Work Anywhere Road Trip, Part 1: Pondering & Preparation

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.

I’ve always believed that working remote meant you can literally work from anywhere, anytime.

I’ve worked 100% remote since 2008 in many settings, including my quiet home office, coffee shops worldwide, in a car, on a flight, and national parks. 

Between 2007 and 2017, I ran a work-from-home (WFH) startup — now acquired by a public company — with awesome employees, processes and tools, which enabled us to build a scalable platform with millions of users worldwide. So, I’m a huge believer of remote work!

I also love to travel domestically and internationally, with my family or solo. I usually take a couple of short, solo trips per year to do some offsite business and life planning. Solo trips help me be more creative, get clarity and return focused on what matters most. 

As it probably did for millions of people, the COVID-19 pandemic killed all my near-term travel plans. I was getting restless — I had to get innovative.

An Idea Is Born

Have you ever aspired to go for one or more things on your bucket list?

Ever since I got my Tesla 3 (in 2018), I had been thinking about taking a long road trip to see how far I could drive it, while working remote in cool places along the way. It became part of my bucket list and something I was determined to check off.

I began wondering if I could drive the car from Virginia (where I live) to Colorado or San Francisco, for the following reasons:

  1. I LOVE the west coast and try to visit places like the Bay Area, Seattle and Boulder, any chance I get. I enjoy working on important business projects at these types of places (e.g. annual company strategy, investor deck, write a book).
  2. We lived in the Bay area for a couple of years and I visit often, since I still have close friends there and have ties to Silicon Valley for my software work.
  3. Coast-to-coast felt like a cooler accomplishment. 

I decided to drive to San Francisco!

Working Up The Nerves

I’m not sure about you but I can be one of the most indecisive people. Sometimes, I wonder how I ever accomplished anything in life.

Even though this was a bucket list item for me for the past couple of years, I was very nervous about taking this trip. There were so many things to worry about: Tesla has no spare tire (my #1 concern), potential Tesla motor/other problems, pandemic safety, political climate in some states, missing work time due to the extensive driving, and so on. 

I was on the fence about taking the trip and kept asking my wife and kids whether I should do it. They were thankfully very encouraging (or, maybe they just wanted me out of the house.?).

However, I still needed something to push me over to one side or the other. I almost backed out till an email from Red Rocks Amphitheatre (in Colorado), dropped in my inbox.

The Push I Needed

I’m not superstitious but sometimes you have to believe in tiny signs from above.

I visit Colorado a couple of times a year to attend a Red Rocks concert or ski in the winter. This year, all concerts were understandably cancelled. As if it was a sign from above, Red Rocks announced a concert, Colorado Symphony Acoustic On The Rocks – Brass & Percussion!

I was pleasantly surprised, given the COVID-19 concerns. Also, normally, I go for Classic Rock, Reggae, Rap, or Jazz concerts but at this point, I was willing to listen to any kind of music at Red Rocks. 

I bought a concert ticket. I was committed.

Research & Planning

Now, came the tedious task of preparation. It wasn’t like I was climbing Mount Everest but it was still nerve-wracking and I wanted to be fully prepared, to make the trip go as smoothly as possible.

You probably have a system for preparing for trips. I’m always curious about the process and tools people use to plan out big projects.

Here’s a list of things I looked into:

  1. Tesla: Service centers
  2. Apps: Tesla (e.g. Go Anywhere map, factory mobile app). Third-party apps; e.g. A Better Route Planner (ABRP), Teslafi, Stats, PlugShare. 
  3. Laws: State, toll roads (e.g. Illinois has annoying tolls).
  4. Money: Notified credit company of my travel plans. Withdrew backup cash, including some small bills for tolls.
  5. Lodging: Hotels around superchargers. I called a couple to check their pandemic cleaning policies.
  6. Emergency: AAA membership. Kit (air compressor, flares, flashlight, tire repair, first aid, etc.).
  7. Documents: Driver’s license, car registration. Medical and auto insurance. 
  8. Tesla: Tire pressure, extra FOB key. I called Tesla to ask whether I needed any servicing before the trip; unsurprisingly, they basically told me: nope, look up service centers on the route and… enjoy the journey.
  9. Return: Car shipping services (e.g. Ship a Car Direct, Reliable) and one-way flight prices, for return trip. I didn’t want to drive back and was willing to risk taking a flight back with a mask on, the whole time and the vent blowing over me.

Road Trip Plan 

Using Tesla’s Go Anywhere map, I found two routes between Tysons Corner, Virginia and San Francisco, both approximately 55 hours (including charging):

  1. Map 1 – through Indianapolis, Kansas & Missouri
  2. Map 2 – through Chicago, Des Moines and Nebraska

One of my favorite family members recently relocated to Des Moines for work — we love hanging out and drinking whiskey and the trip was only an hour longer, so it was an easy decision.

My planned itinerary for the first leg of the trip, looked like this:

My Tesla 3 has an approximate range of 300+ miles, which meant I would likely stop every 2-3+ hours to charge. During the 15-45+ minute supercharging sessions, I planned to either work, get some exercise or grab food.

I also signed up for a A Better Route Planner (ABRP) and Teslafi. Both apps require a username and password (or API key), which was a bit unsettling at first (I’m big on security and privacy) but these apps are highly recommended and widely used, so I went for it. 

If you’re using any other apps or websites, please let me us know via twitter.

Packing List

The last step was to pack and head out first thing the next morning.

Thanks to it being summer time, I was able to pack light in just one medium sized duffle bag and a laptop bag; stuff like snacks, pillows, etc. went in the car.

Here was my final packing list:

  1. Tesla: Charging cable and extension cord (in case I needed to charge from a hotel). Unfortunately, the Tesla spare tire kit I wanted, wasn’t available till a month after my trip, so I decided to do without a spare (even though it was my #1 concern).
  2. Nutrition: Food, water, drinks.
  3. Wear: Clothes, shoes, hats, etc.
  4. Digital: iPhone, Laptop, iPad, AirPods, charging cables, tripod. USB drive (for Tesla Dashcam). 
  5. Cash: Money, credit and debit cards. 
  6. Documents: AAA, insurances, driver’s license.
  7. Pandemic: Masks, rubber gloves.
  8. Sleeping: Pillow, blanket and a twin airbed (in case I wanted to sleep in the car, at a campground — apparently, some people have done that).
  9. Etc.

Onward and Upward

I was nervous about this trip but equally excited about getting out there. My hope is these posts encourage you to push the limits of remote work, now more than ever!

And, if you already have been pushing the limits, please tell us about it on twitter.

Read Part 2

See all parts of this multi-part series.