How to Start Freelancing

December 23, 2015

Culinary tourism is a big part of what Oobites is about. As a consequence, constant travel is key to expanding the amount of information covered here. I live and work as a traveling freelancer.

There are two ways to start freelancing work. They sit at opposite ends of a continuum between effectiveness and comfort.

But first, a tale:

Berber commander Tariq ibn Ziyad led a combination Arab-Berber force against Spain in the eighth century. Upon making landfall the boats were burned behind them. A colorful retelling of the event describes a speech given by Tariq that begins,

Oh my warriors, whither would you flee? Behind you is the sea, before you, the enemy. You have left now only the hope of your courage and your constancy.

Remember that in this country you are more unfortunate than the orphan seated at the table of the avaricious master. Your enemy is before you, protected by an innumerable army; he has men in abundance, but you, as your only aid, have your own swords, and, as your only chance for life, such chance as you can snatch from the hands of your enemy. If the absolute want to which you are reduced is prolonged ever so little, if you delay to seize immediate success, your good fortune will vanish, and your enemies, whom your very presence has filled with fear, will take courage. Put far from you the disgrace from which you flee in dreams, and attack this monarch who has left his strongly fortified city to meet you….

(The quote is pulled from early modern historian al-Maqqari’s The Breath of Perfume, and the emphasis is added here.)

The soldiers went on to victory capturing Spanish cities Cordoba, Granada, Toledo and Guadalajara. The territory still named “Gibraltar” is a Spanish transliteration of the Arabic name Jabal Tariq.

Put Your Back Against the Wall

The history lesson may be a little overkill, but the point remains: without the option to flee the outnumbered army was able to conquer an entrenched force. This instance is very specific, but the event speaks to something about human ability: you have a vast pool of effort to pull from when your back faces away from an empty sea. There’s only forward.

What’s a boat? Boats for you, burgeoning freelancer, are comforts that you’ve assembled for yourself that you’d find difficulty leaving or would readily return to. They can take many forms and vary in importance from person to person. A cushy job, a bounty of nearby friends or family, a super comfortable room, a well-stocked kitchen, or an ongoing personal project that’s unfortunately location-dependent.

The action of “burning” those boats is an action that’s just as varied.

This event or events can be painful, but actually the actuality pales in comparison to what you can imagine. Often we’re bound by threats that much exceed what will actually happen in real life often making it very difficult to act. For some it’s very easy, and if you’re one of them, you may feel that you have no choice to shed these acquired pieces of yourself for something greater.

Slimming down your possessions can change your life. Saying “goodbye”–or more accurately “see you later”–to friends and family better opens the possibility for new connections. Changing your geography is more than simply shifting where you are on a map; often it’s an entire paradigm shift in thinking and action.

Burning boats doesn’t have to be extreme as burning bridges (to borrow another idiom)–though that certainly would work! Quitting a job without the possibility of return makes for great incentive to become a successful freelancer, but maintaining some past connections can help in other ways. (There’s more on that below.)

This technique is not for everyone; some people–more than others–excel in high-stress situations.

Slow and Steady Wins the Race

Not ready to make a jump? The alternative involves setting up your freelancing career within the comfort of your normal routine.

Some of the most successful freelancers are continuing work started while living in the normal 9-to-5; working for an existing company gives plenty of on-the-job experience and a number of helpful contacts–some of which may continue to push the same time of work your way–, and bullet points in work history is never a bad thing.

Though if your current work is unrelated to the services you expect to offer as an independent contractor, pursuing casual interests, building a portfolio, and learning new skills are all helpful when it comes time to make a change.

The Efficacy-Comfort Continuum

In fact, reckless abandon and prior preparation are not discrete pathways towards building a successful freelancing career. They work hand-in-hand with each other and a combination of two is only increases your chances of success, and to be honest, it’s more realistic. Preparing in advance definitely makes for a greater likelihood of building a successful freelancer profile for when the time finally comes, and jumping when things are not so clear can certainly kick-start a tired cycle of over-preparation.

That being said, many err or the side of caution. Its very easy to read posts like these all day and plan for success rather than actually enacting it. This article is not just another guide to the options available to would-be freelancers (though there are certainly many more like that here) but rather a call to action:

Go–and burn the boats behind you.

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