The Career Venn Diagram

Think of all the pressure associated with one particular life choice: What do I want to do for a living?

You could spend four—or more—years pursuing a degree in order to start a career, only to discover you (a) hate it, (b) have no aptitude for it, and (c) are now tens of thousands of dollars in debt. Or more.

I talked about this with my son when he was finishing high school. I’ve spoken to high school students about it while hosting assemblies.

Now I have a college-age step-daughter who’s wondering the same thing: What do I want to do?

And it’s not just 18-24 year olds puzzling over this. Plenty of people in their 30s, 40s, and even 50s stay awake at night, staring at the ceiling, considering a career change but terrified of the potential outcome.

I have no formal training in career management or guidance counseling, but I do have an awful lot of practical experience in two separate—but parallel—careers over several decades. And this is always my suggestion:

Give a lot of thought to going after a career that lies in the intersection of a Venn diagram with three circles. Those three circles represent three different criteria for a successful career path.

Circle Number One: Do you truly enjoy it?

Hey, roll your eyes if you must, but it’s not as obvious as you think. Millions of people drag out of bed every day to do something that kills their soul, hour by hour.

And it’s complicated, too, because our tastes change as we age and evolve. Yet I’m convinced every person has a core collection of things that bring them joy, in many forms.

Since I was a kid, I’ve enjoyed almost anything involving words. Back then, I read everything I could get my hands on, and I loved the writing projects we were assigned at school. I spent a couple of years listening intently to the disc jockeys on KRBC, an AM Top 40 station, and then KNUS-99, a powerhouse FM Top 40 that owned the Dallas airwaves.

My friends were listening only to the music, while I was listening to how these magical radio gods behind the microphones crafted their shows. It spoke to me in ways I didn’t fully understand, but it drove me to put aside my natural shyness and introversion and to apply at a small radio station. I was 16, scared to death, but sure that this was something I’d enjoy. I did. I have. For more than 45 years.

So finding something you enjoy could branch off into several directions. But what’s at the core of your passion? Is it helping others? Is it sitting alone in a private office, focusing on numbers? Is it the outdoors? There are multiple ways to tap into what inspires you, but the key is first finding the larger category before narrowing it down.

That first circle is just one of three.

Circle Number Two: Are you good at it?

This has the potential to be heartbreaking, I know, but I never said I’d blow sunshine up your skirt. I’m bringing a little tough love.

Look, we all have things we like to do but that, unfortunately, are not in our skills wheelhouse. And while plenty of people sell a shit-load of books telling you that you can do anything you want, I’m here with a fierce injection of reality.

You can’t. Sorry, you can do a LOT of things, probably way more than you even realize right now. But you cannot do ANYTHING you want.

Not a popular position, I get it, and the woo-woo crowd (and self-help authors) have already clicked out of this essay. It’s very enlightened (allegedly) to tell every person they have unlimited potential.

Nope. You have things you’re good at and some things you can at least improve on with time and training. And then there are things you just won’t ever be good at. Sorry, but it’s true. There are a ton of things I’d love to do, but I’m mature enough to realize I didn’t inherit that gene.

That’s okay. There are so many other things where I DO have skills. The other stuff? It can be a hobby, and there’s nothing wrong with that. It’s just not a career choice.

So we have two of the three circles: Things we love to do and things where we have some innate ability/talent. We’ve begun our Venn diagram. All we need to add now is the last component, another one that will cause grunts of displeasure and possibly even outrage, which is quite en vogue these days.

Circle Number Three: Can you make a good living at it?

Oh, Dom! How shallow of you! How despicable to assign a value to our passions! Creep!

Yeah, yeah. How’s the weather today in Utopia?

I live in a world where someone always wants to get paid for the things I want. A mortgage company would really like to get paid back for that home loan they gave me. The insurance company is expecting another premium payment to insure my car.

Oh, and the grocery store doesn’t take kindly to me walking out with a basket full of groceries without giving them my credit card.

Sorry, Peter Pan, but unless you’re a trust-fund baby—and I actually have friends who are—you’re gonna need to deposit money INTO your bank account, too. Which means you need to get paid.

Which means money is an inescapable component to this equation.

I know, it takes all the romance out of the subject, but it ain’t too sexy having your furniture repossessed, either.

Now we have all three circles, and for every single person there’s an intersection. It may not be what your high school counselor suggested, and it may go against those dumb Myers-Briggs results you once received.

But you can throw that old shit away. Instead, it’s about sitting down somewhere quiet with a notebook and a pen, and figuring out all of the things that go into the first two circles. Be honest with yourself, don’t fudge.

Because if you lie about how much you enjoy something, you’ll be miserable again in a year or two. And if you b.s. yourself about your talents, you’ll simply fail.

Examine your natural talents or the ones you’ve enhanced to the point where you’re beyond competent and have stretched into the “good” category. Combine those with the areas that bring you joy. What are they? WHY are they is probably a good talk to have with yourself, too.

Then find the careers that embrace those two circles and pay well enough to satisfy your life demands plus a touch more. The three-circle Venn diagram could really open your eyes.

For me, a career with words seemed natural, so I became a morning radio host and a writer. I love both of my careers. I mean, I really love them. I’m happy when I’m on the air, and I’m happy when I write THE END to a new novel. Lots of joy there.

Am I the greatest of all time at either? Nope. But I’m good enough to stay employed (more than 45 years on the radio as I write this) and to have published 25 books—with at least two more coming before the end of 2023. I don’t have to be the best; I just have to be good.

And do those careers pay well? They certainly don’t for some people, that’s true. But the point is they CAN. A successful morning show host can make a good salary, and a hit book series can pay off, too. I’ve found the intersection of all three circles.

Just give it a chance

Is my system perfect? Please, we’re not children; we know life is full of imperfections and sometimes bad things just happen. Radio stations can change formats and good people are canned. Books can get a wave of bad reviews and the author is set back.

But we’re talking about giving yourself, or your kids, a better-than-fighting chance to succeed and find happiness. All of it will take hard work—which could be the fourth circle, except the words “work hard” tend to scare off some people before they even give a career a chance.

I think it’s as good a starting point as anything I’ve read or heard. It takes an honest assessment of yourself and it takes some research into what various careers can pay. Then you work your butt off and give yourself the best possible chance.

Hope this helps at least one or two people. Send me a note if it does. I’m cheering you on.

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If you’ve found the creamy middle of your own career Venn diagram, power to you. If that moves you to buy Dom a tea or a beer, cheers! You can do that right here. And thank you!