Guest blog from Ben Casnocha

Ben Casnocha is a technology entrepreneur. He founded Comcate, Inc., a leading e-government software company, at age 14. PoliticsOnline named him one of the “25 most influential people in the world of internet and politics.” He also incubates and advises internet entrepreneurs at Wasabi Ventures. He is co-author, with LinkedIn chairman Reid Hoffman, of the bestselling career strategy book The Start-Up of You: Adapt to the Future, Invest in Yourself, and Transform Your Career. He is also author of the book My Start-Up Life: What a (Very) Young CEO Learned on His Journey Through Silicon Valley.

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.