10 Things I Wish I Would Have Known in High School


In our culture today, almost nothing is expected of our youth until after they reach adulthood, that glorious day that we have held up for decades, the day one graduates from college. It’s the beautiful day in which all young people are supposed to magically stop wasting all their time, blowing all their money, get their first job, start saving for retirement, start paying their own cell phone bill, car insurance, health insurance, food, rent, and begin paying off that little mountain of student loan debt. They are expected to do this with a perfect job that was going to be handed to them upon graduation. Instead, record numbers are back living with their parents, in debt up to their eyeballs, unemployed or underemployed and completely disillusioned.

If I could go back and advise my younger self, these are ten of the first things I would say.

1. Don’t let anyone rush you into a decision. I learned a long time ago that if someone is trying to rush you into a decision with the hollow threat, you should usually say no. You are going to miss the train and there will never be another one, people will often say. Or this is the last time it’s ever going to be on sale, the salesman says. You need to go to college right away or you will never go, and you will be forever banished to a life of poverty! Wise decisions aren’t made in a rushed, wild panic. This is especially the case when high school students are making important decisions about their lives that will have long lasting implications.

2. Start backwards. Everyone says that you should go to college and then figure out what you want to do the rest of your life. I think students should work until they figure out what they want to do, and only go to college if you absolutely have to for your particular field. Limit your risk. Get an entry level job in the field you want to go into and see if you can stick it out for a year. If you don’t like it and decide to change your mind, you have a pocket full of cash that you’ve saved up over that year instead of 20 grand in student loan debt. Plus you have some job experience.

Ask yourself what you want to spend the rest of your life doing? This is not an easy question and can take years to figure out. If you don’t know for sure, don’t rush off to college and get into debt up to your eyeballs before you have any sort of plan. That would be foolish.  If you don’t have a clear goal, or endpoint in mind, then that needs to be first priority. It doesn’t matter how long it takes for you to figure it out. Remember, don’t let anyone pressure you! I was delivering a dryer to a lady about a year ago who had been pressured into law school by her family. She never finished, got married, had a child, and is not at home with 200k of student loan debt. Two hundred thousand dollars. Give yourself time to wrestle with what you really want to do.

3. Stay out of debt. If you are a high school student right now, hopefully you don’t have any debt. Keep it that way as long as possible. 80 years ago, taking on a little debt to get a college degree was usually a fantastic investment. It almost assured a person a great job and a bright future. Because of this, everyone was encouraged to go to college to get the education that would be this magical ticket to success. Then, over the past 80 years, the world has changed beyond anyone’s possible imagination. The internet has revolutionized people’s access to information and you can now learn almost anything you want from anywhere in the world. The internet has upended the marketplace and allows anyone with a product or a service to reach enormous amounts of potential customers, often for free thanks to websites like Craigslist. The internet has exposed students to a world of possible career paths and is slowly destroying the barriers-to-entry in almost of them. And yet, the advice for young students has not changed. Everyone is to go to college after high school.

All the while the price of a college education has increased 1140% since 1978 thanks largely to unlimited, easy access to student loans that the government is doling out. This, coupled with a very poor, and rapidly changing employment market has caused record enrollment over the past few years. This has caused increased competition for fewer and fewer jobs leading many college graduates to be unemployed or underemployed for years following graduation. So, in summary, a bad job market is driving a record number of college students to take out huge amounts of loans that must be repaid, all to compete for fewer jobs that have wages that are either flat or are decreasing. It’s a bubble and it’s going to pop very soon. Everyone but the computer programmers, a handful of engineers and healthcare professionals are going to get the shaft. These students are basically buying homes right before the bubble is going to burst except they absolutely cannot walk away from student loans. They follow you to your grave.

Stay out of debt.

4. Talk to former college graduates. Interview a good range of them. How much money did they spend on their degree, including room and board, books and lost wages because they weren’t working during school. Are they currently employed? Do they have the job they were hoping for? How much money are they making? Then ask them if things are getting better or worse as far as the job market in their field and the competition.

I have a friend that got his physics engineering degree that told me a story a few years ago. He was in his first or second year of school when a former student emailed the entire department, including all the current students and told them that they were all being lied to. There were no jobs waiting for them! There were way too many qualified applicants for a very small number of jobs and these poor students were still years from even graduating. Needless to say, he along with most of his peers are not working in their field of study.

5. Work hard and make money. There is absolutely no reason that a high school student that is willing to work and use their time wisely couldn’t graduate from high school with 50-100 thousand dollars in the bank. Most high school students live at home and have very little, to no expenses. If you can make $250 bucks a week for 4 years, it will add up to almost 50k. I’m going to soon be featuring some high school students that are now running their own appliance business. They are working hard, learning a trade and putting themselves in a great position to succeed in business.

6. Save your money. One of my biggest regrets from my high school years was how much money I wasted. I blew every penny I earned or was given as fast as it came in. All I could think about were the pleasures of that day, and never considered saving money. You might not be able to go to as many movies with your friends, but when it’s all said and done, and you have a giant pile of cash that you’ve saved through the years and can now invest it, you will not regret it. Ask any person in their 20’s or 30’s and ask them if they wish they would have saved more money when they were young.

7. Increase your marketable skills. Do you enjoy sales? Sales is an incredibly valuable marketable skill. Start your own business where you are forced to learn sales, or get a job for a business where you sell their product. Learn everything there is to know about sales. Read books on the subject. Write down what you learn and focus on what makes a good salesman. Do you enjoy programming? Reach out to some programmers and ask them where to start and what some of the up and coming programming languages are. Focus on becoming as proficient as possible in those programming languages. Not all forms of knowledge and not all skills are equally valued in the marketplace. Some are in short supply and are thus valued much, much higher. Take inventory of your strengths and your interests and focus on increasing your skills that will help you succeed.

8. Get as much work experience as possible. Experience is beginning to trump degrees. As much as people hate it, especially those with college degrees, many degrees are carrying less and less weight as the number of college graduates continues to rise at a rapid pace.  Employers are starting to care more about what you can show them you are able to do, rather than what a piece of paper says you supposedly know. They want to know that you are able to solve problems and not just memorize facts and pass tests. Get as much work experience as you can, as early as you can.

9. Read as much as possible. Read biographies of great men and women that have gone before you. Read the stories of how the greatest companies were started. Read books about problems that are facing people all over the world. Find people you want to be like and read about their lives, read their books, their blogs or follow them on twitter if they are still alive. Through these channels you can learn things and be challenged by people in ways that you will never get from your peers.

10. Focus on quality of friends, not quantity. Pick a small handful of quality friends to hang out with. View them as investments. Choose wisely. Pick friends that will help you go against the foolish current of your peers. Quality friendships take a lot of time to cultivate, but the work will most likely reward you the rest of your life.

One of the reasons I have been writing on this blog these past years is to help and encourage others navigating the seasons of life. Though it doesn’t do much good to dwell on the past, to this day I regret how I wasted so many of my younger years. Spend the early years of your life as productively as possible. Grow up before you graduate. Have fun, enjoy your life, and make your decisions with the long term implications in mind.

What is one piece of advice that you wish you could go back in time and give to your high school self?


  1. It would be sweet to be making money on craigslist in high school. If I were in high school now I would probably demand my parents to let me be home schooled, and I would be checking craigslist while doing my school work at home, and making money. I’d save up the cash, and use it to build a real estate empire.

    Do you know any good books or resources to read on sales? I’d like to study that.

    • I’ll think about a few books today and get back to you with a few suggestions. I was frustrated because when I was leaving high school, Craigslist hadn’t made it to my city yet.

    • The absolute best sales book I could think of owning is “How to Win Friends and Influence People” by Dale Carnegie. It’s largely anecdotal which makes it so easy to read, but it’s chock full of gold.

      $12, maybe $16–cheaper online, I’m sure. Worth every cent.

  2. I would have a few pieces of advice to my younger self and others:

    1). Keep your priorities straight. When you are 40 or 50, no one will really care how sexy your high school girlfriend was, nor how embarrassing it was when she dumped you. It isn’t important in the grand scheme of things.

    2). Find a mentor. Contact them if you can, if not, study them. Emulate what they did to get where they are. There are really no secrets to success, so why not just follow the roadmap written by others?

    3). No matter what you do for work, work hard and be the absolute best dishwasher or dog walker or babysitter you can. People in high places recognize and reward hard work. And, they remember you for many years to come.

    4). Don’t take everything too seriously. Enjoy life. You never know when it will be snatched-away. No one on their death bed has ever said, “I wish I would have worked more.”.

  3. Great points on the college degree. If someone finds their talent like we have in a home-based business that leads to financial independence, then dumping a bunch of money into a degree or taking on a ton of debt to get it just delays the end goal of independence/early retirement. I discovered selling online when I was in college 10 years ago and have expanded it ever since, but I would go back in time even further and advise myself to start reselling in my grade school years just to be that far ahead. Also, I would advise myself to never invest in something I don’t understand or that is sketchy and suspicious. Also don’t make any unsecured loans or loans to family or friends. Also, learn the long term benefits of real estate when purchasing a home rather than looking at short term costs, and get a house instead of a condo – no annoying condo associations levying association fees on you over time, and no shared plumbing problems. Put down the minimum to avoid private mortgage insurance (pmi) payments that stick with until certain conditions are met. Don’t pay all cash for a house if you can get a good mortgage interest rate and invest the money at a higher ratebof return, like real estate investors do.

  4. If you haven’t seen it already, the History Channel series “The Men Who Built America” is worth watching. It details the business deals of Cornelius Vanderbilt, John D Rockefeller, James Carnegie, Henry Ford, JP Morgan, Thomas Edison, Nikola Tesla. It used to be on youtube, but has been removed.

  5. Very insightful.

    I think I would also encourage high schoolers to start saving. Stash like mad.

    I could have had a larger down payment for my home, and would be enjoying a much lower monthly payment if I had been more worried about my future family and less worried about my next Starbucks.

    The latte factor, if you will.

    • Such good advice. It will get you a lower payment, and can help you avoid private mortgage insurance etc. So many benefits to beginning to save early.

  6. Hard to say what I would tell my past self… I didn’t start using Craigslist until the very end of high school/beginning of college, and that was because of my hobby. So I guess I would advise myself to get into that earlier. Craigslist has basically exploded since the old days, which is good because you have more people in the market for stuff. But I do wish I had picked up some sales tips & advice as early as possible. Ken H has some awesome points that I agree with as well.

    On that note, I can’t wait for that feature about the high-schoolers!

  7. Ryan,

    Bookmarked, retweeted. Great lessons.

    This whole list is going to be required reading for my 15 year old. PARTICULARLY the part about having $50K saved before graduating school.

    My son has learned entrepreneurship by working with his Dad… but he spends pretty prolifically.

    When he complained at age 14 that no one would “give” him a job, I told him, “Let’s MAKE you a job” and we advertised on Craigslist and other free posting services (Facebook page, Google Place page)a service-based business that outperformed anything he could make at minimum wage.

    With that influx of cash, and only sporadic influence (I am divorced and he lives with his Mom) from me, he has become quite a spendthrift.

    While my son is still living with his Mom, he could be “weird” and save up a pile of money instead of needing to buy every gadget and go to every concert.

    This post is gonna be printed and put on the wall in the bedroom he has at my place.

    Thanks for this VERY valuable post. Not just the “savings” part but the quality of friends… don’t let anyone rush you into a decision… shucks, all of it. This one-pager should printed out and read by every kid in America over 12 years of age. Thanks again.

    Keep Stepping,


  8. Reading your blog felt like listening to a honest friend’s advice without being trying to rub on feelings! This is coming from a 30yr old who only begun to save in the past 2-3 yrs.

  9. Great pieces of advice! Wish I would’ve had this list years ago! My biggest regret is not saving more money. I’m married and we have our first child and we are still living in an apartment. Our credit score is good, our debt to income ratio is good, the only thing holding us back from getting a house is down payment, closing costs, and reserves. If I would’ve saved my money rather than blowing it, I have no doubt we would have been in a house earlier. Still looking at about a year and a half before we have what we need. I will definitely be sharing this list with my daughter when she is older (she’s only 6 months.) Thanks for this post!

    • Thanks Katie. Yeah, our past spending mistakes definitely put an extra sting in situations where we sure could have used the money. Thanks for sharing your story.

  10. “There is absolutely no reason that a high school student that is willing to work and use their time wisely couldn’t graduate from high school with 50-100 thousand dollars in the bank. ”

    There is virtually no way that a high schooler COULD or SHOULD make 50k-100k throughout high school. Breaking down your numbers, high schoolers should be making $10-$12 all throughout high school, working 40 hours per week.

    Not only is that unrealistic, but it’s foolish. We’re adults from 18 on, why not let kids enjoy their childhood and teenage years, teaching them life skills and managing the money they have, instead of instilling in them the need to make 50k-100k in their teenage years.

    Very disappointing.

    • I said if. Some can make far more than $250 a week..during the school year. Don’t underestimate the capability and intelligence of high school students. Did you read the follow up post about the two kids from Massachusetts that are running an appliance business after school and on the weekends? High school students can start their own businesses and make very good money per hour. That doesn’t even take into account the summer months, where they are free to work as much as they want.

      The whole point is that it’s possible for kids to work and save up large amounts of money, contrary to our cultures low expectations.

      Adults from 18 on? I think that’s foolish. As if they are going to wake up one morning an adult. They are going to wake up a child when they are 18. No responsibility, work experience, job training, marketable skills, no money saved and all of a sudden they are going to get launched out into the world. I know that’s our cultures operating standard, but it’s not working very well. Kids are back living with their parents late into their 20’s, deeply in debt, with very little work experience.

      Kids need to be trained to become adults. The training needs to start when they are young, slowly giving them more and more responsibility until one day they are living on their own, providing for themselves. Encouraging kids to start working, saving and investing at a young age is not going to rob them of a their childhood. As the response to this post will attest to, it would save many from years of regret.

  11. I think saving $50k by the end of college, should you elect to go immediately after high school is a far more attainable goal (and probably healthier too). Kids ought to be transitioning into adulthood during high school, not jumping in with both feet. There are plenty of lessons to be learned in childhood as well as adolescence.

    In fact, if I had realized that those freedoms I enjoyed so much as a teenager didn’t have to disappear when I became an adult (I thought adulthood was job-slavery and bills), I may not have felt so inclined to spend all my time enjoying them while I could!

    This post is full of great advice, but my advice for me would be to repeat what you said here: Start backwards. Find what you love and then find a way to make money doing it. It’ll require effort, but your work doesn’t have to be a job.

  12. Advice to myself when I was in high school would be:

    1) Stay out of debt. If you can’t pay cash for it, you can’t afford it.

    2) I always dreamed of having my own business but I didn’t know how to start. So my advice would be: Ask for help. (Repeatedly, if needed.) People will bend over backwards to help a young person when sometimes they wouldn’t be as quick to help an adult. And “dumb questions” aren’t as dumb when you’re 18 or 20 as they would be at 40 or 50.

    3) Pick friends carefully. “Show me your friends and I’ll show you your future.”

  13. Ryan,
    The part about saving and staying out of debt is critical.

    Example from Dave Ramsey’s book “Financial Peace”: Kid #1. saves $2000 a year at 12%/yr (optimistic, I know) for 8 years and never touches it again until age 65. Kid #2. delays until age 27 (all grown up now?) then saves at same rate every year for 39yrs until he also is 65.

    Who comes out ahead? (Math is such fun).

    Answer: Kid #1. $2,288,996…. Kid #2. $1,532,166. ($756,800 difference)

    Start early…pay yourself first. Even if #1 retired at 50 he’d be pulling $50K+ a year in interest.

    Money’s a great servant and a terrible master. But it’s neutral towards us. It’s not the needs that get us, it’s the wants.

  14. I couldn’t agree more about quality friends. Good friends, even just one or two, can really help to motivate you and keep you focused on what is important in life.


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