Home Articles Want to Be a Snowbird Entrepreneur? Here’s How to Make It Work

Want to Be a Snowbird Entrepreneur? Here’s How to Make It Work


Florida is a temporary home to millions of so-called “snowbirds,” who only live in Florida during the winter months in an attempt to get away from the cold weather.

If you own a business, you might be interested in becoming an entrepreneurial snowbird, living and doing your work in Florida during the roughest months of the year.

But how can you make this work?

Choose the Right Line of Work

First, it’s important to choose the right line of work. Not all businesses and not all industries are suitable for this type of arrangement; in many contexts, it’s better to stay in physical proximity to the core business. Of course, in other contexts, physical presence isn’t necessary at all, and may even be a detriment.

If you’re starting a business from scratch, you can build a business with the explicit intention of making it manageable remotely. Depending on the skills you have, you could start an independent business offering services like freelance photography, freelance writing, consulting, or even financial management. Otherwise, you’ll need to build and develop the business in a way that allows you to sustain the snowbird lifestyle.

Use a Virtual Mailbox Service

One of the best services for sustaining your snowbird lifestyle is a virtual mailbox service.

According to Lucas Seyhun of The Farm SoHo, “We see a lot of NY-based businesspeople using a virtual mailbox for the half of the year – when they’re living in Florida to get away from the cold weather. It’s a solution that allows them to do their work anywhere.”

With a virtual mailbox service, you can establish a consistent business address, where you can receive all the physical mail and packages addressed to your business.

You can have the mail remotely scanned, and then view it at your leisure, wherever you are, as long as you have an internet connection. You can also have the mail forwarded to your current address, wherever it happens to be, or have the mail professionally managed.

When you can store all your packages, cash all your checks, sign physical contracts, and more, being a snowbird entrepreneur becomes much easier.

Prioritize Connection

If you’re going to manage your business remotely and successfully, you need to prioritize your connectivity to the internet. Unless you’re online, you probably won’t be able to stay in touch or access the critical services that keep your business running. That means establishing a secure, reliable internet connection wherever you live and work in Florida – but also having multiple backup plans, such as Wi-Fi hotspots, to keep you connected during outages.

Hire, Train, and Prep the Right Leaders

If you’re going to be away from the business half the time, you’ll typically need good leaders to handle things in your stead. Of course, if you’re a solo entrepreneur, this may not apply to you.

When hiring new people, pay attention to strong, intrinsic leadership qualities. Most people can be sculpted into good leaders with proper training and mentorship, but some people have more of a natural inclination to become good leaders. Focus on these individuals, grant them more autonomy, and help prepare them for roles as interim leaders when you’re away from the office.

Take a Trial Run

If you have a developed organization and a full team to work with, take a trial run before leaving the business without your physical presence for half a year. Consider leaving the office for just a couple of weeks to get a feel for the conditions; what problems arise? What inefficiencies need to be dealt with? How can you optimize this to be better for everyone?

Look Into Insurance

Traveling can present some insurance challenges, so make sure you have solid health, liability, and life insurance policies to cover you. Always check the fine print to make sure your policies remain active in the locations where you choose to be.

Create Clear Emergency Protocols

It’s important for any business to prepare for emergencies, but it’s even more important if you’re going to be away from the physical business for any length of time. Create clear emergency protocols so your leaders are united in how they handle various circumstances that may arise when you’re gone. Additionally, it’s a good idea to make sure you’re able to be informed of the emergency and act accordingly as the situation unfolds, even if you’re in Florida for the winter.

Stay Flexible

Becoming a snowbird entrepreneur can be difficult, and it’s certainly going to present some unexpected challenges if you’ve never lived this lifestyle before. However, with proper planning, attention to detail, and a good team to ground you back home, you should have no trouble eventually making this a success.