The Startup of You Book Notes

An amazing and unorthodox book about career building. Highly recommended to college students, recent graduates, and anybody that’s below 30 years old and wants to make an impact in their lives.

Author: Reid Hoffman, Ben Casnocha.

Date Finished: 21/08/2012

Here’s a link to the Amazon page.

Permanent Beta

Technology companies sometimes keep the beta test phase label on software for a time after the official launch to stress that the product is not finished so much as ready for the next batch of improvements. For entrepreneurs, finished is an F-word. They know that great companies are always evolving.

Finished ought to be an F-word for all of us. We are all works in progress. Each day presents an opportunity to learn more, do more, be more, grow more in our lives and careers. Keeping your career in permanent beta forces you to acknowledge that you have bugs, that there’s new development to do on yourself, that you will need to adapt and evolve. But it’s still a mind-set brimming with optimism because it celebrates the fact that you have the power to improve yourself and, as important, improve the world around you.

Andy Hargadon, head of the entrepreneurship center at the University of California–Davis, says that for many people “twenty years of experience” is really one year of experience repeated twenty times. If you’re in permanent beta in your career, twenty years of experience actually is twenty years of experience because each year will be marked by new, enriching challenges and opportunities. Permanent beta is essentially a lifelong commitment to continuous personal growth.

Get busy livin’, or get busy dyin’. If you’re not growing, you’re contracting. If you’re not moving forward, you’re moving backward.

Develop a Competitive Advantage

If you want to chart a course that differentiates you from other professionals in the marketplace, the first step is being able to complete the sentence, “A company hires me over other professionals because …” How are you first, only, faster, better, or cheaper than other people who want to do what you’re doing in the world? What are you offering that’s hard to come by? What are you offering that’s both rare and valuable?

If you try to be the best at everything and better than everyone (that is, if you believe success means ascending one global, mega leaderboard), you’ll be the best at nothing and better than no one. Instead, compete in local contests—local not just in terms of geography but also in terms of industry segment and skill set. In other words, don’t try to be the greatest marketing executive in the world; try to be the greatest marketing executive of small-to-midsize companies that compete in the health-care industry.

Competitive advantage underpins all career strategy. It helps answer the classic question, “What should I be doing with my life?” It helps you decide which opportunities to pursue. It guides you in how you should be investing in yourself. Because all of these things change, assessing and evaluating your competitive advantage is a lifelong process, not something you do once.

Your competitive advantage is formed by the interplay of three different, ever-changing forces: your assets, your aspirations/values, and the market realities, i.e., the supply and demand for what you offer the marketplace relative to the competition.

Assets

Assets are what you have right now. Before dreaming about the future or making plans, you need to articulate what you already have going for you—as entrepreneurs do. The most brilliant business idea is often the one that builds on the founders’ existing assets in the most brilliant way.

You have two types of career assets to keep track of: soft and hard. Soft assets are things you can’t trade directly for money. They’re the intangible contributors to career success: the knowledge and information in your brain; professional connections and the trust you’ve built up with them; skills you’ve mastered; your reputation and personal brand; your strengths (things that come easily to you).

Hard assets are what you’d typically list on a balance sheet: the cash in your wallet; the stocks you own; physical possessions like your desk and laptop. These matter because when you have an economic cushion, you can more aggressively make moves that entail downside financial risk.

Dominating a professional project at work has little to do with how much dough you’ve socked away in a savings account; what matters are skills, connections, experiences. People list impressive-sounding-yet-vague statements like “I have two years of experience working at a marketing firm …” instead of specifying, explicitly and clearly, what they are able to do because of those two years of experience. Often it’s when you come in contact with challenges other people find hard but you find easy that you know you’re in possession of a valuable soft asset.

A competitive edge emerges when you combine different skills, experiences, and connections.

Your asset mix is not fixed. You can strengthen it by investing in yourself. So if you think you lack certain assets that would make you more competitive, don’t use it as an excuse. Start developing them. In the meantime, see how you can turn a weakness into a strength. For example, you may not see inexperience as an asset to highlight, but the flip side of inexperience tends to be energy, enthusiasm, and a willingness to work and hustle in order to learn.

Your Aspirations and Values

Aspirations and values are the second consideration. Aspirations include your deepest wishes, ideas, goals, and vision of the future, regardless of the state of the external world or your existing asset mix. This piece of the puzzle includes your core values, or what’s important to you in life, be it knowledge, autonomy, money, integrity, power, and so on.

Aspirations and values are both important pieces of your career competitive advantage quite simply because when you’re doing work you care about, you are able to work harder and better. The person passionate about what he or she is doing will outwork and outlast the guy motivated solely by making money.

Contrary to what many bestselling authors and motivational gurus would have you believe, there is not a “true self” deep within that you can uncover via introspection and that will point you in the right direction. Yes, your aspirations shape what you do. But your aspirations are themselves shaped by your actions and experiences. You remake yourself as you grow and as the world changes. Your identity doesn’t get found. It emerges.

Accept the uncertainty, especially early on. Later in your career, you may have more specific, thought-out aspirations. Whatever your values and aspirations, know that they will evolve over time.

The Market Realities

The realities of the world you live in is the final piece of the puzzle. Your skills, experiences, and other soft assets—no matter how special you think they are—won’t give you an edge unless they meet the needs of a paying market.

Keep in mind that the “market” is not an abstract thing. It consists of the people who make decisions that affect you and whose needs you must serve: your boss, your coworkers, your clients, your direct reports, and others. How badly do they need what you have to offer, and if they need it, do you offer value that’s better than the competition?

VC and friend Marc Andreessen likes to say: Markets that don’t exist don’t care how smart you are. Similarly, it doesn’t matter how hard you’ve worked or how passionate you are about an aspiration: If someone won’t pay you for your services in the career marketplace, it’s going to be a very hard slog. You aren’t entitled to anything.

Studying the market realities doesn’t have to be a limiting, negative exercise. There are always industries, places, people, and companies with momentum. Put yourself in a position to ride these waves. Being in a position to ride them—making the market realities work for you as opposed to against you—is key to achieving breakout professional success.

Pick a Hill That Has Less Competition

The most obvious way to improve your competitive advantage is to strengthen and diversify your asset mix—for example, learn new skills. That’s certainly smart. But it’s equally effective to place yourself in a market niche where your existing assets shine brighter than the competition’s.

What Successful Entrepreneurs Do

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.

ABZ 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.

Plan Z is the fallback position: your lifeboat. 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.

Making Plans Based on Your Copetitive Advantage

Career plans should leverage your assets, set you in the direction of your aspirations, and account for the market realities. The problem is these three puzzle pieces are always changing. The best you can do is articulate educated hypotheses about each. “I believe I am skilledat X, I believe I want to do Y, I believe the market needs Z.” 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.

Prioritize Learning

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?”

Learn by Doing

For careers you don’t know what the best plan is until you try.

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.

Think Two Steps Ahead

A goal that can be achieved in a single step is probably not very meaningful—or ambitious.

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.

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. 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.

Pivoting

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. Once you’ve pivoted and are on a new track, that becomes your new Plan A.

When to Pivot

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. And of course expect both good luck and bad luck along the way that will open and close unexpected windows of opportunity.

Of course, given the volatility of today’s career landscape, the decision to pivot often isn’t voluntary.

Andy Grove, the Intel cofounder, refers to these kinds of events as inflection points. 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.” 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.

Starting on the Side

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.

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.

Plan Z

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.

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.

Building a Team

Very few start-ups are started by only one person. Everyone in the entrepreneurial community agrees that assembling a talented team is as important as it gets.

The strength of the cofounders and early employees reflects the individual strength of the CEO; that’s why investors don’t evaluate the CEO in isolation from his or her team. Vinod Khosla, cofounder of Sun Microsystems and a Silicon Valley investor, says, “The team you build is the company you build.”

Networking

Just as entrepreneurs are always recruiting and building a team of stunning people, you want to always be investing in your professional network to grow the start-up that is your career. Quite simply, if you want to accelerate your career, you need the help and support of others.

Relationships matter to your career no matter the organization or level of seniority because every job boils down to interacting with people.

People are the source of key resources, opportunities, information, and the like.

People also act as gatekeepers. Jeffrey Pfeffer, professor of organizational behavior at Stanford, has marshaled evidence that shows that when it comes to getting promoted in your job, strong relationships and being on good terms with your boss can matter more than competence.

Finally, relationships matter because the people you spend time with shape who you are and who you become. Behavior and beliefs are contagious: you easily “catch” the emotional state of your friends, imitate their actions, and absorb their values as your own. If your friends are the types of people who get stuff done, chances are you’ll be that way, too. The fastest way to change yourself is to hang out with people who are already the way you want to be.

I^We (I to the We): You and Your Team

“I” vs. “We” is a false choice. It’s both. Your career success depends on both your individual capabilities and your network’s ability to magnify them. Think of it as I^We. An individual’s power is raised exponentially with the help of a team (a network). But just as zero to the one hundredth power is still zero, there’s no team without the individual.

Building Genuine Relationships

True relationship building in the professional world is like dating. When you’re deciding whether or not to build a professional relationship with someone, there are many considerations: whether you like him or her; the capacity for the person to help you build your assets, reach your aspirations, and position you well competitively, and for you to help back in all the same ways; whether the person is adaptable and could help you adapt your career plan as necessary. And, like with dating, you should always have a long-term perspective.

Building a genuine relationship with another person depends on (at least) two things. The first is seeing the world from the other person’s perspective.

The second requirement is thinking about how you can help and collaborate with the other person rather than thinking about what you can get from him or her. We’re not suggesting you be so saintly that a self-interested thought never crosses your mind. What we’re saying is you should let go of those easy thoughts and think about how you can help first. (And only later think about what help you can ask for in return.) A study on negotiation found that a key difference between skilled negotiators and average negotiators was the time spent searching for shared interests, asking questions of the other person, and forging common ground. The effective negotiators spent more time doing these things—thinking about ways the other person would truly benefit as opposed to just trying to drive a hard bargain out of pure self-interest. Do the same. Start with a friendly gesture toward the other person and genuinely mean it.

In a sentence, as you meet your friends and new people, shift from asking yourself the very natural question of “What’s in it for me?” and ask instead, “What’s in it for us?” All follows from that.

The Structure and Strength of Your Existing Network

If you want to build a strong network that will help you move ahead in your career, it’s vital to first take stock of the connections you already have.

Each type of relationship is different. We’re going to focus on two types of relationships that matter in a professional context.

The first is professional allies. Who would be in your corner in a conflict or when you come under stress? Whom do you invite to dinner to brainstorm career options? Whom do you trust and proactively try to work with if you can? From whom do you solicit feedback on key projects? Whom do you review life goals and plans with? These are your allies. Many people can maintain at most eight to ten strong professional alliances at any given point in time.

The second type of relationship we’ll cover is weaker ties and acquaintances. With whom are you friendly but not full-on friends? With whom do you email occasionally? Of whom can you ask a lightweight professional favor? Can you recall a conversation with this person from a couple years ago? There’s quite a bit of variance in how many of these weak ties you can maintain; you may be able to maintain a maximum of a couple hundred or a couple thousand depending on your personality, your line of work, and the nature of your relationships.

Professional Allies

What are the general characteristics that make their relationship an alliance and that define your own? First, an ally is someone you consult regularly for advice. You trust his or her judgment. Second, you proactively share and collaborate on opportunities together. You keep your antennae especially attuned to an ally’s interests, and when it makes sense to pursue something jointly, you do so. Third, you talk up an ally to other friends. You promote his or her brand. When an ally comes into conflict, you defend him, and stand up for his reputation. And he does the same for you when times get tough. There’s no such thing as a fair-weather alliance; if the relationship isn’t load-bearing under stress, it’s not an alliance. Finally, you are explicit about your bond: “Hey, we’re allies, right? How can we best help each other?”

Weak Ties and Acquaintances

Allies, by the nature of the bond, are few in number. There are many more looser connections and acquaintances who also play a role in your professional life. These are folks you meet at conferences, old classmates, coworkers in other divisions, or just interesting people with interesting ideas who you come upon in day-to-day life. Sociologists refer to these contacts as “weak ties”: people with whom you have spent low amounts of low-intensity time (for example, someone you might only see once or twice a year at a conference, or only know online and not in person) but with whom you’re still friendly.

Because people tend to hang out in cliques, your good friends are usually from the same industry, neighborhood, religious group, and the like. The stronger your tie with someone, the more likely they are to mirror you in various ways, and the more likely you are to want to introduce them to your other friends.

Weak ties can uniquely serve as bridges to other worlds and thus can pass on information or opportunities you have not heard about. We would stress that it’s not that weak ties per se find you jobs; it’s that weak ties are likely to be exposed to information or job listings you haven’t seen. Weak ties in and of themselves are not especially valuable; what is valuable is the breadth and reach of your network.

Weak ties are indeed important, but they are only valuable so long as they offer new information and opportunities. Weak ties are one way to achieve a wideeaching network, but any relationship that bridges you to another world will do.

Whichever way you introduce diversity and breadth, it’s especially important during career transitions. When you pivot to Plan B or Plan Z, you’ll want information about new opportunities. You’ll also want to know people in different niches or fields who will encourage your move.

Your Extended Social Network: Second- and Third-Degree Connections

Your allies, weak ties, and the other people you know right now are your first-degree connections. There are limits to the number of first-degree connections you can have at any one time. But your friends know people you don’t know. These friends of friends are your second-degree connections. And those friends of friends have friends of their own—those friends of friends of friends are your third-degree connections.

How do you actually reach that second- or third-degree connection? The best (and sometimes only) way: via an introduction from someone you know who in turn knows the person you want to reach. When you reach out to someone via an introduction from a mutual friend, it’s like having a passport at the border—you can walk right through. The interaction is immediately endowed with trust.

Anytime you want to meet a new person in your extended network, ask for an introduction. People know they should do this, but most don’t. It’s easier to cold-call. It can be awkward to ask a favor of a friend. Indeed, just because you know someone doesn’t mean they have to introduce you to one of their friends. But you do have to ask—directly and specifically—and you need to present a compelling reason why the introduction makes sense. When you reach out to someone, be clear about how you intend to help the person to whom you’re being introduced—or at least how you’ll ensure it’s not a waste of that person’s time.

If you spend thirty minutes researching a person in your extended network (LinkedIn is a great place to start), and tailor your request for an introduction to something you’ve learned, your request will stand out.

You can conceptualize and map your network all you want, but if you can’t effectively request and broker introductions, it adds up to a lot of nothing. Take it seriously. If you are not receiving or making at least one introduction a month, you are probably not fully engaging your extended professional network.

The Best Professional Network

The best professional network is both narrow/deep (strong connections) and wide/shallow (bridge ties).

Only strong connections provide depth, of course, which is why these more intimate alliances are the most important kind of bond. But they can also be helpful for breadth in ways weak ties cannot. Your stronger connections are more likely to happily introduce you to new people—to your second- and third-degree connections. Weak connections, while valuable sources of new information, will not usually introduce you to other people unless they have a compelling transactional reason (i.e., unless it benefits them in some way). Which is why you should relish opportunities to build trust connections with folks in different fields or social circles. When you hit it off with someone who is meaningfully different from you, know that the relationship has the potential to be both genuinely enriching as well as a way to expand the breadth of information and creativity that flows through your network.

How to Strengthen and Mantain a Network

The best way to strengthen a relationship is to jump-start the long-term process of give-and-take. Do something for another person. Help him or her.

Helping someone out means acknowledging that you are capable of helping. Reject the misconception that if you’re less powerful, less wealthy, or less experienced, you have nothing to offer someone else. Everyone is capable of offering helpful support or constructive feedback. To be sure, you’ll be most helpful if you have the skills and experiences to help your allies.

Next, figure out what kind of help is helpful. To give helpful help you need to have a sense of your friend’s values and priorities so that your offer of help can be relevant and specific. What keeps him up at 2 a.m.? What are his talents? His interests? Asking “How can I help you?!” immediately after meeting someone is overeager. First you must know the person.

Finally, once you understand his needs, challenges, and desires, think about how you can offer him a small gift. We don’t mean an Amazon.com gift card or a box of cigars. We mean something—even something intangible—that costs you almost nothing yet still is valuable to the other person. Classic small gifts include relevant information and articles, introductions, and advice. A really expensive big gift is actually counterproductive—it can feel like a bribe. Inexpensive yet thoughtful is best.

When deciding what kind of gift to give, think about your unique experiences and skills. What might you have that the other person does not? What specific things do you know or have that the other person does not? The secret behind stellar small gifts is that it’s something you can uniquely provide.

Finally, if the best way to strengthen a relationship is to help the other person, the second best way is to let yourself be helped.

Being a Bridge

A good way to help people is to introduce them to people and experiences they wouldn’t otherwise be able to access. In other words, straddle different communities/social circles and then be the bridge that your friends can walk over. Can you develop skill sets, interests, and experiences in two or more domains and then act as a bridge for your connections in one circle who want to access the other? If so, you will be enormously helpful.

Dealing with Powerful People

If you want to maintain relationships with busy, powerful people, you have to pay special attention to the role of status. Status refers to a person’s power, prestige, and rank within a given social setting at a given moment in time. There is no one pecking order in life; status is relative and dynamic.

The business world is rife with power jostling, gamesmanship, and status signaling, like it or not. It’s especially important to understand these dynamics when you work with people more powerful than you.

Remember, even if you aren’t trying to signal you are more powerful, an inadvertent power move is still a power move, and it can irritate decision makers you’d rather impress.

The conclusion is not to suck up to people of higher status. Slavishly affirming everything an important person says is unimpressive, to say nothing of dishonest. Nor is the answer to disrespect people of lower status or to flaunt superiority. Presenting yourself as a Big Deal repels people below you, who won’t feel inspired or loyal. It also repels people above you, who will interpret your braggadocio as insecurity. Rather, the point is that some people require a bit more finesse. If you want to build a relationship with someone of higher status, know that you are supposed to be accommodating.

Curiosity and Opprotunities

There’s one disposition and mind-set that must be “on” like electricity to power all the other opportunity-seeking behaviors: curiosity. Entrepreneurs brim with curiosity: they see opportunity where others see problems, because while others simply complain, entrepreneurs ask Why? Why the heck doesn’t this annoying product/service work as well as it should? Is there a better way? And can I make money off it? You could even say that entrepreneurship begins in frustrated wonderment! For entrepreneurs this mix translates into supreme alertness for new business opportunities. For you in your career, curiosity (with or without frustration) about industries, people, and jobs will make you alert to professional opportunities. It’s hard to learn curiosity. But it’s something you can get infected with by hanging out with passionately curious people. And once you catch curiosity, it’s (luckily) hard to shake.

Even if you don’t have an immediate reason to actively look for an explicit opportunity—even if, say, you’re happily employed and stimulated—it’s important to keep generating professional opportunities anyway. Partly this builds opportunity muscle memory: the more you try, the more you strengthen your intuitive sense of how, where, and why opportunities enter your career. Partly it’s because you never know when you’ll have to pivot to Plan B and go after a new opportunity.

How to Find and Generate Career Opportunities

Court Serendipity and Good Randomness

The key is to raise the likelihood that you stumble upon something valuable—namely, by courting good randomness and seeing the opportunities that reveal themselves.

Serendipity is the delightful word we use to describe accidental good fortune. Serendipity involves being alert to potential opportunity and acting on it.

Even if you are curious and alert, opportunities won’t just fall into your lap. Almost every case of serendipity and opportunity involves someone doing something.

You won’t encounter accidental good fortune—you won’t stumble upon opportunities that rocket your career forward—if you’re lying in bed. When you do something, you stir the pot and introduce the possibility that seemingly random ideas, people, and places will collide and form new combinations and opportunities. By being in motion, you are spinning a web as wide and as tall as possible in order to catch any interesting opportunities that come your way.

If the goal is to court good randomness, you don’t want to be too directed in your motion, either. Most of the time you simply do not know when, where, and how opportunity will knock. At which conference will you fortuitously bump into the friend of your mother who’s hiring in his medical office this summer? Which producer in Hollywood will return your nth voicemail and request a copy of your screenplay? Might a big-name reporter start following you on Twitter and start calling you for quotes? There’s no way of knowing for sure. So be open-minded, but set smart parameters. You can go to a conference and approach random people; but better yet, you can go to a conference, identify someone you know is interesting, and approach the people you see that interesting person talking to. You’re courting randomness, but you’re also being strategic.

Connect to Human Networks: Groups and Associations of People

Opportunities do not float like clouds. They are firmly attached to individuals. If you’re looking for an opportunity, you’re really looking for people. If you’re evaluating an opportunity, you’re really evaluating people. If you’re trying to marshal resources to go after an opportunity, you’re really trying to enlist the support and involvement of other people. A company doesn’t offer you a job, people do.

If you want to increase your opportunity flow, join and participate in as many of these groups and associations as possible.

Finally, the only thing better than joining groups is starting your own. Start your own mafia—your own group, meetup, or association.

Be Resilient

If you want to find out how resourceful you can be, shrink your budget. Move your deadlines up. See how you cope. This may make you more resilient to actual hardships that inevitably arise.

How to Land Breakout Opportunities

Breakout opportunities come and go—if you don’t seize them, you lose them.

The lesson is that great opportunities almost never fit your schedule. It would be nice if you came upon that killer job opportunity right when you were thinking about leaving your current job. It would be nice if that exclusive conference coincided with the week your boss happens to be away. Usually, the timing is imperfect and difficult. Most often, you’ll be in the middle of a different plan—like about to set off on an around-the-world trip.

Frequently, it won’t be completely clear that it’s better than another opportunity. You may be tempted to “keep your options open” and continue to mull things over, as opposed to committing to the breakout you think you’ve identified or generated. That would be a mistake. “Keeping your options open” is frequently more of a risk than committing to a plan of action.

To move forward in your career, you have to commit to specific opportunities as part of an iterative plan, despite doubt and despite inconvenience.

Assesing and Managing Risks

Assessing risk, while always difficult, is not impossible. Entrepreneurs do it every day. But they don’t use fancy risk-analysis models like those found on Wall Street. And neither should you. There’s no mathematical formula that could possibly capture the probabilities and range of outcomes of a dynamic start-up, let alone the dynamic start-up that is your career. It’s impossible to quantify the pros and cons of every opportunity. You will have time constraints. You will have information constraints. Moreover, your intuition is riddled with cognitive biases that get in the way of rational assessment. So here are a few principles to keep in mind to help you evaluate how risky an opportunity really is, and how you manage the risk that does exist.

Overall, it’s probably not as risky as you think.

Sticks get our attention a lot faster than carrots do. Psychologists call this negativity bias, and it pops up all the time in day-to-day life. One stern warning to avoid working with a person makes a stronger impression than one glowing recommendation. Anxiety about how your boss will react to an unconventional proposal will overpower feelings of optimism that he’ll be impressed by your work.

To lead a big and vigorous life, you must work to overcome this negativity bias. The first step is to remind yourself that the downside of a given situation is probably not as bad, or as likely, as it seems.

Is the worst-case scenario tolerable or intolerable?

The first thing you want to ask of a possible opportunity is, If the worst-case scenario happens, would I still be in the game? If the worst-case scenario is the serious tarnishing of your reputation, or loss of all your economic assets, or something otherwise career-ending, don’t accept that risk. If the worst-case scenario is getting fired, losing a little bit of time or money, or experiencing discomfort, as long as you have a solid and reliable Plan Z in place, you will still be in the game, and should be open to taking on that risk.

Can you change or reverse the decision midway through? Is Plan B doable?

When assessing a risk, if you realize you made a mistake, could you reverse your decision easily? Could you get to a Plan B or Plan Z relatively quickly? If the answer is no, the opportunity is riskier and should be approached more cautiously.

You’ll never be fully certain. Don’t conflate uncertainty with risk.

There will always be uncertainty about career opportunities and risks. Uncertainty is an ingredient of risk. And the more compelling and complex the opportunity, the more uncertainty tends to surround it. In all situations, you simply cannot know everything about all possible pros and cons. While you don’t want to make career moves on 0 percent information, you also don’t want to wait till you have 100 percent information—or else you’ll wait forever. Uncertainty makes people uncomfortable. But uncertainty does not automatically mean something is risky. When it’s not clear how something will play out, many people avoid it altogether. But the biggest and best opportunities frequently are the ones with the most question marks. Don’t let uncertainty lull you into overestimating the risk.

Consider age and stage. What will the risks be to you in a few years?

Age and career stage affect your level of risk. Generally, the downside consequence of failure is lower the younger you are. If you make mistakes in your twenties and thirties, you have plenty of time to recover both financially and reputationally. You have parents and family to fall back on. You are less likely to have kids or a mortgage. This is a main reason many young people start companies, travel around the world, and do other relatively “highisk” career moves: the downside is lower. If something worthwhile will be riskier in five years than it is now, be more aggressive about taking it on now. As you age and build more assets, your risk tolerance shifts.

Short-Term Risk Increases Long-Term Stability

The way to intelligently manage risk is to make yourself resilient to these shocks by pursuing those opportunities with some volatility baked in. In the short run, low volatility means stability. In the long run, though, low volatility leads to increased vulnerability, because it renders the system less resilient to unthinkable external shocks.

This paradox—high short-term risk leading to low long-term risk—holds true for careers as well.

Without frequent, contained risk taking, you are setting yourself up for a major dislocation at some point in the future. Inoculating yourself to big risks is like inoculating yourself against the flu virus. By injecting a small bit of flu into your body in the form of a vaccination, you make a big flu outbreak survivable. By introducing regular volatility into your career, you make surprise survivable. You gain the “ability to absorb shocks gracefully.

Some job paths automatically provide regular volatility (e.g., entrepreneurship or freelancing). In other jobs you’ll have to introduce shocks and disruptions manually.

Pretending you can avoid risk causes you to miss opportunities that can change your life. It also lulls you into a dangerously fragile life pattern, leaving you exposed to a huge blow-up in the future. What’s more, you can never perfectly anticipate when inflection points or any other career-threatening event will occur. When you’re resilient, you can play for big opportunities with less worry about the possible consequences of unanticipated hiccups. For the start-up of you, the only long-term answer to risk is resilience.

Remember: If you don’t find risk, risk will find you.

Navigate Professional Challenges with Network Intelligence

Entrepreneurs navigate the day-to-day issues of running a company by gathering intelligence: actionable, timely information on all facets of their business, including industry trends, opportunities, competitors’ activities, customer sentiment, promising young talent, and sales trends. In a business, intelligence serves as a GPS device.

How desirable are my skills in the changing market? How do I know when I should pivot into a new industry niche? What are the best job opportunities and how do I exploit them? These are not easy questions. They’re certainly not questions you can answer by merely reflecting for a few minutes or filling out a worksheet. You, too, need business intelligence to navigate these challenges.

You get it by talking to people in your network. It’s people who help you understand your assets, aspirations, and the market realities; it’s people who help you vet and get introduced to possible allies and trust connections; it’s people who help you track the risk attached to a given opportunity. I^We is the formula for gathering the kind of information that will help you navigate professional challenges.

What you get when you tap in to other people’s brains is called network intelligence. There’s plenty of good information to be found in books and magazines and search engines. Yet your network is frequently a better—and sometimes the only—fount of pivotal intelligence. A book can’t tell you what skills you need to excel in a certain market niche. A magazine can’t help you weigh the risks of moving halfway around the world for a job. A search engine can’t introduce you to the networks that dish breakout opportunities. But, your network can.

Your network is an indispensable source of intelligence because people offer private observations and impressions that would never appear in a public place like the Wall Street Journal or even your company newsletter.

Second, people offer personalized, contextualized advice. Friends and acquaintances know your interests and can tailor their information and advice accordingly.

Third, people can filter information you get from other sources. People can tell you which books to read; which parts of the article are important; which search results to ignore; which people to trust or not trust. People help focus your attention on the intelligence that’s actionable and relevant. In an age of information overload, this is an incredibly valuable benefit.

Finally, many people simply think better thoughts when in dialogue with others.

How to Pull Intelligence from Your Network

There are two basic ways to tap information from your network: (1) ask targeted questions to specific individuals in your network (as when Iris called her friend in the record business, and later her father), and/or (2) cast the net more widely by querying a broad swath of your network all at once (as she did when she sent a mass email to her writer and publishing friends).

Target Direct Questions to Specific Individuals

We all have certain people we call upon for advice or information on certain topics or issues, but not everyone knows who in their network to go to for intelligence on various careerelated decisions.

One way to start thinking about this is to sort the people you know into three (at times overlapping) categories:

  1. Domain experts. These are the pros, the people who really know the topic at hand. Got a question about negotiating your salary? Ask your lawyer friend who has negotiated a million contracts.
  2. People who know you well. Your mother. Your childhood friend. These are the people who may not be up on the latest industry happenings, but they have a good sense of your priorities, personality, and personal history. They can help you unpack feelings of confusion and sometimes even intuit how you’ll likely feel about various outcomes of your decision.
  3. Just really smart people. These people may not be domain experts in the specific topic area and may not know you well. But occasionally sheer analytical horsepower can be useful. At the least, whatever a really smart outsider says stands a chance of being completely different from anything else you’ll hear.

As a general rule, when you want information from your network, when facing a decision, begin by asking domain experts, then talk to people with whom you have strong personal relationships. If you’re still not satisfied, or want yet another perspective, then turn to really smart outsiders.

If you maintain a network that’s both broad and deep, you’ll have plenty of both types to talk to. Remember that breadth introduces acquaintances who hail from different industries, demographics, backgrounds, political orientations, and the like. Amid all that diversity (including second- or third-degree connections) there are bound to be experts in many different domains. With depth, you maintain a set of close relationships with people who know you well.

Online social networks facilitate this by keeping you up-to-date on whom you know and what they know, which allows you to target certain connections more efficiently.

Ask Good Questions

Asking a lot of good questions is the secret to network intelligence, too. It may sound obvious, but if you don’t actually pose your inquiries in ways that generate useful answers, nothing else matters.

Here are some tips for asking better questions:

  • Converse, don’t interrogate. When talking with allies and peers, offer thoughts of your own as a way of encouraging a real conversation. Give some intelligence to the other person and it will nudge them to reciprocate. So even though you want as much helpful information as possible, don’t be a reporter and treat your peers as interviewees. Have an even, true exchange; in the long run, richer information will be exchanged.
  • Adjust the lens. When you’re trying to make a decision, ask wide questions to figure out the criteria you should be using; ask narrow questions to figure out which weight you should give to each. For example, ask primarily domain experts, “What should I be thinking about when assessing the pros and cons of this opportunity?”. Then, once you’ve narrowed down your criteria, ask a more select group (including people you know well) for specific information about factors X and Y.
  • Frame and prime. To get the highest-quality intelligence you’ll want to frame the same question in multiple ways. Ask someone, “What are the top three things you did right when you worked at the company I’m about to join?” Then ask the same person, “What three things did you not get to do at the company and wish you did?” Another way to prime the answerer is to throw out a few sample answers to give a sense of the type of answer you’re looking for. By offering up the kind of answer that’s helpful, you invite an answer of a similar level of specificity.
  • Follow up and probe. It’s rare you’ll get a person’s best intelligence with a single question. Follow up and probe on qualifying words. Dig until a deeper answer takes shape. Some people hesitate to ask too many questions because they fear it will make them look ignorant. It won’t. It’ll make you look like a curious, intelligent person hungering for valuable information.

Occasion Serendipity

Serendipity comes about when you’re in motion, when you’re doing stuff. Serendipitous network intelligence turns up in similar ways—when you’re engaging people. If you’re in touch and top of mind, someone may forward an email with information that’s relevant just because they’re thinking of you.

Just as there are things you can do to court serendipity, there are ways to court serendipitous intelligence. Keep a few general questions in your back pocket to ask people in these kinds of situations or settings. A back-pocket question could be as broad as “What’s the most interesting thing you’ve learned over the past few months?”, or as targeted as “Have you come across any awesome entrepreneurs or start-ups that I should invest in?

Finally, pushing interesting information out to your network increases your chances of serendipitous intelligence. Post an article, email a quote, forward along a job offer, and in other ways share small gifts to your network. Your friends will appreciate it, and you will increase the chances that those same people respond in kind and send you intelligence later on.

Removing Bias from Your Network

Once you have gathered information, the next step is to analyze the validity, helpfulness, and relevance of what each person has said. Remember that everyone has biases—even your parents or best friend. It’s not that they are trying to manipulate you. It’s just the nature of being a human with personal experiences and self-interests. Bias can be obvious or nonobvious, conscious or subconscious. As you pull information and advice from various sources, think about how the person’s personal goals, ambitions, and experience might have colored their position. Bias is not reason to dismiss information or advice altogether; just account for it in your analysis.

Synthesis is the important final step. If you don’t step back and take in the big picture of all you’ve learned, it will feel like you’re worming your way through a cocktail party hearing bits and pieces of several different conversations but not able to make out anything of substance. Synthesizing what you learn involves reconciling contradictory advice and information (which is inevitable if you’re pulling multiple streams from diverse people), ignoring information you believe is completely off base, and weighing each person’s information differently. This is a complex cognitive process.