Remote Control: A Practical Guide to Running Your Business From Afar

By Cameron McCool on July 2, 2015


Right now I’m sitting on a patio in Maui. To my left, a clear blue sky presides over the glistening Pacific Ocean. Below, a valley full of plumeria trees bakes under the hot, summer sun. To my right, an iced coffee sweats onto the patio furniture. And in front of me: my laptop.

This dream state is my office for the next two weeks.

For business owners besieged by employee demands and the minutiae of daily management, getting away from it all while keeping the business afloat can seem like a fantasy at best.

Even if you’re only able to unplug from your business for a short stint, with careful planning you can leverage the remote-work lifestyle to take an extended work-cation with your family, or run your business from another destination for several months at a time.

To help you prolong the summer months and enjoy your well-deserved independence, here’s our mini guide to making it happen.

Reprogram Your Employees

If your employees depend on you to make every decision, they’ll keep depending on your undivided attention and input while you’re working from afar. As a business owner, before you can even consider working remotely, you’ll need to engender a sense of autonomy and ownership in the employees who’ll be responsible for your business while you’re gone.

Start by working from home a few days a week, and see how your employees react. Empower them with clear boundaries and black-and-white guidelines on where their authority lies while you’re out of the picture. Tell your employees that they have the right to make an executive decision if it’s under a certain dollar value. Explain the justifications you use for making important decisions. Be clear on when and how they should reach out to you to seek a second opinion. And train them in using online apps and services (see below) to communicate with you and run the business while you’re out of the office.

What you’re trying to eliminate here is any tendency employees may have to shoulder-tap you for every little thing, while simultaneously encouraging autonomy and smart decision making. You’ll know when your employees are ready for you to work remotely, because the business will run near-seamlessly with very little input from you.

Achieving this state is a critical step in setting up the ability to work remotely, and it’s one that many business owners struggle to accomplish. If you’re overly controlling or involved in every single business decision, this process will be harder for you. The sooner you can get started on it, the better.

A happy side effect of going through this process is that you’ll be able to assess how smoothly your business runs while you’re not at the helm. Making yourself “operationally irrelevant” is one of the key steps to building a sellable business, so whether you find that there are issues to address, or that your business operates well without you being there every single day, your business will be better for it.

Use Apps to Run Your Business Remotely

The following selection of apps and online services can help you run your business from afar. It’s important to ensure that your employees are comfortable using these apps long before you head off on your first remote-work experience.

Slack - Your Virtual Office

The remote team at Zapier, responsible for the industry’s most-comprehensive guide to working remotely, are huge proponents of using Slack as their main communication tool: “Slack is our virtual office. If you’re in Slack, you’re at work.” The app works on desktop and smartphone. And provided that you’re in a similar time zone to your business, communicating via Slack is a great way to check in and chat instantly with employees.

Collaborate on Team Documents

Google Docs and Evernote are all you’ll need.

Manage Your Finances

Use Bench, the online bookkeeping service, to keep your books in order. Use Shoeboxed for snapping and storing digital copies of your business receipts, and FreshBooks for invoicing.

Video conferencing

Skype, FaceTime, and Facebook Messenger are great for handling video calls with employees and clients. If you need to host a video conference for a group of three or more, use Google Hangouts.

International Phone Calls

For those occasions when video conferencing won’t cut it, Google Voice lets you make free international calls to the USA and Canada from your computer. Their rates for calling other countries are extremely low, too.

Cloud Storage and File Transfers

Dropbox is a user-friendly option for storing files online. Google Photos and Flickr both offer huge, free storage limits for keeping your photos online.

Choose a Work-Remote Location that Works for You

Members of NomadList rank the best cities to live and work remotely based on their cost of living, climate, weather, access to ‘fun’ things to do, and even the local internet download speed.

Ultimately you’ll need to decide on a location that fits best with your personal and business needs. Here are a few guiding questions to help you choose a work-remote location that works for you.

Will the Time Difference be a Problem?

If you need to be available while your business is operating back home, it’s much easier to work remotely from a destination that lies in the same time zone as your business. The time difference between San Francisco and Dubai will result in you working odd hours, so that you can be online when your business and your employees need to reach you.

Does the Foreign Currency Work in Your Favour?

If you generate income in USD, and you work from a location where the exchange rate gives you $2 in local currency for every $1 USD, you’ve effectively doubled your income. This neat financial hack is known as income leveraging. Pick your work-remote destination wisely, and you could stretch your income significantly just by working from abroad.

What are the Entry Requirements?

To enter most foreign destinations, you’ll need a visa and a passport that’s valid for six months after the date you’ll be exiting the country in question. Renewing passports and acquiring visas takes time, so make sure your papers are in order well in advance.

Can you Get a Good Deal on Accommodation?

When you look around for accommodation, Airbnb is a good place to start. Make sure your location has enough space for you to set up and work each day. Having a kitchen will help you save on time and the cost of eating out. Don’t be afraid to negotiate a better rate for longer-term stays. Cheaper but less-reliable options include home swapping and house sitting.

Is the Internet Reliable?

An erratic, unreliable internet connection is the bane of a remote worker’s existence. Before you put a down payment on your accommodation, ask the owner or management to run an internet speed test, and have them email you a screenshot that includes the speed test results and a date and time stamp.

What to Pack

Here are the bare-minimum essentials you’ll need to run your business from afar:

  • Macbook air or a similarly light, easy to pack, portable computer. Even though a heavier laptop might not feel heavy, carry it around for an hour or two and you’ll wish you had something lighter.
  • Passport
  • Smartphone
  • Noise canceling headphones: they’ll help you cut out noise when working from busy locales
  • External hard drive
  • Travel insurance

While You’re Away

Adjust your Email Autoresponder

Using Slack for team communication (see above) should limit your need to check your emails frequently. But you can free up more of your time by applying a small tweak to your email autoresponder.

Here’s a modified version of the time-saving email autoresponder developed by entrepreneur Tim Ferriss. It lets people know you’ll check your emails twice a day, max, and provides details on how they can reach you when something is urgent:

Hi there,

I’m currently working from the XX timezone, and in an effort to increase productivity and efficiency, I’ll be checking/responding to email at 11am and 4pm on weekdays (XX timezone). I will try and respond to email in a timely manner, but if you need an immediate time-sensitive response… please don’t hesitate to call me. Phones are more fun anyways.

Hopefully this new approach to email management will result in shorter lead times with more focused & creative work on my part. Cheers & here’s to life outside of my inbox!

Adjust this format according to the needs of your business, and use it to limit the amount of time you spend wading through your inbox each day.

International Money Transfer

You’ll need to withdraw, exchange, and possibly even transfer money in foreign destinations, but banks will gouge you with transfer fees and near-criminal exchange rates. Avoid them where possible. TransferWise is a better solution, but it only works for transfers between a select group of countries. PayPal is second best, although its fees and charges are closer to those offered by banks. Unfortunately, losing money on currency exchange is one place where you’ll never win. Consider it a small price to pay for the privilege of working remotely.


Don’t brag. Be early for meetings. Be readily available. Be so attentive to others that a single issue doesn’t arise as a result of you managing the business from a remote destination.

This is the motto of successful remote workers. Remember that working remotely is a privilege, and it’s one that your employees and clients may not have access to in their own line of work.

Set Boundaries for Your Loved Ones

One of the best things about working remotely is that it allows you to extend your family vacations. A word of warning on this, though: loved ones who see you working on a computer will rarely understand that you’re actually “working.”

When I work from home, I get distracted by my partner all the time. In these situations, I find that the use of noise cancelling headphones, and having a nearby cafe to use as a backup remote workspace, is imperative.

Accept that things can and will go wrong

Even when you’re elbow deep in the day-to-day management of your business, you can’t control everything. Sometimes the things that can go wrong, do go wrong. And it’s highly likely that whatever could go wrong while you’re working remotely will go wrong at least once while you’re away.

When this happens, just like any unexpected hurdle in life, you’ll find a way to deal with it. It might even make your team or business stronger as a result. The trick is to not let the fear prevent you from working remotely in the first place. Be as prepared as you can. And when a problem arises, breathe deeply, and trust that you’ll find a way through.

Above All Else: Enjoy

Once I was on a tour visiting the active lava flow in Hawaii. Everyone had their smartphones and cameras out to record the event. Halfway through the experience, our guide said: “Folks, don’t forget to stop and look at what you’re experiencing with your own eyes, not just through your camera lens.”

What a beautiful reminder.

When I’m stressed out and thinking about the thousand-and-one things on my to do list, remembering this advice helps me to catch my breath and bring my awareness back to the present moment. Strangely, the guide’s advice also helps me to make the most of those times when I find myself working remotely.

As an entrepreneur, I have an unhealthy tendency to overstress and work far more while I’m working remotely than I to do while I’m working from my home base. If you’re a busy type who can relate to this, try not to squander those precious work-remote opportunities you create for yourself by stressing and working more than you need to.

Set healthy boundaries for yourself, ones that help you disconnect, recharge, and enjoy the experience of being in a remote destination during your down time.

Just like running a business, creating the opportunity to work remotely isn’t an easy process. But the pay off once you’re managing your business from a remote destination makes the effort well worth it, so make sure you enjoy your independence. After all, you earned it.

This post is to be used for informational purposes only and does not constitute legal, business, or tax advice. Each person should consult his or her own attorney, business advisor, or tax advisor with respect to matters referenced in this post. Bench assumes no liability for actions taken in reliance upon the information contained herein.

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