The letter has been sitting in my email draft folder for three days. I have rewritten it four separate times. Months of planning, thousands of dollars spent, endless hours of talking to friends, so over, hearing about the “trip” had brought me to this point. I was at the precipice and still could not pull the trigger.
Once again, I hit SAVE and not send.
When I began my dive into the rabbit hole of the bike touring and bikepacking subcultures, I discovered some things upfront. The first being that biking across the country was not all that special. Thousands of people have done it. There are whole routes, maps, blogs, documentaries, and YouTube videos about people who have done it already.
The second thing I discovered, lightening quick, is that biking across America was not really that ambitious. Sure, it's 3700 miles from end to end. But when you binge watch three years’ worth of videos on YouTube about a guy that biked around the world on a unicycle, one continent feels “Meh.”
Traveling across vast swaths of country by bike is something thousands of people do each year. Some bike and stay in hotels. Many camp out in national parks, or campgrounds. A bucket load wild camp, especially in countries outside the US and Europe. Talking to the people who do this is fascinating, but one thing that puzzled me at the beginning of my planning was the time. Biking a thousand or more miles takes time. Lots of it.
Which can only lead to one question and one I asked nearly the moment I joined the Bike Touring and Bikepacking group on Facebook (54,000 members) “Dude, like what do you do about your jobs?”
It did not take long for the question to rack up a few hundred responses. A few went in the direction that you might expect; retirees, people using vacation time, leaves of absences, or sabbaticals. Most of the responses, however, were alike in tone. They went something like this:
Just quit. There’s always another job.
Young or old, high-paying job, or low-paying job, it did not matter. There was general agreement that seeing the country in the way a bike allows you to do is worth two paychecks. Everyone’s advice was simple; save your money, keep expenses low, camp whenever you can, quit the job. Come back, get a new job or the old one back, rinse and repeat.
I do not know why hearing variations of this theme surprised me, but it did. Everyone was so casual about it. And I say that as someone who has never thought of any job or career, short of being POTUS, is the most important thing in the world.
So, what about my job? A job that pays well is with a well-known corporate brand with extreme job security. I have a manager that I like even when she is busting my chops to get a few more sales or to be nicer to other departments. A job with co-workers I like—though Covid keeps me from seeing them for now. How was I going to handle my personal situation?
My company does not have a sabbatical program. Leaves of absences are only for serious medical issues, or new parents. I have vacation time, but not three- or four-months’ worth. My options were to not embark on the trip or quit.
And what about when I’m finished with the trip? When I get back home, I still have bills to pay and a brother for which I am responsible.
These are questions I asked at the beginning of this planning process, it was not however why I could not send my resignation letter to my manager. As important as those concerns are, something else drove my hesitancy. What that is, I do not know.
If you ever find yourself in a similar situation, here is my advice. But discovering what is holding you back aside and instead focus on what you know. I knew I wanted to go on this biking expedition. I knew that waiting a year was not something I wanted to do and doing so would only delay the same decision. I knew I could not picture spending the rest of this summer on the phone in front of a computer. In my mind, I was already pedaling down pathways, through tunnels, and grilling beside creeks and rivers.
I was already gone. It was just time for my body to catch up to my heart and mind. So, I finally hit SEND.
