Work Anywhere Road Trip, Part 2: Virginia to Colorado

Get inspired about the limitless possibilities of working from anywhere at anytime — read this blog series about a 11-day, 2800+ mile cross-country journey, from Virginia to San Francisco.

Boulder Flatirons

After much pondering, planning and preparation (see part 1), I was about to start driving on a cross-country road trip…wow!

Due to the COVID-19 pandemic, many of us might feel cooped up because we can’t travel freely, have to work at home (think Zoom burnout) and might also have kids attending school at home.

However, if you think about it, it’s actually a good time to getaway for a few days, month…or more, if done safely and responsibly. Why not temporarily relocate, if you can?

I hadn’t taken my usual offsite business and personal planning trips all year, so I was definitely getting the urge to travel. I began getting excited about working in remote places with amazing scenery, particularly in states like Colorado, Nevada, Utah, and California.

Ready to leave home for a 11-day, 2800+ mile, cross-country road trip

I also like to inspire readers like yourself to work from anywhere, as I’ve been doing since 2008 — I figured I could blog about it (like I’m doing right now).

It was time to hit the road!

The Drive To Colorado

My goal was to get to Boulder, Colorado, over a three-day period, passing through Des Moines. I planned to stay four nights in Boulder to break up the journey to California, in two parts.

Tesla Go Anywhere Map – Tysons Corner, VA to Boulder, CO

I typically visit Colorado at least once or twice a year to work offsite and enjoy the beautiful outdoors (e.g. hiking, concerts at Red Rocks Amphitheatre, skiing).

Eager to get to Colorado, I mapped out the following three-day plan:

  • Origination: Tysons Corner, Virginia (location of first ever Apple Store in the world)!
  • Destination: Boulder, Colorado.
  • Journey: 1700+ miles. Approximately 34+ hours of driving, including Tesla supercharging.
  • Overnights: Friday (northern Indiana/Illinois), Saturday (Des Moines) and Sunday (Boulder). Not knowing exactly how much I could drive each day, I didn’t book any hotels in advance.

Day one was about building confidence in long distance driving in my Tesla, understanding how the pandemic is being handled by people in various states and seeing how much I can drive in one day.

To my surprise, on day one, I spent 15 hours (including charging stops) traveling 670+ miles and still wasn’t exhausted, since I managed to work in the hotel at night.

I believe this was largely due to the fact that the 30-45 minute Tesla supercharging stops, force you to take breaks versus rushing the journey — a much better way to travel, in my opinion.

Tesla Supercharger, Cranberry Township, PA
Tesla Supercharger, Davenport, IA

I was much more relaxed on day two, since I had gotten comfortable with long distance driving, I was looking forward to seeing a favorite relative in Des Moines and it was the weekend, so I wasn’t worried about work (although I end up working on my phone anyways, often on G Suite and Trello).

I left around 10am from Munster, Indiana, arrived in Des Moines around 5pm and had a great time hanging out with my relative!

Saylorville Lake, Des Moines, Iowa

Day three was going to be a longer, ~14-hour drive type of day…but, I didn’t care since I was really jazzed about reaching Boulder, Colorado. You know how that goes: when you’re excited about something, you’re willing to put in the effort.

I left around 7am. On the way, I managed to get a nice hike in on a beautiful nature trail, at a supercharger stop.

Old Stone Arch Nature Trail, IA

After a long day of driving, I finally made it to Boulder!

It was quite a sense of accomplishment to see the Flatirons, right around sunset…in my own car, versus a rental car rented from the Denver airport.

Flatirons, Boulder. End of leg 1.

I was excited about spending the next three days (four nights), in Boulder. My plan was to:

  1. Work in the hotel, coffee shops and around nature
  2. Do some walking and hiking daily
  3. Watch a concert at Red Rocks Amphitheatre (in the middle of the pandemic!)

Working Anywhere

I had planned to work pretty much anywhere I felt like…on scheduled and unscheduled blocks of time or whenever I had a brilliant idea…on my laptop, phone or iPad.

Nowadays, cloud/mobile apps make it easy to work anywhere, anytime.

In Boulder, I had planned to work in coffee shops, my hotel, national parks, and Red Rocks.

Working In The Car

At the 30-45 minute Tesla supercharger stops during my three days of driving, I worked in the car, if I was not grabbing food or walking. I find these short periods of work are nice to continue on a larger project or to get “quick hits” of work done (e.g. call, emails, Slack).

Working in the car using personal hotspot on a supercharger stop
Working momentarily while driving on Autopilot

Working In The Hotel

What would work travel be without working at your hotel?

I figured if I’m going to work in the hotel, it might as well be with a view of the Flatirons.

Working on a business plan deck out of the hotel

I was able to get some business planning done one afternoon, after a Skype video interview that morning.

Interviewing Gene Reichert from the hotel on Skype video (with blurred background)

Working On A Mountaintop

I worked on our website design and part 1 of this blog series, on top of the Flatirons, for a couple of hours. I also responded to some emails and Slack messages.

Working on website design (WordPress) on top of Flatirons
Working on website design (WordPress) on top of Flatirons

I used personal hotspot on my iPhone with AT&T. I had approximately two to three connectivity bars — it can get spotty on mountaintops but I find moving to a different location helps.

Working In A Coffee Shop

Working in coffee shops on Pearl Street in Boulder is one of my absolute favorite things to do!

Three of my regular coffee shops include OZO Coffee, The Laughing Goat and Boxcar Coffee Roasters. I was able to spend a late afternoon working at OZO, on this trip.

I love these occasions, since I can typically get a couple of hours of focused and productive work done, often on some business strategy, important project/presentation or a blog post (like this one).

Sometimes, it’s just nice to daydream and imagine where you want to take your startup or how you want to improve your personal life.

Working on website design at OZO Coffee, Boulder, using their WiFi

Sadly and unsurprisingly, with the pandemic, it just didn’t feel the same working in coffee shops, since they were only doing takeout orders with limited outside seating. Nevertheless, I was glad to have their awesome coffee while watching the sunset over Flatirons.

Working Elsewhere

There were occasions while driving, when I stopped at a scenic spot and worked standing up, just to take a break from all the sitting.

Editing blog photos at Red Rocks before concert starts

All in all, I was able to conduct meetings, work on the website, write blogs, do business planning, delegate tasks to my staff, and more, without missing a beat.

I used the following tools:

  • iPhone: Phone, Maps, Mail, Notes, Health, Compass, etc.
  • Laptop: MacBook Pro, Personal Hotspot, Safari, G Suite, Trello, Slack, WordPress, Medium, Buzzsprout, Google Analytics, Calendly, LinkedIn, Twitter.
  • Tesla: factory app, A Better Route Planner, Teslafi.
  • Other: iOS Photos, Google Photos, Spotify, Yelp, Skype, etc.

Work-Life Balance

If you have ever worked in a startup, you probably know it’ll take everything you can give it.

I regrettably learned a bit late in life that having the right work-life balance is vital to good physical and mental wellbeing. Nowadays, I advise everyone to have the right work-life balance and not make the same mistakes I did.

I had planned to work partially on driving days (e.g. at supercharger stops and hotels), full days on non-driving days and a bit on weekends and evenings. However, it was very important for me to set aside ample time for exercise, nature and entertainment, to enjoy the journey.


Nowadays, I love to walk every morning and evening, while listening to music or nonfiction audio books.

On the first few days of this trip, I was able to get an average of ~12k steps per day, mostly on supercharger breaks (1-5k steps per stop) and the remainder after I arrived at the hotel.

Of course, keeping myself and others safe in the pandemic was priority #1, in the wellbeing department. It was interesting to see the different mask laws in different states, with Colorado being the strictest on my route, so far.

Mask laws in Colorado

On the wellbeing side, there’s nothing as rejuvenating as the great outdoors. As you know, long drives can provide hours of beautiful scenery. I took in as much as I could while driving and also on scenic stops.

Scenic drive

Colorado is all about outdoors, so I hiked every day, namely at Chautauqua Park and Red Rocks area.

Having visited places like Rocky Mountain National Park, Pikes Peak, and Garden of the Gods, several times before, I decided to skip those this time, to limit the driving, take in the local scenery, chill, and work.

Deers on a hike at Chautauqua Park

Of course, if you love music and food like I do, you’ll get your fair share on the road.

Delicious Indian food in Boulder area


I got countless hours of enjoyment listening to classic rock and chill/lounge music (on Spotify), while driving and walking. I don’t listen to classic rock much these days, so the experience was a bit nostalgic and rejuvenating (even if it made me feel old).

Ssshhhh…I was even able to watch my Sunday morning news shows on an iPad (YouTube TV, personal hotspot), while driving on Autopilot.

One of the highlights of this leg of the trip was a music concert at Red Rocks Amphitheatre: Colorado Symphony Acoustic On The Rocks – Brass & Percussion. This wasn’t my preferred rock, reggae, rap, or pop music, but given the lack of music concerts due to the pandemic, I was willing to listen to anything.

Concert at Red Rocks in the middle of the COVID-19 pandemic

On one hand, I was glad to see a concert in the middle of a pandemic, on the other hand, it was depressing to realize that masks and limited capacity seating, were a new reality for the near future. For example, compare the couple of hundred attendees with masks in the photo above, to a concert at Red Rocks I saw in 2019 (photo below).

Thievery Corporation at Red Rocks

Takeaways From First Leg

Within the first few hours of being on the road, and certainly by day two, I was extremely comfortable and thankful my wife and kids encouraged me to do this because it was the push I needed.

My main takeaways from the first leg of this trip were:

  1. Fear: “Only Thing We Have to Fear Is Fear Itself” -Franklin D. Roosevelt
  2. Travel: The first three days of driving were a lot easier and smoother than I had hoped. I really enjoyed working and doing outdoors stuff in Colorado. I also had good conversations with people at Tesla superchargers, restaurants and other common areas.
  3. Productivity: There’s nothing like traveling to build your confidence, get clarity and gain focus. You can really get your creative juices flowing by thinking outside the box, when you’re working in remote places.
  4. Nature: Needless to say, it’s really rejuvenating to be in the great outdoors.
  5. Pandemic: The pandemic had turned bustling places into somewhat of a ghost towns with 10-20% of the capacity (e.g. small town downtowns, concerts, hotels). It’s one thing to see the effects of the pandemic in your hometown but it’s another thing to see an entire country operating that way.
  6. Tesla: I’ve enjoyed driving my Tesla every single day since I got it (in 2018) but I fell in love with it all over again, on this trip. Telsa’s Autopilot feature does 90% of driving for you and the extensive supercharger network enables you to take a break every couple of hours, making the entire road trip a breeze.

Now, it was time to continue on with the second leg of my trip…driving from Boulder to California!

Read Part 1 | Part 3

Read other parts of this multi-part series.