For almost every workout, I want to know at the outset two things: how long/far is it going to be, and how hard should it feel? And when it’s over, I know two things: did I finish it? And how long did it take?

I’m old enough to remember when the packing list for Camp Catoctin recommended that campers bring old sneakers for hiking, hand-me-down tshirts, and “nothing you can’t bear to lose.” Since then, I’ve learned that expensive gear isn’t often truly necessary but it can make things more comfortable. But for a trip of this scale, I’m trying to balance what I’ll truly need with an open mind about spending money to make it more enjoyable. Here is an overview of what I’m planning to buy and why. 

I’ll go into a lot more detail about this later, but I use eMoney^[1] for my own financial planning. In Toler Financial Group’s financial planning process, when clients come to us with questions about how to absorb a new, big expense (like a baby starting daycare, for example), we always ask clients to review their most recent 90 days of spending and make any relevant updates to living expenses.

I’m taking March and April off next year to bike from San Diego, CA to St. Augustine, FL. Between now and then, I’ll be blogging about training and planning so that others who might be interested in doing a cross country tour or sabbatical can learn from my experience and figure out how you can take — and fund — significant time off. This trip lives at the intersection of “can I physically do this?” with “can I afford it?”

I’ve put together details of the tax provisions most relevant to our clients and network. As you can imagine, there’s some good news, and some bad news.