Yesterday was my husband’s last day at his day job. Should you quit your job to travel? Have you been planning a long road trip and dream of being able to travel for more than two weeks?
Most people cannot afford to simply quit their job and travel full time, where is the money coming from?
My husband and I have done a lot of creative scheduling to fit in more family time and more travel.
By creating a flexible schedule at your current job, working remotely or planning ahead you can travel and keep your job. If you get creative, you can find ways to stretch your two weeks of annual vacation into epic adventures for yourself and your family.
If you’re determined to quit, skip to tip 7!
Get Creative with Your Current Job
If you are hoping to take a long vacation, but you are stuck at a job with 2 weeks of annual vacation, see if you can change your schedule.
Maybe you love your job, you don’t want to lose it, but you need a break, or you need a trip.
My husband and I were able to negotiate going from 5 days a week to 4 days a week for a few months. He was the only one doing this schedule, and it was a very traditional blue collar job. This could be a great way to get in a lot of adventures without losing your job.
I gave a few more details on our journey in this post.
Look at your job and see if there are any slow days?
Could you work remotely one day a week?
Come in 90 minutes early all week and have Friday off?
What about a slow season at work, could you take an unpaid week off?
If you are an excellent employee, your employer may prefer to have you 4 days a week rather than zero.
Plan to Quit
If you are not happy at your job and you plan to quit, write out a budget for that dream vacation.
Work just long enough to save that money plus a month of expenses and when you quit, take the vacation, then come back and start the new job.
This is easy in some professions where the demand for employees is very high. In many professions it is not negative to have a short gap in employment if it can be explained.
Plan out that vacation, it will be such a great motivator to save that money fast!
If you are more cautious, start the search for the next job and get a feel for the job market. In some industries it is not uncommon to be hired then start work a month later, and some want you to start right away.
You can also fill out applications and enter a later start date. For example, if you are quitting in July, fill out applications and indicate that you are not available to start work until September.
If you are not a natural budgeter, use my tool to budget for a whole year of vacations so that you already have that cash ready.
Find a Remote Job
This might be the most obvious one on the list.
Since March 2020 more and more companies are offering remote jobs.
When I talk to people who are traveling often or full time, the biggest question is ALWAYS about income. How do you afford to travel full time?
The answers always roll in:
Health Coach
Small Business
Freelance Writing
Mortgage Underwriter
MLM
The truth is, there are a lot of ways to work while traveling. Here are some great ideas that are not scams.
Become a Teacher
If you have ever considered entering the teaching profession, this might be the time. Many states have career switcher programs that hire professionals and pay for their teacher training.
You do not have to already have your teaching license to be hired in a school district.
We all know that teacher pay is low, and the numbers will be posted publicly for each school district because teachers are government employees. Take a look and see if the salary is comparable to your current job.
Teaching is a tough profession, but the schedule is great for traveling. You have 2 months off every summer and 2 weeks at Christmas time. You get Spring break too!
This is a very rewarding profession and gives you a great opportunity to live a meaningful life and travel the world.
Check out this amazing video from Real Rap with Reynolds who is the coolest, most inspiring teacher I know on YouTube.
Max Out 3 Day Weekends
Consider planning your whole year of vacations at once.
Sit down with a calendar and mark out all the three day weekends, breaks, birthdays, holidays and other special occasions that offer a vacation opportunity.
Could you beef up these weekends with a few personal days? Could you split up your 5 vacation days over 2 three day weekends and end up with 2 long vacations?
Do everything you can to take advantage of scheduled days off.
This strategy will truly maximize your vacation time. Using these built in days can turn a three day weekend into a week long getaway.
Here is a quick list of all the American three day weekends in 2021
The obvious drawback of this strategy is that you will be traveling at very busy times. If you have ever driven to the beach on Memorial Day, you probably know this.
That is exactly why we need to add those vacation days, you will skip lots of traffic by driving on a Wednesday night and getting home on Tuesday.
Travel for Work
If none of the other options offer you enough travel time, find a job where you travel!
There are a lot of jobs that involve lots of travel:
Truck Driving
Travel Nursing
World Wide Opportunities for Organic Farming
Tour Guide
Cruise Ship Employee
Flight Attendant
Au-Pair
These jobs are great for adventurous singles or flexible couples. If you can snag one of these opportunities then buckle up for some big adventures.
My husband and his father are both career truck drivers and the hours are long. It can be a great way to see the country and getting the proper licence only takes 4-6 weeks. It could be a great gap year job.
Families who want to travel more often might need to find remote work to pay the bills while road tripping.
Joining any RVing Facebook group will give you lots of ideas for making money on the road.
Work Towards a Big Payout
Now, you are sure you want to quit, can’t take it no more, no turning back, then you need to start to stash cash.
Plan out what you want to do after you quit, cruise for a month? Visit Europe? Write it down and see how much it costs. Post pictures on your fridge and get to work.
Give yourself a timeline, maybe 2 months, and do everything you can to earn extra money.
Pick up an extra shift, add a side hustle like Uber Eats and fill up that bank account.
Keep your eyes on the prize and cut your expenses to the bare minimum.
Then take 2 or 3 months off. Live the dream.
Bonus Tip: Use Anticipation
I know that there are jobs that are just soul crushing. It is just a struggle to go to work each day.
If this is where you find yourself, plan a vacation.
I read a bunch of research for this post and I am really proud of the great tips in this post.
Research tells us that building anticipation for a trip makes the trip less stressful and spreads out the benefits of relaxation, better sleep and reduced stress.
It is easy to be happy when you have something great to look forward to, so put something on the calendar.
I have some great ideas for almost free vacations, $100 vacations, and a budgeting printable for planning a whole year of vacation.
Plan trips and look forward to going on them.
I hope this post is helpful for you.
This site is all about encouraging families to live their dreams.
Maybe it is time to quit your job, but maybe you can get creative and still live the dream with a bit more financial security.
