Highly Skilled Freedom Seekers:

Enslaved persons with skills had the most advantages when running away. For instance, skilled enslaved persons such as watermen ran away with the intent of eloping and making it to free geography in greater percentages. Likewise, other skilled enslaved people that were more accustomed to the happenings of the white world had skills that could be employed "on the free labor market more readily than most other slaves." Thus, they also had advantages to escaping slavery. This is because they had more mobility and gained a greater level of trust from whites.

For instance, "Special talents of watermen, their boating skills and geographical sophistication, somewhat countervailed against these inhibitions and enabled them to run off with uncommon frequency." 

Watermen had opportunities to establish relationships with captains of larger vessels and increase the success of their escape. For instance, enslaved boatmen working in the Great Dismal Swamp under owner S.S. Simons often used his schooners to carry corn, wheat, and lumber to ports like New York, Norfolk, or Philadelphia. As a result, "boats [like the one from Simmons] engaged in the lumber trade sometimes brought refugees from New Bern, North Carolina, to Philadelphia. Captain Austin Bease, who was active in the rescue of stowaways from Wilmington, North Carolina."
 

It should be noted that knowledge of the capability and resources available to whites, who would use any means to prevent running away from any success, also created much hesitancy to running among skilled enslaved persons. Thus, knowledge was a double-edged sword, "the howling dog knows what he sees." 

Lesser Skilled Freedom Seekers:

It is a fact that enslaved persons with skills had great advantages materially and intellectually. Nevertheless, enslaved persons who worked the fields may or may not have had the same advantage as higher-skilled slaves, yet they ran away with great frequency, utilized native intelligence and what they learned from the book of nature to aid them in their journey. Lesser skilled freedom seekers learned about geography from short travels, traveling at night, and enslaved persons who traveled or were sold frequently. They learned from other plantations in times of leisure or labor and when they found time to travel and move about on Sundays [typical day off]. 

Plans:

Skilled or lesser skilled enslaved persons planned their escapes in many cases. Planning to escape was all about finding the best opportunities and anticipating obstacles. Granted, there were many times when plans could not be made, and escapes were spontaneous. However, thoroughly organized plans were temporary, as freedom seekers had to navigate many different situations such as random patrols, injuries, dogs, the weather of all sorts, failed rendezvous, potential betrayals, fatigue, hunger, and so on.

Nevertheless, plans were still necessary, even if they only served freedom seekers temporarily. For instance, James Curry noted that he planned his escape around the travel of his slave owner:

"I firmly resolved that I would no longer be a slave. I would now escape or die in the attempt. They might shoot me down if they chose, but I would not live as a slave. The next morning, I decided that, as my master was preparing for one of his slave-driving expeditions to Alabama, I would wait until he was gone; that when he was fairly started on his journey, I would start on mine, he for the south, and I for the north. In the meantime, I instructed my two younger brothers in my plans. It happened that on the afternoon of the 14th of June…."

Allen Parker also discussed his plans, noting the following: 

"During the month of August 1862 slaves living on the adjoining plantation together with myself began to form plans of in some way getting to the "Yankees". We used to get together when we could and talk our plans over, but for a time we did nothing else. But finally finding that lots of the slaves from the neighboring plantation were running away we concluded that we would take our chance as soon as we could get any."