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Antifragile: Author Nassim Taleb’s term for organisms that do not simply withstand change and survive it; they become better because of it.

Asymmetric Upside: In Antifragile, author Nassim Taleb talks about the principle of “optionality,” opportunities that provide much more to potentially gain than lose. As Taleb describes it, “Optionality is the property of asymmetric upside (preferably unlimited) with correspondingly limited downside (preferably tiny).” What does this mean in layman’s pivot terms? Look for career pilots that have high potential upside with limited downside. Taking out a second mortgage on your home to pursue a business idea is a very risky endeavor: it may expose you to a great deal of debt, high interest rates, or bankruptcy if your idea does not succeed. On the other hand, taking a small chunk of your savings to pilot a prototype offering—to see if there is interest and if you enjoy it—does not expose you to risk in such a vulnerable way.



Bartering: If you are short on cash, or even if not, and you have a unique skill to trade for another expert’s services, bartering can be a way to get professional help while keeping expenses down. In a study of 1,000 freelancers, 83 percent said they refer work to fellow freelancers, 52 percent team up on projects, and 37 percent trade services by bartering. Bartering agreements work best when there is a clear start and end date or deliverable on both sides.

Board of Advisors: As one-off mentoring relationships progress, you will develop deeper relationships with a handful of people that you can consult regularly and exchange ideas and feedback with, ideally to benefit them as well. In doing so, they can become members of your board of advisors. This is your brain trust, your mentor clan, your strategic “been-there-done-that” crew who offers lessons from their triumphs and missteps. Think of people you admire: perhaps you have no contact with them, but their actions and career approaches still serve as guiding lights.

Boiling Frog: Many of us do not fully appreciate the magnitude of the change even though we are completely immersed in it.

Bridge Income: The term bridge loan refers to short-term commercial real estate financing. A bridge loan is meant to be paid back quickly, bridging the timing gap while investors implement their plan to improve a property’s performance before securing a long-term loan. Bridge income tides you over while making a change, but is not your desired primary long-term solution.

Burn Rate: In Silicon Valley parlance, burn rate is defined as the rate at which an enterprise spends money, especially venture capital, in excess of income. In Pivot terms, are you being financially prudent or spending like the Wolf of Wall Street? The higher your burn rate, the faster your runway will disappear.



Calfee: an amalgam of call and coffee, for connecting with potential friendtors and mentors

Career Conversations, Career Coaching: Career conversations are separate from performance reviews and focus on an individuals’ strengths, goals and growth-opportunities within and outside of the organization. These are expansive and exploratory (not advice-based or prescriptive unless that’s what the person is asking for), and allow individuals to identify stretchy-but-exciting next moves. Career conversations are best when held on a regular basis; ideally at least every six months.

Career in the Age of the App: Careers are no longer straightforward, linear, and predictable like a ladder. They are now much more modular, customizable, and dynamic, like smartphones. Our education and our upbringing are the out-of-the-box model. After that, it is up to us to download the apps—for skills, interests, experiences and education—that we want and need to feel fulfilled.

Career Karma: The idea that when we give freely, we reinforce the idea that plenty is on the way back. Plant enough seeds of generosity, without expectation, and it comes back tenfold, often in ways you will not see coming.

Career Operating Modes: How are you currently showing up in your day-to-day work? Are you operating at your desired energy levels, creative output, and impact? There are four categories: inactive, reactive, proactive and innovative. The first two are impacter stressors, the latter two are sweet spots.

  • Inactive: Does not seek changes; paralyzed by fear, uncertainty, and self-doubt; covers up career or life dissatisfaction with unhealthy habits, such as numbing out with excessive amounts of food, alcohol, TV, video games, etc; feels and acts like a victim of their circumstances.

  • Reactive: Mimics others’ models for success without originality; follows instructions to the letter; waits for inspiration to strike; “phones it in” at work; feels unhappy but does not inquire into why or what to do about it; lets fear overrule planning for the future and subsequent action steps.

  • Proactive: Seeks new projects; actively learns new skills; open to change; improves existing programs; makes connections with others; takes ownership even within existing leadership structures; has a giver mentality, willing and interested in helping others. May not be fully using innate talents, but is exploring what they are and how to amplify them.

  • Innovative: In addition to proactive mode qualities, fully taps into their unique strengths; focuses on purpose-driven work and making meaningful contributions; is energized by a strong vision for new projects with a clear plan for making them happen; does not just improve existing structures, but creates new solutions to benefit others.

Career Pivot: doubling down on what is working to make a purposeful shift in a new, related direction. Pivoting, as we will refer to it in this book, is an intentional, methodical process for nimbly navigating career changes. By doubling-down on what is working best while thinking about how to develop into what’s next, you accelerate the experimentation and change process. A pivot is change you make of your own volition when you have reached a point in your career where you are ready for increased challenge and impact.

Career Portfolio: Your career portfolio is the aggregate of your strengths, prior work experience, and existing connections.

Career Roomba Syndrome: Roombas are the robotic vacuum cleaners that scan floors on their own, switching directions whenever they hit an obstacle. Brad Zomick defines Career Roomba Syndrome as, “An occupational affliction that is characterized by a string of different job roles, some related, some starkly different than the last. The afflicted lacks passion for these jobs, and each time they hit a dead-end at a job, they back up and redirect their career path, but more often than not, the new path is not determined by any clear strategy.”

Childhood Interests: Start honing in on your innate talents by looking at what activities you enjoyed as a kid; your career strengths have probably been expressing themselves in some way long before adulthood.

Combinatorial Play, or Hobbies: Albert Einstein would often discover innovative ideas during his violin breaks. This practice was so important to his process that he famously said, “Combinatory play seems to be the essential feature in productive thought.”

Continuous Pivot: Cycle through the first three stages—Plant, Scan, Pilot—as many times as necessary to feel secure when you launch. You can also work through the Pivot process any time you get stuck, not just during major moves, but also within businesses, side hustles, and smaller projects and goals. The Pivot Method will help you be a scientist in your life—a steady observer and experimenter—as you direct future changes gracefully, methodically, and with greater confidence, clarity and insight.



Decision-Fatigue: also referred to as ego-depletion, refers to the dwindling effectiveness of our decision-making abilities throughout the day without proper recharging

Difficult Conversations: There are five distinct parts to difficult launch-related conversations: Making the decision based on your gut instinct, figuring out how to express the difficult decision in words, clearly and directly, figuring out when to have the conversation, communicating the decision to the other/s involved, and responding to their reaction and any ensuing consequences or follow-up.

Diminishing Returns: Sometimes we obsess over these potential gains out of fear or emotional attachment to what feels safe. We clutch at security while ignoring the fact that, like the boiling frog, our surrounding environment is no longer hospitable. In economics, the law of diminishing returns asserts that past a certain point in production, adding more resources will no longer yield favorable results. In fact, every added effort or input yields increasingly lower returns.

Discoverable: Pairing up in the career sense works the same way. You will have an easier time navigating between career moves or clients if you are discoverable, which means putting your ideas out into the world through your own platform, or piggybacking on an existing one. Both require that you stand for something and commit to sharing your unique ideas and expertise.

Downing Effect, or Illusory Superiority: Some of the smartest, most self-aware people I know also report sometimes feeling the most unsure or insecure. This is the Downing Effect at work. The Downing Effect, also known as “illusory superiority,” says that the more intelligent someone is, the lower they rate themselves on the intelligence scale. The lower someone’s IQ, the higher they rate themselves. Ignorance truly is self-assessment bliss.

Drafting: If you have seen the Tour de France, you know about drafting: riders clumping behind the lead bike, not passing on purpose, so they can benefit from reduced headwind and effort. They are mimicking a technique used by many bird species. The lead biker or bird is doing the hardest work, while the others flock closely behind to reduce their drag and the energy needed to achieve the same speed. Career drafting can be a mutually beneficial technique, though it should not devolve into stalking, stealing, plagiarizing, or leeching. Think of someone farther along in their career, either in your industry or the one you may want to be in, who is doing what you are hoping to achieve, and ask if you can help with any overflow he or she does not have the time or desire to tackle.

  • Apprenticeship: working for potentially little compensation in exchange for total access and mentoring about how the lead runs their business or career.

  • Overflow: when the lead has incoming work demand that they cannot fulfill, if you are skilled in your trade but not yet generating the same flow of incoming interest, the lead can recommend you in their place.

Drop the Bucket: Imagine that there is a bucket in your brain where you place an unanswered question. If you “drop the bucket” into the well of your brain, like a wishing well, when it is ready it will rise with the answer; maybe in an hour, maybe when you are in the shower, or maybe a week or month later.



Expert: becoming an expert in your desired field—not just technically the best, but recognized and publicly known for it by generously sharing that expertise with others—will become your most powerful generator for new opportunities. Instead of feeling like you must constantly pound down doors to get hired, others will swing those doors open for you.



Fauxspiration: When you have a tornado of great ideas and good intentions swirling around in your mind, but are having a trouble translating them to the real world. You might be afflicted with fauxspiration if you get stuck in analysis-paralysis in the name of research or draft mode . . . which might just be the big bad wolves of procrastination; fear in sheep’s clothing. Combat this by identifying one small next action step you can take.

FONT: Impacters are not afflicted with FOMO: Fear of Missing Out. They have FONT: Fear of Not Trying. Jeff Bezos, founder of Amazon, shares similar sentiments, and applies what he calls a Regret Minimization Framework: imagining himself at 80 years old and making decisions to minimize regret.

Friendtors: friends who can also wear the mentor hat professionally by providing domain-specific advice. You may have friendtors in your local area already; if not, start seeking like-minded people in online communities or meetup groups focused on your interest areas. Your closest friendtors may also be part of your Board of Advisors, who you turn to when facing big decisions.



Give-Receive-Achieve: A framework for vision-setting. What do you want to give, or contribute? What do you want to receive and how do you want to feel? What do you want to be recognized for?

Grounded Theory: you first observe the “lived experience” and use that to make conclusions, which may or may not clash with existing theories. “It is all about resonance and fit—do the concepts that you are coming up with resonate with the studied population?” Brown explained. “Do people see themselves in the lives and stories that you are creating with your data?” According to Brown, trust and emergence are two of the most important axioms of Grounded Theory. “Trust in whatever emerges from the data, trust in people’s lived experiences, and their perceptions of those experiences,” she said.

Growth Mindset: Stanford University psychologist Carol Dweck, author of Mindset: The Psychology of Success, discovered in her research that the most successful people are those with a growth mindset. These are people who “believe that their most basic abilities can be developed through dedication and hard work,” rather than believing their gifts (or lack of them) are fixed traits



Happiness Formula: Your happiness formula is the unique mix of environmental factors and activities that are most likely to invigorate you and reset your energy batteries when they are running low. As you plan your pivot, think of your happiness formula on a micro-level—day-to-day routines and five to 20 minute habits—and on a macro-level of bigger choices like where to live and work.

Hotter/Colder: the guessing game many of us played as kids. You hide something and as the other person wanders around looking, you guide them by saying only “cold, colder, FREEZING,” or “hot, hotter, ON FIRE!” Your career moves speak to you in the same way.



Impacters: shorthand for individuals who optimize for high net growth and impact, not just high net worth. Impacters love learning, taking action, tackling new projects, and solving problems. They are generous and cooperative, and imbued with a strong desire to make a difference. Impacters aim first and foremost for a sense of momentum and expansion. They ask, “Am I learning?” When their inward desire for growth is being met, they turn their attention outward, seeking to make a positive impact on their families, companies, communities and global societies.

Income-Anxiety Seesaw: When it comes to money and pivoting, imagine a seesaw with anxiety on one end and income on the other. The Anxiety-Income Seesaw is a checkpoint to determine when you need to correct course.

Internal Mobility: Internal mobility within organizations reflects the ease with which employees can pivot internally; how visible are opportunities within the company? Are there open channels of communication when someone feels they have hit a plateau? When they do want to move teams, is there internal support for making the switch or are they bogged down by bureaucracy? Internal mobility can also include programs such as job shadowing, rotation programs, and working abroad.



Known vs. Unknown Variables: Knowns are your must-haves for your next pivot. Unknowns are elements you are still uncertain about in your one-year vision. Consider knowns and unknowns across categories such as location, finances, projects, success metrics, and lifestyle.



Launch: Launching involves a healthy dose of faith, smart risks, and adrenaline. Ultimately, you will know it is time to launch when you are ready to risk failure—and knowing that you had the courage to go for it—for the possibility of success, challenge, and personal growth. Or, as Joseph Campbell put it, for the “rapture of being alive.”

Launch Stage: Eventually it is time for a bigger move, or launch. The first three stages of the Pivot Method, repeated as many times as necessary, help reduce risk and give you a greater chance of success, often taking you 80 to 90 percent of the way toward your goal. Launch is where you pull the trigger on the remaining 10 to 20 percent. These are the bigger decisions that require commitment even in the face of remaining uncertainty.

Launch Timing Criteria: determining your launch timing criteria allows you to observe your pilots and detect when you are making true progress toward a bigger decision. You will have a clearer idea for your launch based on reaching certain thresholds, and when you need to adjust if your experiments are not going as planned. Common Launch decision-making criteria includes: financial benchmarks, date-based timing, progress milestones, gut instinct, and decisions that hinge on others.

Lean Pilot: one that does not cost a tremendous amount of time or money, but that you could run to determine if you enjoy this area, have the skills to succeed and differentiate yourself within it, and have the potential to earn income (or any other top priority value).

Leapfrog Approach: If you are still having trouble culling opportunities or clarifying a project-based purpose that is aligned with your vision, consider the Leapfrog Approach. Many people actually do have an idea of what they want two “moves” from now, even if they do not have a clear understanding of what they want in the moment. Imagine a frog hopping on lily pads. Oftentimes people can identify the lily pad that is two leaps away, they just can’t see the one right in front of them that should come next in order to reach their farther goal. The Leapfrog Approach will help you scan for opportunity two moves out, then work backward to find a transitional in-between pivot.

Levels of Learning: The four stages of learning one goes through when learning a new skill or undertaking a big goal. A fifth stage might be considered conscious mastery: you continue honing your craft and finding new ways to grow even once you have reached expert status.

  • Unconscious incompetence: You don’t know what you don’t know; ignorance is bliss. You are not yet aware of the skill or what is required to master it.

  • Conscious incompetence: The dip. As you start practicing, you become aware of how much you have to learn. You might feel incompetent, frustrated or discouraged as you realize you need more time or practice to excel.

  • Conscious competence: You have started to master the new skill, but you still have to actively think about whether you are doing it right. Similar to the first days after getting your driver’s license, you are capable, but vigilant attention is required.

  • Unconscious competence: You do not have to actively think about the skill any longer. Applying it comes naturally; as a result, meeting your objectives becomes attainable and enjoyable. Momentum builds.

Leverage: being able to parlay your reputation and platform into greater exposure, and therefore opportunities. Like the pole-vaulter who uses a pole to catapult over the high bar, your platform gives you leverage to find new and previously unseen opportunities.

Linear Thinking: Asking open-ended questions does not always come naturally. One common Pivot pitfall occurs when people skip the question-asking step altogether, instead selling themselves short with a laundry list of precursory qualifications. They wait too long for more training, more experience, or more certifications, instead of building from their current strengths. You know you are falling into this someday trap if you are putting linear conditions on a desired outcome, such as “When I earn $150,000 a year, then I can travel more,” or “If I get an MBA, then I can start my own business.” Some of us fall into perfectionistic thinking as a delay tactic:



Make-or-Break Marker: Plan your worst-case scenario from the outset. In what order are you going to cash out your assets? What is your Make-or-Break Marker to change strategy if things are not going as planned?

Marketable Skills: A marketable skill is a specific service you provide at the intersection of talents, strengths, and education, that a customer or company will pay you for.

Mastermind Groups: In addition to casual Friendtor relationships, I have also found great value in more formalized peer mastermind groups. For many years now, I have set recurring weekly or bi-weekly calls with one or two friends who are doing similar work or who share similar goals. These mastermind groups provide consistent accountability, encouragement, and brainstorm buddies

Mind Map: A freeform brainstorming exercise that involves writing a word or theme in the middle of a page, then drawing secondary spokes that connect to big themes, followed by tertiary spokes that elucidate each of those themes. Can be done for values, yearly planning, and project brainstorming.

MIPs: Author and professor Brené Brown’s strategy for dealing with naysayers and unproductive people-pleasing is identifying her five Most Important People. She suggests making a short list of those who really matter in your life, or as she puts it, “would help you move a body.” Brown says when you ruffle feathers or do something that invites haters, ask what the people on your MIP short list would say. If they are on board, you can lean on them for the courage to proceed.

Monthly Nut: How much do you need to earn each month to cover your basic expenses (minimum needed, nice-to-have, jump out of bed with glee). Business strategist Nick Reese calculates the ideal monthly nut a person needs to pay living expenses (and taxes, if self-employed) as 3.4 times their monthly rent or mortgage. For parents, or for people living in expensive cities, the multiplier is 5. For bootstrappers willing to live frugally or “lean,” the multiplier can be 2.5 x rent. To calculate your yearly nut, multiply your monthly rent by 41. If you have debt, such as a mortgage, Reese suggests multiplying your monthly rent or mortgage payment by at least 50.

MVP, or “Get Scrappy”: In The Lean Startup, Eric Ries popularized the concept of the MVP, or Minimum Viable Product. By his definition, the MVP “helps start the process of learning as quickly as possible. It is not necessarily the smallest product imaginable, though; it is simply the fastest way to get through the Build-Measure-Learn feedback loop with the minimal amount of effort.” During my time at Google we referred to this as “being scrappy.” We knew the conditions or output of our work would not be perfect, but it was important to release anyway, to “launch and iterate.” Just get something out, then test it, get feedback, revise, and do it over again. Holding a mindset of launch and iterate



Network Email: When you are clear on what opportunities you are most interested in, send a clear, focused email to your closest friends, family and trusted professional contacts with the following sections:

  • An introduction succinctly stating the pivot you hope to make: what you are doing now and where you want to go (one to two sentences max)

  • Your background: three to five brief bullet points on your strengths and experiences

  • The type of company or clients you are looking for—a few bullets on types of work, location, how you can make an impact

  • Call to action: how recipients can be most helpful. For example: forward the email, and keep their eyes and ears open as opportunities come up



One-Off Mentor: someone that you admire who has achieved something you aspire to, or who knows more about an area of interest than you. Allow one-off mentorships to evolve naturally if both parties are interested in developing the relationship further

180s: Avoid pivots that are too sharp—too far past your stretch zone—what I call 180s. These are dramatic leaps-of-faith that have little to do with your current role or skillset, which means there are too many unknowns that you would be gambling on when you launch. However, even what sometimes looks like a 180 from the outside might actually be, in execution, a pivot comprised of a series of smaller steps that paved the way for larger change.



Pilot: For our purposes, the primary goal of the Pilot phase is ignition and validation: generating ideas, testing those ideas, then taking small, smart risks to eventually inform bigger decisions about what’s next. When considering a pilot, aim for the following criteria: Tie experiments to the Plant stage: How many touch points does it have to your strengths, career portfolio, and one-year vision? Start small: How can you pilot in a low-cost way in terms of money, energy, and time? Tip the risk scales in your favor: What small experiments would have the most potential upside with limited downside?

Pilot Evaluation: The Three E’s: Enjoyment: Do I like doing it? Is it engaging? Am I excited to return to it?  Expertise: Am I good at it? If not, can I increase my skills in this area? Am I excited to do so? Is this a natural extension of my strengths? Expansion: Is there more market opportunity where that came from? Can I earn a living or find employment doing it?

Pilot Stage: small, low-risk experiments to dip a toe in the water of your new direction. Pilots help gather real-time data and feedback, allowing you to adjust incrementally as you go, instead of relying on blind leaps.

Pivot Degree or Intensity: One way to visualize the amount of risk, reward, and work required for your pivot is to imagine plotting your move on a graph. With time on the x-axis, and growth on the y-axis, the degree, or incline, of your next move can be viewed as the amount of resources it consumes in time, money, energy, and effort. A pivot can be subtle, say a twenty-degree turn, such as moving to a new team at work. Or a pivot can be sharper, say 70-degrees, such as switching industries or leaving your job to start a business.

Pivot Hexagon: There are three reciprocal pairs of values I see people express frequently in the midst of career change, and they sometimes conflict with one another: Security vs. Freedom, Money vs. Time, Structure vs. Adventure. Three represent our desire for security, and three represent our desire for freedom. Make short-term tradeoffs if necessary.

Pivot Method: A four stage process—Plant, Scan, Pilot, and Launch—to systematically bridge the gaps from where you are now toward where you want to be. In basketball, a pivot refers to a player keeping one foot firmly in place while moving the other in any direction to explore passing options. Much like a basketball player, successful pivots start by planting your feet—setting a strong foundation—then scanning the court for opportunities, staying rooted while exploring new options. Scanning alone will not put points on the board, so eventually you start passing the ball around the court—piloting, or testing ideas and getting feedback—generating perspectives and opportunities to eventually make a shot—launching in the new direction.

Pivot Point, Plateau: The way you are working is no longer working. Approaching (or already at) a place of feeling stagnant, ready for change. Could manifest as not being as engaged with your day-to-day work as you know is possible; not operating from your strengths a majority of the time; or operating from your strengths but not feeling challenged and like you are making as big of an impact as you are capable of.

Pivot Scales: Comfort vs. Risk - Imagine a scale with your comfort zone on one side of the balance, and your willingness to take a career risk on the other. As the risk surrounding a new direction starts to outweigh the comfort of staying in place

Pivot Timing: will depend on the scope of your change, how far your ideal end state is from where you are now, your risk threshold, your savings runway, your expertise and reputation, and the complexity of what you are building toward

Plant Stage: Creating a foundation from your values, strengths, and interests, and your vision for the future. The most successful pivots start from a strong foundation of who you already are, what is already working, and how you will define success for this next phase of your life.

Platform: Developing a public-facing platform, a corner of the world from which you can share your ideas and expertise with a community you cultivate, greatly amplifies your leverage during and after a pivot.

Project-Based Purpose: For some, the pressure to define a purpose or mission statement is stifling, and causes much unnecessary angst. In many cases, particularly mid-pivot, trying to get too specific with one End-All Be-All Purpose causes more anxiety than anything else. So ditch it. Focus on shorter-term aims instead. If your one-year vision is the what, or the desired destination of your next career pursuit, your project-based purpose is the why. In a world of shorter-term work, defining your why with project-based purpose will help you better sift potential opportunities while scanning, without the pressure to guide your entire life by one magical all-encompassing sentence.

Purpose: The motivation behind what you do. What is the impact you want the work you are doing to have, and for whom? Purpose is your personal mission statement. It goes deeper than your one-year vision, connecting all the work you do to an underlying theme.



Reciprocal transformation: According to Lisa Danylchuk, a San Francisco based psychotherapist, “The principle of reciprocal transformation says that one person’s growth is another’s. Learn to see the other person’s awesomeness or good fortune as a reflection of your own possibility.”

Redundancy: In engineering, redundancy is defined as the inclusion of extra components that are not strictly necessary for normal functioning, but are included in case of component failure. While it is not always possible to have complete career redundancy in terms of timing a move, it can help to aim for at least some overlap. By piloting new ideas simultaneously, in addition to your current source of career stability, you gain important information before betting big on a new direction. Best to avoid panic about your next paycheck in the midst of major change, whether transitioning to a new client base if working for yourself, to finding a new job if working for someone else

Reputation: When you consistently help others achieve results, you develop a reputation as a must-hire. Reputation refers to how others see you; the strengths they acknowledge and seek you out for.

Reputation Capital: expanding your sphere of influence by mastering your current role; establishing yourself as an expert; developing a name as someone with a unique skillset at the top of your field.

Results: Results are the meaningful impact that you have had on people or projects. These can be qualitative and quantitative, whether improving existing systems or launching new initiatives. Qualitative results might relate to soft skills, such as leadership and teamwork, while quantitative results are often characterized by increasing effectiveness, efficiency, revenue or reach, or a combination of all the above.

Riskometer: Take your risk temperature by identifying which of the four zones you currently fall into: playing it too safe (when you might find yourself slipping from the comfort zone into stagnation), when something feels edgy but exciting (stretch zone), or when a next step seems too overwhelming or extreme (panic zone).

  • Stagnation Zone: feeling restless, antsy, trapped, anxious, or bored. May start manifesting as physical symptoms and health problems.

  • Comfort Zone: feeling good about the status quo; daily life doesn’t demand much deep thinking about the direction of your career. Work is “fine.”

  • Stretch Zone: feeling challenged, excited, and motivated to get out of bed every day. Actively learning; work may be unpredictable, but you feel engaged.

  • Panic Zone: anxiety is starting to dominate your thoughts; you are not able to think long-term about the future because you are dealing with things that are “on fire” in your day-to-day life. Or, if contemplating next steps, you feel so paralyzed by fear that you end up doing nothing.

Runway: How long will your savings support you if you do not earn any income? The rule-of-thumb is three to six months until recent years, when the average unemployment duration hit 31 weeks, or nearly eight months.



Scan Stage: researching new and related skills, talking to others, and mapping out potential opportunities. This is the exploration phase: identifying and plugging knowledge and skill gaps, and having a wide variety of conversations.

Shadowing: Find people in roles you might want to ask about details of their daily experience, perhaps even by shadowing for a day or more. This will help determine whether the day-to-day realities of their work match how things appear from the outside. Does the reality of this role fit your strengths and interests?

Shoot the Moon: I am a firm believer in paying attention to practicalities while not neutering ourselves or our dreams. One of the most invigorating things you can do is go for something so outlandishly enormous that just to attempt the feat strengthens your resolve and forces an entirely new dimension of creative thinking.

Side Hustle: The term side hustle refers to modern-day moonlighting, earning income on the side of maintaining a full-time job. This is often not sustainable indefinitely, though some people will be perfectly happy with a light side hustle that brings them joy without ever having to quit their job, such as making and selling jewelry. Side hustles represent a calculated risk: you willingly invest some of your spare time (and maybe money) into a project that you are excited about, with the hope of making a greater proportion of your living off of this someday, or to land your next full-time role

Sliding Doors Careers: In the movie Sliding Doors, Gwyneth Paltrow’s character’s story plays out in two parallel universes based on whether or not she catches a certain London train. Imagine you get to live in an alternate reality, one parallel to the one you are living now, where you get to pursue any type of work that you want. What would you do? What do you daydream about?

Slow Build, or Incremental Piloting: Sometimes you will want to pilot quickly, acquiring information and feedback as soon as possible, in a lean and scrappy manner. At other times, you may take a more deliberate approach to piloting, aiming not to make change happen within the year, but rather as a long-term approach to developing your career portfolio. In the latter, you may sacrifice quality by moving too quickly, trying to force ideas and income streams to ripen before they are ready.

Sphere of Influence: As former FBI executive director Shawn Henry defines it, your sphere of influence is the circle of individuals that you can reach through your current position. Focus on expanding your sphere of influence within every role, whether it is two people or two hundred.

Strengths: Your natural talents and marketable skills; ways you uniquely add value and solve problems.



Talent: As peak-performance expert Laura Garnett defines it, is the unique way you solve problems. By identifying the types of challenges you are attracted to and how you tackle them, you can steer toward these areas for greater fulfillment and impact with your work.

Thought Leadership, Expert: publicly expressing your ideas; giving potential clients or companies an idea of what you stand for; making it clear who should seek work with you, who you enjoy working with, and how you can add value.

Travel Pilots: If you are not generating the traction you seek from piloting, travel can be a tremendous way to spice things up. Travel pilots are different than vacations in that they stretch you out of your comfort zone. The stretch zone might be how long you travel, where you go, or your intentions for the trip. Perhaps there is a class you want to take abroad, or an industry you want to explore further as a potential next career move or location. Travel pilots allow you to experiment with long-term or long-distance travel without committing to a giant leap, such as moving to a foreign country outright, though sometimes that can be just the shocking cold-water plunge your system needs.

Tyranny of the Hows: Getting caught up in how you will achieve vision-related goals too early in the Pivot process. Hat tip to Jeff Jacobson for the term.



Unrealized Gains: If you are at all successful in your current position—which you probably are, as an impacter—it is likely that you have unrealized gains on the table. In investing terms, unrealized gains refers to profit that exists on paper, but that has not been cashed in, such as a winning stock that has not yet been sold. In a career sense, unrealized gains typically fall into three categories: Financial Incentives: Large commission, bonus, stock options vesting, Results and Reputation: Completing a project, an upcoming promotion, making an impact, Growth: Gaining skills and experience that will be helpful for long-term career goals.



Values: Think about values as life filters; the search criteria that help clarify your priorities. They are rules-of-thumb for what makes you most fulfilled, the core operating principles by which you live your life.

Vision: If your values are your compass, your vision is your desired destination. Once you know where you are going, the Pivot process can take you there—but first, you need to pinpoint where you want to end up. Your vision attaches a specific future-based form to your values



Warm Connections: mutually beneficial relationships you nurture over time, where you both derive a sense of fulfillment and even exchange from your interactions.

Work History: The sum total of your work experiences across various industries, job roles, relationships, and results that you have achieved.



“Yes And” Technique: The Yes And technique means that anything your improv partner says goes. Between the two of you, you can combine crazy, unrelated concepts if you build on what the other is saying. In fact, that is the only effective way to keep the story moving. The same goes for your biggest pivot questions. While some reflection is good, as is some future planning, the real gold lies in the middle—your present reality. Only by adding to your current reality, asking combinatorial questions from seemingly contradictory statements, do you move the conversation forward.



Zone of Genius: These are the activities you are uniquely suited to, that draw upon your special gifts and strengths. When you feel most “in the zone,” while working, losing track of time.