One of the biggest obstacles standing in the way when people begin to think about traveling, is money.

Do you have enough saved? Do you have anything saved? Will you need to supplement your savings by working while abroad?

And if so, how long do you intend to work? Will you get a working visa, or look for cash-in-hand jobs?

These are crucial questions to ask yourself in planning a trip. And the answers bear a good deal of weight in deciding the length of your trip and what you decide to do once you’ve embarked.

First of all, the amount you have saved is usually the main determining factor in deciding how long your trip will last.

There are a few fixed expenses, such as airfare and gear for your trip but the majority of your funds will be gobbled up by daily expenses such as hostels, transportation, food and entertainment (i.e. alcohol).

This amount increases with the amount of time you travel, so the length of your trip is usually decided by constructing a rough daily budget and determining how far your dollars can take you (hint: overestimate the cost of everything, just to be safe.)

Alternately, if you’re like me and decided to take a fairly long trip on short notice, you will probably be planning to work while traveling rather than relying on your meager savings to tide you through.

There are two ways to go about doing this, either (1) apply for a working holiday visa or (2) look for jobs that pay cash under the table.

Applying For a Working Holiday Visa

Rules differ in each country so make sure you read all the fine print before applying, but usually you are eligible to receive a limited amount of working holiday visa’s in your lifetime – in some cases, only one – so plan to work for at least a few months in order to make it worthwhile.

Why get one at all? Well, many “regular” jobs require you to have one in order to legally employ you, your job pool is increased by being able to legally work and the ease with which you’ll be able to find employment will increase with the amount of jobs available to you.

The downside is that you will be taxed on your earnings. Some countries are eligible to apply for this tax back but it can be quite a lengthy process.

Cash Under The Table

If you choose not to apply for a visa, you’ll be relying on finding cash-in-hand work. This means you’ll get paid in cash for any work you do and accordingly, you won’t be taxed on your earnings.

Strictly speaking, this is illegal in most countries, but it’s also a commonly used way to earn extra cash while traveling – whether or not you’re okay with that is a personal decision.

Cash-in-hand jobs are usually for shorter durations and the work tends to be casual, but it is usually possible to find steady employment that pays enough to finance your nightly accommodation and bar tab.

Finding these jobs is a bit tougher as they can’t be advertised through regular channels like help-wanted ads or online postings. Hostel job boards are a great resource, as are other travelers – when they move on they often leave a job opening in their wake.

One last tip: be open minded. Jobs you have while traveling don’t need to be career-advancing, life-fulfilling work; they just need to pay enough to feed and house you for the duration of your trip.

It’s always useful to draw on your experience, interests and talent, but don’t be afraid to leave you comfort zone and try something new.

If nothing else, a weird and wonderful job will make a great story to take back home.

Madeleine Somerville is a big city girl living in small city British Columbia, where she works as a newpaper columnist. She has travelled to Thailand and Japan and most recently came back from a few months of sun and sand Down Under.

Do you have any tips for earning income on the road? Share in the comments!