My dad built a small family business renting tools and equipment to contractors. He bought a house with some land and raised a family (Thanks Mom!). Now he’s pretty much chillin’ full-time while my brother and I run the family business, thus completing the American Dream.

Forever grateful and far from lazy, we Millennials have a new American Dream: Working from home. Working remotely, and the tech required to get there, can expand your abilities, improve efficiencies, and create opportunities. If you’re the young gun in your organization who wants to #WFH…well, this is how I did it. Hopefully it’s helpful for you.

Make a plan.

Get a list going of all your responsibilities. Now close your eyes and imagine yourself outside of the office. How do you take care of business with nothing but an internet connection?

Tons of organizations already embrace remote work. They did a lot of the heavy lifting, so quite often you can find digital solutions with a quick google search. Googling “cloud-based accounting system” or “cloud-based phone system” should get you heading in the right direction.

Some important tools for me included…

  • Cloud-based point-of-sale (POS) system
  • VoIP phone system
  • Cloud-based storage service
  • Cloud-based accounting system

Tip: A lot of SMB software is very new to market. Know who/what is supporting your software and keep a backup plan in case their business fails.

Get the greenlight.

You’ll probably need to convince a manager, owner, or parent to approve your plan. This is a big ask, so make sure you’ve done thorough research and have all your answers prepared. Carefully assess your plan from the owner’s perspective and the customer’s perspective. Your plan should include a timeline with benchmarks.

Tip: You’ll need a strong commitment from your owner saying that they’ll give you a legitimate shot at pulling this off. If you’re in the middle of busting your (Deleted by editor: This is a family blog, Robert.) in Hulk-like execution mode, it can be difficult to deal with an owner getting cold feet.


I took it piece by piece. I started by converting us to a cloud-based POS system. While my dad was learning about the benefits of our new POS system, I was already moving on to cloud-based accounting, circling back to the POS system to answer any questions or address his concerns. By the time Dad wrapped his head around the new POS system, I was ready to introduce him to our new accounting system. Now we’ve got momentum! This is the best part because “things are changing” and you’re leading the charge.

Tip: If possible, run systems in parallel. We were always able to keep existing systems in place, running parallel to our new systems until Dad was comfortable with letting go of the old.

Now I can take reservations for my family store in Georgia while at a beach with friends in New York (actual story). With the right tools and implementation process, you can be working from anywhere in no time. Good luck!

Robert Douville helps run Able 2 Rent All in Fayetteville, Georgia and uses Rental Essentials as part of his suite of products to allow him to work from his home in New York. He’s a member of the ARA YPN and will be attending the event in Clearwater Beach, Florida this December. Register for the YPN event here: