Content warning: This article discusses topics of substance abuse and alcoholism.
Like most of the Gallaghers - and in fact, all other characters of Shameless - Lip works his fair share of odd jobs during his time on the show. As a school student, he makes what little money he can by tutoring and taking other people's SATs illegally. As he grows, Lip must step up to contribute more to the Gallaghers' finances.
His time in college is a juggling act of studies, managing his dysfunctional family back home, finding ways to make money, and maintaining some kind of social life. After college, Lip tries to fill Fiona's shoes as she moves out of the house to pursue her own ambitions while Lip's future starts to look less promising. Like his siblings, Lip often turns to illegal methods to make ends meet.
10 Construction Worker
When Lip gets back to Chicago after getting kicked out of college, Tommy offers him a job at a construction site he's working on. The work is laborious and way too physically challenging for Lip's comfort.
Not to mention, it's dangerous because of the sketchy working conditions. Lip isn't protected from the risk of physical injury and muscle strain, nor from the loose heavy objects being thrown around. The job is unpleasant, unfavorable, and doesn't pay very well.
9 Cafeteria Bus Boy
At the beginning of his time away at college, Lip works as a busboy at the cafeteria. It's not a terrible job, but he's never happy when he's there. The job itself frustrates and stresses him out, especially when he feels he could be making better use of his time.
It also represents one of Lip's lowest points. He's intensely homesick, lonely, and feeling very alienated in this new environment. This is where he starts to rely heavily on alcohol and other substances. Lip is not yet very good at managing his time or priorities, and as a result, working often gets in the way of completing his schoolwork, and vice versa.
8 Tech Startup Intern
Lip's internship isn't technically a job, since it's unpaid, which is a major drawback for him and his family. However, Lip believes that it could lead to better, full-time employment later down the line - the kind of employment that could set him and the Gallaghers up for life.
Unfortunately, this tech startup is just as sketchy as every other workplace in the show. The FBI is leading formal investigations into the way things are run at the company, which Lip realizes isn't the safest place for him to be starting his career. His time there is short-lived and not in any way beneficial.
7 Sorority Houseboy
One of the advantages of being a sorority houseboy is that Lip gets free accommodation. However, he's essentially alone, except for the many members of the sorority who pay him unexpected visits.
Lip feels objectified, which he sometimes enjoys but mostly finds annoying. The advantages are outweighed by his compromised privacy, the distractions from his studies, and his own weakening of character.
6 Ice Cream Van Operator
While Lip may enjoy this job, it's illegal and immoral. Lip helps Kevin operate an "ice cream van," where they do actually sell some sweets and ice cream, but the real money is made selling other items.
Young children are the customers who arrive at the van's window unsupervised, and Lip has no problem supplying them with drugs. As a means of making money, it's easy work, but it's not honest or good.
5 Teaching Assistant
This is one of Lip's most promising jobs, but it leads to a lot of problems later on in his life. The employment is convenient and seems like it will actually be useful for his career - not to mention, Lip is a natural when he's given the opportunity to step up and teach. He clearly enjoys talking about his passions and sharing them.
However, the work environment is not always positive. Youens becomes like a friend and mentor to Lip, but he also passes on a number of toxic habits. Lip follows in his footsteps and sabotages his own career, then begins abusing substances and glorying his aimless misery.
4 Tutor
Being a tutor is Lip's first job in the show, and at its core, it's like being a teaching assistant, but better. Here, Lip doesn't have to deal with any stress - he only does the job because he enjoys it, and at this point in the show, he doesn't do many things that he doesn't choose to do.
Lip is clearly passionate and has a talent for understanding things that others don't. He sees things differently than some of his peers, which is why he's so academically advanced. The only downside is that tutoring isn't a steady means of employment.
3 Test Taker
Although taking other people's SATs is illegal, it's one of the easiest ways for Lip to earn cash. He can score big in a single day, and he seems to enjoy challenging himself to take the test as many times as he can.
Unfortunately, apart from being a good way to make money, this job is illegal, immoral, and not reliable. It may be fun while he's still in school, but it shouldn't be considered formal employment.
2 Dishwasher At Patsy's
Patsy's becomes such a big part of Shameless that it's almost like a second home to the Gallaghers for a while. All of them walk through the doors at one point or another, many of them following Fiona's suit to work there.
Lip is a dishwasher, which may not be the most pleasant job, but it's not particularly hard and the environment is pleasant enough. It's also where he meets Sierra, who is one of Lip's best romantic partners.
1 Mechanic At Born Free Cycles
Becoming a mechanic is one of the best things to happen to Lip. It's Lip's first proper, steady job, and it's one he seems interested in. He may not have ended up pursuing any of his prior academic ambitions, but as a job, Free Born gives him everything he needs.
Even better, Lip gets to work with his best friend, Brad. The workplace is properly looked after, safe, well managed, and takes care of its staff. Lip has a decent salary and is able to support his family - both of them.
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