PDF Summary:The Squiggly Career, by Helen Tupper and Sarah Ellis

Since the early 2000s, the nature of work has changed greatly, and as a result, so has the nature of careers. Factors like increased flexibility and access to opportunities due to the internet have changed how and why people work. Rather than sticking to a single profession and climbing the corporate ladder to achieve financial stability, people frequently move between professions looking for a job that brings passion and fulfillment. In The Squiggly Career, Helen Tupper and Sarah Ellis argue that ensuring career success in this new era requires workers to develop five abilities: unique talents, strong values, self-confidence, networking, and foresight.

In this guide, we’ll explain why the nature of careers has changed, the five abilities you need to succeed amid these changes, and how to apply these abilities in your professional life. In our commentary, we’ll supplement the authors’ recommendations with advice from other personal development experts like Jack Canfield (The Success Principles) and Tony Robbins (Awaken the Giant Within).

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Identify Your Core Values

Tupper and Ellis explain that core values are the most important things in your life that you prioritize over all else, therefore, you can only have three to five core values. Further, core values are universal. They’ll guide your actions and decisions in all areas of your life, whether personal or professional. The authors recommend following a four-part exercise to identify your values.

(Shortform note: In Dare to Lead, Brené Brown reiterates the importance of only having a few core values. She elaborates that this is crucial because having too many values makes them meaningless—they become feel-good words rather than principles that truly guide your behaviors, intentions, and commitments. Further, Brown recommends narrowing your core values even further than the authors—she says you should have only two.)

First, the authors say to consider all the jobs you’ve done in your life. How happy or unhappy did you feel in each one and why? Based on the best and worst job experiences you’ve had, what are three things you require to be happy and three things you want to avoid at all costs?

Second, evaluate your previous response and consider what’s most important to you about four factors: the people you work with, the roles you perform, the company you work for, and your work environment. Which factors are more or less important to you?

Evaluate Your Life to Identify Your Values

While the authors’ approach to identifying core values is career-focused, Russ Harris provides a more general, and scientifically backed, approach to identifying values in The Happiness Trap.

First, while the authors recommend analyzing values under the domain of career and in relation to four factors, Harris recommends considering values in four domains identified by psychologists—work being only one of them. You should also consider your values under the domains of relationships, personal development and wellness, and leisure.

Then, Haris recommends asking yourself numerous questions to identify values in each domain. For example, under the work domain, ask yourself: What kind of person do you want to be? If you could be that person without obstacles, how would you treat people and behave? What kind of relationships are important to you? What skills or knowledge do you want to gain?

The third step of Tupper and Ellis’s exercise is to brainstorm a list of 10 traits that encompass the different concepts you’ve recorded in the previous steps. For example, if something important to you is being friends with your coworkers, you might want to write something like “authenticity.”

(Shortform note: This tool sorts 230 core values into 12 categories and may be helpful for drawing connections between values and combining them into core values. So, if most of your values seem to fall under the category of feelings, consider the different core values under this category and select the one you feel best represents the values you’ve outlined.)

(Shortform note: The authors provide an original list of 72 example values in the book.)

Finally, the authors say to identify your core values from the list of traits by weighing each trait against the others to identify which is more important. To start, compare trait one to trait two and mark a check next to the more important one. Then compare trait one to trait three and so on until you’ve reached trait 10. For round two, compare trait two to traits 3-10. Repeat the process for each trait until they’ve all been weighed against each other. At the end of the exercise, the traits with the most checks will indicate your core values.

(Shortform note: You can use this chart to help complete your values analysis digitally. To use this tool, first replace the 10 value labels with the 10 values you’ll compare. Then, move down each row comparing the value next to the “row 1” indication to the value indicated in the top of the chart. If the value of that row is more important, mark it with a 1, if it’s not, leave it empty. Then, tally the 1’s in each row and mark the total for each value in the “total” column on the right to determine your top-ranking values.)

Once you have your core values, the authors add, define exactly what they mean to you and what they require you to do. For example, you might define your core value of “genuine connection” as “relationships and environments where you can be your authentic self and speak your mind without feeling pressure to hold back or be something you’re not, and where others do the same.” This core value might require you to leave relationships and work environments where others or the organization are inauthentic, or where you feel pressure to censor your authenticity.

(Shortform note: Brené Brown also recommends defining your values and what they require you to do in Dare to Lead. To be even more specific, she recommends including the following elements in your definition: several behaviors that support the value, behaviors that would go against the value, and a few examples of moments of integrity where you exemplified this value.)

Leverage Your Values

The authors explain that identifying your values isn’t as simple as doing an exercise—you may realize over time that what you prioritize in real life differs from what you identified on paper. As such, you must regularly reflect on your daily life and how your core values play into it—how many of your core values can you remember off the top of your head and how often are they contributing to your life? If you find that one of your core values on paper isn’t a core value in real life, you should reevaluate.

(Shortform note: If you find yourself having to regularly reevaluate your core values, you may be confusing goals with values. In The Happiness Trap, Harris explains that this is a common mistake people make when identifying their values—especially in Western societies, which tend to be more concerned with status and achievement. For example, if one of your values is financial stability you may find this “value” is no longer relevant in guiding your actions once you’ve attained wealth—this is because it’s a goal. Whereas goals are objectives that can be considered “completed,” values dictate ongoing behavior.)

Further, the authors recommend making the effort to integrate your values into your life—especially in areas that may stray from your values. The authors say that when decisions arise, you should use your values to guide your choices. For example, in prioritizing authenticity, you may have to decide between agreeing with someone to maintain peace or speaking your mind and risking conflict. Following your values would require you to speak your mind respectfully.

(Shortform note: In The Six Pillars of Self-Esteem, Nathaniel Branden explains that living by your values is especially important because when you fail to do so, you compromise your integrity. When this happens, you end up damaging your self-respect and self-esteem—both of which directly contradict Tupper and Ellis’s third ability: self-confidence. Branden says that to regain integrity if you accidentally act against your values, take responsibility for your behavior and the consequences, do what you can to reduce any damage you’ve caused, examine why you did what you did, and commit to integrity in the future.)

Ability 3: Self-Confidence

Tupper and Ellis’s third ability for succeeding in a nonlinear career is self-confidence—believing in your capacity to achieve your goals, acknowledging your success, and being resilient in the face of challenges. Self-confidence is crucial in non-linear careers for three reasons.

First, self-confidence inspires you to take action toward your goals with less deliberation, helping you forge your own path and achieve goals faster. Second, self-confidence helps you persevere when you encounter setbacks and challenges. Third, being confident in yourself inspires others to be confident in you as well, making you a valuable asset to teams and organizations.

(Shortform note: In The Six Pillars of Self-Esteem, Branden argues that to achieve true success in life, you need to have more than just self-confidence—you need to have self-esteem. His concept of self-esteem includes Tupper and Ellis’s definition of self-confidence and also encompasses the belief that you’re an inherently good and valuable person who deserves happiness. Having self-esteem is beneficial because, in addition to the results of self-confidence listed by the authors, self-esteem increases independence, creativity and intuition, and rationality.)

Tupper and Ellis offer three main methods you can use to build your confidence.

Method 1: Overcome Limiting Beliefs

Tupper and Ellis’s first method for building your confidence is overcoming your limiting beliefs—thoughts that diminish your self-worth and hold you back from reaching your goals. For example, believing you can’t learn a hard skill or that others will always be better than you.

The first step in overcoming your limiting beliefs is identifying them. To do so, consider what you’re afraid of, what you want to do but don’t, and what negative thoughts you have about yourself. Then, ask yourself why you believe these things—for example, you don’t like talking to new people because you’re afraid they’ll reject you.

(Shortform note: In Awaken the Giant Within, Robbins provides additional recommendations for releasing limiting beliefs. He says that once you’ve identified them, consider not only why you believe these things, but why they might be ridiculous, who you learned each belief from and whether they’re a good influence, the costs and benefits of holding onto the beliefs, and the costs and benefits of letting them go. This will help you better direct your efforts to overcoming the belief, for example, by giving you confidence to face your fears and detach from negative influences in your life.)

Next, Tupper and Ellis say you must face your fears and challenge your limiting beliefs to disprove them. For example, face your fear of talking to new people by finding someone new to start a conversation with. Most of the time, you’ll realize that your fear doesn’t manifest or that it’s actually not as bad as you thought. This will help you build confidence in yourself and overcome the things holding you back. Regularly challenge yourself to continue making progress.

(Shortform note: In The Comfort Crisis, Michael Easter explains that facing your fears is difficult for most people because we dread the anxiety that comes from leaving our comfort zone. However, there are small things you can do regularly to strengthen your ability to break out of your comfort zone. For example, going into nature on a regular basis better equips you to face your fears by reducing anxiety, depression, and anger. In particular, Easter recommends spending 20 minutes in nature (even if it’s a city park) at least three times a week, at least five hours in a rural area (outside the city) every month, and at least one three-day trip to the wilderness (outside of civilization) every year.)

Method 2: Acknowledge Your Success

The authors’ second method to build self-confidence is to acknowledge your successes. Many people struggle with self-confidence because we have the tendency to remember our failures more than our successes, therefore building a false negative track record for ourselves in our minds.

(Shortform note: We tend to remember our failures more than our success due to the negativity bias—a natural cognitive bias that causes negative events to more significantly impact us than positive events. Experts theorize that this bias developed as an evolutionary adaptation—we’re more focused on negativity so we can avoid what can harm us and keep ourselves safe.)

To counter this, the authors say you should start recording all your successes of the day—how you helped yourself, and others, in different contexts. Further, remember that success is subjective—rather than comparing yourself to others or an objective idea of success, consider what success means to you.

(Shortform note: In Steal Like an Artist, Austin Kleon also recommends overcoming our tendency toward negativity by keeping track of positive experiences in a “praise file”—this way, all your positive reminders are in one, easily accessible digital file. He specifically recommends keeping track of positive comments you receive from others; however, you can use it to record any success or positive experience.)

Method 3: Build a Support System

Finally, Tupper and Ellis argue that it’s crucial to have a solid system of supporters in order to build self-confidence. You should ensure your support system includes at least one person who can offer unconditional love (like a parent), one who can empathize with your circumstances, one who can give situational advice, and one who can give honest feedback.

(Shortform note: In Bold, Peter Diamandis and Steven Kotler also recommend building a system of close supporters to help you succeed in your career. However, they note that these people are useful for more than just building self-confidence—they can also help you build your business or personal brand by offering critical feedback, personal connections to build your network (which is important for Ability 4), and resources you may need along your journey.)

Further, say Tupper and Ellis, ensure there’s balance in these relationships—don’t rely too frequently or heavily on someone. You also want to ensure that the relationship is somewhat mutual—that you or the other person isn’t expecting support without returning it. Failing to do these things can create dependent relationships that hinder autonomy.

(Shortform note: Even if you’re in mutually supportive relationships, you can still end up overly dependent. For example, if you struggle to make decisions without others’ input, struggle to start things on your own, feel the need for others’ approval, or are unable to enforce personal boundaries, you may have a dependency problem.)

Ability 4: Networking

Tupper and Ellis’s fourth skill for succeeding in a nonlinear career is the ability to network. Networking is building a social web of people who offer mutual benefits—they help you build your career, and you do the same for them. This can be by providing advice, mentorship, skills, other connections, and so on. Networking is important for three reasons.

First, strong networking skills help you to build meaningful relationships with people. This is important because having a smaller network of close connections who are willing to help you is more effective than a large network of loose connections that you can’t leverage. Second, your network will provide a diverse web of knowledge and perspectives that help you develop your career and branch into new territory. Third, networking helps you spread your name—the more that people know you, your goals, and your talents, the more opportunities will come your way.

(Shortform note: In Never Eat Alone, Keith Ferrazzi also emphasizes the crucial nature of networking. In addition to the benefits discussed by the authors, Ferrazzi explains that another important benefit of networking is that it improves your public image—it makes other people think positively about you. In particular, having a reputation for being well-connected will make you popular and influence more people to want to join your circle. You’ll also be seen as having good social skills, which not only makes people like you but is a sought-after professional skill.)

Build Your Network

The authors provide a few recommendations to build your network.

First, be calculated when deciding who you build relationships with. You can only keep up with a certain number of people, so it’s crucial that the people you let into your network are highly valuable to you. To ensure your network is intentional, identify the skills and benchmarks you need to meet to achieve your goals and seek relationships with people who can help you.

One way to do this is by considering what you need to reach your goals in three areas: your current job, your future career, and your personal life. You should seek out people with the specific experience, knowledge, or connections that you need to progress in one or more of these areas. For example, if you’re interested in transitioning into a new industry for your future career, look for someone with experience in that industry who can give you advice or help you build more connections in that area.

(Shortform note: In Never Eat Alone, Ferrazzi also emphasizes the importance of having a network of meaningful contacts rather than shallow connections. To ensure this, he says that you should build a social network that includes four groups of people: people who can help you meet specific goals, mentors, people with a large network who can share their contacts (super-connectors), and people who are well-known and share their insider knowledge and clout with you. As long as each person in your network falls into one or more of these categories, you’re guaranteed to have numerous people who can help you with your personal life, current career, and future career.)

Further, once you have a network, the authors note that it’s important to use it. One way to do so is to share your skills and interests with people, and ask if they have recommendations or connections that may be of use to you—even if they don’t in the moment, they’ll think of you if something does arise in the future and spread your name to others in relevant situations. This will attract more opportunities back to you. You can also start a side project that will help you develop your skills and ask one of your network members to help you.

(Shortform note: Under Ferrazzi’s framework in Never Eat Alone, this is the type of conversation you'd want to have with your super-connector contacts. He notes that there are a few types of super-connectors whom you’d especially benefit from having this discussion with—for example, headhunters, political lobbyists, journalists, or social media gurus. These people are guaranteed to know many people in many disciplines who they can connect you with.)

Finally, write Tupper and Ellis, be sure to find ways for your network to benefit from you so the relationship is mutual. Sharing your skills is one way to do this—once they know your expertise, people can ask for assistance when it's relevant. You can also directly ask people what you can do to help them.

How to Request Benefits and Give Them in Return

In Never Eat Alone, Ferrazzi explains that super-connectors are the best types of contacts to ask for opportunities and connections. In particular, he discusses a few types of super-connectors that are especially beneficial to have in your network and the types of benefits you can offer them to ensure the connection is mutual.

For example, headhunters are a great super-connector to have in your network—to ensure the connection is mutual, you can provide them with business leads and connect them to valuable people you know who need a job. Social media gurus are another great super-connector to have—to ensure the connection is mutual, you can share their content on your feed.

Ability 5: Foresight

The authors’ final ability for succeeding in a nonlinear career is foresight—the ability to strategically envision your desired future and possible career paths so you can develop truly fulfilling goals in the present. These goals will be based on genuine interests rather than objective metrics of success (like a promotion) and will be enjoyable and fulfilling to work toward.

Having foresight in a nonlinear career is crucial for three main reasons. First, it allows you to plan a fulfilling career trajectory autonomously. Second, when you work toward an interest-based goal and enjoy the process, you’ll discover additional interests and meaningful opportunities along the journey. Third, when you’re focused on pursuing your genuine interests, you ensure that your decisions guide you toward a career you truly want—many people switch to equally unsatisfying jobs just to escape their current one.

In the following section, we’ll discuss how to practice foresight by identifying possible career paths and developing the skills necessary to pursue them.

(Shortform note: In The Magic of Thinking Big, David J. Schwartz reiterates the importance and benefits of envisioning meaningful, passion-driven future goals and career paths, adding that there are five excuses people make that prevent them from doing so. First is self-deprecation—thinking you're not good or smart enough to achieve your goal. Second is the desire for security, which prevents you from branching out into new territory. Third is the belief that competition is too stiff to succeed. Fourth is letting your parents set your goal rather than creating it yourself. Fifth is allowing family obligations or expectations to prevent you from pursuing your dreams.)

Develop Foresight

According to the authors, the first part of developing foresight is identifying the possible directions your career could go in. There are four directions you should consider: 1) the logical next step based on your current job, 2) a job you’ve thought about pursuing but made excuses not to, 3) the job you’d do in your dream world, and 4) a job that’s parallel to your current job—it’s a different industry or career path but uses your skills and strengths.

(Shortform note: In the previous commentary, we discussed five excuses from The Magic of Thinking Big that Schwartz says prevent us from developing foresight. If you find yourself using these excuses, Schwartz recommends altering your underlying attitude from scarcity (what you don’t have) to abundance (what you do have). You should overcome excuses and focus on your values in four main areas: health, intelligence, age, and luck.)

Further, the authors write, the most valuable possible career directions are those that promote the five abilities of nonlinear careers. To ensure the possible career direction will benefit you long term, consider the following: 1) How often will it have you practicing and developing your unique talents? 2) In what ways will it allow you to live your values? 3) How will it help build your self-confidence? 4) How will it help you use and give back to your network? 5) What future opportunities might it open up for you?

Classifying the Ideal Career

In What Color Is Your Parachute?, Richard Nelson Bolles says the ideal career must align with five facets, some of which align with the skills the authors discuss. Combining the authors’ and Bolles’s requirements will ensure you choose a career that’s most valuable to you.

The first two facets of a valuable career, according to Bolles, are alignment with the people and workplace conditions—what kind of person are you, what kind of people do you get along with, and which environmental conditions make or break a company for you? These are the types of people and factors you’ll want to be present in your career. While the authors recommend considering these factors when developing your core values, they also say you can only have five core values. Even if these factors don’t make it into your core values, Bolles says they’re still important when selecting your career.

Two more facets Bolles says make a career valuable are the skills and knowledge it requires you to use. You want to use the skills you’re best at and the knowledge you have that excites you. You’ll also want to ensure your career helps you further develop your skills and knowledge. Ensuring this will also arguably help you develop your self-confidence and your ability to benefit your contacts by sharing your expertise. While the authors say your career should rely on your unique talents (skills), they don’t discuss the importance of knowledge that excites you.

Bolles says you should also choose a career that aligns with your life purpose. This means that the career should not only align with your values, as the authors discuss, but it should also help you achieve your underlying mission in life.

Bolles recommends ensuring a career aligns with one additional factor that the authors don’t discuss—money. While the authors prioritize all the other factors above money, Bolles reminds us that money is still important to fund the things we want to be able to do in life.