Career Break Advice: 10 Steps for planning your trip

Nov 10, 2013

Planning what you’ll do on your trip and where you’ll go is easy and fun. Planning to make the trip possible isn’t as glamorous but far more crucial. A good plan can’t be overlooked. You need to figure out how to save the money you’ll need for the trip and how to keep yourself inspired. Follow these tips to get things going and stay motivated. 

  1. First, pick a date. Set your sights on the day you want to leave and work towards it. Be realistic though. Missing an overly aggressive date can drain your resolve and may cause your plans to fall apart. 
  2. Be flexible with your date. Have a general idea of when you plan to leave but remember that between now and then, other things will happen and you may need to adjust a little. Don’t let this go too far though; if you have to move your date try not to let it move by more than a month or two.
  3. Socialize your plans starting with the people closest to you. This step allows you to bounce the idea off other people and creates social pressure to keep you on track. If you’re in a serious relationship, married, or just planning the trip with someone close to you, make sure they have bought into the idea and are fully on-board. The buddy system works and if you’re anything like us, your weak moments will be offset by your partners strength. As you socialize the idea outwards to others in your circle of friends, you start creating positive social pressures that will keep you on track.
  4. Set small goals by breaking your plan down and setting more easily achieved milestones. Reaching these milestones will keep you on track by preventing your determination from being eroded when you look at the calendar.
  5. Figure out the cash and start saving but focus on debts first. How much attention you need to give debt is different for everyone but I chose to open a savings account specifically for the trip and pay into it a little every pay-period while I hacked away at the debt I had. Now my debts were pretty small, I owed about $10k on my truck, $1700 on some furniture, and about $1k on a no-interest credit card. Once I put all my effort into it, paying those debts down took very little time. Jen on the other hand started with some serious school debt and her main focus has been paying it off before we go. If you’re in the same boat, then you’ve got your work cut-out for you but don’t let it stand in your way.
  6. Reign in that spending. Seriously, decide what you have that you can’t live without and consider everything else expendable. Do you really need cable? Unless having it helps you make money then the answer is no, you don’t need it. You don’t have to cut out all entertainment but at the very least, compromise for Netflix or allow yourself a RedBox rental every few days. Another big drain on your spending is going out. We still go out but when we do, we spend very little, maybe $15 dollars between the two of us, which is about one drink apiece. How you ask? Well a little self-control goes a long way but you can also get creative and pick up a flask. We like Rum Runner flasks. Friends may look at you funny and ask what the heck is wrong with you but you’ll be laughing all the way to the bank and during your epic trip while they sit in the same crummy bar catching up on your awesome photos from the road.
  7. Get a second job, or even a third. I know, it sucks, but you really need more money and the extra cash will go to good use. Not to mention, the extra time you spend working will be time you won’t have to spend money. I, for example, took a Valet job that required me to work most Friday and Saturday evenings; prime times to spend your hard earned dough and cut into your savings. Jen took on a few jobs like coaching volleyball and a part-time gig working the front desk at a yoga studio.
  8. Find a way to keep yourself on task. Don’t get derailed by things that may seem important at the time. You may think that a short 2 week trip somewhere is essential to keeping yourself on track but it’s probably going to set you back way more than it’s worth and could jeopardize the entire plan. Keep reaching those milestones and don’t let your focus shift, especially when you see your bank account growing.
  9. As you get closer to the date you set initially, start getting rid of stuff. You can do this earlier and I encourage some purging of “stuff” at regular intervals while you’re working/saving but when you get to within a few months of your departure date, sell everything fire-sale style. Storing crap can be expensive and the money you’ll save will go to far better use.
  10. Within about two months, carry out your exit strategy. Remember to be respectful of your employer when the time comes.  Give them adequate notice and be sympathetic to the challenges they’ll face in filling your role. You may want to say, “take this job and shove-it” but don’t. Sure, it might feel good for a second or two but you shouldn’t burn any bridges. The trip doesn’t start until the wheels on the plane come up and who knows, you might come home and want your job back.

There are a million ways to attack this and everyone’s situation will be a little different so we kept things very general here. If you want more specific information about each one of these steps or what we did, look for similar posts with the key words “Planning your trip” in the title. Have a comment or a question, leave it below.


Roam On. 


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