been Working Remotely Since 2015 — Here Are 15 Things I Wish I Knew In The Beginning

Step 1: LEAVE THE HOUSE.

After working office jobs that required long commutes and stringent 9-to-5 work schedules, I woke up and decided it wasn't how I wanted to spend the next 50 years of my life.

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I love office camaraderie as much as anyone, but an over one-hour commute before and after a more than eight-hour workday leaves little time for fun, and the belief that a workday has to fall between certain hours feels super outdated to me.

So I joined the remote work world in 2015 — transitioning from freelancing to a full-time work-from-home job and back again.

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While there are definite differences between the two options, they both offer MUCH more flexibility than a traditional office job.

But I would be lying if I said working remotely was always easy. Here's what I wish I knew in the beginning:

1. Don't be afraid to ask if you can alter your working hours to make time for things that are important to you.

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This one depends on your boss and company, but chances are, if you consistently show up, put in your time, and get your work done, they'll be flexible with you.

If you're training for a half-marathon, ask if you can shift your hours from 9–5 to 10–6 so you can get in a long, early-morning run. Or, if there's a boxing class every Thursday at 5 p.m., ask if you can start your workday an hour earlier so you can cut out early every Thursday.  

2. You don't have to use paid time off for things like travel days — or even certain vacation days.

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Figuring this out was huge. Say you're flying to visit friends for a long weekend. With a traditional job, you might have to use a PTO day for a Friday travel day and a second one on Monday to travel home. But when you work remotely, you can book your flights so they're easily outside working hours, OR you can ask your boss if you can clock in early (or work late) to make up for time you'll need to get through check-in and security before logging in at the gate, and then again on the plane. 

Suddenly, a trip that might typically require two days of PTO isn't costing you anything.

And to take it one step further, if you're traveling during the workweek, you may be able to wake up early and get in four hours of work before your friends mosey out of bed. It takes discipline, but it feels amazing to use up a half day rather than a full day of PTO.

3. Long-term travel is easier to pull off than a weekend away, and you can do it without using much PTO.

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This one sounds unbelievable and takes some serious planning, but I've done it. I spent a full month living in Paris and later a month in Jordan while working for a company full time. I just had to adjust my working hours to match Eastern Standard Time and couldn't stay longer than a month (per a company policy).

In fact, I've found long-term travel is easier to pull off while working because you'll be in one place for a long chunk of time, allowing you to create a consistent work schedule. 

4. Your lunch break can be whatever you want it to be.

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Eating at your desk sucks, but it's worth it if you can spend your lunch break doing something you love (or taking care of something that's been stressing you out). You can get in a workout, do the laundry, go on a hike, or even spend the time making yourself a decadent work-from-home lunch. 

No matter how you choose to spend it, it'll beat sitting in the office cafeteria eating a turkey sandwich (or, worse yet, eating in front of your computer).

5. But anytime you want to travel and switch up your schedule, you have to communicate with your boss.

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There is a lot of flexibility to be had in remote work, but you can't just drop off in the middle of the day because you want to take a yoga class. In most cases, you still need to let someone know what you have planned and how (and if) you're going to make up any work time you miss. 

Obviously, every company and boss have different expectations, but I've found that most are willing to be flexible if you are clear about what you want to do and what your plan is for making it happen without neglecting your work. 

6. Just because you work from home doesn't mean you have to literally work from home.

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I understand that there's a certain safety that comes with working from home — it's quiet, your internet is reliable (hopefully), and you have your comfy home office setup. But I've found that working a half day or two from a coffee shop, a drop-in coworking space, or even a mellow restaurant or hotel lobby can do wonders for your mental health and just get you out of the house. What a concept.

7. Meeting up with other remote workers on "work dates" can do wonders for your mental health.

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I have a remote work friend who will meet me at a coffee shop or wine bar (shh!) once a week for a half day of work. We usually chitchat for a few minutes, then dive into work. It's like having an officemate you actually really like, and it helps both of us get out of the house.

8. Backup internet is the secret to life.

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When you work remotely, Wi-Fi is your lifeblood. Anytime I travel, I get straight-up anxiety over the quality of the internet, where I'm going to work, and what is going to happen if — god forbid — my internet cuts out in the middle of a call.

This is where backup internet comes in. I make sure that wherever I'm staying has internet (le duh) and then scout out a nearby coffee shop, hotel, or restaurant where I can work if my home internet goes out. AND because it gives me such anxiety, I also ended up purchasing a Skyroam Solis, which uses local cellphone towers to provide Wi-Fi in over 130 countries for under $10 a day. I only use the Solis in dire situations, but it has saved me.

9. Download work apps on your phone so you can check in on the go.

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This one is tough. On one hand, downloading apps for work allows you to stay connected when you have to run to the store in the middle of the day (win), but it also means you'll get notified if someone messages you after hours (loss). 

Weigh your options, but having apps like Slack, Zoom, Google Docs, and Hangouts on my phone has saved me multiple times. I've also played with muting notifications from these apps after hours so I can detach from work.

10. Creating a separate work space in your home is key, no matter how small it has to be.

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I spent the first year of my remote work life moving from the bed to the kitchen table to the couch. Not only was it horrible for my back (duh), but I also had a hard time transitioning out of work and into life at the end of the day.

This is why it's crucial to find a space that's dedicated to work. If you're in a tiny studio or one-bedroom apartment, research tiny-space-friendly desks that can tuck into the corner. 

11. Springing for a computer monitor, keyboard, and mouse is sooo worth it.

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I love the on-the-go nature of my laptop, so I resisted buying a computer monitor, keyboard, or mouse for YEARS (like literally five full years). It took signs of carpal tunnel, overworked eyes, and a pandemic for me to finally invest in a desktop setup. I bought a big Asus monitor that's supposed to be gentle on the eyes, as well as a keyboard and mouse from Apple that I connect via Bluetooth to my laptop.

It cost me a few hundred dollars, but I can't tell you how much better my body feels, AND I am a million times more productive.

12. And invest in a good office chair or standing-desk setup.

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In all honesty, this is a piece of advice I should take myself. I used to have a transitional sitting-to-standing desk (which was amazing), but then I found an adorable retro blue chair on Facebook Marketplace and couldn't resist. I like to think the cuteness of the chair makes up for any added aches and pains, but the truth is, I'm on the brink of going back to my transitional sitting-to-standing desk. 

If you think that you'll be spending eight-plus hours a day sitting in this chair, it makes the cost (and research into what works for you) well worth it.

13. Getting dressed makes a huge difference. (So does showering and getting ready.)

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For a long time, I loved the freedom of working in my PJs, not wearing makeup, and sleeping in until five minutes before I was supposed to start work. But by the time the afternoon rolled around, I felt horrible, and I felt even worse if someone unexpectedly dropped by my house.

Even if I have no calls and no one will see me all day, I've made a habit of at least washing my face and getting dressed.

14. Set boundaries between your work and personal lives, and keep them sacred.

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This is a hard one, and to be honest, I don't have this fully figured out either. But I'm much better than I used to be. There is always more work to do, but if you're honest with yourself, it can wait until tomorrow.

This is what works for me: Every evening, before I clock out for the day, I look at what I need to do the following day and break it into chunks of time — one hour for catching up on emails, four hours to write an article, lunch, three hours of editing time, etc. Then I set a hard end time. 

There are, of course, certain days when starting early or working late is a necessity, but in most cases, the work can and should wait until tomorrow.

15. Finally, be clear with family and friends who live close by that yes, you have a real job, and no, they can't swing by to chat in the middle of the day.

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It's not unusual for people to assume that because you work from home, you don't have a "real" job or "real" things to do and can do what you want during the day. 

This one is tough. For starters, you need to draw the line and let people know they can't drop by during working hours. If people don't listen and you have a big call or project, put a note on your door letting people know you can't be disturbed. 

The same goes for personal phone calls and even texts. Even though you could pick up that call from your aunt in the middle of the workday, it's probably best to call her back when you clock out. Treat your remote workday as you would an office workday.

Do you have any remote work tips to share? I'm all ears!

For more stories about work and money, check out the rest of our personal finance posts.