Seven things I want my sons to know about making their way

I wrote this five years ago, when my sons were in high school and thinking about their futures. I’m thrilled to see how much of this advice they took, and how relevant it remains today.

Now that you’re both teenagers, my job as your dad is changing. When you were little, my job was more about teaching you some basics, keeping you safe, and showing you love. Now it’s about slowly letting go and coaching from the sidelines so you can go in your own direction and hopefully find success and satisfaction.

The day is coming when you will have to make your own way. You are both bright and capable, so you have a leg up. But here are some things you need to know.

1. When you do your best today, more doors will be open to you tomorrow.

How well you do in high school determines what opportunities are available to you when you graduate. This is changing; more on that in a minute. But giving your best effort always pays sooner or later. So give your best to your schoolwork. I’ll be satisfied with whatever your best can deliver, even if it’s a D average.

If you go to college (and I hope you do), better grades will get you into better schools and bring better financial aid to pay for it. You need as much financial aid as you can get, because I can’t afford to pay for all of college.

If you skip college, doing your best now will build disciplines that will carry you into whatever you do after high school, be it the military, vocational school, or just getting a job.

But don’t just get a job after high school. If you don’t have a good degree, a good trade, or the good care of Uncle Sam, the jobs available to you involve saying, “Do you want fries with that?” or “Thank you for shopping with us.” They will pay poorly and you will struggle. There are paths to move up in those worlds but they are hard and slow. This will suck; avoid it if you can.

2. People who express themselves well, verbally and in writing, get ahead.

Srsly. cuz in the real world u will need 2 work with old farts my age and if you use speling and grammer right you will pwn your txtspeak friends. and we will not lol at u behind ur back.

Translated: You will probably start out working for someone closer to my age than to yours. When you speak and write well, we will think you are smart and capable, and we will give you opportunities we won’t give to your less-eloquent friends.

Dad and Sons
Me with my sons, now both in college

3. The world is bigger than today’s pop culture.

Pop culture is great fun. You know I love the pop culture of my generation – I’ve made you sit through all the cartoons I used to watch as a kid (the good ones, anyway) and as we ride around in the car I play the music from my youth.

But there is so much more culture to experience. Try other forms of music, film, theater, and art from around the world and from times before the 21st century. There’s lots to like out there.

More importantly, see beyond pop culture. Know what’s going on in the world. Form opinions about how the world should work, find causes that are important to you, and give of your time and resources to make things better. You will find no end of opportunity to make a difference.

4. Be who you are.

This means you have to find out who you are, which will take the rest of your life. As you figure it out, do not compromise – be that person. The worst pain and difficulty I’ve experienced in my life has come from times when I’ve tried to be someone I’m not.

You have a natural personality type that makes you good at some things and not good at others, and makes you fit easily into some environments and poorly into others. The better you know yourself, the easier it is for you to choose things that you are good at and find environments where you fit.

This isn’t license to be lazy or selfish. You will grow more and achieve more when you push and stretch yourself. I’m just saying that when you know yourself and honor the way you’re wired, you are more likely to find happiness and success on your own terms.

5. Following your dreams is overrated.

I’m lucky. I knew at age 15 that I wanted to make software for a living. Through smarts, work, and luck, I’ve been doing it for more than half my life. And it so happens that living my dream pays the bills just fine. But I’m a rarity.

Except that I thought I’d be a programmer. It turns out I was only an average programmer. But I understand geeks and fit in with them really well, so I stuck with it. And then I was handed an opportunity to manage geeks – and to my surprise, I’m very good at it. I’m really lucky I got an opportunity to find that out. But you could argue that I’m not really living my dream. Whatever. I adapted. I started toward my dream but then let the streams of life take me where they would flow.

Look, most people’s dreams don’t come true. And for most people, if their dreams came true they wouldn’t pay the bills very well anyway.

You absolutely need to have ideas about what you’d like to do with your life. Let them guide your general direction, but always be willing to take a chance on the opportunities that find you – they will find you. The good ones use what you’re good at and are in environments where you fit well. Doing this will give you an interesting life full of meaning and satisfaction.

6. Enjoy the journey.

If you fill your life with meaningful things that you enjoy, happiness will find you.

You will have to take some risks to find those things. The path that feels secure may be less scary, but my experience has been that it’s less joyful, too.

That’s not to say life will always be unicorns and rainbows. Some risks won’t pay off, some random bad things will simply happen, and you will have some unhappy days! But bad times always end, especially when you keep pushing, keep trying, keep rising above the discouragement you will feel.

Here’s the crazy thing: The ups and downs can be exhilarating! Learn to ride them, and to enjoy the ride.

7. You are going to make the world’s new rules for success.

You live in an unprecedented time when the old rules of success are quickly becoming invalid.

For a few generations, the rules have been: Go to college and study pretty much anything. Your degree will lead to corporate jobs that pay well enough for at least a middle-class lifestyle. As you gain experience, you might even get bigger and better jobs that pay more. Along the way, save money for retirement, and when you’re old you can afford to play golf every day.

Those days are pretty much over.

I’ll pay for as much of your college education as I can, and you’ll probably get some financial aid. But you will need to borrow money to cover the rest. Your first monthly payment will be due one month after you graduate. You need a plan that leads to work that pays well enough for you to have a place to live, feed yourself, probably own a car, and make your college loan payment.

The college degrees that lead to jobs that pay enough for all that are in disciplines such as engineering, business, medicine, finance, law, and science. It’s harder to get a good-enough-paying job when you major in history, literature, art, and so on. If you have a burning desire to study them, minor in them while you major in something that leads to good-paying work.

But even then, don’t count on corporate jobs. Their relative security has been fading slowly since the 1980s, and I think that security will fade to nothing in the years to come.

Fortunately, resources are available to you that my generation only imagined, thanks in no small part to the Internet. You can now do so much as an entrepreneur.

Say you want to write a book. Did you know that my first dream was to write stories? I wrote a novel when I was in the 7th grade. (It was terrible!) But in those days, becoming a successful author of fiction was as hard as getting to play for the NFL. Very, very few people got publishing contracts compared to the huge group of people who wanted them.

You no longer have to try to convince a publishing company to give you a contract. Now you can start a blog, create a Facebook page for it, build an audience, and then publish your book yourself and sell it to your blog readers.

Or say you want to make software. When I started doing it, you pretty much had to have a college degree in computer science or engineering and join a software company. Today, you can write an app for the iPhone and make money off it a dollar or two at a time, and build your own software business from there. When I think of the best young programmers that I know, most of them skipped college!

These paths, and others like them, take a ton of work. But they are possible now when they never were before. They open new pathways to success. As they replace the old, dead pathways, your generation will get to write the new rules.

I envy you; it sounds like great fun!


17 responses to “Seven things I want my sons to know about making their way”

  1. J P Cavanaugh Avatar

    Excellent advice, this. Although I received parts of it in my own youth, I wish I had been given this entire essay when I was 16. The next question is whether I would have listened to it, but that is another thing.

    1. Jim Grey Avatar

      My dad gave me a Sidney Harris column he cut out of the paper when I was 18 and it was a list of advice kind of like this. I really took it to heart. Wish I kept it.

  2. Jason Shafer Avatar
    Jason Shafer

    Jim, this is hands-down some of the best advice I’ve seen in a very long time. It will likely be shared with a teen who lives under my roof!

    1. Jim Grey Avatar

      Wow, awesome!

  3. tcastleman Avatar

    Excellent advice that I will share with my teens.

    Have to admit that the hard truth of needing a good-paying job straight out of college (we can’t pay for all of tuition either) makes me sad.

    My liberal arts education has taken me unimaginable places and what I studied is where both my talents and my passions are found. My first jobs (I often had to work two) barely paid the rent. If my loan payments had equaled what young people pay today, I would’ve been in a quandary.

    Worse, I have one daughter who is very interested in teaching special education. She already shows signs of being a gifted teacher. However, after looking at what she is likely to owe and comparing it to a beginning teacher’s salary, she has informed me that it’s not feasible. Maybe teaching can be a second career she says, but she needs to look at other options for now.

    When higher education has become so expensive and lower education has become such a low-paying field that people can’t afford to enter the profession, then who educates our grandchildren’s generation so they can follow their dreams?

    1. Jim Grey Avatar

      I admit to a bias: I went to engineering school. It doesn’t get much more practical than that, from the perspective of higher education. And that set my viewpoint of what education is for. I realize that a liberal-arts education has value, but the world truly has changed since we graduated and a liberal-arts education will now primarily leave one saddled with too much debt to function.

      Our youngest son was accepted to my alma mater, but he is not going. It is primarily because the cost of one year is now what my four years cost in the 80s, and their financial aid offer had our son borrowing about $45k just for his first year. No way in hell, I said.

      I think higher education is a bubble that will soon burst. It may not come in time for your children. It certainly won’t come in time for ours. But it’s coming, and society will have to shift significantly when it does.

      It makes me wonder if paradigms will change. Who will educate our children? Does it have to be professional teachers? Will we see a shift toward homeschooling? Will we see the reemergence of the one-salary household as a result?

  4. seatacphoto1951 Avatar

    This is good advice for anyone at any stage of life. Thank you.

    1. Jim Grey Avatar

      Glad you liked it!

  5. SilverFox Avatar

    I wrote something like this for my daughter recently as she turned 21, the emphasis was more around go out there and I’ll be here kind of thing. Wish I had read this before though as you have some great points in here that I would have included/adapted :).

    1. Jim Grey Avatar

      I’m flattered to hear you say that!

      1. SilverFox Avatar

        Not at all; they are wise words that I would imagine anyone would find useful and would want their offspring to hear

  6. Heide Avatar

    Your sons won the jackpot when they got you for a dad, Jim. This is some of the best advice I’ve read anywhere, and much of it applies to people of any age. Thank you for reposting this!

    1. Jim Grey Avatar

      Oh, thank you, H. I’m good at this stuff and less good at other fathering stuff. At least I’ve always been earnest about being a dad.

      1. Heide Avatar

        As you said to your sons, you can’t be great at everything — but you’ve certainly nailed this part of fathering. (Hopefully there’s considerably less spitting up now, so you can let THAT skill go …)

        1. Jim Grey Avatar

          Boy do I not miss the baby years!

  7. Rain Avatar

    I found this post interesting and it made me think of myself. 5 years ago I was in high-school too, struggling to choose my future field of study and career. I’m 22 now, I wish I could get back to those days and do somethings differently. Your post made me ask myself that didn’t I get some advice that could help me to make better decisions?
    the answer is yes I did, but still I didn’t take some of them seriously and I took some other advice seriously which later I wished I wouldn’t.
    I mean that’s the problem you know? As a teenager you get a lot of opinions about stuff and future, plus your own thoughts and feelings, and the hardest part is when you don’t know which one you should trust and which one you should ignore.

    1. Jim Grey Avatar

      What a profoundly honest comment. Thank you for leaving it.

      I didn’t take all of my dad’s advice either when I was young. What kid does? As a parent, we say what we can say to our kids and hope some of it gets through and makes a difference. But each kid is his or her own self, separate and different from the parent, and it really is up to them to decide what to take.

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