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The 14 Hard Life Lessons College Didn’t Teach Me

In my first year of college, I moved in with my band. Yeah, that’s right. I was actually planning to be a rock star, but agreed to get an education as my “backup.” You know how rock stars be 😉

Someone in our hometown had a 15-passenger van for sale – $300! A steal! So we bought it, and I drove it 10 hours to where our new band house was. 1 hour away from my destination, I heard an ungodly noise coming from it and it exploded in the middle of a 6-lane highway. Life lesson #1. Put oil in your vehicle.

Poor ol’ betsy never rode again.

I moved into a house with 7 other guys and agreed to put all the bills in my name. Why not, I thought. They’re good for it! That stupid decision ruined my credit score and left me paying bills out of pocket (and dodging collectors) for years to come.

Life lesson #2. Pay bills on time.

I was a poor kid from a small mining town. My parents sent me to college — hoping my life would be better than theirs. But the world wasn’t that simple. Truth is, I’m 37, and I feel like it’s taken me this long to figure a lot of shit out. Things like money, success, getting jobs, using my education, and a bunch of other stuff that I’ve learned the hard way over the past few decades.

So, if you’re in your teens or twenties, I hope you can learn from my mistakes. If you’re my age or older. I hope these life lessons are interesting to you. I’m sure you have some of your own I could learn from.

Here are the life lessons I’ve learned — some of them the hard way. And — in case you’re wondering — there’s no college credit for this shit.

1. There’s no shame in work

Would you believe that my college education was actively against work?

*Gasp* you say?

Seriously. For some stupid reason, my liberal arts professors didn’t think their job was to prepare ME for a job. They thought it was beneath them.

And surprise, I had no freaking clue what to do when I finished. So I went to grad school–the thing those same professors said was the most valuable way to use your brain.

$80k in student loans later and I STILL had a degree I couldn’t use. I had to learn how to put it to work.

Guess what? If you’re lower to middle-class like I was and there’s no parents’ money or trust fund coming to save you… you’re going to have to work. And there’s no shame in that.

Work hard. But make sure you also learn how to work on the stuff that moves the needle for wealth.

2. College is worth it, sometimes

I devoted a lot of time to asking whether college is worth it. But really, it’s a stupid question.

What the fuck does “worth it” mean? If you get a technical engineering degree at a local college that costs you $2,000/year and leads to a salary of +100k, of course, that’s probably worth it! If you go $200k into debt for a PhD in English, that’s stupid.

In general, I’m in favor of an undergrad degree. It opens up your world, teaches you to think, and statistically does lead to a higher income. In general, I’m cautious about grad degrees — some can pay off, but many are shit.

But be careful. Choose your major carefully and get lots of other experience. I’ve often quoted the statistic that many grads have jobs they could have gotten with their high-school degree. This is true for 44% of all grads.

Life lesson – go to college if you can. But do it on the cheap. Look at your in-state tuition instead of trying to go to your dream school that’s going to sink you.

3. It’s better to own the machine than work in the machine

When I read Seth Godin’s book, Linchpin for the first time, he argued something that I’d never heard.

Education isn’t created to make you unique. It’s not to build your leadership abilities. It’s to turn you into a reproducible cog in an industrial age machine.

Now I know I’m going to sound like I’m contradicting myself, but bear with me. At their very best, college and universities are usually trying to plug you into a job. Which, as I already said, there’s nothing wrong with.

However, getting a job is a way to go and build someone else’s world-creating machine. And, the second of these life lessons, some of you should build your own.

While shocking at first, I’ve come to believe that there’s a lot of truth in Godin’s claim. Education doesn’t teach you to build the world. In fact, there’s some evidence to suggest that most small business owners did not go to college.

There’s even a running list of college dropouts who have gone on to be wildly successful.

The reality is, as Seth Godin writes in Linchpin, that the world doesn’t actually reward people who stay in their lane and follow all the rules. And education is fundamentally about following rules.

One of my biggest frustrations with degrees is that students who hold them know what needs to be done in the world.

They can identify every social inequity and even some ways to fix them.

But most don’t know how to take the massive action to create the world that they want to see. It’s a life lesson they’ve never learned. Instead, they look for a job to match their skills.

So if you’re angrily tweeting about some problem on a regular basis, maybe it’s a sign that you need to grow your leadership skills to the point where you can step out and help fix that thing!

If you hate the work that X company does in an area or see a big need for X in another area, maybe you’ll be the one to solve it.

Change needs to happen. So go and make it happen!

Imagine if people with degrees and big ideas had the ability and knowledge to execute and build their vision in the world!

4. Learn about money… now

This is perhaps the most vital of life lessons, and you probably didn’t learn it in school (unless you studied business or finance). And, if you were raised like me, you probably didn’t hear it from your parents.

We live in a capitalist system and very few people get an education in how to actually succeed in that system.

By the time I’d finished my undergrad, I’d read Marx and Weber. But I’d never learned how to turn my knowledge and skills into a value proposition in the marketplace. I could talk about exploitation, but I had no fricken clue that I could make money work for me.

I’d never learned how to get paid, or how to grow wealth.

I was just taught to complain about how unfair it was that everyone else had it and I didn’t.

Check out our four favorite personal finance books here!

5. Great success often needs a team

Damn I hate group work.

One time, I had a group project. My team included a guy who was useless…

I mean, really useless.

This guy wouldn’t show up for our group meetings, wouldn’t talk to us, and in the end, we just planned the project without him–then he showed up and presented something half-assed that he’d done himself. 

I hated working in a team. I loved working by myself when I had total control of the outcome and didn’t have to socialize too much.

Now some of you reading this understand me completely, and the other half of you are scratching your head.

That’s good! You learned to work on a team. It will serve you well.

The world requires a certain amount of teamwork and playing well with others.

Even at its best, college doesn’t usually include the kind of group work that makes the world work. The greatest partnerships are made up of people with different and complementary skill sets.

If you did group work in college, it was probably with people who were exactly like you.

As an entrepreneur, I love having people who know things I don’t on my team. Bookkeepers, graphic designers, lawyers, accountants, bankers… they know stuff I don’t. And I know stuff they don’t. That’s what makes a team function. 

Life lesson: Do the stuff you’re good at. And get other people to do the stuff you’re not good at.

6. Networking is vital

A great segue from the last point.

Networks matter. Networks and connections give you what you need in life.

Of course, this starts out with the ability to build a career and maybe get your first job. Most of the readers of Roostervane are thinking in this vein.

But, over the course of a lifetime, your network then becomes your ability to make shit happen.

  • Want to start a non-profit? It helps to have community partners to work with.
  • Want to start a business? It’s great to have some potential clients.
  • Want to get a higher-paying job? It’s nice to be able to flip a message to interested parties telling them you’re looking and getting job offers back.
  • Want your company to start a new product line? It’s nice to know some people in the field you can chat with about it.

Did you know all this stuff comes from networking?

Probably not. They won’t teach you that in school.

You imagine networking as standing in a room talking to strangers and handing out business cards.

In reality, networking is just stepping into the sandbox of life. Everyone’s building their own stuff, but it doesn’t mean you don’t lend a shovel or borrow a bucket. You come together to build the turret of an enormous sandcastle, but then you go off and dig your own moat. But you work with others to build the world you want and help them build the world they want.

7. Leadership is decision making

“We build the leaders of the future.”

You’ll see something like this on the masthead of a lot of universities and colleges.

But I meet too many grads who have crushed confidence from their education that takes years to recover.

To be honest, I’m not even sure if leadership is something you can learn in a class.

I think you’d be better learning leadership by stepping into the real world and getting tossed around a bit. If you are given a position with real responsibility, or if you try to start a business, you’ll learn leadership pretty quick.

A lot of grads do eventually grow leadership skills, but I’m not sure how many of them get them from school.

Too often, students are trained to sit and wait to be told what to do, usually with very clear instructions. This isn’t how the world works.

The world rewards decision-making.

One of the first and most important places to make decisions is about your career. Don’t just wait for it to happen to you.

  • Decide the type of work you want to do.
  • Decide the impact you want to have.
  • Decide how much money you’re worth.
  • Decide how you demand to be treated.

One great podcast that gives advice for growing leadership is the EntreLeadership podcast. And I’m pretty sure that Dave Ramsey was one of the first people I heard defining leadership as decision-making.

8. The world only cares about results

In Canada, it’s common to go to university for a four-year undergrad.

And it’s also common to go to a community college AFTER that four-year degree, to gain some sort of high-income skill, experience, and placement that will actually be valuable in the real world.

When was the last time you created a project you could show an employer in university? When did you last create something that had the same title of something that people actually use in jobs?

My spouse is a graphic designer. She fell into this career after being a social worker and hating it.

As we do, her first instinct was to go to college for graphic design so she could start a business. But after some research, she realized that clients don’t care if you went to design school or not. They care if you’re good at making stuff.

And she worked as hard as she could to become amazing! (She also made the Roostervane logo.)

Education can do a lot in this world. But at some point, you’re going to need to learn to produce things, produce them well. This is why resumes are such a tricky thing for new grads.

Employers don’t care if you “did research.” But they do care of you “produced a high-impact report that was implemented by my program.”

The first of these is a task. The second is a result.

If your degree doesn’t include producing things that can demonstrate your skills in the marketplace, you might need to take it upon yourself to do it.

9. The world my parents prepared me for doesn’t exist anymore

I was born in 1985, which google tells me is the year that the original Nintendo NES system came out. I played video games in an age that you had to stick a huge square thing called a cartridge in a slot and–sometimes–you had to take it out and blow on it to make it work. The first cellphone I ever saw was in a suitcase.

Over my short 37 years, life has changed more than anyone could have ever imagined.

My parents’ knowledge of how the world worked was that someone gave you a job, you worked at it for life, you got married, had kids, worked for your pension, and retired at 55 if you were lucky, or 65 if you weren’t.

Massive technological disruption was happening at the same time as my parents and teachers were teaching me about the world that they knew. It came just as I enrolled in a university to study an undergraduate degree in history that was becoming obsolete.

Nobody saw it coming.  

My guidance counselor had no idea–he funneled me into the old-world career path he knew.

So here we are.

Those of us who are Millennials, who have lived through this transition, are left with a world that no longer looks like what we were trained to expect. Even Gen Z is being taught a lot of the same stuff; most education systems haven’t caught up to the disruption yet.

We’re the monks who spent years learning to copy manuscripts by hand right as the printing press was invented.

Succeeding in this world will take constant reinvention. It will take disciplined self-learning to grow in the areas where the world is going, rather than waiting for the education system to catch up. It will take endless creativity and adaptability. And yes, it will take an attitude of embracing the change rather than wishing it wasn’t happening.

10. You need an income and a calling

“What do you do?”

Ahh the question of every dinner party I’ve ever gone to, and the one I dreaded the most.

“I’m doing a PhD” was usually met by a blank stare or a question:

“What are you going to do with that?”

When I worked for a think tank I got similar blank stares.

But when I worked for the government, I finally had an answer that was satisfactory. People my parents’ age understand that government jobs are good jobs with pensions and benefits—they check all their boxes. So telling people that I work for the government was usually met by smiles, nods, and exclamations of “oh nice.”

This is how another generation understood themselves and the individuals they engaged with: through job titles.

But–refer to point one above–that world is quickly disappearing. And the world of work is changing so fast that, even if you do have a steady job, there’s a chance nobody knows what it is anyway.

I’ve come to believe that the way we think about work and jobs need to change.

On reflecting, I think you need an income and a calling.

An income is to pay the bills.

A calling is what gives life meaning and purpose.

If those are both in the same place, great. If it happens to be working for an employer you love, good. If the thing you love is working as a policy analyst for the government or a researcher for a Pharmaceutical, great. Your job and your calling match up. This is an efficient way to do this.

For some people, though, it doesn’t work like that. Some people do a job that they feel okay about because it’s amazing money, and use that money to chase their calling, whether it’s feeding the hungry or building model railroads in their garage. These people keep their income separate from their calling.

When I worked for the government, I met a lot of people who enjoyed being able to work 9-5 and not take the work home with them. They worked to live, and spent their free time doing other things. I also met people who loved the job and wouldn’t do anything else. It was their calling.

Both of these scenarios are fine. It depends on what a person wants.

There’s more.

Money doesn’t necessarily come from working by the hour. People with big chunks of money in investments make interest on it. For some people that interest can be enough to live on, maybe even more than what most people make in a year. For some people, owning rental properties brings in an income that gives them financial freedom. Some people choose to make very little money, but also live a compressed life of extreme frugality. They have all the money they need.

All of my money gets funneled into my corporation and I pay myself and my wife a salary from it. Our bank account doesn’t know whether it’s money that comes from my consulting work or if it’s passive income from this blog.

Money is money. You need some.

Find or create these two things: an income to give you what you need and a calling that will make you come alive.

11. Stop admiring useless degrees

I’ve spent a lot of time chasing degrees that are somewhat useless, so I feel particularly qualified to say this.

I’m not sure why the university degree is so connected to my sense of self-worth, probably because of the good degree=good job bullshit of my parents’ generation. I was an oldest child who wanted to impress adults, and everyone seemed to be impressed by university–so I did it.

I recently read similar reflections from Michelle Obama in her book, Becoming. She explained that many of her education choices were shaped by the responses adults had when she told them what she wanted to study.

There’s nothing wrong with being educated.

But if you’re stuck in life, for the love of God, a degree won’t necessarily fix it. Don’t do further studies because you don’t know what else to do. That’s a way to be disappointed.

My generation thinks that the answer to “I’m having a tough time getting a job with my English degree” is “Jiminy Cricket, I can go to grad school!”

NO! STOP IT! If you know where you’re going in the world, go to school for it. Don’t go to school to fill the void. Go out in the world and figure it out.

12. Everyone thinks they’re extraordinary. Few do extraordinary things

Many of us have a deep desire to be significant.  

But being extraordinary isn’t just a quality of being. Being is ordinary. What makes us extraordinary is the things that we do.

This isn’t to try to make you feel inadequate. Every life has tremendous value in and of itself. I’m not saying that “being” isn’t valuable. It is the beautiful, ordinary state of every individual on this planet.

Extraordinary is usually a quality of doing. That Greta Thunberg is a teenage girl is ordinary and special in and of itself. That she single-handedly sparked a global climate revolution is extraordinary.

The older I get, the less I care about being extraordinary. But if it’s important to you, you’ll have to do extraordinary things.

13. Stop feeling sorry for yourself

I’ve felt sorry for myself way too many times in my life. One of the most recent was while I was studying for my PhD, and realized that there was an academic jobs crisis in universities. I got really mad at the world, at my department, at my supervisor, at my peers, and I felt like I’d been the victim of a system that sold me a degree I didn’t need, promised me jobs that weren’t there, and then made me feel guilty for looking outside of academia for work that could actually put a roof over my family’s head and food on our table.

Whatever struggles you’ve gone through in your career, you don’t deserve them.

But at the same time, feeling sorry for yourself helps nothing. It won’t change where you’re at.

Getting mad at the world doesn’t do much either. And hating people who are more successful than you hurts you, not them.

It’s only once you ditch this attitude and start to cultivate optimism and hope that you can change your life.

Instead of feeling sorry for yourself, focus on the positive.

You have a tremendous skill set and an excellent mind that will be valuable once you learn how to use it and apply it to the marketplace.

And, you have gifts to offer the world that we desperately need.

14. Teach yourself what you need to know

Last but hella not least, you can teach yourself anything you need to know in this world. You can go on YouTube and access more information than our parents had in the encyclopedias that once sat on their shelves. People will teach you to make money, be happy, build businesses, make friends, speak in public, really just about anything you could ever want to do.


We tell kids to stay in school. I want to tell them to get the hell out. Run far. Work first. Travel in between. Find ways to get out of school, and only then will you be able to determine if you need it. 

These life lessons won’t come from college. They come from the school of hard knocks. But I hope they’re useful and interesting to you. And I hope the fact that I made some of these mistakes means that you won’t have to!

Read More: How to Find Your Passion When You Feel Lost

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