Five Jobs for Young People: Thoughts from a Modern Jack of All Trades

Are you young and looking for a job?  Aren’t we all?  This economy still sucks for young people, plain and simple.

But there ARE jobs out there, if you are willing to work anywhere and don’t mind trying something unconventional or getting your hands dirty.  I should know: during my early twenties and late teens, while in college and in the time before and after, I held five different jobs that all helped me pay the bills.  In the resource that follows, I’ll share my reviews of five different jobs I’ve worked in the past half decade or so, and share my opinions about the work’s “pros” and “cons.”  These are all my opinions, based on experience.  Feel free to ask questions in the comments below!

Waiting Tables: The Pros and Cons of Restaurant Work

Busy_WaiterWhat Are Common Restaurant Jobs? What is “Waiting?”

Waiting tables is a unique job in that ALMOST everyone (in the U.S.A. where I live anyhow) has been waited on at sometime in their life, and a very large number of people have worked in restaurants themselves. In the restaurant hierarchy, waiters and waitresses rank somewhere in the middle. As a waiter or waitress, you usually report to a floor manager or restaurant proprietor, must tip-toe around cooks and chefs and kitchen staff that you depend on, and pull rank on bussers and hosts/hostesses.

But the waiting job is unique in that you have the most amount of contact with customers, are largely responsible for setting the mood of the customers experience, and depend on tips for a large amount of your income. As someone who has worked in restaurants of varying quality for more than 10 years off and on, I’ll share some of my experiences with waiting tables, and take you through the good, the bad, and the ugly of working in a restaurant. If you are thinking about becoming a waiter or waitress, want to know more about what the job takes, or are just curious about what exactly a waiter does, read on!

Pros and Cons of Waiting Tables

Here is a quick list of the pros and cons of waiting tables. I will spend time diving in to each point below.


  • Food!
  • Fast Paced Work
  • Tips =)
  • Meet Interesting People
  • Applicable skills/resume building


  • Power dynamics
  • Sexism/racism
  • Tips =(
  • High stress
  • Little advancement potential (often)

Read on for explanations and insights related to each point, based on my personal experience as a restaurant worker.

Ryan Secrest, Justin Long, and Anna Ferris Star in the Fun (But Somewhat Unrealistic) “Waiting”

Pro of Waiting Tables: Food!

Who doesn’t love a well cooked meal? Working in a restaurant usually means you get a free or cheap meal for every shift you work, and if you work at the same restaurant for a little while, you will become intimately familiar with the menu and be able to order your favorites how ever you like them. Especially if you become close with the kitchen staff (WHICH IS A MUST) you can often order things that are off the menu as well.

At a brunch restaurant I worked at in highs school, I would order a smoked salmon omelette every week that to this day remains one of my favorite things in the world to order at any breakfast joint that has lox on the menu. Good food is what draws many people to the restaurant business in the first place, and being a waiter or waitress means you will get to enjoy good eats!

Pro of Waiting Tables: Fast Paced Work

Sadly for young workers or those looking for a new career, many entry level jobs are dead boring, slow, monotonous, and generally mind numbing. However, waiting tables is an entry level job that can be very exciting and interesting. This is because waiting is often a very fast paced job: when you get slammed with a lunch rush, you are on your toes for hours and time moves very quickly.

While it can be stressful to work in such a fast paced environment (more about this later) most serving staff get accustomed to the adrenaline rush that comes along with working quickly and efficiently. Personally, the fast paced times of day were always my favorites at all of the restaurants I have worked at. The fast paced nature of waiting tables means things will stay exciting and you won’t get bored, and time will pass faster.

Pro of Waiting Tables: Tips =)

Big parties with lots of alcohol drinkers are every servers dream.  Tips!
Big parties with lots of alcohol drinkers are every servers dream. Tips!

Tips are one of the most exciting and misunderstood aspects of restaurant work, but if the conditions are right, they are a MAJOR entry in the “pro” column. Tips are what make it possible for some waiters and waitresses to make waiting a professional career: if you are working at a high end restaurant that stays busy, it is possible to pull several hundred dollars in tips per shift fairly easily. As a server, parties are your best friend. In most states, it is legal and expected that for parties of 6+, a waiter or waitress will automatically add 18% for tip on to the check, guaranteeing a good amount of tip money.

Of course, to get big tips, there is a certain level of finesse and art required. My two cents: be friendly and try to make a connection, and try alcohol/apps/extras. Here are some of the internet’s hubbers’ thoughts on the “art” behind getting good tips:

Pro of Waiting Tables: Meet Interesting People

As a server, your restaurant will likely have many “regulars,” or people who come to eat at your establishment frequently. As a waiter or waitress, you will have ample opportunity to get to know these people well, and can make some genuine friends. Even if you don’t become best buds with your customers, you will get to meet any number of interesting people that walk through the door, and will small talk with all kinds of folks.

Celebrities, local politicians, authors, people with interesting and unique careers and life stories: all of these customers are likely to be sat at your table sometime during your career. At a nice brunch restaurant I worked at, I had the pleasure of meeting George Lucas, Carlos Santana, and others, which makes for great stories.

Pro of Waiting Tables: Resume Building!

Waiting tables can be a summer job, or a lifelong career, all depending on personal ambitions and opportunities. As I mentioned, professional high level servers make fairly good money, and these skills are learned at a more entry level waiting position. No matter what career path you are looking in to, it is likely that there are some skills required of a waiter or waitress that would be transferable: from time and stress management, to people skills, to basic accounting, servers do a lot that is important in other lines of work. Even as a stand alone resume bullet point, waiting can be very useful: there are restaurants all around the world, and waiting tables can be a great fall back plan or part time job at all different phases in a person’s life.

Con of Waiting Tables: Power Dynamics

1200px-Sad_WomanOne of the biggest cons of waiting tables that can really get to some people (but doesn’t seem to bother others) is the inherent power dynamic at play that affects servers. First, you are literally “waiting hand and foot” on your customers: it is your job to make them happy no matter what, and this kind of relationship can be very demeaning. If your customers are crazy and have crazy demands, you are forced to cater to them or give up tips, putting you in a stressful position.

Second, there is a power dynamic within restaurants (which I mentioned earlier) between managers and owners/proprietors and servers. As the front lines in what a restaurant does and the employee who interacts with costumers the most, owners and managers are relying on you to bring in the money and create a good customer experience, and if you don’t do this managers will be very angry with you.

Even if you do your job well, there is a certain amount of ass-kissing that goes along with being a server: you have to keep managers happy to ensure they give you shifts, and have to be constantly on your toes to make sure that those above you are in a manager’s good graces. While this is not too uncommon in any position, it is especially exaggerated in servers, and in general working waiting tables can feel demeaning and make servers feel inferior.

Con of Waiting Tables: Sexism and Racism

This “con” could be considered a sub-category of “power dynamics,” but has some particularly nasty manifestations in the restaurant business. It has been widely commented upon that gender and race plays a wide role in the positions that people are likely to occupy in the restaurant hierarchy: women are more likely to be hostesses vs male hosts, males are more likely to be head chefs, minorities are more likely to be bussers or dish washers. In general, these patterns can create a disturbing atmosphere for servers. Additionally, sexism especially can dominate many of the interactions in a restaurant.

As a white male I was never the victim of this kind of thing in my restaurant work, but I saw my female co-workers get treated in a demeaning way by managers and customers alike, often being sexualized and objectified against their liking.

Con of Waiting Tables: Tips =(

I have received 25 cents on a 50 dollar check. Everyone who has waited tables has a story of getting pennies where they should have gotten dollars. DON'T BE THAT PERSON.
I have received 25 cents on a 50 dollar check. Everyone who has waited tables has a story of getting pennies where they should have gotten dollars. DON’T BE THAT PERSON.

While tips can be a major boon for waitresses and waiters, they can be a huge disappointment as well. As a “tipped” worker, you will be making less than minimum wage from your hourly pay meaning you literally rely on tips, and this can be a huge negative for servers. First, you don’t get to keep all of your tips: despite popular opinion, your tips are taxed usually, and additionally most restaurants have a policy where servers split a percentage of their rips with bussers and hosts/hostesses (which is a good and fair thing in most situations but is a drag when your tips are very low as a server).

Second, when business is slow you may not be getting enough tables or costumers to make any decent tip money, and there isn’t much you can do about this. Third, tips play in to the power dynamic I mentioned above: you literally have to cater to a costumer’s every whim for their tips, and this can be demeaning and discouraging if tips are low. Finally, some costumers just don’t tip what they should, which is sad and sucks and happens way more than you might think.

Con of Waiting Tables: High Stress

While the fast paced environment of serving tables can be a fun thing, it can also drive people insane. Waiting tables can be a VERY high stress job, with stress levels much higher that the money you are making deserves. This is because of a variety of reasons: you have to constantly suck up to customers and mangers, make sure cooks and chefs like you (or you won’t get orders when you should), literally run when things get slammed and you have a lot of tables, go for hours without a break during rushes, and in general do a million things at once. The work can be very stressful for some.

Con of Waiting Tables: Little Advancement Potential

For many workers, there is nothing worse than a “dead end” job. And at many restaurants, that’s exactly what a waiting job is: not terrible pay, not a terrible job, but no chance of moving up or getting anything better. Especially in smaller restaurants, the only real position above a server may be an owner/proprietor, meaning there is literally 0% chance for a server to get a promotion. Even at bigger restaurants with designated managers, there is often little possibility for servers to move up the ranks without a huge time commitment or additional education/training. This lack of career advancement can turn many people off of waiting work quickly, and make the field not very appealing.

The Cons of Waiting Tables Can Drive Some People A Little Crazy…

Waiting Tables: a Good Job With Some HUGE Negatives

Overall, I enjoyed my time working in restaurants, but there are many reasons why I don’t wait tables now. The good? If you work at a decent restaurant and are able to get good shifts, the tip money can be very good once you hone your craft. The fast pace work is exciting to some people, myself included, and combined with the chance to meet interesting and unique people, waiting tables is not likely to get boring like many other jobs with similar education or skill requirements may. For millions of Americans, waiting tables is a great temporary job or a fulfilling career.

But the story isn’t all sunshine and roses. The bad? Well, the tips for one. Yes, they can be good. Or they can be REALLY, REALLY bad. If the restaurant you work at is usually slow or doesn’t have a lot of tables, you aren’t likely to get rich off of tip money. Plus, the fast pace has a flip side for many as well: lots of excitement can mean lots of stress, and the wear and tear that serving can exert on a person both physically and mentally can be too exhausting to make the job worth it.

Unfortunately, there is a lot about waiting tables which is unique in a bad way. The ugly? Every restaurant has a power dynamic, between servers and management and servers and customers, which can lead waiters and waitresses to feel demeaned and lowly. You will have to scramble and kiss up to your costumers for tips, and tiptoe around your managers as well as kitchen staff, just to be sure you can do your job. Plus, there is a lot about the hierarchy of many restaurants that is sexist and racist, which can make for a disheartening work environment even if you are a white male like me not directly affected by a manager’s prejudice. The power dynamic in serving can break many people’s spirit, and make the work feel empty and disheartening.

However, on the whole, waiting tables can be the perfect job for some people at some times in their lives, and I do recommend it to anyone who has read this guide thoroughly and still wants to give it a try.

Pedi-cabbing: The Pros and Cons of Driving a Bike Taxi  

What is a Pedicab Driver? What is “Pedi-cabbing?”

In many countries, the term
In many countries, the term “rickshaw” is more common for a bike taxi, but in the US “pedi-cab” is the most common nomenclature.

Pedicab driving, pedi-cabbing, and rickshawing are all terms for the same unique job: driving a bike taxi. Like a traditional taxi, pedi-cabbers charge riders a fare to take them from point A to point B, thought that’s about as much as pedi-cabbing has in common with driving an automotive cab. In recent years, pedi-cabbing has taken off in many major cities. From Austin to Portland to San Francisco to New York City and beyond, residents in major urban areas would probably recognize a bike taxi if they saw one.

But what exactly is pedi-cabbing, what does a pedi-cabber do, and what are the pros and cons of the job? As a pedi-cab driver myself, I’ll share some of my experiences with rickshawing, and take you through the good, the bad, and the ugly of driving a bike taxi. If you are thinking of becoming a pedi-cabber, curious about the alternative transportation craze sweeping the nation, or just want to learn more about this interesting occupation, read on!

Pros and Cons of Pedi-cabbing:

Here is a quick list of the pros and cons of pedi-cabbing. I will spend time diving in to each point below.


  • Terrible money (sometimes)
  • Very physically demanding
  • Meet TERRIBLE people
  • You WILL piss people off.
  • Managers/owners


  • Good money (sometimes)
  • Lots of exercise and get to work outside
  • Meet interesting people
  • Doesn’t get boring (most of the time)
  • Get to know your city/area better

Read on for explanations and insights related to each point, based on my personal experience as a pedi-cabber.

Conan O’Brien Spends a Day Pedicabbing in NYC

Pro of Pedi-cabbing: Good Money! (Sometimes)

While the money you make from pedi-cabbing can be very unpredictable (more about this in “cons”) it is possible to pull a good chunk of change out of a night of rickshaw driving, if you are good at it and the stars align in your favor. Last weekend, I walked home with close to 400 dollars in my pocket after about 10 hours of work. Keep in mind: this is NOT easy money. I had to bust my back (or more accurately, my legs) to make those four bills, but none the less, the money is sometimes very good if you are willing to put the work in.

Walking home with a big bank roll like I did last week depends on a lot of things. First, you have to be decent at what you do. You have to be in good enough shape to move a lot of costumers on any given night, and get to places where customers will be (more about this in “cons”). Additionally, you have to be good at talking to people, approaching people and asking them if they want a ride (similar to “cold calling” or any basic sales) and in general be able to pedal your heart out while simultaneously chatting up customers, obeying traffic laws and keeping your customers and you safe, and maintaining a fast working pace for long periods of time.

The really frustrating thing about pedi-cabbing though is that even if you are great, the money just isn’t there sometimes. I was able to walk away with a nice wad of cash last Saturday night because there were several big events going on down town where I ride that all lined up in my favor, meaning there were a lot of people on the streets willing to spend big. When the stars to line up like this, pedi-cabbing can be very good money.

Pro of Pedi-cabbing: Good Exercise! Work Outside!

If you have noticed, I have used the term “drive” instead of “ride” when referring to pedi-cabbing, because the experience of rickshawing is very different from riding the bike you grew up on. The high weight, three wheels, and general lack of maneuverability makes pedi-cabs harder and less fun to cruise around on than bicycles (most importantly pedi-cabs do not “bank in to turns” so you can’t steer through leaning: the cab will go wherever the steering wheel points only).

Never the less, you are moving a great amount of weight with your own two legs, and pedaling like crazy, which all adds up to some great cardio and leg muscle building exercise. Working out while you work: what could be more fun than that? Additionally, you get to be outside, which is a huge perk in my opinion. Weather isn’t really a factor: pedi-cabbing will only make you money when it is moderately warm and not raining anyways, as no customers are going to want a soggy chilly ride, so you will only be enjoying the best parts of the out doors.

Pro of Pedi-cabbing: Meet Interesting People

I once drove a man that looked and talked EXACTLY like the mob bosses out of the movies. I'm not telling you his name for fear of getting wacked.
I once drove a man that looked and talked EXACTLY like the mob bosses out of the movies. I’m not telling you his name for fear of getting wacked.

You have to be somewhat of a “people person” to enjoy pedi-cabbing and be good at it, but if you DO like talking to and meeting interesting people, there is plenty of opportunity to do so here. Part of your job is making small talk with customers in the hopes they will tip you more, but by doing so you will learn all sorts of interesting things about interesting people. I have had local celebrities, friends of friends that I have never met but have been at the same parties with and never bumped in to, former roomate’s girlfriends cousins, and all other manner of odd and interesting people jump on the back of my cab, and getting them talking and learning about their lives and what makes them interesting can be a real joy.

Pro of Pedi-cabbing: Doesn’t Get Boring!

I have had a hundred jobs that weren’t terrible, but which I couldn’t stick to because they just got flat out boring. Pedi-cabbing is not one of those jobs. Since you usually have free reign to drive around wherever you like, get to talk to interesting people, are being physically active, and all of the other things that come with pedi-cabbing, you probably won’t be getting bored or feeling like the work is monotonous. There ARE times when you will have a good amount of time without a ride, which can be a drag, or when you are waiting for an event to let out and are sitting around aimlessly. But despite the occasional boring stretches, on a whole pedi-cabbing is an exciting job.

Pro of Pedi-cabbing: Get to Know Your City!

Downtown San Jose, California, where I pedi-cab
Downtown San Jose, California, where I pedi-cab

One of my favorite things about pedi-cabbing is a huge perk that I didn’t necessarily expect, but which I appreciate immensely: driving a rickshaw has given me the chance to get to know my city a lot better. On an obvious level, you have to know where things are and how to get there, as people will give you addresses or slang terms for hot spots without giving you directions and expect you to get there.

On a deeper level though, meeting so many different people, seeing my city at all hours and from a unique angle, and spending so much time in my city’s core has made me feel very connected with the place I live. Every time a friend asks me directions and I can spit out turn by turn answers without asking Siri, I have cabbing to thank. Every time someone asks me what I love about my city and my eyes glaze over as I tell stories of night time romps and beautiful historic spots, the same is true.

Con of Pedi-cabbing: Terrible Money (Sometimes)

Wait a minute…didn’t I put “good money” as a pedi-cabbing pro?? The truth is, sometimes the money rocks and sometimes it sucks. A couple facts of pedi-cabbing make this a truism. First, I pedi-cabbers don’t own the rickshaws we drive: instead we are independent contractors who lease them by the night or day from a company. When there is a lot of money down town, this lease is a pretty small percentage of profits, or you walk away with so much that it doesn’t matter. But if you are having a very slow night and the lease is high, it can really hit your wallet. I have had friends end up in the hole, even though they were doing everything right, based on lease rates.

Second, you can’t post rates as a pedi-cabber. While this is different in every city, typically pedi-cabbing is by donation basis only. This sounds crazy, but it is usually easy to work around: when someone asks you how much the ride costs you use vague language like “typically, I would get $20 dollars for two people for that ride,” and they will usually pay up. But some smart customers know the law and will abuse it and pay you close to nothing. Finally, there are many days when the stars just don’t align.

If there aren’t many events going on downtown, if it has been raining recently, if there is a major televised event that is keeping everyone home, if there was a big local event last month that everyone spent their money on: there are a lot of factors which can contribute to slow nights, and when things go wrong pedi-cabbing can be small to terrible money.

Con of Pedi-cabbing: Physically Demanding

With great exercise comes great wear and tear on the body. If there is a big event going on and the money is flowing, you may be riding for 12+ hours at a time, and this is obviously very challenging physically. Even if you are in great biking shape and your legs almost never give out (mine don’t), spending so much time outside in the elements while exerting yourself means your skin may peel like crazy (mine does) or you may get saddle sores from sitting on a bike seat for so long. Additionally, you will be burning a lot of calories, which sounds like fun at first but means you will have to pay a lot of attention to your nutrition and make sure you are refueling frequently and intellegently in order to avoid serious injury.

Con of Pedi-cabbing: Meet TERRIBLE People

I’m not going to dwell on this one, as I like to keep my faith in humanity at as a high of a level as I can muster. But it should be noted that you will be around a lot of drunk people as a rickshaw driver, as the majority of your work is down town at night. Drunk people can be terrible people: from the angry dudes who yell at girls to the cheap bastards who flag you down with no intention of paying you, you will meet some terrible people.

Con of Pedi-cabbing: You WILL Piss People Off

There is a lot about pedi-cabbing that can get under people’s skin. For one, you are approaching people constantly and asking them if they want a ride, and not everyone responds very well to getting cold called. I have had people tell me to f*** off multiple times when I politely offered them a lift. Additionally, you are a big boat looking tricycle that will take up a lane of traffic, and a lot of drivers will hold this against you. You will be honked at and cursed at by drivers, even if you are within the bounds of the law and using the road correctly. You will grow thick skin to this kind of thing, but in general it is never fun to piss people off.

Pedi-cabbers Piss Some People Off. This Is A Fact Of Life.

Con of Pedi-cabbing: Managers/Owners

The owner from the pedi-cab company you rent from may be a Burns, and make it impossible for you to have a good time
The owner from the pedi-cab company you rent from may be a Burns, and make it impossible for you to have a good time

Disclaimer: this is not something I personally have to deal with, but some of my friends who ride in different cities or for different companies complain constantly about the owners/managers of the companies they lease from. Since you are paying a lease usually for a whole night independent of how much money you make, some pedi-cab companies will try to lure you in to lease a cab for a night with promises of big events and big money, but then charge you an incredibly unreasonable lease. In general, pedi-cabbers are independent contractors, which can mean very precarious relationships with management. Often rickshaw drivers are at the mercy of the cab owners, and shouts of “it’s not fair!” ring loud and often in the pedi-cabbing community.

Pedi-cabbing: A Unique and Exciting Job, but Not For Everyone

Overall, I have enjoyed my time as a pedi-cabber, and there is a lot about the work that appeals to me. The good? There is something exciting and entrepreneurial about the nature of the work: since you lease a cab, you are responsible for working hard to make your bank, and that motivates me. Plus you get to be outside, get great exercise, meet interesting people, and explore the streets of your city. The money can be very good if you are good at the job and you are cabbing on a good day. Pedi-cabbing is without a doubt an exciting and unique way to make money.

But it isn’t for everyone. The bad? So, so, so, so, soooooo physically demanding. If you do not handle extreme physical exertion over long periods of time very well, this is NOT the job for you. Additionally, many people are turned off by the independent contractor aspect of the work, as there are no real labor protections (think no bathroom breaks) and you may have to negotiate your lease with a terrible boss. Finally, the money isn’t always great: if you aren’t good at small talk with strangers, can’t pedal like crazy for hours on end, and aren’t willing to learn an ungodly amount about street names and how to get places, you aren’t going to make a lot of money pedi-cabbing.

And there are admittedly things that are flat out unpleasant about the work. The ugly? Saddle sores, for starters. I am an experienced cyclist, and I wear protective shorts when I ride, but spending 12 hours on a bike seat is going to cause some wear and tear on your groin, and I often end up with an uncomfortable chafe rash after a few days of long riding.

And let’s not forget about the drunk people: whether its a pack of frat bros yelling racial slurs at people as you bike by (this has happened to me…) or a group of girls who wave you down and ask to be pedaled 20 blocks away but then decide that they flirted with you a bit so don’t have to pay you (this has happened to me too…) you can see the best as well as the worst of people when you drive a pedi-cab.

However, despite some of the negatives, I have enjoyed my experience and will continue to pedi-cab in my city or whatever city I end up in next, and I do recommend it to anyone who has read this guide thoroughly and still wants to give it a try.

Working as an RA: The Pros and Cons of Being a Residential Assistant

What is a Resident Assistant? What does an RA do?

University of California, Santa Cruz, where I was an RA
University of California, Santa Cruz, where I was an RA

The “Resident Assistant,” or RA, goes by many names at different Universities: community assistant, residential adviser, community adviser, resident mentor, peer adviser and more are all names for the same position. While the RA does different things on different college campuses, there are some basic tenants to the job which are consistent. RAs are responsible for enforcing University policies, planning events, and acting as mentors to younger students. But what exactly does a Resident Assistant do, and what are the pros and cons of the job? As a former RA who held the position for two years, I’ll share some of my experiences and insights about the job, and take you through the good, the bad, and the ugly of working in residential life. If you are thinking of becoming an RA, curious about what it takes to be an RA, or just interested in learning more about exactly what and RA does, read on!

Pros and Cons of Being an RA

Here is a quick list of the pros and cons of being an RA. I will spend time diving in to each point below.


  • The “compensation”
  • The lifestyle
  • Lose friends
  • High stress
  • Lose other opportunities


  • The compensation!
  • Leadership development
  • Make friends
  • Networking opportunities
  • Unique resume building opportunity

Read on for explanations and insights related to each point, based on my personal experience as an RA.

RAs Have a Unique Lifestyle, to Say the Least

Pro of Being an RA: The Compensation!

While compensation packages vary from school to school, the details of the package I received while being an RA was fairly typical, and most campuses will offer something similar. As a Resident Assistant, you are not paid an hourly or salaried wage: instead, you are given a package deal to thank you for your time that usually includes a large reduction in the cost of attending the university you are working for.

My package consisted of room and board, meaning that for being an RA the university paid for my housing and meal plan costs. Talking to RAs at other schools, I can say that this kind of awesome package is fairly typical, though some campuses offer tuition discounts or work study grants instead of in-kind packages like I received. Overall, the value of the compensation package I received was close to $15,000, which made it financially possible for me to attend University and broke down to the best money I have ever earned when I calculated how much I made/hour of RA work.

Pro of Being an RA: Leadership Development

Being an RA is a unique chance to develop your leadership skills, which is an important part of attending college and will assist you in whatever career path you take. As an RA you serve as a mentor to your “residents,” or (typically) younger students who live on your floor or in your area, and as a mentor you must constantly embody what it means to be a leader and role model. Additionally, your managers know that leadership is important to being an RA, and many schools have special leadership development opportunities for Resident Assistants like extra classes, group workshops and events, and other formal and informal training and development opportunities. The leadership principles that will be drilled in to you as an RA will help you in the post grad world immensely.

Pro of Being an RA: Make Friends!

My RA team from 2011. I am still close with many of these people.
My RA team from 2011. I am still close with many of these people.

There is a definite social and community aspect to being an RA that can manifest itself in a variety of ways. First, you can become friendly with your residents while you are an RA, and these bonds can develop in to genuine and long lasting friendships once they aren’t your residents anymore (being bff’s with your residents while you have authority over them isn’t recommended, but your RA manager will talk about that).

Second, you will inevitably become close to the other RAs that work in your college or area; you will be planning a lot of events and working as a community with other RAs and will build a good working relationship. And since you are going through something unique and at times taxing (more about that in “cons”) with your co-workers, genuine friendships are bound to form. I met my current girlfriend of two years when we worked together as RAs, and have a number of close friends that were RAs with me.

Pro of Being an RA: Networking Opportunities

Residential Education can be a rewarding career in itself, and as an RA all of my supervisors and their supervisors and their supervisors were RAs at one point, meaning that if you really love the work and being part of a college student community, there is a lot of opportunity to turn your student job into a post-grad career. Even if you don’t want to be an RA for life though, there is a lot of opportunity to network while working as a Resident Assistant.

Guest speakers and presenters that you coordinate with for events will be useful contacts in a variety of fields. People that work at your University, from administration to professors and everything in between, will be happy to chat with you about potential career paths and will be very beneficial for you to start adding to your contact book while you are an undergrad. In general, being an RA gives you a sense of professionalism that many of your college aged peers may lack, and will allow you to start the important work of networking while you are still in school.

Pro of Being an RA: Resume Building

The skills you can develop while being an RA will make your graduation a lot more valuable and your transition to professional life a lot easier.
The skills you can develop while being an RA will make your graduation a lot more valuable and your transition to professional life a lot easier.

As an RA, you will be doing a lot of different things: from event planning, to enforcing university policy, to acting as a mentor, there is a lot of detail work and responsibility that goes in to the job. As a result, you will have a lot of opportunity to develop skills that you can put on your resume. Things like “crisis management,” “themed event planning,” “community building,” “collaborative project design:” the list goes on. By working as an RA, you will have the chance to hone these skills and others, and have a great opportunity to gain professional level skills that will give you a big leg up on the competition come graduation time. This is something that I have been able to leverage quite successfully as I have transitioned from student to professional life, so feel free to ask me about putting RA things on your resume!

Con of Being an RA: The “Compensation”

While the compensation package that comes with being an RA is enticing to some, it does have it’s drawbacks. First, the value of your compensation is taxed, which comes as a surprise for some and may mean you owe the IRS money at the end of the year. As a side effect of the taxable nature of your package, your financial aid package will likely be lower in the future as well. Second, you won’t be making any cold hard cash as an RA, which can be a major downer. RA management often makes it a requirement that RAs not hold any outside jobs, so you may not have any cash coming in at all while you work as a Resident Assistant.  Which will make it difficult to socialize and buy necessary things in college.

Third, the nature of your package as a stipend and not an hourly or salaried wage means that you don’t have a lot of worker rights, so your managers can do things like require you to be on duty (holding a “duty phone” or being on extra patrols in your community) for days on end. Finally, the packages are usually non-negotiable, and if you get a lot of grant money or financial aid money that would usually cover things that your RA compensation package covers, you may not get as great of a deal out of the job as it first appears.

Con of Being an RA: The Lifestyle

As an RA, you can kiss your weekend keg rituals goodbye
As an RA, you can kiss your weekend keg rituals goodbye

Overall, the total hours that you will work as an RA probably won’t be too many considering your compensation, but the nature of the hours and the work can still have a HUGE impact on your lifestyle. Most RAs have a required amount of time per year or month where they are required to be “on duty,” which means they can’t leave their community area, usually have a phone and are “on call” for any number of community issues, and generally can’t do anything other than be an RA.

This has a huge impact on friendships and academics. Additionally, a lot of the events that you are required to host and coordinate will be on weekends or other times when you would rather be social, and you will be forced to organize and staff these “programs” instead of enjoying the usual social benefits of college. Finally, as an RA you are usually an upperclassmen, and the fact that you have to live on campus and eat campus food for another year may not be appealing. The RA lifestyle can really wear a person down, and I had several RA friends quit the job because they hated the sacrifices that came with it.

Con of Being an RA: Lose Friends

While you will make new friends while being an RA, you will likely lose some previous college friends and acquaintances as well. The strains on your life style mentioned above will put stress on even the closest friendships, as people complain that you “can never hang out anymore,” and for the kind of college friendish-acquaintances you will make your freshman year aren’t likely to remain your friends if they don’t see you at parties, etc. Plus, since it is your job to enforce university policy, you probably can’t attend on campus social gatherings where drugs and alcohol may be present (um, all of college?) so you will push away a lot of people.

Of course, it could be said that any friend that won’t stand by you isn’t worth it in the long run, but the shedding of friends and acquaintances that comes with being an RA can make a person feel lonely and isolated and like they are missing out on the college experience.

Con of Being an RA: High Stress

You may want to pull out your hair as the stress of being an RA takes its toll
You may want to pull out your hair as the stress of being an RA takes its toll

In addition to the general emotional wear and tear that comes with the RA lifestyle, there are a lot of high stress situations that you will be thrown in to as a Resident Assistant. From breaking up parties (not as fun as it sounds) to giving CPR to your passed out residents (this happens more than you may think…) to responding to 4am calls on the duty phone, you will be in some stressful scenarios. This “crisis management” aspect of being an RA can be good experience, but it can also wear a person thin, and cause some serious emotional damage. I had RA friends who started the job with a smile and left at the end of the year in tears because they had one too many people throw up in front of their door or get in a fight on their floor, or had one too many 911 calls involving their residents.

Con of Being an RA: Losing Other Opportunities

While there is a lot about being an RA that can advance your future career and add to your college experience, it isn’t the only way to get experiences at a University by a long shot. College is all about seizing opportunities: from forming a band to making life long friends to working in a lab to starting your writing career to enjoying some of the best parties you will ever be able to attend, there is a million memorable and unique things that attending a university will allow you to do. However, as an RA, you won’t have a lot of time to do other things, and may give up a lot or all of these other opportunities. Of course, you won’t be able to do anything while in college, and being an RA is still a good opportunity, but overall you will be giving up a lot of other experiences while being a resident adviser and the trade off won’t be worth it for some.

Everyone Has Met a Super Corny, “Kill Me Now” Inducing RA

Resident Adviser: Great Opportunity, but Stressful and Not All That’s Out There

On the whole, I enjoyed my time as an RA, and it allowed me to afford college and gain some great experience. The good? The importance of developing your professional skills while still in your undergrad can not be over stated, and being an RA gives you a chance to work on a lot of valuable career focused resume points, from networking to honing applicable attributes. Plus, the compensation can be quite good; in my case, the room and board stipend kept me afloat, and I wouldn’t have been able to attend University without it. Finally, you will have a great chance to be part of a community while being an RA, and will make lifelong friends with your residents and co-workers if you keep an open mind.

Of course, there are ALWAYS negatives. The bad? For starters, that compensation package which looks so appealing is taxable, may screw up your financial aid, and isn’t cold hard cash which you can spend on beer or books. And the friends you make while working as an RA will of course be great people, but may be replacing friends you had before becoming an RA that can’t or don’t want to adjust to your new lifestyle. Speaking of which, being an RA can be demanding, take all your time, and force you to forego other opportunities: you may not be able to take that lab internship which will help your career and lead to a dream job if you are working as an RA and your manager is concerned about you taking outside commitments.

And there are some very dark sides of being an RA that many who haven’t held the job won’t be able to understand fully. The emotional toll of constantly acting as a front line for community crises can put a person on edge, make you feel exhausted, and impact a lot of other aspects of your life. You will likely feel isolated and alone at times as an RA since your job is unique and many of your friends don’t know what you are going through, and the high stress combined with the disconnected feelings that come with being an RA can lead to major depression and emotional hardship. The toll can be too high for some, and it was disheartening for me as an RA to see some of my peers wearing thin and obviously coping with very challenging things emotionally and psychologically

However, I don’t regret being an RA in the least, I would do it all again if I started college over, and I do recommend it to anyone who has read this guide thoroughly and still wants to give it a try.

Working in Retail: the Pros and Cons of a Retail Job

What Makes Retail Unique? What Are Some Common Retail Jobs?

If you plan on working retail, get very comfortable with looking at a cash register.
If you plan on working retail, get very comfortable with looking at a cash register.

Retail work is some of the most basic and easy to obtain work in the economy, and often requires little or no former work experience. A retail job typically has some room for advancement, though turning a cash register gig in to a full time career may not be advisable. Retail has a lot of variety, both between positions at one store or company and between stores and varieties of retail.

At a big box retail store like Old Navy, a retail worker’s responsibilities fall in to several different categories, usually including stocking, cleaning, and operating a register or front counter. As someone who has worked in retail in different settings for about 5 years in total, I’ll share some of my experiences with retail work, and take you through the good, the bad, and the ugly of working retail. If you are thinking about starting a retail job, want to know more about what the job takes, or are just curious about retail work looks like, read on!

Pros and Cons of Working Retail

Here is a quick list of the pros and cons of working retail. I will spend time diving in to each point below.


  • Boring.
  • Little professional development
  • Poor money
  • Zero glory.
  • Meet annoying people.


  • Doesn’t require extensive resume or previous work experience
  • Has promotion potential
  • Practice people skills
  • Develop business savyness
  • Meet good people!

Read on for explanations and insights related to each point, based on my personal experience working in retail.

“Clerks” Offers an Amusing Look at Retail Work

Pro of Working Retail: No Resume Required

Well, not literally: you should have a resume for whatever job you apply to, even if your “resume” consists of classes you have taken and volunteer work you have done rather than previous work experience. One of the most attractive things about working retail though is you don’t need a lot or any previous work experience. The job can be learned quickly and a variety of different personalities will be able to succeed in the retail environment’s many different roles, so managers and owners of retail businesses are likely to hire individuals without extensive resumes. Working retail can be a perfect first job to start building that ever important work history, as most people can find some kind of retail work that suits them with a manager willing to hire.

Pro of Working Retail: Potential for Advancement

Especially in big box retail stores and corporate settings, there is a lot of room for advancement in the retail world compared to other entry level positions. Basic floor and counter retail workers can aspire to shift management positions, better and higher paying commision based retail positions within the same company (for example, moving from the clothing to the jewelry department at Macy’s), and potential advancement to higher paying and more interesting positions within the company they work for.

A college friend of mine started working at Urban Outfitters less than a year ago as a basic cash register and floor stocking grunt, and quickly was able to impress her managers and get promoted in to more interesting projects: now, less than a year after starting at Urban, this friend works as a buyer/fashion rater, flying to cities around the country on the company dime and looking at different pieces of clothing from different designers that Urban is interested in buying. It isn’t likely that you could an opportunity like this after a year of fast food work, or something else with an entry barrier as low as retail.

Pro of Working Retail: Practice People Skills

The big crowds during rush times in retail stores will force you to practice your people skills.
The big crowds during rush times in retail stores will force you to practice your people skills.

While there may not be a large amount of transferable skills from retail work to more professional careers, one thing you will get to practice a lot in a retail job that will help you for the rest of your life are your “people skills;” your ability to talk and interact with people and costumers efficiently and effectively especially in a costumer service environment. “Good people skills” are required in a wide variety of careers and situations, and almost every employer and future contact will respond well to a person who can communicate effectively.

When on cash register duty in a retail situation, you will have to practice interacting with people while completing a variety of other tasks, forcing you to develop the ability to multitask while remaining polite and professional. When on the retail floor, you will be expected to react quickly and in a detail oriented manner to the questions and concerns of costumers, forcing you to operate well under pressure while still exercising good people skills. This experience will be invaluable and widely applicable across a wide range of opportunities.

Pro of Working Retail: Develop Business Savviness

If you are hoping to get in to an eventual career in marketing or business administration, you can learn a lot from even the most basic entry level retail positions. Many small business owners and entrepreneurs started out working a cash register in some forgotten store long before they founded their own businesses. In addition to practicing the people skills discussed above, working retail will expose you to many of the bare bones elements of running a successful company, from managing employees to promoting products to maintaining efficiency, IF you are an astute observer and want to get some initial exposure to how a business is run, working retail will allow you to develop some business savviness.

Pro of Working Retail: Meet Good People!

There is a lot about working retail that isn’t great (more on this in the “cons” section) but all of the rough and rugged elements of retail have a knack for creating a tight and unique community among employees. Any job where you spend a lot of time together will inevitably lead to friendships, but retail work has a particular knack for fostering such bonds. The down times in retail allow for a lot of free time, which will inevitably be filled with conversation between you and your co-workers.

A friend of mine who started a relationship with one of her co-workers at Abercrombie when she worked there in high school is about to get married to that same co-worker, and many of the people I worked with during my retail job in college are still close friends. Working retail, you are bound to meet some good people who you click with.

Con of Working Retail: Boring.

Working retail will make you pull your hair out with boredom at times
Working retail will make you pull your hair out with boredom at times

Retail can be so, so, so, so boring. More than any other entry level position, retail can be mind numbingly slow and tedious for a variety of reasons. First, the tasks do not vary much at all; if you work a cash register, there isn’t much you can do to spice up the position, as you will be doing the same thing over and over again. Second, retail work often has long stretches of slow down time.

While tedium is a trademark of many entry level jobs, there is typically more empty time in retail than many other positions; if there are no costumers in your store, there isn’t much for you to do to fight off boredom, and retail has long stretches with very little costumer interaction. When you combine the routine nature of retail with the long stretches of empty, mindless time, you end up with one of the most boring positions imaginable.

Con of Working Retail: Little Professional Development

Wait, didn’t I just get done telling you in the “pro” column that there is a lot that can be learned from working retail? While it is true that an astute observer can get a lot out of this position, your boss in a retail job probably isn’t too invested in your professional development or advancement: while some positions have extensive company trainings and advancement programs to insure that workers are aware of their opportunities for promotions and are able to develop their professional skills, retail work is not likely to have a strong focus on these kinds of initiatives. While in any position, you should be thinking about how the skills you are learning can be transferred to a later position, but a major “con: of retail work is that this isn’t always obvious and there aren’t many professional development opportunities to make the connection more clear.

Con of Working Retail: Poor Money

Get used to looking at the 1's and 5's. Retail money isn't huge.
Get used to looking at the 1’s and 5’s. Retail money isn’t huge.

Of course, any entry level job you get isn’t going to make you rich, but retail has some especially low pay rates considering the nature of the work. As opposed to working in a restaurant setting, you won’t get tips working a retail counter, and will likely be earning minimum wage. Combine minimum wage with the fact that paths to promotions may not always be obvious (read above) and you may be earning poor money in retail for a lot longer than you would in a different setting. Working isn’t all about earning, despite popular opinion, but if you are getting a retail job primarily to save some money and pay the bills, you may be better off applying to other positions.

Con of Working Retail: Zero Glory

While the idea of “glory” isn’t usually something you would relate to entry level work in the first place, working retail is particularly unromantic. Let me explain what I mean by “glory.” In many positions, you will have the opportunity to distinguish yourself, and earn the praise of your boss and co-workers. Not so in retail. In many positions, you will be put in positions that will let you feel proud of your abilities, and will give you something to take home from work that is less tangible than wages; good stories, satisfaction with your work, and a feeling of fulfillment.

Not so with retail. Without these opportunities to stand out, you probably won’t be very happy with your job. Of course, there are counter examples; some retail settings have commission based positions or other metrics for you to judge your performance, improve your work, and have something to brag about and work towards. However, typical, entry level retail jobs are often mundane and without any sense of “glory” what so ever.

Con of Retail: Meet Annoying People

If retail work is particularly likely to give you the opportunity to make friends with your co-workers, it is also particularly likely to provide costumer interactions that will drive you crazy. See, people who are shopping are almost always in a hurry or on a time schedule, and they are likely to mistreat retail workers as a result. Rushed and agitated costumers aren’t the only ones likely to annoy retail workers either. When I worked retail during college, we had several “regulars” who would come in to our store and browse and ask a lot of questions, but NEVER bought anything.

While this sounds harmless enough at first, your manager probably doesn’t think so. Everyone time I was unfortunate enough to be working the retail floor when one of these costumers came in, I knew they wouldn’t buy anything, and that my manager would blame me for being unable to “sell” a product to someone who wasn’t planning on buying in the first place. Working retail, you will gather a lot of stories about costumers being rude or annoying or insane, and the treatment retail workers receive is a major “con” of the job.

You Will Meet Some Crazy People Working Retail

Retail: It’s Not Fun, But It’s Not Hard

Overall, a retail job is better than no job, but it isn’t the greatest work. The good? A retail job can be easy to get, and doesn’t require an extensive resume to nail down in most cases. While working retail, you will have a lot of chances to build your employment skill set, especially your people skills. And if you are a really keen observer and want to start your own business some day, you can learn a lot about running a business from even the most basic retail position. Basically, retail jobs are easy to get and can lead to better things if you apply yourself.

However, there is a reason why many people don’t stay in retail for long. The bad? Well, it is really boring for a start. Compared to many other entry level positions that have faster work environments, you will literally have nothing to do for a large part of the day as a retail worker. combine this with the fact you are likely to earn minimum wage and not have very many opportunities to be proud of your work, and the mind numbing and very unromantic nature if retail are unavoidable “cons” of the position. Oh, and the costumers. They can suck. More than in most positions, you will meet a lot of crazy and annoying people working a retail counter.

Additionally, there is a lot about retail that is downright ugly. Your managers probably won’t be very invested in your success. Yes, you can learn a lot from retail if you are astute and apply yourself, but it is likely that you won’t have any help to get there. This lack of investment on the part of your higher ups adds to a pervasive feeling in retail work that you are unimportant and replaceable. You won’t have many opportunities to gain any psychological satisfaction from your work, as the tasks of a retail bee are so menial. These factors make retail a job with little to no “glory,” and you will feel like you don’t matter in your work as a retail employee.

However, on the whole, if you need work retail is a lot better than nothing and can lead other places, and I do recommend it to anyone who has read this guide thoroughly and still wants to give it a try.

Working as an Independent Contractor:  The Pros and Cons of Freelance Work

What is an Independent Contractor? What is a Freelancer?

Hunter S. Thompson, one of the most famous journalists of the 20th century, worked as a freelancer
Hunter S. Thompson, one of the most famous journalists of the 20th century, worked as a freelancer

Being an “independent contractor” can mean many things; by definition the field is varied, and involves any activity where you can produce some income while working under your own terms. As an independent contractor, you can do whatever you are good at, as long as you are creative and proactive enough to find a way to monetize your talents. “Independent Contractor” means you are working ‘independently’ from a traditional management structure (read: you are your own boss) while being contracted to complete a project, whether that is editing a document for a client or producing a crafted product for a costumer.

“Freelance” work is similar in that you are allowed a great degree of freedom, but as a freelancer you are usually working to meet the specific guidelines of an assignment or specific task. As a freelancer, you will be working to contribute something to an existing agency, company, or publication; as a member of the broader independent contractor category, you could be doing this or anything else you are interested in doing.

As someone who currently works as an independent contractor and has in varying capacity throughout my life, I’ll share some of my experiences with freelancing and working as an independent contractor, and take you through the good, the bad, and the ugly of this unique way to make a buck. If you are thinking of starting work as an independent contractor, want to know more about how this field can generate revenue, or are just curious about what being an independent contractor takes, read on!

Pros and Cons of Being an Independent Contractor

Here is a quick list of the pros and cons of working as an independent contractor. I will spend time diving in to each point below.


  • Money
  • Instability
  • Isolation
  • TOO MUCH Freedom
  • Taxes


  • You are your own boss
  • Freedom
  • Express yourself
  • Build your resume
  • Become an entrepreneur

 Read on for explanations and insights related to each point, based on my personal experience working as an independent contractor.

If Richard Branson can do it, so can you! (…right?)

Pro of Being an Independent Contractor: You Are Your Own Boss!

EVERYONE has stories of a boss that drove them crazy, work conditions that they couldn’t stand, or the exorbitant and malicious manager who made their work life feel like the seven circles of hell. But as an independent contractor, you won’t have to worry about a boss that will drive you crazy, since you will be your own boss! One of the most stressful elements of working in any job is the power dynamic that exists between workers and managers; even if you have a “good” boss who isn’t disrespectful or unreasonable, you will probably find yourself tiptoeing at times, or working hard to make your boss happy.

As an independent contractor, this stress won’t exist at all. Even if you are in an employment relationship where you are working for a company or service as an independent contractor, and have someone to report to, by definition your role as an independent contractor and not an employee means that the company or service you are contracted with can not legally tell you how to work.

Pro of Being an Independent Contractor: Freedom!

While this is closely related to being your own boss, it is worth mentioning that being an independent contractor has the special perk of offering you a LOT of freedom. In many freelance or independent contracting positions, you can work for home and set your hours. Since no one can legally tell you exactly what to do, you can set your own work conditions. Feel like doing that data analysis at 3 am in your pajamas while eating Ben and Jerry’s? Go for it. Think you can complete a contracted project without showering for a week? It’s your call. Overall, setting your own work conditions means that you will have the freedom to work however you likes, which can be a very liberating and enjoyable element of working as an independent contractor.

Pro of Being an Independent Contractor: Express Yourself

Madonna had it right. Express your self!
Madonna had it right. Express your self!

Let’s face it: most jobs you will have in your life aren’t exactly going to encourage your creative side all the time. Being an independent contractor means you get to do what YOU want to do, and will have a lot of room to express yourself through your work. Do you love making hand crafted bracelets? You can do that, sell them online or in person at festivals, and earn an income while doing so as an independent contractor.

Whether you love writing, playing music, creating things with your hands or mind, cooking, or anything else you can monetize, you can express your passions and creativity as an independent contractor. Again this ties in to being your own boss and crafting your own product, but no matter how you look at it or what you find yourself doing as an independent contractor, you will have a great opportunity to express yourself.

Pro of Being an Independent Contractor: Build Your Resume

Are you at the point in your career or life where you feel you have the skills and abilities to land a great job, but you don’t have the resume or experience to secure the role you want? Being an independent contractor may be the perfect venture for you. As an independent contractor, you will have the ability to focus on developing skill sets that will be applicable to your later career and ambitions. Want to work as an accountant?

Consider starting your own small business, producing or doing whatever you like, and keep a detailed ledger to show your skill development. Want to be a musician? Work independently to record your abilities, and use your product as a demonstration of your potential. No matter what career you aspire to, you can build some of the skills necessary to break in to your dream field by starting as an independent contractor and adding to your resume.

Pro of Being an Independent Contractor: Become an Entrepreneur!

Many of the greatest entrepreneurs of our era worked very independently.
Many of the greatest entrepreneurs of our era worked very independently.

While this is related to resume building in general, the opportunity that being an independent contractor affords to develop an entrepreneurial mind state is unique and can’t be emphasized enough. In this day and age, almost every career expects you to accomplish core responsibilities AND be a business person, and this kind of entrepreneurial spirit is something that being an independent contractor will force you to practice. As an independent contractor, you are responsible for developing your own business goals and turning them in to profit margins.

You are your own boss, but you are also your own sales manager and accountant and creative developer; you will get familiar with the many facets necessary to turn a product in to a profit, and if you are observant and apply yourself you can easily translate the entrepreneurial spirit of being an independent contractor in to your future endeavors. Being an independent contractor will force you to become an entrepreneur, which is invaluable in the modern economy.

Con of Being an Independent Contractor: Money

If you are proactive, entrepreneurial, talented, and have a good bit of luck on your side, you can make very good money as an independent contractor. Unfortunately, it is far more likely that, by working as an independent contractor, you are trading an increase in freedom and creativity for a decrease in earnings. Put simply: you aren’t going to get rich as an independent contractor, or at least you won’t very quickly. If you are offering a highly skilled service, you can expect a decent compensation, but you would more likely earn more working for a company directly providing that service than you will by contracting to complete it as a free agent.

For example, I was once paid a monthly salary as an independent contractor while I was working on a project for a large start-up company. I could do the work form home, and whenever I chose. But when I worked out the actual per hour wage I was receiving for the work I was contracted to do, it was much below market rate for the service I was providing and much below what other employees with similar responsibility who worked for the company directly were paid. So, if you intend to work as an independent contractor, keep in mind the money won’t always be great.

Con of Being an Independent Contractor: Instability

The stress related to instability that comes with freelancing is a major drawback
The stress related to instability that comes with freelancing is a major drawback

If there is one thing that can be said for the routine of a standard waged job, it is that it leads to routine benefits: you can expect a check every payday, a decently predictable work schedule even in the worst jobs, and a predictable level of stress. Not true if you are working as an independent contractor. Part of the fun of the job lies in the fact that it is unpredictable and forces you to think on your feet and be your own biggest promoter, but these conditions also mean that nothing is guaranteed, and you can’t expect anything to be regular or routine.

This instability can lead to a lot of unnecessary stress. When is the next time I will land a big project? When and where will I be able to sell my products? Questions like this plague the independent contractor, and this instability is a major drawback of the position.

Con of Being an Independent Contractor: Isolation

For better or worse, work and earning money is a big part of almost everyone’s life. And in most jobs, there is a large social aspect to working: you will make friends in any position, will have people to complain to and about, will share an experience (working) that will bring you together. Not so for being an independent contractor. That “independent” part means your work is almost entirely without camaraderie. Yes, you can finish projects at any hour of the night that you like, but you will be working on them alone.

This kind of individual work can be very isolating, and have a large negative effect on a person’s psyche, leading to depression and loneliness. The total isolation of working as an independent contractor isn’t based on monotony or work conditions, but is instead a more real and obvious isolation: you are working alone, and there is no way getting around the fact that being an independent contractor is a lonely way to make money,

Con of Being an Independent Contractor: Too Much Freedom

All the freedom that comes with being
All the freedom that comes with being “independent” may come tumbling down if you aren’t careful

Is there really such a thing as “too much” freedom? In the world of work, it just so happens that an excess of liberty can be a major issue. As an independent contractor, you are in complete control of your hours much of the time, which can mean procrastination for even those with the best worth ethic. You may push yourself to work near deadlines and produce sub-par work as a result You may promise big results that you find yourself unable to obtain. You may very quickly come to realize that freedom, while an attractive quality of working as an independent contractor, can become a burden. You will have a lot of responsibilities as an independent contractor, and they can quickly fall by the wayside if you aren’t careful.

Con of Being an Independent Contractor: Taxes

If I haven’t scared you off already with the cons of being an independent contractor I have listed above, there is one more big drawback I have to discuss about doing freelance work, and it is a BIG one: taxes. While it can be frustrating to get a paycheck from a waged job and have close to a third of your earnings go directly to the government via taxes, it is even more disheartening to realize that when you earn money as an independent contractor, you will STILL need to pay the tax man.

However, you will be responsible for managing your taxes yourself, and sending your tax payment to the IRS or in some cases your state tax board directly. This means you are going to have to keep meticulous track of everything you earn and everything you spend, and you are going to have to keep a close handle on all of the right paperwork to document your earnings. Depending on how much you are making as an independent contractor, you may have to pay taxes annually or quarterly. The whole process can be, frankly, quite taxing.

Every Independent Contractor’s Catchphrase: “I Work Alone!”

Independent Contractor: Freedom Comes at a Price

Overall, working as an independent contractor is a unique way to earn money, but has some drawbacks as well. The good? The “independent” part of the job means you will be in charge of most of your work conditions: you can set your own schedule, work where you like and how you like, and be your own boss. This freedom means you will be able to express yourself a lot more than in most positions.

As an independent contractor, you will be providing services that you WANT to provide, and as a result will be able to inject some creativity in to your work. Furthermore, all of this freedom means you won’t have to deal with some of the demeaning elements of a standard job. No sucking up to your boss, scrambling for shifts, or begging for raises. You are your own marketer, boss, and creator as an independent contractor, which can be a great experience and a great opportunity.

However, all of that freedom comes with at a price. The bad? As an independent contractor, you are in charge of your business, and in charge of creating business in the first place. This means you will constantly have to be “on your hustle” to ensure you have work, and this instability can be very stressful. Adding to the stress of working as an independent contractor, you have no one to share your experiences with: the role is incredibly isolating, and unlike traditional waged labor roles, you will not have anyone to bond with at work, complain to about a particularly horrible project, or celebrate with after a great accomplishment.

The combination of instability and isolation mean that working as an independent contractor will be very stressful. And don’t get me started on taxes. No really, don’t get me started: working as an independent contractor now, taxes terrify me, and are a big burden to handle for anyone in this role.

Even worse than stress and taxes, there are some elements of working as an independent contractor that are downright ugly. All that “freedom” that you get by being “independent?” It can have it’s downsides; you will make significantly less for any service you provide as an independent contractor compared to a standard employee providing the same service, and you will often be forced to work longer hours than you would like when deadline’s approach. The fact is that since you aren’t a standard employee, a lot of employment law won’t apply to you.

It is conceivable that you will earn less than minimum wage on some projects if you have bitten off more than you can chew or accepted too many responsibilities. It may seem that you are getting taken advantage of as an independent contractor, earning less than you should and working long hours. And that’s because you probably are.

However, I have enjoyed the experience of being an independent contractor and feel I have a stronger resume and sharper set of skills as a result, and I do recommend it to anyone who has read this guide thoroughly and still wants to give it a try.

Questions?  Ask them below!