What to do if You’re a College Student Who Isn't Excited by 9-5 Corporate Work

By Nat Eliason in College

Published or Updated on Apr 24, 2015

I don’t meet many people who are “excited” about going corporate.

Many treat is as a means to an end, just a way to earn money and live comfortably.

Or it’s seen as the only option, usually because it’s what our parents did and it’s what we see our peers doing.

But there are a world of options out there, all providing a greater degree of personal freedom than corporate work.

On some level, everyone wants to work for themselves, have creative freedom, have time and location freedom, but very, very few get it.

I haven’t mastered it (though my current work will be in a future article) but I’ve certainly learned a ton about working for yourself and getting that creative freedom.

So if I could go back three years and give myself a roadmap to get a few years ahead of where I am now, and be even more able to work independently before graduation, here’s what I’d say.

Different Types of Work

There are many “types” of work, and you need to identify which one interests you the most.

As I see it, there are seven main categories. The first three are the most obvious to everyone as options. The second four we know are options, but usually seen as impossible or massively hard to get.

Manual Labor

I’m going to assume you don’t want to do this though I have to admit that periodically engaging in it ala Levin from Anna Karenina does sound attractive.

But breaking rocks or cleaning houses or any other physical labor for an hourly wage… I It’s not something we tend to aspire towards. Let’s just rule it out and move on.

White-Collar Corporate Work

White-collar work is the one that, from people I talk to, students have admonitions about pursuing.

They don’t hate the idea, they just see it as a necessary evil. Even though it’s the most common, there’s something unsatisfying about it.

There’s little time freedom. Limited upward mobility (mostly from time limits on how fast you can advance). You’re only working with people your level or marginally more intelligent (or, as you might tell a friend over beers, much less intelligent). And you have a mostly set career path.

There are benefits, of course. You have some income security, there could be perks like health care, maybe you have a hot secretary (male or female, let’s not get sexist here) but do they outweigh the downsides? Up to you, but I assume that if you’ve read this far then your answer is “probably not” so let’s continue.

Trade Professional Skills

These are the lawyers, doctors, engineers, professors, and so on. They’re not working typical corporate jobs, but they’re still in a “system” of sorts. If you’re interested in this, go for it. I commend you. I don’t have the patience for that much education (or, honestly, the inhuman hours of lawyering and doctoring).

Just get the degree, get good grades, and you’ll do fine. It takes hard work, yes, but there is a clear system that you can follow. Though you might do better competing on other criteria.

One-on-One or Mentorship Work

Now we’re breaking out of the traditional structures. Depending on what type of independent, self-directed work you’re interested in, you might look at doing one-on-one or mentorship work.

This type of job is any kind where you work directly for someone who’s been successful in your field of interest. So if you want to write, maybe you work as a book researcher for an author you admire. Or if you want to pursue entrepreneurship, you do a low-wage “internship” with a successful one where you do whatever they want in to gain their knowledge / experience / network. Charlie Hoehn has a useful book on this.

You can do Mentorship or One-on-One work in any field, you could even do it in the traditionally white collar corporate jobs like Finance. Instead of being a first year at JP, go work directly under the head of a small hedge fund. The hours and climate might be the same, but you gain the benefit of much more direct mentorship.

Mentorship is the key here. You do this to get a mentor, someone who knows the ropes, how the system works, and what you need to learn so you can shoot to the top quicker than you thought possible. If you can make that happen, you can achieve in two years what would take ten or more in the traditional system.


If you’re adventurous, you might want just to start your own company. There’s an absurd amount of money floating around out there right now, so if you can get good mentors and a good team you can certainly go for it.

Don’t assume you have to know what you’re doing first. That’s where the mentors come in. And if you have a great idea and a great team and you’re making progress you’ll easily be able to get mentors (they want to bask in your glory when you make it big).

Startups are one of the highest risk options on the list, since you could blow up and lose your company, but it’s also potentially the highest reward if you do it right.

The key here is to take as few risks as possible, protect your downside and don’t spend your own money. Get other people to give you theirs.

Lifestyle Businesses

A lifestyle business is like a startup, but it can be run by one or two people, doesn’t intend on getting investor money, and should make enough money per year to sustain your lifestyle (thus, lifestyle business).

This is the safer, lower risk, though also smaller upside version of a startup. You can start one in a weekend if you know what you’re doing, and you can grow it to a 6 figure business in less than a year if you’re excellent. But it’s never going to go IPO and give you tens of millions of dollars (well, not usually).

One key component here is automation. A lifestyle business typically requires a massive amount of upfront work, and then can run on its own indefinitely with minimal input from you. In The 4-Hour Workweek, Ferriss explains that the goal is to create a business that requires less than four hours a week to manage.

This, in my opinion, is the best place for college students to start. Why? Because if you do it well then you have the funds to start a creative career, or a startup, or anything else without worrying about starving. We’ll come back to “how” later.

Creative Work

These are the artists, writers, inventors, and anyone else who could theoretically sit alone in a room and create something of value.

They’re the only ones on the list who can truly have 100% control over their life and work. Something we all aspire to.

But it’s just ask risky as a startup, at least in the beginning. These fields are incredibly crowded and standing out is nearly impossible.

If you can, though, you end up in a situation where you can create something once and make money off of it for life. After J.K. Rowling wrote the Harry Potter books she didn’t have to do much else. She could sit back and become a billionaire.

How To Get the Interesting Work

So now I’m sure you’re all hot and bothered about the last four options: mentorship work, startups, lifestyle businesses, and creative work. If not, stop reading, and keep editing those god-awful powerpoint slides your boss asked for.

For each of these types of work, you’ll have to think differently than most college students and approach getting work differently. There are no job boards, no career fairs, none of the typical infrastructure that your peers will be taking advantage of when getting their jobs.

It will be hard work! But the freedom, faster learning, and higher income are worth it. Not to mention getting to do much more interesting of work.

Four General Concepts:

Don’t worry about grades. No one cares about your grades when they’re buying from you, working from you, or reading your book. Even in the case of working with a mentor / small team they’ll be more interested in what you can DO rather than how well you can work the school system

Get good at marketable skills. This can be literally anything: writing, programming, design, marketing, teaching, juggling, but the important element here is that you need to get good at them in the context of working with people. Programming for a client or on a team is different from taking a computer science class. Working as a freelance designer is different from what you do in design classes.

Be okay with failing. Failing is fine in the real world, it means you’re learning. Most of the things I’ve started or pursued have failed, but they’ve each paid amazing dividends in the experience and knowledge that came with them. And you’ll find that in all of these lines of work, people fail all the time and recognize it’s value. More on examples of failure later.

Have an online presence. In all of these areas, you need to exist online. You don’t have to write a blog, but you should have some sort of portfolio of your work out there so people can find you.

Finding One-on-One or Mentorship Work

This is essentially the same as having a mentor, but instead of an ethereal relationship where they tell you what to do, you’re providing value for them while also getting the chance to soak up their knowledge.

It can take different forms, and I outlined some of them above (researching for an author, helping an entrepreneur with random tasks, maybe doing some writing for a marketing pro). But at the core of it you’re finding someone really good at something you want to be really good at, and then convincing them to hire you.

So, first, you must be good enough to get hired for something. This goes back to having marketable skills. If you don’t have this then it’s never going to happen.

Then you find people for these relationships one of three ways:

They reach out to you. Much less likely in the beginning when you’re just starting to build a brand, but after a couple of these gigs it becomes possible

You get connected to someone. This is where it pays to have a network. See who your mutuals are on LinkedIn (don’t have a LinkedIn? Get on that), see who your parents know (no shame), see who your friends know, etc.

You cold email them. This is most likely what you’ll end up doing. It won’t work most of the time, so get ready for rejection, but when it does work out you’ll be elated.In the first two cases, you have some credibility to help you stand on your own. But what do you do if you need to cold email someone? I’m gonna plug Charlie Hoehn’s book again, it provides a robust method for making this happen. But in short, send them an email something like this (let’s say I want to do research for an author):

Dear Mr. X,

My name is Nathaniel Eliason, I’m a philosophy major at Carnegie Mellon University. I’ve read all of your books, my favorite was X because Y.

I wanted to reach out because I want to become an author in a similar genre myself. I really admire the work that you do and feel like I could learn magnitudes more from working with you than from any class at school.

I don’t know if you’re working on a new book currently, but if you are, I’d love to be your book researcher. I’m happy to work for dirt cheap or even free just for the experience. As a college student I have to do a lot of research for different papers and articles I work on, so I work quickly and keep detailed notes.

In addition, if there are any other small tasks or projects I can help you with, I’d be happy to do that too. Working under you and learning from you could rapidly improve my writing, and I want to provide as much value for you as possible in the process.

If you’re hesitant, I’m happy to do a two week unpaid trial period. Just let me know what you want me to go do some research or work on and I’ll take care of it. If you like the results, we can keep going. If not, no hard feelings.

Let me know if this sounds interesting to you too. And if you want to hop on a call my number is XXX-XXX-XXXX and I can make time to talk whenever is best for you.

Thanks for your time, and have a great day!

You would obviously modify it to fit your voice, but with enough persistence it will pay off eventually. You can use the same system in any line of work where you want to get experience working for a professional.

Doing a Startup

There’s a ton that’s been said, and that will be said, on this topic, so I’m not going to explain “how to start a startup,” especially considering I’m not qualified to talk about it.

But there are a few core points to consider if you want to go for it:

You don’t need to have any idea what you’re doing. Most people don’t when they’re starting out, and you’ll figure it out as you go.

Read a few books. I recommend against The Lean Startup if you’re already familiar with the concepts since it’s basically one idea rehashed in a couple hundred pages. The Lean Entrepreneur and The Startup Owners Manual are great. If you need to get users, read Traction.

Get a mentor. More importantly, a GOOD mentor. When you get into startups many people will want to “mentor” you but have no idea what they’re doing. Be sure to check the source of knowledge.

Be selective about who you work with. You might be spending the next 5 years with these people, don’t rush into it. Make sure they know their shit and that their skill set complements yours. Most importantly, make sure they’re hard working and self-educating. If they need a class to teach them something that should set off alarm bells.

Just do it. You’ll get a much better idea if you fail a couple times (assuming you have the self-awareness to know why you failed) and you’ll be more ready for the future ones you start.

Lifestyle Businesses

Then there are the mini-startups. A lifestyle business is any business that you can run on your own or with a partner that provides a steady (though not necessarily reliable) income.

Typically, a lifestyle business requires a large amount of work on the front end to get it set up, but once it’s set up, you can automate it to run mostly on its own

This should be attractive to everyone. Done right it’s a source of income that you can live off of without having to work a fixed number of hours. It breaks you out of hourly work, freeing up your time to do whatever you want.

The downside? It’s damn hard to do. When someone tells you it’s easy they’re trying to sell you a guide on how to do it.

But how do you do it? First, read The 4-Hour WorkWeek. That’s still the best source on the topic.

Once that’s done, just start trying ideas. The key is to not spend too much money testing the idea and getting it up and running.

For some examples:

  • Fratboxes could have turned into a lifestyle business, I just didn’t have the time to pursue it. I’d just have to get some freelancers to handle distribution and sourcing.
  • A couple friends and I once spun up a site where we would send people healthy recipes for a week for a small fee. We were just hooking into the Yummly API to automatically generate the meal plans so it was zero work. Turned out no one wanted to pay for it though, lesson learned!
  • A friend of mine is sourcing custom high end (something, it’s a secret) from China to sell on Amazon. All he needs to do is get the manufacturers to ship to Amazon and they’ll do the fulfillment. So long as he can game the ratings well enough he’ll just make a passive cut from the sales.
  • Another friend and I are working on a tool for designers that we’ll source from China. Minimum order is ~$1,000, so we’re just going to run a Tilt to pay for that batch then sell through Amazon. Assuming it sells. If it doesn’t, nothing lost since we didn’t order any yet.

If you want more ideas, check out The Smart Passive Income.

The key is to just get started. The sooner you start playing with different lifestyle business ideas the sooner you’ll hit on something that works, and the better idea you’ll get about how to execute. And this is particularly easy to do as a college students since it requires little up-front capital and doesn’t require an eight hour a day commitment.

Creative Work

Last there’s the purely creative work.

Obviously if you want to make money from this then you must become good at whatever it is you want to do, whether that’s art, writing, etc.

But you don’t need to become the best. If you’re in the top 5-10% that’s fine, and it doesn’t take that long to get to that level.

The important element here, that most creatives neglect, is an understanding of marketing. You’ll have a hard time standing out in any creative realm if you don’t know how to promote and sell your work to the right audience, and if you don’t know how to understand your audience.

This is why you only need to reach the top 5-10%. If you’re good enough, and good enough at marketing, you’ll do well. But if you’re the best writer in the world with no marketing skills you’ll starve.

This is true even if you have an agent / book deal. The more of your own marketing that you can do, the better position you’ll be in to stand out. They’ll only do so much.

As a college student with no exposure, you’ll have to create it yourself. That might mean sharing your work freely online, contributing to other people’s work, gaming sales platforms like Amazon, joining new sales platforms like Easely, and any other way you can stand out.

If you want to stand out in the highly competitive creative fields it’s not enough that you’re good. You have to do something different. Without that you’ll be lost in the noise.

Putting an Order to It

You can pursue any of these channels independently, but you can set yourself up for greater success in some of them by adding an order to it based on what’s easier to break into.

Startups and pure creative work are, by far, the hardest to make it in on the list. They also carry the biggest risk. If you dedicate a year of your life to something that doesn’t pan out, you’ll certainly learn, but you’ll be set back financially.

So how do you use the other types of work to set yourself up for the highest risk highest reward ones? Here are a few ways.

Corporate -> Lifestyle Business

Getting a lifestyle business right might take a couple years, and if you’re a junior or senior you might not make it in time. You certainly could, but there’s always that risk.

A corporate job (in the right industry) can provide a cushy source of income since if you’re highly productive you can work 2-3 hours a day and no one will notice. Then you can use those other 5-6 hours to work on your lifestyle businesses. Once one gets up and running, you can quit the job and live off of that!

Just make sure you pick a job where you work largely on your own, or at least behind a computer. If you need to spend a significant amount of time talking to people then it will be harder to do other work.

Lifestyle Business -> Startup

If you want to do a big tech startup, it’s not a bad idea to set up a lifestyle business first.

One of the concerns in the early years of a startup, before you have enough money to pay yourselves is how are you going to afford to eat as well as fund the company?

If you take investor dollars early you give up large amounts of equity for little money, which is a situation no one wants.

By having a lifestyle business you have a reliable source of money for food (and even funding the startup) so you’re not as worried about being equity rich and cash poor.

Lifestyle Business -> Creative Work

Since it might take a couple years to build a reputation as a creative to the point where you can make a living, you don’t want to suffer as a starving artist.

A good lifestyle business that takes <10 hours a week to maintain can set you up with the money you need to stay comfortable while pursuing your creative passion.

Ideally, you’ll be able to set up one that’s related to your craft. It could be something to help other writers, other artists, other actors, there are infinite possibilities. Obviously that’s not required though, any lifestyle business will do.

Mentorship/ One-on-One -> Creative Work / Startup

This one should be obvious, but your odds of success in both creative work and startups go way up if you have a strong connection with a professional who’s already done it.

They know all of the problems you’ll run into, the mistakes you’ll likely make, who you need to talk to, what you need to focus on, and most importantly, they can help you get exposure by leveraging their existing audience.

Get Started

You have what you need to get started lining up work that’s radically different from the typical 9-5 jobs that your peers will be going for.

This is only the beginning though. As you start down each path there will be much, much more to learn, but this is enough to get started.

If you already accepted an internship offer for this summer and are going “oh shit why did I do that,” don’t worry, just do the bare minimum necessary to impress them and work on this stuff when they’re not looking. You’ll be glad you have that money to fall back on.

First Steps:

Mentorship / One-on-One work: Read Charlie Hoehn’s “Recession Proof Graduate” and start implementing his method.

Startups: Find someone you can trust who complements your skill set, read The Lean Entrepreneur, and start thinking up at least 10 startup ideas a day until you hit on one that speaks to you at a primal level. But I swear if you build another messaging, to-do, or tinder-swyping app I will hunt you down.

Lifestyle Business: Read The 4-Hour Workweek and follow his steps. Just keep running cheap tests until you get some validation (actual sales or massive numbers of interest signups).

Creative Work: Keep practicing, put your work out there, and read 1000 True Fans.

Most importantly, don’t give up.


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