The bestselling career book of all time goes by the whimsical name What Color Is Your Parachute? But when it comes to charting a career plan, that’s the wrong question. What you should be asking yourself is whether your parachute can keep you aloft in changing conditions. The unfortunate truth is that in today’s career landscape, your parachute—no matter its color—may be shredded and tattered. And if it isn’t that way already, it could get that way at any time.
In his first chapter, Parachute author Richard Bolles writes, “It is important, before you enter the job hunt, to decide exactly what you are looking for—whether you call it your passion, or your purpose in life, or your mission.… Passion first, job-hunt later.”1 After four decades in print, this is still the accepted wisdom today. You see similar advice all over. Habit number two of Stephen Covey’s Seven Habits of Highly Effective People is, “Begin with the end in mind”: you should produce a personal mission statement that puts your goals in focus. In The Purpose-Driven Life, Rick Warren advances the idea that each of us has a God-given purpose for being on this planet.
The primary message of these books (of which there are more than 50 million copies in circulation) and countless others is to listen to your heart and follow your passion. Find your true north by filling out worksheets or engaging in deep, thoughtful introspection. Once you’ve got a mission in mind, these books urge, you’re supposed to develop a long-term plan for fulfilling it. You’re supposed to craft detailed, specific goals. You’re urged to figure out who you are and where you want to be in ten years, and then work backward to develop a roadmap for getting there.
This philosophy has some serious strengths. It’s important to have worthy aspirations. If you are passionate about something, you’ll have fun, stay committed, and achieve more. It’s also right to invest for the long term: to find out whether you’re good at something and whether you like it, you need to stick with it for a meaningful amount of time.
But while these strengths may have made them the right philosophies in past decades, today there are some huge problems with this approach to career planning. First, it presumes a static world, and as we saw in Chapter 1, the career landscape isn’t what it used to be. Deciding where you want to be in ten years and then formulating a plan for getting there might work if our environments were unchanging. It might work if getting from point A to point B in your career were like crossing a lake in a boat on a calm summer’s day. But you’re not in a calm lake. You’re in a chaotic ocean. Conventional career planning can work under conditions of relative stability, but in times of uncertainty and rapid change, it is severely limiting, if not dangerous. You will change. The environment around you will change. Your allies and competitors will change.
Second, this philosophy presumes that fixed, accurate self-knowledge can be easily attained. In fact, lofty questions about identity and moral purpose, along with deceptively simple ones like “What am I passionate about?” take time to work out, and the answers frequently change. It’s unwise, no matter your stage of life, to try to pinpoint a single dream around which your existence revolves.
Third, as we learned in the last chapter, just because your heart comes alive at a calling doesn’t mean someone will pay you to do it. If you can’t find someone who wants to employ you to pursue your dream job, or if you can’t financially sustain yourself—that is, earn a salary that allows you to live the lifestyle you prefer—then trying to turn your passion into a career doesn’t really get you very far.
So which is it? Should you follow a plan or stay flexible? Should you listen to your heart or listen to the market? The answer is both. They’re false choices—the same false choices entrepreneurs are frequently dealt. Entrepreneurs are told they must be really persistent in fulfilling their vision, but also be ready to change their business based on market feedback. They are told to do a business they’re passionate about, but also to adapt to customer needs.
The successful ones do both. They are flexibly persistent: they start companies that are true to their values and vision, yet they remain flexible enough to adapt. They are obsessed with customer feedback, yet they also know when not to listen to their customers. They draw up light plans with the intent of developing true competitive advantage in the marketplace, but they’re also nimble enough to stray from those plans when appropriate. And they are always driving toward developing true competitive advantage in the marketplace.
To run a successful start-up of you in today’s world, you can—and must—do the same in planning your career. This chapter will show you how.
Flickr is one of the most widely used photo hosting and sharing websites, with an estimated five billion–plus images on its servers. But the company wasn’t started by photography pros. In fact, its founders, Caterina Fake and Stewart Butterfield (who teamed up with Jason Classon), didn’t set out to start a photo-sharing service at all.
Their original product, rolled out in 2002, was a multiplayer online game called Game Neverending. Most gaming platforms at that time allowed one or at most a few people to play the same game together at the same time. But Caterina and Stewart wanted to create a game that hundreds of people could play at the same time. To this end, the plan was to build something they saw less as a game and more as a “social space designed to facilitate and enable play.” To attract and retain players to this social space, they pumped out social features like groups and instant messaging, including one add-on to the instant messenger application that allowed players to share photographs with one another. As with most features of the game, the photo-sharing add-on was developed very quickly—it only took eight weeks from idea to implementation.
When photo sharing was first added to Game Neverending in 2004, it was no big deal—photographs were just another thing players could trade with one another, like the objects they would collect during the course of the game. However, it didn’t take long for the photo-sharing capability to eclipse the game itself in popularity. As this became increasingly apparent to the leadership team, they were faced with a decision: Should they try to expand their new photo-sharing platform while sticking to their long-term plan and continuing to develop Game Neverending, or should they put the game (and its twenty thousand avid users) on hold to devote the majority of their precious resources to photo sharing? They decided to deviate from the original plan and focus exclusively on building the photo application and the photo-sharing community that went along with it. They called it Flickr. (I invested just as it became the photo service.)
Flickr soon became the photo-sharing service of choice for millions of Internet users. Its social features—tagging and sharing—grew naturally out of the social DNA that defined the original online game, even as they differentiated the service in response to market feedback. In 2005 Yahoo! acquired the company, making it a Web 2.0 poster child. But more than just a Silicon Valley success story, the evolution of Flickr is a case study in smart adapting: its founders were in constant motion early on, tried many things to see what would work, and nimbly shifted their plans based on what they learned.
These are the very same strategies that define some of the most inspiring careers. Take, for example, Sheryl Sandberg. Today, Sheryl is chief operating officer of Facebook, where she is in charge of the company’s business operations. She serves on the boards of Disney and Starbucks. Fortune named her one of the most powerful women in business.
You might think someone so successful knew her goals and aspirations from day one, and followed a rigorous and ambitious career plan to achieve them. But you’d be wrong. Sheryl hasn’t stuck to a conventional career plan. In fact, as an idealistic undergraduate majoring in economics she never imagined that she would one day be working in the private sector, much less as a top executive for one of the world’s most valuable companies. Sheryl began her career in India, about as far as one could get from Silicon Valley. There she went to work on public health projects for the World Bank. It was a first job consistent with deeply embedded values: to give back to those less fortunate and to make a difference in the world. Sheryl had grown up in a home where political activism was as normal as eating or breathing. Her father was a doctor who regularly took his family on vacations to Third World destinations, where he would provide surgical services for free to the poor. Sheryl’s mother was involved in a movement to support Soviet dissidents by helping them smuggle into the USSR contraband white chocolate disguised as soap—which could then be sold on the black market for much-needed cash. Sheryl knew that she was lucky to have been born in the United States, with its freedom and wealth of opportunities, and she was driven by an intense desire to give back in some way.
Yet after a couple of years with the World Bank, Sheryl shifted course and left the public sector to enroll at Harvard Business School, where she earned an MBA. From academia, her next stop was the business world. But after a one-year stint at management consulting firm McKinsey, she realized the corporate career track wasn’t for her; so she shifted yet again, this time to Washington, DC, where she served as then U.S. Secretary of Treasury Larry Summers’s chief of staff from 1996 through 2001. It wasn’t providing health care to the impoverished of India, but she was helping to shape policy in ways that would have a meaningful effect on the lives of many Americans. (It should be noted that working for Summers wasn’t an accident: he had been her economics professor in college and had also hired her at the World Bank. As always, Sheryl was thoughtfully tapping her connections to find the next opportunity, something we talk more about later.)
After President Clinton left office, Sheryl asked then Google CEO Eric Schmidt, whom she had met at Treasury, for advice on her next career move. She recalls Schmidt’s reaction as she made a detailed presentation of the pros and cons of her various options: “No, no! Get out of the weeds. Go where there’s fast growth, because fast growth creates all opportunities,”2 he told her. It was outstanding advice: Work in a market with natural momentum. Ride the big waves.
As it turned out, in 2002 Google was that place. Schmidt made Sheryl an offer. She accepted and became Google’s vice president of global online sales and operations. She grew the company’s online sales and operations group from four individuals in California to a global team of thousands of people and played crucial roles in developing and growing both of Google’s online advertising programs, AdWords and Ad-Sense, still the sources of the majority of Google’s revenues.
Shifting from the public to the private sector, from the high-powered corridors of Washington, DC, to the organized chaos of Silicon Valley, might strike you as abrupt, or even random. But in fact, each move made sense given the interplay of her assets, aspirations, and the market realities. Her honed management skills would be useful for a fast-growing company; her economics background would help develop a sales model for a new type of online advertising; and Google’s mission was rooted in making the world a better place. After six years at Google, Mark Zuckerberg hired Sheryl to be COO at Facebook, where she remains today.
What Flickr and Sheryl have in common is that they each challenge common assumptions about the path to success. Flickr contradicts the idea that winning start-ups come out of nowhere and ride the founders’ brilliant idea to take over the world. In reality, most companies don’t execute a single brilliant master plan. They go through stops and starts, a couple near-death experiences, and a great deal of adaptation. Pixar started as a company that sold a special computer for doing digital animation; it took a while till they got into the moviemaking business. Similarly, Starbucks originally sold only coffee beans and coffee equipment; they hadn’t planned to sell coffee by the cup.
Sheryl’s story contradicts the analogous assumption that massively successful people find their calling at an early age, devise a bulletproof life plan, and then follow it unwaveringly until attainment. Sheryl’s career plan wasn’t something she crafted once in her early twenties and then followed blindly. She didn’t assemble a bunch of dominos, knock over the first piece, and then sit back and watch the rest fall into place over time. Instead of locking herself in to a single career path, she evaluated new opportunities as they presented themselves, taking into consideration her (ever-growing) set of intellectual and experiential assets. She pivoted to new professional tracks without ever losing sight of what really mattered to her. “The reason I don’t have a plan is because if I have a plan I’m limited to today’s options,” she says.3
Among some of the most notable professionals, she is the rule, not the exception. Sure, Bill Clinton decided on politics at age sixteen, and set his sights on the presidency almost as young. But most of us zig and zag our way through life. Tony Blair spent a year trying to make a go of it as a rock music promoter before entering politics. Jerry Springer was mayor of Cincinnati before attaining daytime television fame. Andrea Bocelli practiced law before he became a world-famous singer. Winning careers, like winning start-ups, are in permanent beta: always a work in progress.
It’s important to understand, though, that while entrepreneurial companies and people are always evolving, the choices they’re making are disciplined, not random. There is real planning going on, even if there are no firm plans. We call this kind of disciplined, adaptive planning ABZ Planning, and it’s what we’ll cover in the balance of the chapter.
ABZ Planning is the antidote to the “what color is your parachute” approach to career planning. It is an adaptive approach to planning that promotes trial and error. It allows you to aggressively pursue upside and mitigate against possible downside risks. ABZ Planning isn’t something you do once early in your career. It’s a process as important for someone in their forties or fifties as for a newly minted college grad. There is no beginning, middle, or end to a career journey; no matter how old you are or at what stage, you will always be planning and adapting.
So what do A, B, and Z refer to exactly? Plan A is what you’re doing right now. It’s your current implementation of your competitive advantage. Within a Plan A you make minor adjustments as you learn; you iterate regularly. Plan B is what you pivot to when you need to change either your goal or the route for getting there. Plan B tends to be in the same general ballpark as Plan A. Sometimes you pivot because Plan A isn’t working; sometimes you pivot because you’ve discovered a new opportunity that’s just better than what you’re doing now. In either case, don’t write out an elaborate Plan B—things will change too much after the ink dries—but do give thought to your parameters of motion and alternatives. Once you pivot to a Plan B and stick with it, that becomes your new Plan A. Twenty years ago Sheryl Sandberg’s Plan A was the World Bank. Today, her Plan A is Facebook, because it’s where she is right now.
Plan Z is the fallback position: your lifeboat. In business and life, you always want to keep playing the game. If failure means you end up on the street, that’s an unacceptable failure. So what’s your certain, reliable, stable plan if all your career plans go to hell or if you want to do a major life change? That’s Plan Z. The certainty of Plan Z is what allows you to take on uncertainty and risk in your Plans A and B.
Later in the chapter we’ll go into more detail about each of these stages, but first we want to offer some general tips that apply at all stages of your career plan—whether it’s A, B, or even Z.
Career plans should leverage your assets, set you in the direction of your aspirations, and account for the market realities. The problem is, as we learned in the last chapter, these three puzzle pieces are always changing. The best you can do is articulate educated hypotheses about each. “I believe I am skilled at X, I believe I want to do Y, I believe the market needs Z.” All plans contain these sorts of assumptions; good ones make them explicit so that you can track them over time. Essentially, you want to make explicit the things that need to be true for your plan to work. These hypotheses should lead you to specific actions. Companies often have broad missions like maximizing shareholder value, but as Jack Welch has said, maximizing shareholder value “is not a strategy that tells you what to do when you come to work every day.”4 Similarly, you may have broad aspirations, like “help interesting people do interesting things” or “design human ecosystems.” But real planning means plotting the specific steps it will take to make those aspirations happen.
Many people defer collecting full-time wages by spending twenty-three consecutive years in school. A high school dropout can make more money in the short run than the guy stuck studying chemistry. But in the long run, the logic goes, a person with a foundation of knowledge and skills will make more money and most likely live a more meaningful life. It’s true. And there’s a similar belief in start-ups: technology companies focus on learning over profitability in the early years to maximize revenue in the later years.
Unfortunately, for far too many, focused learning ends at college graduation. They read about stocks and bonds instead of reading books that improve their mind. They compare their cash salary to their peers’ instead of comparing lessons learned. They invest in the stock market and neglect investing in themselves. They focus, in short, on hard assets instead of soft assets. This is a mistake. We’re not suggesting you be a starving, unshaven graduate student forever; you do need to earn money and build economic assets. But as much as you can, prioritize plans that offer the best chance at learning about yourself and the world. Not only will you make more money in the long run, but your career journey will be more fulfilling. Ask yourself, “Which plan will grow my soft assets the fastest?” Even simpler: “Which plan offers the most learning potential?”
Entrepreneurs penetrate the fog of the unknown by testing their hypotheses through trial and error. Any entrepreneur (and any expert on cognition/learning) will tell you that practical knowledge is best developed by doing, not just thinking or planning. At Flickr, there was an assumption that a multiplayer online game would have the most uptake. It was only by launching it, gauging user feedback, and building new side features like photo sharing every several weeks, that the team learned where the real opportunity lay. In the early days of LinkedIn, the plan was to have members invite their trusted connections by email—an invitation mechanism would fuel membership growth. But it turned out that the best way to enable viral spread was actually to enable members to upload their address books and see who else was on the service already.
For careers, too, you don’t know what the best plan is until you try. It was only after I spent time in that graduate program that I learned academia wasn’t the path for me. When I moved to the business world, I mistakenly thought my competitive advantage was being able to hold complexity in my head and master abstractions. But when I started working, I discovered my real advantage in the Internet industry was having the ability to think simultaneously about individual psychology and social dynamics on a massive scale.
Learn by doing. Not sure if you can break into the pharmaceutical industry? Spend six months interning at Pfizer making connections and see what happens. Curious whether marketing or product development is a better fit than what you currently do? If you work in a company where those functions exist, offer to help out for free. Whatever the situation, actions, not plans, generate lessons that help you test your hypotheses against reality. Actions help you discover where you want to go and how to get there.
Occasional missteps are to be expected when you take this experimental approach to career planning. It’s the “error” part of trial and error. But these errors needn’t be permanent. Good Plan A’s can be stopped or reversed or morphed into a Plan B. A good Plan A minimizes the cost of failure. Don’t bet the farm. Iterate bit by bit, learn experience by experience. Start with a trial period. Keep your day job. ABZ Planning embraces recoverable failure so long as it generates real lessons.
Planning and adapting means thinking carefully about your future. Lunging at the first well-paid and/or high-status job you come upon may offer immediate gratification, but it won’t get you any closer to building a meaningful career. A goal that can be achieved in a single step is probably not very meaningful—or ambitious. The business professor Clayton Christensen once told graduating students at Harvard Business School, “If you study the root causes of business disasters, over and over you’ll find [a] predisposition toward endeavors that offer immediate gratification.” At the same time, though, don’t do the opposite and think ahead too far in the future. Again, you will change, the world will change, the competition will change. It’s why Plan C, Plan D, or Plan E are not part of this framework.
The best thing to do is to think and plan two steps ahead. If you’d like to be promoted from analyst to associate, it may mean a first step of building a relationship with a key partner, or taking a night course to pick up advanced financial management skills before taking that step of marching into the boss’s office and asking for that promotion. Sometimes the first step toward a goal is rather simple. A question people sometimes ask us is, “What’s the best way to get into Silicon Valley start-ups?” Well, there are various ways, but the first step is this: move here!
If you’re unsure what your first, or even your second, step should be, pick a first step with high option value, meaning that it could lead to a broad range of options. Management consulting is a classic example of a career move that maximizes “optionality” because the skills and experiences of consulting can be helpful in and applied toward many other next steps, even if you’re not sure what those steps are yet. A good Plan A is one that offers flexibility to pivot to a range of possible Plan B’s; similarly, a good first step generates a large number of possible follow-on second steps.
There was a great article in the Onion in November 2008 about how medical personnel had to be dispatched to help Obama campaign workers found lying on park benches and wandering city streets aimlessly, their lives devoid of meaning after election victory. It was a joke, of course, but it actually highlights a serious point: Throwing your heart into something is great, but when any one thing becomes all that you stand for, you’re vulnerable to an identity crisis when you pivot to a Plan B. Establish an identity independent of your employer, city, and industry. For example, make the headline of your LinkedIn profile not a specific job title (e.g., “VP of Marketing at Company X”) but personal-brand or asset-focused (e.g., “Entrepreneur. Product Strategist. Investor.”). Start a personal blog and begin developing a public reputation and public portfolio of work that’s not tied to your employer. This way, you’ll have a professional identity that you can carry with you as you shift jobs. You own yourself. It’s the start-up of you.
Now let’s look at how you can apply all these strategies at different points along the A–B–Z timeline.
PayPal is the leading online-payments company, processing more than 20 percent of all e-commerce transactions in the United States. People around the world have sent hundreds of billions of dollars to one another over the Web—instantly and safely—thanks to PayPal’s innovative technology. When PayPal went public in 2002 (one of only two companies to do so that year), it gave hope to a technology industry in recession. When eBay acquired the company for $1.5 billion, PayPal staked its claim as a great Silicon Valley success story. Yet the PayPal Plan A did not look anything like the company looks today.
In 1998 programmer Max Levchin teamed with derivatives trader Peter Thiel to create a “digital wallet”—an encryption platform that allowed you to store cash and information securely on your mobile phone. That soon evolved to software that allowed you to send and receive digital cash wirelessly and securely via a Palm Pilot (the first of several iterations) so that two friends could split a dinner tab using their PDAs. It was a neat idea that leveraged Max’s and Peter’s technology and finance backgrounds, respectively (complementary assets that gave them a competitive edge as founders). Max and Peter named the company Confinity—a mix of confidence and infinity. But the Palm Pilot wasn’t catching on.
So Max and Peter iterated again. They developed an online payment transfer service that didn’t require a Palm or any other mobile phone application. It let you send money securely over the Web to anyone with an email address. Recipients could in turn transfer the money wirelessly to their checking accounts. To make the service, which they dubbed PayPal, even more useful to businesses, they added credit card processing. No merchant accounts needed to process a credit card payment: just a simple, universal online interface.
Confinity signed up early adopters for peer-to-peer money transfers on both the Palm Pilot application and the PayPal online payment transfer service, although not as quickly as expected for the Palm Pilot. The company struggled to find and articulate a mass-market use case; the general public was not accustomed to electronically and wirelessly sending cash to one another.
In short, PayPal’s Plan A had played out. There were no more iterations to make, no more small bets to take. Many lessons had been learned. But the game wasn’t over yet, thanks to an auction site called eBay that kept growing and growing. But more on that in a minute.
Somewhat earlier, I was at a similar crossroads in my career. My Plan A (after leaving academia) had been to go into the computer industry, but I had one big concern. I was unsure I had the technical skills to compete in a place like Silicon Valley. Creating technology that millions of people would use was an aspiration. There was clearly growing market demand for folks who had experience with the Internet. But did I have the skills, and could I make enough connections in the tech industry, to become a hitter? To find out, I tried. I got a job (via a friend of a friend) at Apple Computer in Cupertino.
Apple hired me into their user experience group, but shortly after starting on the job I learned that product/market fit—the focus of product management—mattered more than user experience or design. You can develop great and important user interfaces, and Apple certainly did, but if customers don’t need or want the product, they won’t buy. At Apple, and in most companies, the product/market fit questions fall under the purview of the product management group, not user experience. And because product management is vital in any product organization, work experience in the area tends to lead to more diverse career opportunities.
So, much in the way that the earliest version of PayPal iterated from a digital wallet to an online payment transfer service, I attempted to iterate into a product management role within Apple (Plan “A1”). But the product management jobs required product management experience. It’s a common catch-22: for jobs that require prior experience, how do you get the experience the first time? My solution: do the job for free on the side. I sought out the head of product management within the eWorld group at Apple, James Isaacs, and told him I had a few product ideas. I offered to write them up in addition to everything else I was doing, and I did. Product managers reviewed my ideas and gave me feedback and encouragement. It was a small, reversible bet, an experiment within my job, and it worked well.
The experience taught me that I did indeed have the skills and intuitions to make a go of it in the tech industry (assets). I learned that product management was closer to the heart of technology companies than the job I was initially hired for (a market reality). And I learned that product strategy was a path that could propel me to the highest levels of seniority in the business world—which in turn would help me realize my vision of making a huge impact (aspirations). All important lessons I wouldn’t have gained any way other than by setting foot in the industry.
After almost two years at Apple I left to go to Fujitsu in Silicon Valley to work as a full-time product manager (Plan A2). I was still on Plan A: I was still experimenting within the tech industry. But all the while I was honing my assets and aspirations for what I might like to do next: my Plan B.
While you’ll always be tinkering and adjusting your Plan A, should you decide you need to make a bigger change, that’s when you pivot to Plan B. Pivoting isn’t throwing a dart on the map and then going there. It’s changing direction or changing your path to get somewhere based on what you’ve learned along the way.5 Once you’ve pivoted and are on a new track, that becomes your new Plan A.
PayPal’s pivot to Plan B happened because of eBay. At the time, eBay was the busiest person-to-person marketplace on the Web. Yet auctions demanded a person-to-person financial transaction. This meant that a buyer in one city usually mailed a check or money order to a seller in another city. This process was inconvenient, time-intensive, and unreliable. As eBay grew in size, sellers became increasingly frustrated with money-collection options. They wanted a more efficient way to accept payments.
When the PayPal team saw that growing numbers of eBay users were trying to use PayPal to handle payments, the first reaction was “Why the heck are they using our product?!” (Remember, PayPal’s first focus was on mobile payments.) That quickly turned into “Ooh—maybe those people are our customers!” Which in turn led to a realization that the company should pivot to Plan B: offer the eBay community an easy way to pay for the items they bought in online auctions. In 1999 PayPal ditched the Palm Pilot app (the original Plan A) and focused on eBay. Plan B wasn’t something random, like an online chat application. It stayed true to PayPal’s initial encryption roots while shifting to capitalize on what appeared to be the real market need.
As it happened, my career Plan B intersected with PayPal’s Plan B. A few years before PayPal took off, after stints at Apple and Fujitsu, I had decided to pivot into the adjacent world of entrepreneurship and start a company of my own. In 1997 I cofounded Socialnet.com, an online dating site. At the time, my Plan A was Socialnet. On the side, I was helping Peter and Max get PayPal off the ground, promising to return their calls by midnight the same day and serving on their founding board of directors. In my mind, I had two possible Plan B’s. One would be to deepen my relationship with PayPal—i.e., join full-time. Another would be to get a general job in the tech industry. My experiences cofounding Socialnet would make either career move a natural pivot. About a year before Socialnet closed down (an experience that taught me a tremendous amount), in January 2000, I decided to join Max and Peter full-time at PayPal and became executive vice president.
Both PayPal’s Plan B and my own career Plan B worked out well. At PayPal, online payment processing for eBay users (and beyond!) was a big winner. This isn’t to say it was smooth sailing the rest of the way; quite the opposite. PayPal changed its business model, brought on new executives, merged with another company, and endured millions of dollars of losses due to fraud. Probably the lowest point was when the company spent $12 million in cash in one month without a dime of revenue. (The situation was so dire that I pointed out to Peter at the time that we could spend a day throwing fistfuls of cash off the roof of a building and not come close to matching the company’s burn rate.) The team flexibly dealt with—and learned from—these challenges while persistently pursuing the vision of delivering online payment transfer in multiple currencies.
From a career standpoint, I hit similar bumps in the road, but they were all instructive. I learned to adapt to the speed of the start-up world. I learned about how to attract and hire the right talent. I learned about the right and wrong kinds of impatience. And much more. What I learned from the PayPal experience equipped me for my next pivot: trying again to start my own company. That company was LinkedIn.
How do you know when to pivot from Plan A (what you’re doing now) to a Plan B? When is it time to change divisions, change jobs, or even change the industry you work in? You’ll rarely know for sure when to pivot or when to persist in what you’re doing. In general, a lesson from the technology industry is that it’s better to be in front of a big change than to be behind it. But the question of when to shift exactly is a question of both art and science, intuitive judgment combined with the best feedback or data you can collect—something we’ll discuss in the network intelligence chapter. And of course expect both good luck and bad luck along the way that will open and close unexpected windows of opportunity.
The common presumption is that you shift to Plan B when something isn’t working. That’s frequently the case but not always. What you’re doing now doesn’t have to be failing for it to make sense to shift. Sheryl was hardly failing when she pivoted to the Google opportunity. If you find that the grass really is greener somewhere else, go there!
Of course, given the volatility of today’s career landscape, the decision to pivot often isn’t voluntary. Sometimes we’re forced to go to Plan B. We could be fired, new technology could automate or offshore our routinized job, or the entire industry we work in could be disrupted. Or we might undergo a major life change, like having children, that reorders life priorities and necessitates a pivot into a situation that offers more work/life balance.
Andy Grove, the Intel cofounder, refers to these kinds of events as inflection points. In a business context, Grove says a strategic inflection point is what happens when a “10×” force (ten times bigger) disrupts a business. For example, for a small-town general store, a Walmart setting up shop nearby is a 10× force on the general store. For a midsize financial firm, a huge corporate takeover is a 10× force. Countless once-giants like Blockbuster, Kodak, and the New York Times are all in the midst of environmental inflection points brought about by the 10× force of the digital revolution.
In the same way that external forces threaten companies, so too can they have profound effects on your career. For an autoworker in Detroit, the closing of a major plant is a 10× force. For a public school teacher, the slashing of school budgets is a 10× force. As Grove says, “[A] career inflection point results from a subtle but profound shift in the operating environment, where the future of your career will be determined by the actions you take in response.”6 An inflection point at your company or industry usually will require you to either change your skills or change your environment. In other words, it will often require you to pivot.
It’s impossible to know exactly when an inflection point will disrupt your career. The only thing you can safely know about the future is that it will be sooner and stranger than you think. So instead of trying to do the impossible and predict when an inflection point will threaten, prepare for the unknown. Build up your soft assets and proactively embrace new technology so that if and when the inflection point does come, you are ready to swiftly parlay skills into a Plan B.
James Gaines is a model example of someone who has adapted his plans in anticipation of disruptive forces. During the reign of print magazines, Gaines was king. He was managing editor of People magazine, then Life magazine, and finally Time magazine—at the time, one of the most influential print publications in the world. There, he interviewed heads of state and directed an editorial staff of more than six hundred journalists. He left the magazine in 1996 to run the corporate editorial side of the Time Inc. empire, sharing oversight of the company’s twenty-six magazine operations. A year of that reminded him that writing—not management—was his passion. So he went independent and began writing books. Since he could write from anywhere, he moved his family to Paris to provide a more colorful upbringing for his children and a more inspiring backdrop for his writing.
While living in Paris in 2002, Gaines and his son went to see the first Harry Potter film. That night turned out to be a pivotal career experience for Gaines. In one scene, Harry opens a book and a three-dimensional human face leaps out of the page and wiggles its face. Gaines recalls the scene triggering an epiphany: an interactive book! At the time, he was writing a book about Johann Sebastian Bach and he found it frustrating that the reader couldn’t hear the music described in the text. Perhaps technology could transform books for the better; perhaps it could add a touch of Potter magic to the reader experience.
By the summer of 2008, just shy of his sixty-first birthday, Gaines moved back to the United States with two published books to his name. With a lifetime of print journalism and publishing experience, he could have held any number of senior posts in the trade. But he saw that the future had arrived and that old media may not have a place in it. So he pivoted to Plan B. He was excited, not panicked. Rather than mourn the past, he embraced the unique storytelling possibilities of a digital canvas. This positive mind-set sustained him during his learning curve.
He went on to become editor in chief of Flyp, a start-up online magazine that produced video and audio narratives on politics, finance, and social issues. At an online, multimedia magazine, Gaines had a lot to learn. And there was no formal training or classes. His youthful subordinates were his on-the-job teachers, instructing him on how to do video editing, audio editing, understand MySQL databases, and learn the pros and cons of other Internet protocols. To hear Gaines tell it, you’d think picking up these new skills was a piece of cake. But think about his ego. He had decades of experience. A long list of accomplishments. Yet he found himself, in a sense, powerless and young again. It was Day 1 for Gaines. He was in permanent beta.
Instead of waiting for an inflection point to disrupt his career, Gaines adapted. Rather than try to preserve what has always been, Gaines parlayed his skills into new media. Throughout, he never lost sight of his competitive advantage in the career marketplace: his ability to tell stories that move people, regardless of the medium.
Flickr’s Plan A was an online multiplayer game. My original career Plan A was to be an academic. Sheryl’s was to help the underprivileged, starting in India. James Gaines’s was to be a magazine editor. None is on the original plan now, and at first glance the current plans seem unrelated; but if you look closely you’ll see a logical evolution through the various pivots. I am still spreading knowledge and ideas about social life through LinkedIn, through the companies I choose to fund, and now through this book with Ben. Sheryl is still helping the underprivileged in places like Syria and Egypt who are using Facebook to organize and rally against oppressive governments. The best Plan B is different but very much related to what you’re already doing. As you think about your own Plan B alternatives, favor options that let you keep one foot planted while the other one swings to the new territory. Pivot into an adjacent niche.
Unless you need to take immediate action, one way to begin the process of pivoting is to start your potential Plan B on the side. Start learning a skill during the evenings and weekends. Start building relationships with people who work in an adjacent industry. Apply for a part-time internship. Start a side consulting practice. This is what I did when I began advising PayPal while still working at Socialnet: it was a side project that had the potential to become a full-blown Plan B later on (which it ultimately did).
Companies ranging from 3M to Gore-Tex, Google to LinkedIn, pay employees to spend a portion of their time experimenting on side projects. Why not make this a personal career policy? Set aside one day a week or month or even every few months to work on something that could be part of your Plan B. If you have a business idea you want to pursue, a skill you want to learn, a relationship you want to form, or some other curiosity or aspiration, start on it as a side project and see where it goes. At a minimum, just start talking to people. Take a day and arrange five coffee meetings with people who work in an adjacent industry.
If you want an even smaller baby step, take a “vocation vacation.” A company by the same name lets you test-drive dream jobs—whether it’s being a symphony composer or a real estate broker or a travel writer. If you think you might like to open your own spa business, for example, they’ll connect you with a spa owner in Texas and fly you out to spend two days with her, observing the ins and outs of the business and discussing in depth what it takes to succeed in the industry. It’s a great way to explore potential Plan B’s without making a big or irreversible commitment.
The reason many people do not embrace trial and error, learning by doing, adaptation, and the other themes of this chapter is because these strategies introduce real uncertainty. It’s easy to say “learn by doing”—but what if you’re not sure what you’ll learn or what you should do? As we’ll talk about in the risk chapter, uncertainty never goes away. Fear of failure never goes away. The way to feel comfortable with these entrepreneurial strategies is to have one plan in your life that’s highly certain. That’s Plan Z: a reliable plan you shift to when you no longer have confidence in Plan A and B, or when your plans get severely disrupted. The certainty of the Plan Z backstop is what enables you to be aggressive—not tentative—about Plans A and B. With a Plan Z, you’ll at least know you can tolerate failure. Without it, you could be frozen in fear contemplating the worst-case scenarios.
When I started my first company, my father offered up an extra room in his house in the event it didn’t work out—living there and finding a job somewhere else to earn money was my Plan Z. This allowed me to be aggressive in my entrepreneurial pursuits, as I knew I could draw my assets down to zero if necessary and still have a roof over my head. Becoming homeless or bankrupt or permanently unemployable is an unacceptable outcome when one of your career plans fails. Your Plan Z is there to prevent these unacceptable outcomes from becoming realities.
If you’re in your twenties and single, getting a job at Starbucks and moving back in with your parents might be a viable Plan Z. If you’re in your thirties or forties with children, on the other hand, it might mean cashing in your 401(k). Whatever it is for you, think of it as a lifeboat, not a long-term plan. Invoking Plan Z should allow you to retreat, regroup, and develop an entirely new Plan A. It’s not an endpoint—it’s what will keep you afloat while you reload and then relaunch yourself on a brand-new voyage, a brand-new Plan A.
• Make a list of your key uncertainties, doubts, and questions you have about your career at the present moment. Make a list of the hypotheses you’re developing around these uncertainties—what are the things you’re looking for to figure out whether you should stick with your Plan A, or pivot to Plan B?
• Write out your current Plan A and Plan Z, and jot some notes about what possible Plan B moves might be in your current situation.
• Schedule a coffee meeting with someone who used to work in your professional niche who pivoted to a new career plan. How did he or she make the shift? Why? Was it a good move? What were the signs that the time was right?
• Make a plan to develop more transferable skills, those skills and experiences that are broadly useful to potential other jobs. Writing skills, general management experience, technical and computer skills, people smarts, and international experience or language skills are examples of skills with high option value—that is, they are transferable to a wide range of possible Plan B’s. Once you’ve figured out which transferable skills to invest in, make a concrete action plan you can stick to, whether by signing up for a course or conference, or simply by pledging to spend one hour each week self-learning.
• Begin on an experimental side project that you work on during some nights and weekends. Orient it around a skill or experience that is different but related—something that either enhances what you do now or can serve as a possible Plan B if your Plan A doesn’t work out. Ideally, collaborate on this project with someone else in your network.
• Establish an identity independent of your employer, city, industry. Reserve a personal domain name (yourname.com). Print up a second set of business cards with just your name on it and a personal email address.
Reach out to five people who work in adjacent niches and ask them to coffee. Compare your plans with theirs. Keep up these relationships over time so you can access diverse information and so you’re in a better position to potentially pivot to those niches when necessary.