The Jammed Career Escalator: Old Premises, New Realities

Centuries of immigrants risked everything to come to America with the belief that if they worked hard, they would enjoy a better life than their parents had. Since the country’s birth, each generation of Americans has generally made more money, been better educated, and enjoyed a higher standard of living than the generation that came before it. This expectation of lockstep increases in prosperity had become part of the American Dream.

For the last sixty or so years, the job market for educated workers worked like an escalator. After graduating from college, you landed an entry-level job at the bottom of the escalator at an IBM or a GE or a Goldman Sachs. There you were groomed and mentored, receiving training and professional development from your employer. As you gained experience, you were whisked up the organizational hierarchy, clearing room for the ambitious young graduates who followed to fill the same entry-level positions. So long as you played nice, you moved steadily up the escalator, and each step brought with it more power, income, and job security. Eventually, around age sixty-five, you stepped off the escalator, allowing those middle-ranked employees to fill the same senior positions you just vacated. You, meanwhile, coasted into a comfortable retirement financed by a company pension and government-funded Social Security.

People didn’t assume all of this necessarily happened automatically. But there was a sense that if you were basically competent, put forth a good effort, and weren’t unlucky, the strong winds at your back would eventually shoot you to the top. For the most part this was a justified expectation.

But now that escalator is jammed at every level. Many young people, even the most highly educated, are stuck at the bottom, underemployed, or jobless, as Ronald Brownstein noted in the Atlantic. At the same time, men and women in their sixties and seventies, with empty pensions and a government safety net that looks like Swiss cheese, are staying in or rejoining the workforce in record numbers. At best, this keeps middle-aged workers stuck in promotionless limbo; at worst, it squeezes them out in order to make room for more senior talent. Today, it’s hard for the young to get on the escalator, it’s hard for the middle-aged to ascend, and it’s hard for anyone over sixty to get off. “Rather than advancing in smooth procession, everyone is stepping on everybody else,” Brownstein says. (I’ll address why it got jammed in a future post.)

What’s replaced the career escalator? There’s no single metaphor that universally describes the 21st century career journey. For those who lack globally competitive skills (and yet who are simultaneously overqualified for low-skill labor), the current environment feels like slogging through a tar pit. For people with the relevant skills, the journey is like a vast ocean voyage: unpredictable waves, multiple routes to arrive at a destination, the need to keep investing in your vessel lest it capsize, the allies who form an armada around you to cross perilous straits. A recent Fast Company cover story called the winners of the post-escalator job market “Generation Flux,” a reference to their ability to acquire new skills, adapt to change, and reinvent themselves.

Whatever you call the current climate, the point is that the old premises of the career escalator have given way to new realities, and with new realities come new rules. The new rules are ones entrepreneurs have mastered for years and they are the inspiration behind The Start-Up of You.

Old Premises, New Realities

Old: Ready, Aim, Fire…Retire
New: Almost-Ready, Aim, Fire, Aim, Fire, Aim, Fire

Classic career strategy is Ready, Aim, Fire. Ready is mental, introspective (e.g. pondering “what am I passionate about?”). Aim refers to crafting a long-term career plan. Fire means executing on the plan. Ready-aim-fire (and then retire) no longer works. You can’t plan your life or career like you used to. These days, the better approach is almost ready-aim-fire-aim-fire-aim-fire. Entrepreneurial career strategy involves learning while going, executing while planning, finishing while starting, aiming while firing. There are no clear start and finish points; no designated “ready” or “set” phase followed by a “go” phase. Still, despite the need for constant recalibration, you can be disciplined about how where you choose to direct your energies and how you choose to adapt to unpredictable changes.

Old: Be Loyal to Your Employer and They’ll Be Loyal to You
New: The Employer-Employee Pact is Over; Extend Loyalty to Your Network

LeBron James grew up in Ohio. He married his high school sweetheart from Akron. The Cleveland Cavaliers picked him first in the 2003 NBA draft. A couple years later, LeBron James was widely viewed as the greatest basketball player alive. In Ohio, he was God. (A giant billboard in Cleveland with his photo was headlined, “We Are All Witnesses.”) Yet even as he racked up accolades, the one thing he wanted more than any other–an NBA Championship–eluded him. In mid-2010 LeBron James announced that he was leaving Ohio. He said he was taking his talents to the Miami Heat, a team with a stronger supporting cast, because he wanted to “win now and in the future.” Ohio fans felt betrayed. Sure, he was technically a free agent. But what about loyalty? What about roots? To LeBron, a better career opportunity meant more than his loyalty to Cleveland. While this was a case of a superstar athlete abandoning his team and city, teams have initiated break-ups just as often. The New York Knicks traded away NBA-great Patrick Ewing, even though he had played a record 1,039 games in a Knick uniform.

Today, every young, talented professional is like LeBron. There used to be a long-term economic and psychological pact between the employee and employer–the mutual expectation that a job within the “family” culture of corporations like Ford or IBM guaranteed lifetime employment (and generous benefits once you retired). It’s been replaced by a performance-based, one-day contract that’s perpetually up for renewal by both employee and employer. If you want to keep working at a company, you have to prove your worth–or else they’ll show you to the door. These are competitive times. An organization can’t afford deadweight, regardless of a person’s seniority, loyalty, or prior competency. By the same token, if you are valuable and a company wants to keep you as an employee, it has to earn your loyalty: it has to offer a competitive salary, engaging opportunities, meaningful work–or else you’ll head to the door.

Old: Network Your Way to the Top
New: Build a Network of Allies and Looser Connections

Because loyalty is no longer flowing vertically from you to your employer and vice versa, direct your loyalty horizontally, as Dan Pink suggests, to your professional network–to friends, current and former colleagues, and allies who may work in different companies or industries. Those are the people with whom you want to maintain authentic lifelong connections even as you move from company to company.

We’re all now cynical about “networking.” Yet, despite our cynicism about networking in a self-serving, “what can you do for my career” sense, online social networks are huge. And one’s professional network still matters more than almost anything else. Building a valuable network of allies and weak ties is a different project than classic networking.

Old: It’s Not What You Know, It’s Who You Know
New: The What-You-Know Comes From the Who-You-Know

When knowledge and information were scarce, you could distinguish yourself on the “what you know”–the knowledge and information you had in your head. When knowledge and information became abundant and free, business gurus re-emphasized the “who you know.” Anybody can Google information, they said, yet not everybody can have a vibrant network of relationships. In reality, both information and relationships matter, and they work in tandem. That’s because some important knowledge and information resides not on the internet but in the heads of the people you know. For example an experienced business veteran who knows the company you work for may be the best person to offer subjective insight on a financial dilemma (e.g. “How should I respond to the latest bid?”). Or a colleague at work may be the only person who could advise you on negotiating with your boss over a disputed point. People are frequently better founts of career intelligence than objective, static information sources.

Old: Search for Jobs When You’re Unemployed
New: Continually Search for and Generate Breakout Opportunities

Career strategy used to be a topic you discussed when you were looking for a job. But entrepreneurial professionals know they must always be investing in themselves. Instead of “job hunting” when they’re out of work, they’re continually on the look-out for “opportunities.”

Success begins with opportunities. Opportunities are like the snap to the quarterback in football. You still have to move the ball down the field; you still have to execute. But without a snap to the quarterback, there’s no touchdown. For a young lawyer, an opportunity could mean being assigned to work with the smartest partner in the firm. For an artist, it could be a last-minute offer (perhaps due to a cancellation) to exhibit at a prominent museum. For a student, it could mean being awarded a rare scholarship to travel and research.

Remarkable careers are punctuated by breakout opportunities. If you ask people of note to reflect on their career, you do not hear about a sequence of equally important jobs. Instead, they highlight specific breakout opportunities that led to unusual career growth. These killer opportunities didn’t fall into their lap; they knew how to spot and create them through a series of specific behaviors.

Old: Risk is Bad, Minimize Risk
New: Risk is Unavoidable; Proactively Take Intelligent Risk

Risk wasn’t a relevant concept in the days of the career escalator. The idea was to avoid risk, and avoid “high risk” career moves like freelancing. This is exactly opposite of how winners think today. Every opportunity contains downside risk. To effectively exploit opportunities, you have to be take on the right kind of risk, and manage it prudently. In so doing, you build resilience to the seismic industry and competitive changes that destroy professionals on a more brittle ”low risk” path.

There is an entrepreneurial approach to intelligent risk taking, and you may be surprised at how different it is from the stereotyped bet-the-farm, throw caution to the wind approach that people tend to think of when they think of entrepreneurs.

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Chris Rock on Job vs. Career

Chris Rock, in his unique blend of wisdom, riffs on the difference between having a job and having a career:

He seems to define a job as something you hate and a career as something you love. I'm not sure that's the most useful distinction and definition. But, I love Rock's point that loving what you do causes you to always think there's not enough hours in the day. And his story about dropping out of the tenth grade and how he should have just dropped out of the second grade, while exaggerated, is perversely true. 

(hat tip: Marci Alboher)

Top Performers Maniacally Prepare for Job Interviews

Ramit is killing it over at his blog. In his recent post How to ace the world's toughest interviews, he says top performers maniacally prepare and hustle in order to land jobs at competitive companies. Below is a story he recounts.


A few months ago, I met a college student at a conference. He was telling me about his job search. “I have a few companies I want to go after,” he said excitedly. “I’m pretty sure I can get a job offer from all of them. Then I'll have to pick! I just have to start working on my interviews. What do you suggest?”

I asked him if he’d researched the interview process. Had he done any practice interviews with friends? What about reaching out to older friends who worked there? He shook his head no impatiently. Then he told me he’d get to all that, but did I have any “tips” to share with him?

I didn’t know what to tell him. He had no idea what he was getting into.

The companies he named were some of the most competitive in the Bay Area. He had little experience (which is fine for college students) and a competitive GPA. But his communication skills were terrible. As we talked — with him talking at me instead of with me — I compared him to a group of friends I had in college.

During interview season, this group of friends and I sat around the dining halls and shared our best interview techniques on a regular basis. We shared the craziest questions we got, the best answers we’d given, and the strategies that alumni — the hiring managers — had let us in on. My friends from this group went on to get jobs at McKinsey, BCG, Google, Goldman, and other extraordinary companies.

This isn’t meant to brag. But let me share what was happening in these dining-hall meetings. Each of us was relentlessly focused on becoming the world’s best interviewees. We studied interview techniques — for hours every week. We tested our best material with interviewers. (Many students would schedule interviews with companies they have no interest in to use as “practice interviews.” Like it or not, it works.) Then we brought it back to the group, compared notes, practiced our cadence, rhythm, and tone, tore each other’s answers apart, and systematically improved our interview skills. Over and over.

So when this random guy at a conference was telling me his interview strategy, there was a game going on around him that he didn’t even realize. Serious applicants to companies like McKinsey were practicing their case-interview techniques for MONTHS before they ever stepped foot in the interview room. These same applicants that had talked to alumni/friends currently at their target companies to get the inside scoop on what really mattered in the interviews. They’d read books and Vault Guides and had attended info sessions. By the time they got to the interview, they were absolutely ready.

And, as with virtually any other complex transaction, 85% of the work was done before these serious candidates ever stepped foot into the interview room.

And the scary thing is, this is what most top performers do.

What does this mean for you?

Am I saying that you need connections and dozens of hours of interview prep to get a job with these companies?

Of course not.

But it sure stacks the odds in your favor.

The Mindset of the Ambitious Educational Elite

James Kwak on Peter Orszag's decision to join Citibank:

This is the mindset of the ambitious educational elite: You go to Harvard (or Stanford), maybe to Oxford (or Cambridge) for a Rhodes (or Marshall), then to Goldman (or McKinsey, or TFA), then to Harvard Business School (or Yale Law School), then back to Goldman (or Google), and on and on. You keep doing the thing that is more prestigious, opens more doors, has more (supposed) impact on the world, and eventually will make you more and more famous and powerful. Money is something that happens along the way, but it’s not your primary motivation. Then you get to Peter Orszag’s position, where you can do anything, and you want to go work for Citigroup? Why do our society and culture shape high-achieving people so they want to be executives at big, big companies that are decades past their prime? Why is that the thing people aspire to? Orszag wanting to work at a megabank — instead of starting a new company, or joining a foundation, or joining an NGO, or becoming an executive at a struggling manufacturing company that makes things, or even being a consultant to countries with sovereign debt problems — is the same as an engineer from a top school going to Goldman instead of a real company. It’s not his fault, but it’s a symptom of something that’s bad for our country.

Tyler Cowen, in his long, informative piece on inequality, mentioned something similar:

…in so-called normal times, the finance sector attracts a big chunk of the smartest, most hard-working and most talented individuals. That represents a huge human capital opportunity cost to society and the economy at large.

How to Draw An Owl

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One interpretation of the image and caption is that it reinforces how some folks perceive the progression from novice to expert:

Stage 1: You suck.
Stage 2: You're an expert.

In fact, mastering a skill involves hundreds of stages of incremental improvement over a very long period of time.

I believe a key reason so many people on the road to mastery call it quits is not because drawing a beautiful owl in pencil is superhumanly hard. It's because they thought it would be easy.

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Another interpretation of the image is that it's showing that step one is always "start," and step two is always "keep going and going and going until you've nailed it."

(image hat tip to Alexia Tsotsis)

What’s Remained Constant?

From a 1997 interview between Dan Pink and Richard Bolles of What Color Is Your Parachute? fame:

Pink: Despite all the things we've discussed so far, you're not totally sold on the idea that the world of work is awash in change, are you?

Bolles: No, I'm not. There is a basic truth about what a human needs in order to survive; our culture seems unable to understand that. Human nature survives and has survived through the ages by being able to hold on tenaciously to two concepts: What is there about my life or world that has remained constant? and What is there about my life or world that has changed or is changing? I have always argued that change becomes stressful or overwhelming only when you've lost any sense of the constancy in your life. You need firm ground to stand on. From there, you can deal with that change. Observing the constants in your life gives you that firm ground. The thing about the great faiths is that they talk about what's constant in the world: God, grace, prayer. But our culture, in general — and the profession of career counseling, in particular — gets absorbed with a single question: What's changing? Nobody remembers to ask the other question, What's remained constant?

How to Get Hired

Derek Sivers, who started CD Baby and sold it to eBay, generally writes great stuff. However, I think he misfires in his recent post How to Get Hired. His advice for landing a job is:

1. Focus on one company

2. Tell them how much you want to work for them

3. Be persistent (though succinct)

4. Do this until hired

There's more detail under each step over at his post. I agree with the general principle that instead of blasting your resume out to a hundred firms you should be more strategic and proactive and very persistent in your follow-up.

The gaping hole in the advice is simple: How do you know which company to focus on and relentlessly pitch? Under Step 1, he writes: "Do some soul-searching to decide what you really want to do." Those are 12 words of a 432 word post. Yet it's the hardest thing to do.

Calling it "soul searching" is problematic. Had he said, "Figure out which company you want to work for," it would have left open the possibility to arrive at the answer in various ways. But by saying one needs to search one's soul, it furthers two myths that I see.

The first is that we all have one or two things we are destined to do. In fact, I think you can become good (and thus) really interested in a range of things. The second is that the way to find what you "really want to do" is through inspection and reflection. In fact, introspection seems never to bear the fruit you're promised; personal discoveries and self-knowledge seem sooner found via experiments and activity.

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Here's Derek's great post on how to hire a programmer to make your idea happen. Here's his thoughtful post titled A real person, a lot like you, about how the web can sometimes make us forget that a real person is behind the other computer you're interacting with.

Singular Competence = Passion = Happiness

Eric Falkenstein channels Arthur Brooks' new book to discuss the connection between happiness and finding your comparative advantage at work:

He states that the key factor in one's happiness–not experiential happiness, but 'remembered happiness' that is more correlated with 'life satisfaction', see Kahneman on the difference–is 'perceived earned success'. This is the willingness and ability to create value in your life or the life of others. He states that if you ask someone if they feel like they are creating such value, they are happy, regardless of how much they make. Giving people money, via welfare or inheritance, does not make people happy, because this if anything discourages the effort needed to find and develop such a niche. …

Finding alpha is about finding your comparative advantage in your work. As David Ricardo noted about comparative advantage, it exists regardless of one's absolute advantage, it's what one is relatively best at, basically, one's most productive activity. When you find it, you are literally being all you can be.

Invariably, one finds one is good at what they like and vice versa, because you can only get good at something via a lot of effort, and if the task is perceived as onerous or boring you won't put in enough effort; if you are good at it, you'll find you like the appreciation you receive from others that is greater than in any other activity. Thus, finding your alpha is like Brook's 'perceived earned success'. If you find what you would do for nothing and get so good people pay you for it, you will probably be happy.

One important refinement of this idea is that there's a difference between current and permanent value: Pets.com vs. Google, the works of John Kenneth Galbraith vs. Ludwig von Mises. They might, at one time, have generated the same appreciation, but one faded, the other proved highly prescient. One's sense of whether one is creating permanent value, irrespective of current rewards, is important as well, because its rather ghastly to think one's lifework will be seen like past experts in quack homeopathy, irrelevant if not a joke.

There's more, then this conclusion:

The key is doing the best with what you can, the self-awareness and motivation to develop one's strengths so that your hard work generates a maximum payoff going forward. As Muhammad Ali once said, "You can be the best garbage man or you can be the best model–it doesn't matter as long as you're the best." 'The best' is mathematically improbable, 'really good' generates the same result. If you are really good at your job your day is filled with sincere gratitude by colleagues and customers, and hopefully you can also have a family that appreciates you as well (but for vary different reasons).

The Cal Newport shorthand would probably be something like: Singular Competence = "Passion" About Work = Personal Happiness.

I thank Cardiff Garcia for the pointer. Here's Cardiff's post on scalable careers which draws on the same Taleb chapter I blogged about last year.

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Justin Wehr's sound advice: "When in a sour mood, stop everything and ask if you are in need of food, sleep, a potty break, fresh air, or exercise."

Career Lessons from Elena Kagan vs. Richard Posner

Consider the career paths and attitudes of two of the most prominent legal scholars in America.

Kaganhead Elena Kagan, recently nominated to the Supreme Court, according to profiles has been carefully plotting a career since, well, forever. Her youthful dream was to be a Supreme Court justice. At 17 she posed for her high school yearbook in a judge’s robe with a gavel and a quotation from Felix Frankfurter. She relentlessly worked toward this goal in her adult life, knowing what she would have to do to get there. "She was one of the most strategic people I’ve ever met, and that’s true across lots of aspects of her life. She is very effective at playing her cards in every setting I’ve seen," said John Palfrey, a law professor at Harvard. She published rarely; she did not speak out on controversial issues; she has been "extraordinarily — almost artistically — careful. I don’t know anyone who has had a conversation with her in which she expressed a personal conviction on a question of constitutional law in the past decade." Thus: she stands a good chance at enduring Senate confirmation hearings because she has given her opposition little ammunition. David Brooks called this willingness to suppress her mind for her career "kind of disturbing." Andrew Sullivan called her pure careerism "depressing."

Posnerhead Richard Posner, an appellate judge and Univ of Chicago law professor, may have been similarly ambitious when young (I'm not sure), but based on how he's lived his adult life it's clear that he values the pursuit of truth over a carefully cultivated resume. Posner is someone people agree is bright enough to be a Supreme Court justice but too eccentric so as to never pass a confirmation hearing. With jaw-dropping productivity he's shared his thoughts on nearly every topic under the sun. He applies his considerable intellectual heft to timely public debates. He's come out in support of legalizing marijuana, gay marriage, and other rational (if unpopular) ideas. In addition to his court opinions, where are the most cited in the land, he churns out a book a year and a blog post a week. With all this output, he inevitably gets some stuff wrong (sometimes a lot of stuff wrong), offends everyone at least once, and makes himself impossible to pin down. But what an inspiring mind and life!

The career results for each: Kagan will likely assume the top judicial position in the land. Posner will stay put at a close-to-the-top judicial position. The pure careerist achieves her goal. But at what cost?

I'd rather be close to the top and be able to live honestly and with the freedom to take risks than live a neutered life for 35 years in order to rise to the very top. I'd rather be myself than be a shallow, approval-seeking imitation of what is supposedly required to advance to the next level.

Bottom Line: In many professions it seems the sacrifices to go from A- to A+, from 2nd place to 1st place, are just not worth it.

Who Are the Masters in Your Field and How Do You Learn from Them?

When contemplating your own field, ask yourself: are you the wannabe screenwriter reading how-to guides on the subway, or are you, like Thomas, throwing yourself among the masters, and proclaiming: I know nothing, but you do, and I’m not going anywhere until I do too?

That's Cal Newport in his latest entry on building a remarkable life. He rightly emphasizes that if you want to get good at something you should immerse yourself in an environment where people are good, deconstruct their keys to success, and learn from them. Modern craftsmanship: "Learning crafts takes not only time, but exposure to master craftsman." Perhaps another question you could then ask of someone is, "Who are the masters in your field and how do you learn from them?"

The other day Slate did a summary of the new theories of success which focus on the importance of hard work.

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Excellent Stratfor analysis of the crisis in Europe and European identity.  Self-identified progressives do not understand economics. Mickey Kaus op/ed about the outdated union system.

DaveJ comments on yesterday's post about mood and creativity: "You are talking about mere mood variation, and it makes sense that mood cycles enhance creativity, because they shift context and stimulate novel patterns of activity in your brain. I suspect that it is not the middle of the emotional continuum that produces creativity but the variation itself."