How Vacation Can Benefit Business & Tools To Make It Work

I recently got back from a 6-week cross country road trip.  Some people might assume that running your own company provides unlimited flexibility when it comes to time and location, but that’s hardly ever the case– this trip was a rare treat.

If location-independence and free-time is your sole objective — and there’s nothing wrong with that — it’s certainly an attainable goal if you structure your business accordingly and maintain modest expectations.  But if you want to disrupt entire industries or forge brand new ones, chances are you’ll have to remain in place, grind out ungodly work hours, and build a team around yourself.

With that being said, even if you’re aiming to make your mark in the universe, not only will you see a productivity boost from the relaxation and stress reduction that comes with a vacation, but your business can benefit from the vacation too.

Here’s how a vacation can fundamentally improve the operations and profitability of your startup or small business:

Identifying choke points in your business processes

While on vacation, even if you wanted to get work done, there are times when that just won’t be possible.  Put a few of those days in a row, and you’ll quickly see where your business’s operational choke points are.  Even if your goal is to create the next disruptive conglomerate and you plan to be present and grind it out all day everyday, there’s always benefits to optimizing processes as much as possible.  Addressing these choke points is as much of an insurance policy as it is a growth tactic.  Unless you address these choke points, your business will never grow as fast as it otherwise could.

Limiting your work hours puts things in perspective

When you decide to get a bit of work done while on vacation, you’ll have to prioritize what’s truly important since you won’t have nearly as much time available as usual.

Once you do this a few times, you’ll quickly see how much time you waste on petty tasks during a normal business day.

Now imagine that on a normal work day, you only spent that same amount of time on those most important tasks– how much time would that free up for other strategic and higher-level tasks necessary to grow?  If you want to scale, your goal should be to set up streamlined systems, whether they are through software or hiring help, to be able to spend your time more wisely.

Tools for streamlined processes and stress-free vacations

When it comes to scaling a startup, the goal is to eliminate yourself from as many operational processes as possible, not only for life-balance but also to compound the growth of the company.

Here are some tools I’ve implemented into my own business over the years to address choke points and streamline business processes in order to make vacations possible–

Google Alerts

Google Alerts allows you to have Google alert you if any specific terms, phrases or keywords are mentioned in the news.  This is especially useful to monitor when you or your business are mentioned. It’s also useful to keep tabs on your competition.  Or if content creation is a pivotal part of your marketing strategy, defining some keywords related to topics you’d like to write about would provide you with a steady source of content.

Automated RSS emails

All email marketing software that we recommend will allow you to pull an RSS feed from anywhere, automatically build it into a nicely designed email template, and mail it out to your list on predetermined intervals.  If you run a blog, you should be cultivating an email list and emailing them new content when it’s published, and this feature makes that happen automatically.


Currently my favorite social media management platform.  The feature that saves the most time is their “Automatic Scheduler” feature, where all you do is click Schedule and it determines the best time to post something based on a number of metrics.  If you’re going to be scheduling a ton of posts at once, choosing a date and time for each adds up, but this makes the process a breeze.


Saving things in the cloud makes them infinitely more accessibile from any device, and Dropbox is the king of cloud storage.  Dropbox’s native desktop and mobile apps are intuitive and functional, but what makes Dropbox better than the rest is that almost every other app connects to it seamlessly, making the files on Dropbox as accessible as possible.  Need to post a picture on Instagram from your phone?  Easily access the pictures from Dropbox.  Same thing with Twitter, Photoshop, Pinterest. Need to share files with a team? Dropbox keeps everyone on the same page.


When you’re in your hometown working, there’s nothing like having a workspace to call your own.  The free beer, coffee, events, and other members are just added benefits.  But you really see the value of WeWork when you travel.  My road trip would have been much more difficult on business if I didn’t always have a reliable place to access internet, printers and coffee.  Even with day trips to any major US city, chances are there will be a WeWork close by, ready to provide you a productive space to work.


I’ve been through so many free and paid customer relationship management (CRM) suites, yet nothing compares to the utility of Pipedrive.  Unlike all other CRMs, it’s very visual, so with a quick glance you can see where each account is in the sales cycle.  The entire platform is very customizable too– you can set what information to display, what information to collect, and pull reports to keep track of key metrics on your sales process.  If you want the most efficient and profitable sales process ever, you need to be using Pipedrive.

Accounting in the cloud

The days of having Quickbooks on your desktop and not having it accessible on any other device instantly are dead and gone.  Today, it’s possible to use an accounting system that pulls real-time information from all of your bank accounts, your CRM, your email marketing software, your website and everything else, automatically completing a lot of tasks that used to be done manually.  My favorites are Xero and Quickbooks Online.


If you’re starting out small, chances are you can’t have one landline for your business phone number because you might not always be at your desk to answer it.  Ringcentral allows you to route your business number to your cell phone or multiple landline phones, giving you complete freedom on where you can answer business calls.

Google Docs

Even though I prefer Dropbox for cloud storage, I prefer Google Docs when it comes to building documents.  When they’re on Google, not only are they easy to collaborate on, but they are automatically backed up so you can revert to a past version whenever you want.


Trello is a great platform for streamlining an organized workflow. Many people use it for managing team collaboration on things like content generation, but it’s a very flexible platform so you can customize it to fit your needs.


In many major cities, it’s usually cheaper and faster to take an Uber than to take almost any other form of transportation.  Time is money, so this is a no-brainer.  If you’ve never taken Uber before, do yourself a favor and download it and try it once– use code ta4q2 for a free ride up to $20!


Airbnb is usually cheaper, easier and more comfortable than a hotel. You have the option to rent out a common space, a private room or an entire home, so whatever you need and your budget permits, Airbnb can accommodate you and make your travels cheaper and more comfortable.

There you have it.  Did I miss any?  Which tools are most useful for you?  Leave them in the comments below!

Join Our Weekly Email Of DC Startup News & Political Analysis
I agree to have my personal information transfered to MailChimp ( more information )
Get our once-a-week email of the latest DC startup news and political analysis
Completely free. You can unsubscribe at anytime.
Stephen Steinberg

Stephen Steinberg

Stephen is the Founder of Vapor Fresh, a line of safer plant based cleaning products for the sports & fitness industry, as well as Founder of Animate Yerba Mate, a brand bringing quality unsmoked organic Yerba Mate teas to the USA.