1) Jobs never quite line up.
When transitioning from job A to job B it is usually never a smooth transition. Job A ends, rather than you give them a two week notice and can plan for a short time between jobs. Job B begins, usually at an inopportune time. So you're left waiting. You still have to pay your bills, but you're not making any money and it's just a long enough time that applying for unemployment isn't worth it. And so you live on your friends and families couches who've taken you in again. Because of this I have a room in Ludlow, Barre, Brookfield, Emerado and soon to be Charlotte.
2) Jobs never quite line up.
Sometimes the opposite happens. Job A starts before Job B ends, or because you've applied and been hired so late there is no physical way to get there before Job A starts. Some jobs you can leave early and it's not a problem. They're winding down and it's beneficial for the company to let you go early, no hard feelings, everybody wins. This is generally how it happens after you've been somewhere for awhile, if you've been an employee a company isn't as annoyed to give you a little slack. There are circumstances where companies cannot give you that time. Say for example, you're scheduled to be in the backcountry and you can't leave. Then you get to choose which company you're going to screw over. This is a delicate decision, if you piss off the one you're working for you may not get to come back, or if you piss off the job that you're going to you might be in for a long season of kiss-ass.
When there is no physical way to get there say for example it's Friday and they want you in New Hampshire on Monday and you're in North Dakota, companies are very understanding.
3) Gear
Every job is a little different and so you have to plan for the gear you're going to bring. Now after doing this a time or two I have the big ticket items, backpack, sleeping bag, warm clothes. But then there's always that thing that you don't have. This job it's rubber boots, and yes I really do need them.
4) Organization
Being a free spirit doesn't usually lend itself to organization. Filling out paper work and getting your drivers license and social security card, then filling out other forms that you'll see later when you file your taxes needs to be done before you arrive. It's not like you can walk down the street and hand the stuff over a few days before you start.
5) Travel
I have to get from where I am to where my job is by a certain day. If you have enough time they expect you to be there. Now the question becomes, should I drive? If you drive you have to figure out how many days it's going to take you. If you fly now you have figure out a place to leave your car.
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