Updated 2026: In 2009, I was genuinely excited to discover that American Airlines had rolled out in-flight WiFi through GoGo (originally GoGoInFlight.com). I wrote a quick blog post from the plane, marveling at the ability to work at 30,000 feet for the low price of $12.95. Looking back, that moment captured a shift in how internet entrepreneurs could work, and the reality of working anywhere has changed dramatically since then.

The State of In-Flight WiFi in 2009

When GoGo launched on domestic flights, it felt like a luxury. In-flight WiFi was new, unreliable, and expensive relative to what you got. The connection was slow enough that anything beyond email and light web browsing was painful. But for someone building an internet business in the margins of a busy schedule, those few hours of flight time suddenly became productive hours instead of dead time.

I remember being on that flight thinking about how to angle the GoGo service as an affiliate opportunity. That instinct to spot monetization opportunities everywhere is something I still encourage in new internet marketers. It did not pan out for GoGo specifically, but the habit of asking “is there a business here?” is a good one.

How Remote Work and Travel Connectivity Have Changed

The in-flight WiFi that felt revolutionary in 2009 is now a standard expectation. Most major airlines offer WiFi, and many include it free with premium cabins or loyalty program status. Speeds have improved to the point where video calls and streaming are viable on many flights.

More broadly, the infrastructure for working from anywhere has improved beyond what I could have imagined in 2009:

• Cellular hotspots and 5G provide fast internet access in most populated areas worldwide.
• Cloud-based tools like Google Workspace, Notion, and project management platforms mean your office is wherever you have a browser.
• Video conferencing through Zoom and similar tools has replaced much of the business travel that used to be mandatory.
• Coworking spaces exist in virtually every major city and many smaller towns, giving travelers a professional workspace on demand.

Productivity Lessons for the Traveling Entrepreneur

Having built my internet business while traveling regularly for my day job, I have learned a few things about staying productive on the road:

• Batch your offline work. Despite better connectivity, you will still hit dead zones. Have tasks ready that do not require internet access: writing content, planning strategy, reviewing analytics screenshots you saved earlier.
• Protect your focused time. A plane with WiFi can be a distraction machine just as easily as it can be a productivity tool. Set a clear goal for what you want to accomplish during the flight before you board.
• Use travel time for thinking, not just doing. Some of my best business ideas have come during flights when I closed the laptop and just thought about where I wanted my business to go. Not every minute needs to be “productive” in the task-completion sense.

The Bottom Line

That 2009 flight was a small moment, but it represented something bigger: the internet was becoming truly portable, and that changed the game for anyone building a business on the side. You no longer had to be at your desk to make progress. Today, that portability is so complete that many people run entire businesses from their phones.

If you are building an internet business in the margins of your schedule, whether on planes, in hotel rooms, or late at night after the family is asleep, know that the tools and connectivity have never been better. The only thing that has not changed is that you still have to do the work.

For more on building an online business part-time, subscribe to the Late Night Internet Marketing podcast on Apple Podcasts.