A Letter to my College Self on 5 Lessons Learned the Hard Way

Before I launch into today’s post where I write about 5 lessons learned the hard way while in business school, I wanted to make a quick announcement. I’ve launched a NEW podcast! 10 episodes are already available so check them out via this link. If you love what you hear, then definetly leave a review. Either way, I hope you enjoy it and I appreciate any feedback! (For those without iTunes, we are working on pushing the content to more locations so more viewers can download/listen so stay tuned!)

With the upcoming Winter break, I can’t help but feel a bit nostalgic. I’m talking about the feeling I had this time of year year back in college. I also think to myself, “Man, what if I could go back in time and write a letter to my college self?” To my knowledge, time travel is still a thing of science fiction, but I figured I’d give it a shot anyway.

First, I have to put myself in my college self’s shoes. At this point I’m stuck in the library CRAMMING for finals.

Full panic mode.

The Fall semester is coming to a close and I am catching myself daydreaming about Winter break. I’m planning on either reading a few books OR (if these are my earlier days) I’m thinking of which Top 100 IMDB movies I’ll tackle when I get home.

If I could add one more item to that daydream, it would be this:

5 lessons learned the hard way:


This list is in no particular order of importance. Each lesson has been equally important in my life.

To start — Learn from the mistakes of others, but don’t beat yourself up too much for making your own.


My freshman year of college was filled with asking a lot of questions. I loved to talk with older students and ask them questions about their experience.

Many of them would reflect back and give the common phrases, “enjoy it while you can.”

It often took a few minutes of prodding, but then the real answers would open up.

“When you take Econ 301, make sure you avoid professor Y.” (I was going to put the standard X there, but I did not attend X-Mansion for my undergrad.)

Or, “start recruiting for a job NOW.”

Those were the real valuable pieces of advice that helped me land a great job right after graduation.

But, naturally, despite how many questions I asked, I couldn’t figure out the optimal solution to EVERY potential situation.

I stumbled. I fell. I got D’s on exams that required an immense amount of work and ended up with a C overall.

Early on, I would take each failure a bit too personally. I would think I’m not cut out for my major or that I wasn’t as smart as the other kids in the class. I mean, objectively, I had an exam in front of me indicating I was near the bottom.

My problem wasn’t me, it was my strategy.

Over time, I quickly learned I could make adjustments to my approach and receive a better result. I would tweak my studying habits or go in to office hours for additional questions. I would talk to my peers to see what problems they were having and set up group study sessions.

The trick I developed was when I received negative feedback via a poor result on a quiz or exam, I would immediately think to how I can change my approach to receive a positive result. I eliminated all the self-talk saying how I should have studied more or that I was stupid. Those thoughts were not going to help me get an A on the next test.

Learn to appreciate the moment, but don’t find yourself idle or lazy for too long.


At one point, during my Sophomore year, my first class started at 4:30pm. Ahhhh, those were the days.

Sadly, I quickly learned, that sleeping in a slippery slope.

Left unchecked, my college self became a bit TOO lazy. I began to sleep in a bit longer than I should have and it started to show.

By not doing the right work upfront, I left a mountain of work to do down the road.

Being proactive is one of the most vital ingredients to success. Sadly, I learned this only by being completely reactive to my environment.

When the environment starts to make us soft, then the smart thing to do is to put the pressure on ourselves. Over time, things will catch up and we’ll be happy we did the work to prepare.

Learn that nothing is good or bad, but thinking makes it so.


Ok. I’ll admit. This one comes from Shakespeare. Wait, what is a CPA doing reading Shakespeare? I know. I’m shocked this quote stuck with me this long, but the lesson is so eloquently stated.

We often find ourselves surprised by outside circumstance. Some of us respond by rolling with the punches and finding a way to get the job done. Others (cough, cough, me in college, cough) might spend quite a bit of time looking for someone to blame or some outside factor that made our situation worse.

Easier said than done, but I would tell my college self to not take things too seriously.

Pick yourself up, brush the dirt off, and keep moving forward.

Learn to work with others, but only trust yourself.


This one isn’t very collaborate at first glance, but hear me out and you’ll see it is very collaborative at the end.

In college, we often had team assignments and even team projects that could be worth as much as 50% of our grade. Naturally, this meant a high level of collaboration.

Still to this day, this structure led to a lot of learning about coordinating team schedules and dealing with many types of people.

By Sophomore year, I learned the correct response when someone was a “no show”,was to take notes and fill them in later. Yelling at them the next day in class is not an OPTIMAL solution to receiving a good team grade.

Similarly, when it comes to getting the assignment done, the smart move is to develop the right structure to pull out any weeds before the final submission. In other words, don’t rely on another teammate to get the job done perfectly. Lean on each other and self-review each aspect of the project.

With this approach, you can collaborate everyone’s strengths while simultaneously filtering out any noticeable weaknesses.

This process also means you don’t have any sudden hiccups hours before the project is due. The final hours are spent refining the work and bolting on any necessary changes. The alternative in my earlier college days was typically stressing out and nearly burning bridges with semester long colleagues.

Learn the difference between productive procrastination and productivity, but still make time for both.


Ahhh productive procrastination. That beautiful middle ground between doing what needs to be done and doing something that doesn’t need to be done right this second.

For the longest time, I felt I was being productive and learning when I was really just wasting my study time. Now that it is finals week, that study time becomes its worth in gold. So, what was the ultimate culprit to my productive procrastination?

TED Talks.

I used to swear by these. Sometimes I would have 15 minutes between classes and think to myself, “YES! Enough time for 1 TED Talk.”

Hell, even in the middle of a 90 minute lecture (I know), I’d open a new tab on my laptop and (I know) launch into a 20 minute TED talk on how creativity is born (I know, I wasn’t the GREATEST student, but I still had good grades!).

Great TED talk, but it didn’t move me any closer to understanding why the limit does not exist.

Feeling productive is not the same thing as BEING productive.

I learned that lesson a few too many times. My hope is that by now, it is engrained in my mind. My solution now is to do the hard things first, then enjoy the rest of my time.


I should build a time machine to avoid my past self from experiencing the pain from learning new life lessons.

Juuust kidding.

College is a place where I learned how to learn. That might sound trite, but it is true in my case. I just wish it didn’t cost me $100k+ to learn such valuable lessons.

This post was part of a project inspired by Earnest, a student loan refinancing company. If you fall into the 70% of grads with student loans and want to learn more, check them out here.

What would you tell yourself if you could go back? Would you rather you learned the lessons the hard way early on or would you spare yourself the turmoil?


10 comments… add one
  • PeterB Dec 14, 2016, 7:07 am

    I thinking about this “writing a letter to past me” thing from time to time. Man, how much better could be those years if we have the opportunity to actually do that. But also, the way we lived our lives made us the persons who we are, so those mistakes and tough lessons were necessary after all. But the “what if?” question still scratching my brain. Probably we will not find out the answer until time travel become real.

    PS: Congratulations Matt for the podcast. Good stuff, listening to them right now.

  • Mrs. Picky Pincher Dec 14, 2016, 8:32 am

    This is an awesome point! I’m sure we all wish we could go back in time and give our college-selves advice–woe if I could. 🙂

    First of all, I would have slapped myself for going to a private university. I had received a full ride to a univeristy in Indiana, which I had declined for a much pricier school closer to home in Texas. Ugh, stupid 18-year-old self.

    I would have also told myself to have fun. I hoarded in my room all the time during college and the first year in particular was really hard. It’s important to get out a little and see the world.

    But most importantly, I would have ingrained better money habits. I was fortunate enough to get $300/mo from my parents for everyday expenses. When your food, room, and board are already paid for, that’s a lot of money for a college student. But I blew all of it on impulse purchases and Amazon orders. If I could go back in time I would have saved that money to pay for an apartment out of college or to start a Roth IRA. Good money habits start early!

  • Matt Dec 14, 2016, 8:56 am

    Awesome job on the podcast, I’m excited to listen!

    I can relate with the college nostalgia, one because I’m at the age where my college experience started a decade ago so it’s easy to get reflective and two, I also daydream about what I would do with a month long winter break!

    The thing that really hits home for me about the idea of “writing a letter to your past self” is that it’s easier to look back at all the things you could have done than to appreciate what you were doing right (and maybe better than you’re currently doing).

    Even through the mistakes and the lessons learned and the hard work I still think it’s important to “feel lucky”. Yes, I could have spent a lot less money on school or started investing earlier, but I’ve also been fortunate enough to stumble upon the resources to get my finances together in my twenties – for a lot of people when it finally “clicks”, it’s too late.

  • Financial Panther Dec 14, 2016, 9:50 am

    Gosh, if I could go back, I would’ve told myself not to spend every buck I had trying to act like a big shot. I had way too many clothes that have been tossed over the years. Going back over my college years, I probably made at least 20k and yet, by the time I graduated, it was all gone. Would have been nice to have invested that money properly.

    Also, great job on the podcast Matt. I listened to all 10 episodes while cleaning up my house last night.

  • Financial Slacker Dec 14, 2016, 12:27 pm

    I can easily relate to the “productive procrastination” tendency. I still fall into that trap even today.

    My most glaring example is the website. I can spend hours working on little technical aspects of the site which really have no bearing on anything, but they make me feel like I’m being productive.

    Instead, that time would be much better put to use writing a post or as you have done, starting a podcast.

    Congratulations! Can’t wait to check it out.

  • Jay Dec 14, 2016, 6:35 pm

    These are some awesome lessons Matt. I think your college self would be lucky to receive these words of wisdom. And kudos to you for documenting them so effectively. I like that most of them have a theme of balance and perspective. It sounds like all that stoicism you’ve been reading lately is paying off nicely 🙂

  • Jon @ Be Net Worthy Dec 14, 2016, 8:01 pm

    Interesting question. I’m not sure I’d give myself any advice. I certainly do everything “right”, but I wouldn’t be the person I am today without that experience. Luckily, I made it through those years relatively unscathed. You hear you forget, you see you remember, you do you understand. Nothing beats experience and I’m not sure I’d want to cheat my younger self of that.

  • Derek Hopper Dec 15, 2016, 4:44 pm

    “Others (cough, cough, me in college, cough) might spend quite a bit of time looking for someone to blame or some outside factor that made our situation worse.”

    This post is definitely relevant to me right now. I’m currently reading 7 Habits of Highly Effective People. I can’t say I’ve fully comprehended everything yet, but everything you say here rings true. As humans, we have total control over how we feel – as much as outside factors try to influence us.

    Thinking back to college, I’m sure I was very similar to you.

  • Financial Samurai Dec 26, 2016, 9:19 am

    Those aren’t bad things at all! Just life I say! I wish I had even MORE fun in college. It was so nuts! Traveling abroad, dating, partying. I loved college so much. I wish I stayed for a 5th year! haha.

    • Distilled Dollar Dec 27, 2016, 6:50 am

      College might be wasted on the young, but that’s just the way it is. 🙂

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