Career Advice You’ll Love or Hate; Your Choice

Scott Wolfe Jr
The Startup
Published in
13 min readDec 12, 2019

Careers are a tricky subject.

It’s a bit unclear where “careers” truly start or end, and from point to point, careers twist, turn, and do somersaults, get interrupted by life events, get suffocated by bad work or personal circumstances, or maybe get a big breakthrough to the fault of a little luck.

And all along the way, there is advice. Oh, is there advice.

It’s even a career path to give career advice!

Follow your passion. Do what you love. Pay the bills. Make sure there is a 401k. Move jobs quickly to maximize your pay and title. Stay with companies a long time to prove you can stick it out and maximize your learning. Make sure you have a career path. Don’t worry about your career path. Get a mentor. Read. It’s what you know. Network. It’s who you know.

Even the word “career” can be tricky.

As a noun, the word means “ an occupation undertaken for a significant period of a person’s life and with opportunities for progress,” but as a verb, it means, “ move swiftly and in an uncontrolled way in a specific direction.”

Careers are a tricky subject. Careers, like success, are somewhat in the eyes of the beholder. But, I think, unlike Vietnam, there are some rules.

WARNING: Don’t Answer This Question Right Away — What Are You Interested In?

The most popular place for career advice is in commencement speeches, and the most popular advice is to “follow your passion” or “do what you love.”

The “follow your passion” advice seems appropriate and nice, but it turns out to be bad advice.

The speaker never really explains how someone can figure out what their passion actually is, and that’s because it’s not something you just find by looking. Passion, it turns out, is not something you discover, it’s something you develop.

Angela Duckworth explores this in her excellent study of passion and perseverance, Grit:

Commencement speakers may say about their vocation, ‘I can’t imagine doing anything else,’ but, in fact, there was a time earlier in life when they could…Most grit paragons…told me they spent years exploring several different interests, and the one that eventually came to occupy all of their waking (and sometimes sleeping) thoughts wasn’t recognizably their life’s destiny on first acquaintance.

Duckworth dives into a few examples, but I really like the example she makes of Julia Child. In Julia & Julia, a comedy quasi-related to Child’s life, the opening scene has her dining with her husband at a fancy French restaurant, and then her “passion” strikes like lightning after taking one bite of a decadent sole meuniére.

But, of course, that’s not what happened.

It took a lot of time for Child to actually develop her passion. Child, after all, dreamed about becoming a novelist. Child once remarked that, as a child, she had “zero interest in the stove.” Was the sole meuniére dish really that good? Was it the first bite of delicious food she ever had, really?

Duckworth acknowledges we can’t know for sure exactly when Child’s passion sparked to life, but it’s clear that as to her “romance with French food, that first bite of sole was just a first kiss.” Quoting Julia Child, “Really, the more I cook, the more I like to cook….to think it has taken me forty years to find my true passion.”

To think it has taken me forty years to find my true passion!

I think I’m starting to piece together a nice “career” myself, and I feel like I’m doing something I’m passionate about, but honestly, the how is not exactly clear to me.

I wasn’t born this way. I didn’t come out of my high school or college graduation with an inextinguishable zeal to impact construction payment. Construction payment? Construction? Y.A.W.N. I didn’t know that I wanted to be a tech and startup CEO. Hell, I still don’t know if I want to do that.

Reflecting back, my entire career feels like it’s built on a series of accidents. If it weren’t for a friend in high school who was into programming I would have never developed a clue about it. If it weren’t for Hurricane Katrina, I would have never found my way into construction. If it weren’t for such and such and such, there would never be such and such.

And something interesting has happened to me along the way. I developed a passion.

Paul Silvia, a psychologist who is a leading authority on the emotion of interest, says “For the beginner, novelty is anything that hasn’t been encountered before. For the expert, novelty is nuance.”

This reminds me of the Arthur Miller quote I used in a previous LinkedIn post about things I’ve learned from books recently, which is that you must “ specialize in something until one day you find it specializing in you.”

This also reminds me of the one commencement speech that actually hits the nail on the head. I show it to every new employee who starts working with us. It’s the commencement address at Harvard Business School given by Facebook COO Sheryl Sandberg.

At 07:30 she says this:

[There is a] great metaphor for careers. [It’s] not a ladder. [It’s] a jungle gym. As you start your career. Look for opportunities. Look for growth. Look for impact. Look for mission. Move sideways, move down, move on, move off. Build your skills NOT your resume. Evaluate what you can do, not the title they’re going to give you. Do real work. Take a sales quota, a line role, an ops job. Don’t plan too much and don’t expect a direct climb. If I had mapped out my career when I was sitting where you are, I would have missed my career.

Passion isn’t found. It isn’t mapped. It isn’t given.

It’s developed.

And here’s how.

Have Hard, Miserable Curiosity To Get Deep Understanding

Were you an overachiever in school?

If so, I have some bad news for you. You’re likely to underachieve in life. And that’s because you’re probably too pragmatic, too much of a rule follower, and you care more about getting A’s (or a promotion) than you do about developing skills, interest, and deep understanding.

I didn’t just make that up.

In his book about the science of success, Barking Up The Wrong Tree, Eric Barker examined research on the professional success of high achievers from school days. In a study of high school valedictorians and salutatorians from graduation onward, the findings showed that a great majority of these folks “do not appear headed for the very top of adult achievement arenas.”

Why?

One reason is that schools reward being a generalist and there is ‘little recognition of student passion or expertise.’ For those intellectual students who actually enjoy learning, they struggle in school, and ‘they have passions they want to focus on, are more interested in achieving mastery, and find the structure of school stifling. Meanwhile, the valedictorians are intensely pragmatic. They follow the rules and prize A’s over skills anddeep understanding.’

Deep understanding.

Deep understanding.

Deep understanding.

At our company we have a core value, Make Complex Things Simple. This value appears straightforward, but we ask our team to look closer. The anchor here is in the “complexity.” The only way to make complexity simple is to have a deep understanding of everything that makes the complicated, complex.

And what is a deep understanding of something? How much understanding is enough for it to be deep? Exactly how do you get a deep understanding in something?

To answer these questions I’ll point to Walter Isaacson’s great Leonardo Da Vinci biography.

Isaacson hits right dead center on that core value and the nature of complexity when describing Da Vinci’s work on the human anatomy, explaining that “ complexity is magically transformed into an elegance that is unrivaled by any anatomical drawings of his time — or ours.”

We don’t have to wonder how Da Vinci accomplished this magical transformation. We know it was through his extreme curiosity, and his deep understanding of everything that made depicting the anatomy complicated. And we know this because of some beautiful career advice given by Da Vinci himself to someone else in his era who was interested in a career in anatomical study. Here that’s advice:

You will perhaps be deterred by your stomach; and if this does not deter you, you may be deterred by the fear of living through the night hours in the company of quartered and flayed corpses, fearful to behold. And if this does not deter you, perhaps you will lack the good draftsmanship that such a depiction requires; and even if you have the skill in drawing, it may not be accompanied by a knowledge of perspective; and if it were so accompanied, you may lack the methods of geometrical demonstration and of calculating the forces and strengths of muscles; or perhaps you will lack patience so you will not be diligent.

Look at Da Vinci’s descriptions. To be successful in this career, you’ll be physically ill, you’ll be scared to death, you’ll need skills in drawing, you’ll need knowledge of perspective, you’ll need expertise in engineering and calculations, you’ll need patience and diligence.

And, guess what, it’s going to take you quite some time to get through all of that (thus, the need for patience!).

So, would you like to sign up for this career?

Michelangelo once remarked that “[i]f people knew how hard I worked to achieve my mastery, it wouldn’t seem so wonderful after all.

Passions are developed. Novelty is in the nuance. Careers aren’t planned. And curiosity, that little thing that leads you to more and more knowledge, and eventually, a deep understanding of something, is hard, grueling, and sometimes miserable work.

Eric Barker discusses the work required in Barking Up The Wrong Tree:

Hours alone aren’t enough. Those hours need to be hard. You need to be pushing yourself to be better…You’ve spent a lot of hours in your life driving, right? Are you ready to compete in NASCAR or Formula 1? Probably not. Trying to improve isn’t something we are doing in the vast majority of activities we engage in every day — including work.

But be mindful of where you put in your hours and what exactly you think is important. Be cautious about the promise of jumping from one opportunity to the next too quickly, without giving yourself time to deeply understanding anything. As Duckworth warns in Grit, “Some people get twenty years of experience, while others get one year of experience…twenty times in a row.”

Persevering Is The Whole Battle

The funny thing about building a career is that so much boils down to just continuing on. Ideas, talent, abilities, and your “marketing automation skills” are all a dime a dozen. The real rare commodity in the marketplace is endurance.

The actor Will Smith had a great sound clip about the power of perseverance and endurance:

The only thing I see that is distinctly different about me is: I’m not afraid to die on a treadmill. I will not be outworked, period. You might have more talent than me, you might be smarter than me, you might be sexier than me. You might be all of those things. You got it on me in nine categories. But if we get on the treadmill tougher, there’s two things: You’re getting off first, or I’m going to die. It’s really that simple.

The problem is we so rarely see all of the endurance and perseverance behind every success story and amazing career. It’s too easy to write a magazine article about a young startup founder who shot into the headlines, seemingly overnight. Sometimes, it seems like amazing careers are just growing on trees so long as you “have the right talent,” or you “follow your passion,” or you “have a great idea.”

Remember what Tyler Durden said in Fight Club?

We’ve all been raised on television to believe that one day we’d all be millionaires, and movie gods, and rock stars, but we won’t. And we’re slowing learning that fact. And we’re very, very pissed off.

This isn’t new.

Nietzsche observed that “with everything perfect we do not ask how it came to be, [instead] we rejoice in the present fact as though it came out of the ground by magic.” The eternal and gnawing overnight success myth!

In fact, though, nothing comes about by magic. There’s a perseverance plot in every success story. Every stellar career had to punch through extremely hard times.

“Anyone can sail with the wind to his back,” Randy Komisar wrote in The Monk and The Riddle, but “startups usually sail into a stiff wind, leaking like a sieve, in high seas, without food or water.” And so they, like you, have to be built for that kind of journey.

There’s a great interview clip with Steve Jobs about perseverance and passion. He’s convinced that pure perseverance is what separates the “successful from the non-successful.” What I find intriguing is the chemistry between perseverance and passion.

People say you have to have a lot of passion for what you’re doing and it’s totally true, and the reason is, is because it’s so hard, that if you don’t, any rational person would give up. It’s really hard. And you have to do it over a sustained period of time. And so if you don’t love it…you’re going to give up. And that is what happens to most people…the ones who were successful love what they did so they could persevere when it got really tough, and the ones who didn’t love it, quit, because they’re sane…it’s a lot of hard work, and a lot of worrying, constantly. If you don’t love it, you’re going to fail. So you’ve got to love it and got to have passion. And I think that is the high order bit.

And dammit, we just went through how much perseverance you need to get passion, and now you need passion for perseverance?? What gives!

This all seems so damned hard.

So What Do You Actually Want?

Henry David Thoreau observed that “ the price of anything is the amount of life you exchange for it.

So, as you work on your “career” and plot out your dreams and ambitions, the ultimate question for you is this: what do you really want? And more specifically, what is the amount of life you’re willing to exchange for it?

Careers are a tricky subject, but perhaps the more tricky subject is “work.”

How much should you work, how important should work be, and is work a means to an end (i.e. the ability to live your other life) or is it an end itself (i.e. an integral, important, and passionate part of your life)?

An interesting debate is raging on this subject.

Just this week, Derek Thompson published an essay in The Atlantic with its thesis built into the title, “ Workism Is Making Americans Miserable.” According to Thompson, workism is the “belief that work is not only necessary to economic production, but also the centerpiece of one’s identity and life’s purpose.”

And I get it, Thompson.

Just as humankind has been on an eternal quest to find the fountain of youth, the species has always dreamed of a world without “work.”

Maybe that dream came in the form of someone looking up to royalty or the super rich and dreaming of leisure. Or, it came in the form of the 1930s economics study that opens the Atlantic article, John Maynard Keynes’ essay “Economic Possibilities of our Grandchildren,” which predicted a 15-hour workweek in the 21st century and the promise of having the “real, permanent problem [of] how to occupy the leisure.” Or, maybe it is the present day political conversation about needing universal basic income because technology is going to start doing all the work for us. Or, the new “FIRE” Movement, which promises “financial independence, retire early,” that promises to help you get work out of the way quickly, so you can go on focusing on your “life.”

You know, your “Life.” That thing you can exchange for anything.

What would you like to buy with it?

Thompson’s conclusion in the Atlantic article makes his point about why “workism” is making people miserable. It’s because “Americans have forgotten an old-fashioned goal of working: It’s about buying free time.”

You exchange some of your “life,” in other words, to buy time to live your “actual life.”

That’s interesting.

It reminds me of a great Warren Buffet quip, “I always worry about people who say, ‘I’m going to do this for ten years; I really don’t like it very well. And then I’ll do this…’ That’s a lot like saving sex up for your old age. Not a very good idea.”

Or maybe the advice from IKEA Founder Ingvar Kamprad, who wrote in a 1976 memo to his employees, The Testament of a Funiture Dealer, that “[a] job must never be just a livelihood. If you are not enthusiastic about your job, a third of your life goes to waste, and a magazine in your desk drawer can never make up for that.”

And herein lies your career problem. Your work problem. The problem of searching for that gold at the end of the “workism” / FIRE Movement rainbow.

In the New York Times article about the FIRE Movement, How to Retire in Your 30s With $1 Million in the Bank, they interview Jason Long, who has shunned material things and the false god of work, and now is “retired” and able to “live his life.” Here is what he is doing with his well-earned and purchased “free time:”

That morning, he’d woken up on his own, “not when an alarm clock told me that I had a responsibility.” He’d read the news online for 30 minutes, went on a seven-mile run, took a nap and “watched the ceiling fan spin around for a little bit…He had been watching the movies from They Shoot Pictures, Don’t They? a website that ranks what it calls the 1,000 greatest films. He’d watched 600 or so. He had work to do.

Sign me up?!

Yikes.

Maybe Mr. Long’s problem, like the problem with workism and work itself, isn’t work. Maybe the problem is Mr. Long hasn’t developed any passion, and his “career.”

After all, in the same New York Times interview, “Mr. Long acknowledged it was possible that he’d simply burned out, that all of this FIRE stuff was just a needed break until he found a more satisfying career. When he was recently offered a job back in the pharmaceutical field, it induced a mild panic attack…”

That makes sense.

Everyone works. Everyone dies. You work. You die.

And in-between working and dying, you can have anything you want, for the price.

It’s your choice.

Originally published at https://www.linkedin.com.

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Scott Wolfe Jr
The Startup

Co-Founder of ClaimSpot.com. Board Director, Advisor, Helper. Former CEO/Founder of Levelset (Acquired by PCOR, $500M).