The Squiggly Career

Ditch the Ladder, Embrace Opportunity and Carve Your Own Path Through the Squiggly World of Work

Welcome the Advantages of a Non-Linear Career

On average, we spend about 90,000 hours of our lives working. That’s a significant amount of time to achieve our professional goals and become experts in our fields. However, the nature of careers has changed. They’re no longer linear but increasingly squiggly.

The days of working for a single organization until retirement, culminating in a gold watch and a generous pension, are long gone. So, in this rapidly changing professional landscape, how do we make the most of those 90,000 hours?

This book explores the thrill and potential of a squiggly career, demonstrating how embracing non-linearity and agility is the key to success in the new job market.

In this book, you’ll learn:

  • How to incorporate your values into your work
  • The real barrier to confidence
  • The true value of money in relation to happiness


We Have More Control Over Our Careers Than Previous Generations

In the past, careers progressed according to internal corporate structures and promotions. This approach is increasingly becoming obsolete. Now, more than ever, we have the power to decide where we want to be, what we want to do, when we want to do it, with whom we want to do it, and, perhaps most importantly, why we want to do it.

The key takeaway here is: We have more control over our careers than previous generations.

Job-hopping, once a surefire way to have your application disregarded by hiring managers, is now not only more common but increasingly seen as a positive trait in an applicant. After all, multiple career starts indicate a refusal to settle for anything less than the best. Trying different routes suggests adaptability and open-mindedness, and it usually means you’ve picked up new skills and perspectives along the way.

Automation is continually transforming and replacing professions. According to a study by management consulting firm McKinsey & Company, as many as 375 million people might have to change their career fields in the next ten years. Rather than having proficiency in a specific area, work is now more centered around projects and relevant skills. Learning to adapt to new technologies and industries will ensure that you have opportunities well into the future. Your career will always be a work in progress, so it’s a good idea to give lifelong learning a permanent timeslot in your daily routine.

These changes are leading to more flexibility in how we work, which can positively impact both employees and companies. A YouGov study found that implementing flexible working hours increased employee productivity by 72 percent. For some, this new freedom means they can work from home, a café, or even a tropical island.

But having more flexibility presents its own challenges. Too much remote working can lead to loneliness, due to the sheer lack of human interaction. Many people also find it difficult to unplug and keep their work life and downtime separate.

Navigating your big-picture plans without a road map can be a daunting task, so start small. Identify practical changes you can make to begin squiggling your way through a rewarding career.


Identify Your Strengths and Concentrate on Developing Them

Would you prefer to be a jack of all trades or a specialist in your field? It’s tempting to try to be good at everything, but this approach is increasingly impractical. No matter how skilled we become at some things, we’ll always struggle with others. Rather than spreading ourselves too thin, we should focus on developing – and truly mastering – our strengths.

The key takeaway here is: Identify your strengths, and focus your energy on developing what you’re already good at.

Of course, not all strengths are created equally. We have natural talents – things we do well innately – and then we have learned talents, which we pick up in life or on the job. Ultimately, our strengths are a combination of talent, experience, attitude, and behavior.

According to a study by analytics company Gallup, employees who lean on their strengths at work are six times more engaged in their jobs than their colleagues whose tasks don’t align with their natural proclivities. They’re also more productive. The authors recommend spending 80 percent of your time enhancing your strengths; this leaves 20 percent to identify and tackle the weaknesses that get in the way of your performance.

It’s typically easier for us to call out our weaknesses than to think up our own strengths on the spot. But in every weakness there’s an opposing strength. Perhaps, for example, you’re not as detail-oriented as you’d like to be – maybe this also means you’re a visionary who thrives in environments that require big-picture thinking. Try jotting down what you consider to be your greatest weaknesses. Now, find their counterpart strengths. Any surprises?

“Super strengths” are qualities your colleagues and family associate with you when you’re not in the room. You’re not just good at them; you’re really good at them. Super strengths should be used frequently and visibly. Don’t keep them a secret! Your coworkers and even LinkedIn connections should know what you do best.

Think back to how often you’ve used your super strengths over the past week. If your current job doesn’t routinely harness them, you could try to tweak your work approach or ask your boss how to better incorporate them into your assignments. Otherwise, it might be time to start looking for greener pastures.


Recognize and Integrate Your Values into Your Daily Work

Imagine you’ve just started a new job, and the pay is better than you dared to hope. You get a snazzy company car and free lunches, and everyone is friendly and competent. But something is missing – something essential. The work itself just isn’t meaningful or interesting to you. Can a few nice perks really compensate for 90,000 hours of meaningless toil?

The key takeaway here is: Recognize and integrate your values into your daily work.

According to the authors, by the time we’re in our mid-twenties, we’re equipped with three to five core values that start informing our behavior – as well as how we experience happiness. These values, which shape our motivations and judgment both at work and at home, are cultivated in three main phases in life.

The first period is the imprint phase, which begins at birth and continues until we’re about seven years old. Our parents, as well as others we spend time with, provide our first taste of right and wrong. For the most part, we don’t challenge what we see and hear; we soak it up like a sponge.

The second period is the copy-cat phase,

also known as the modeling period. From ages eight to thirteen, we start acting in various different ways, copying the behavior of people we look up to. We imitate teachers, other kids at school, or older siblings.

The final period is the rebel phase. It starts in our teenage years when we become more influenced by friends, the media, and friends of the media. We then have to iron out the friction between what we used to believe and what we now think is right.

Our values are a double-edged sword that can work for or against us. For example, if you value honesty, you could help out a colleague with some constructive feedback. But you might also unwittingly upset someone by telling them the bitter truth at the wrong time. Becoming aware of how this works can help you more clearly articulate your feelings and understand others’ values. This makes it easier to connect with people and work with them productively.

Just as defining your values will provide a deeper understanding of yourself, actively living those values will also benefit those around you.


Confidence: A Skill to be Mastered, Not a Trait to be Envied

We’ve all been there, trapped in the clutches of self-doubt. The silver lining? Fears such as stage fright or self-consciousness are not life sentences. With the right training, you can tame your insecurities and mitigate their impact on your performance.

The crux of the matter is: Confidence can be honed and enhanced through practice.

Sure, some folks are naturally confident, but we all have fears that muzzle our potential. By recognizing and taming our unique confidence gremlins, we can bolster our self-assurance. Your colleague’s confidence gremlin might be your superpower, or perhaps you both grapple with the same gremlins, albeit in different ways.

What triggers your gremlins? How do they hinder you? One strategy to rein in your gremlins is to challenge them. If public speaking sends shivers down your spine, delve into why. Unraveling the reasons behind your gremlins can help devise practical actions to curb their influence.

Here’s the exciting part: each time you confront one of your gremlins, reward yourself! Suppose you have a daunting presentation to deliver at the office. The pressure is on to make it flawless, and to top it all off, there’s no microphone. Once you’re done, treat yourself to something tangible, like a chocolate croissant. If things didn’t go as planned, reflect on why. Was the task too ambitious? Or was it the right level of challenge, and you could nail it with another try?

Confidence isn’t solely an internal phenomenon; it’s also nurtured by your support network. Visualize your sources of support by sketching a support solar system. What types of confidence do different people in your life provide, and how often? Who do you support in return?

In every support solar system, there should be three types of people. The person who “gets it” understands the hurdles you face. The person who “asks the tough questions” pushes and motivates you. The person who has “been there” offers valuable advice based on their experience.

Confidence boosters can also help you maintain composure in high-stakes situations. You exude more confidence when you complete your sentences, avoid indecisive words like “could” or “should,” and listen to others before speaking. Your body language radiates self-assurance when you adopt a powerful posture. Presentations improve with practice, so rehearse aloud and frequently – in front of a mirror or with friends or colleagues. Seek feedback, and reciprocate.

Cultivating your confidence and fostering a robust support network are crucial at every stage of a squiggly career.


Networking: A Mutual Exchange of Support, Not a One-Way Street

It’s late at night, and you’re on day twelve of your job hunt. You’ve spruced up your LinkedIn profile, and now you’re scrolling through your connections. You spot some colleagues from a job you had a decade ago, a classmate from a college project, and a recruiter offering an entry-level position in Montana.

How did you get here? Well, networks are more akin to gardens than cobwebs; they require regular maintenance to flourish.

The essence here is: Networking is a mutual exchange of help, and offering support can foster valuable relationships.

The depth of your network connections trumps their breadth. According to anthropologist and psychologist Robin Dunbar, we have a limited capacity for each type of friend. His research suggests we can have a maximum of 150 casual friends, 50 close friends, 15 confidantes, and just 5 best friends.

Your network should align with your learning objectives. You don’t need to be an extrovert to build and nurture mutually beneficial relationships. Instead of speed networking, identify people in your network who can assist with specific needs or issues. Be precise in your requests rather than vaguely asking someone to mentor you. For instance, you could reach out to someone working in your desired field or position, and ask about their journey. What skills and experience would you need to emulate their path?

Ensure your network is diverse. A study by McKinsey & Company surveyed 1,000 companies across twelve countries and found that organizations in the top quartile for gender diversity were 21% more likely to achieve “above-average profitability” than those in the bottom quartile. This figure jumps to 33% for those in the top quartile for ethnic diversity.

Reflect on why you were hired. Did you join as a consumer, benefiting from the existing network value? Do you have skills or ideas to contribute? Are you there to connect people? Understanding your role in a network will help you decipher why you’re there in the first place.


Embrace the Future: Explore Possibilities, Not Just Plans

In the modern era, we’re likely to switch careers five times during our working lives. The traditional life track of “education-work-retirement” is becoming a relic. So, how do we navigate our careers for a future that’s yet to be?

The key takeaway is: Focus on exploring future possibilities rather than adhering to linear plans.

Envisioning potential futures for your career demands creativity and taking ownership of your future. What other jobs or professions could you envision yourself in? Consider different types of possibilities to get the ball rolling.

Your obvious possibility is the next logical step from your current position. If you continue on your current path, where will you end up? Your pivot possibility is a new role that leverages your skills and strengths in a novel way. Your ambitious possibility is something you’ve always considered but have dismissed for some reason, usually due to a hurdle such as lack of experience or education. Finally, your dream possibility is the job you’d choose if there were no constraints. It could be your current job, or something entirely new. Maybe you’re an accountant with dreams of becoming a pilot. The sky’s the limit!

With all these possibilities, the reason you go to work remains as important, if not more so, than what you do at work. Your ‘whys’ are intimately connected to your values and articulate the impact you aspire to make. For instance, Google might say their ‘what’ is “to create an amazing search engine that everyone uses.” But their ‘why’ would be “to make data more accessible and better organized.”

In the face of the uncertainty that comes with a squiggly career, determining what matters most to you – and why – will serve as your career compass.


The Power Trio: Curiosity, Feedback, and Grit

The world seems to be changing at a pace that’s hard to keep up with, especially when we switch jobs every few years. Each new role brings requests for new skills and different working styles. How do we ensure we’re ready for our next opportunity when it knocks?

The core message is: Curiosity, feedback, and grit are increasingly sought-after workplace skills.

Stay curious to avoid tunnel vision – if you focus solely on your work, you’ll miss out on new trends and opportunities. Research by Francesca Gino, a Harvard Business School professor, shows that companies encouraging curiosity among employees have lower conflict rates and more innovative problem-solving approaches.

So, how can you stay curious? The options are limitless. Subscribe to a magazine on an unfamiliar topic. Discover new podcasts. Engage in conversations with strangers or new acquaintances. You get the drift.

Another way to maintain your relevance is to enhance your feedback skills

, both in giving and receiving. Many shy away from seeking feedback due to past traumatic criticism. Feedback can be a powerful tool for positive change, but it can also dent your confidence.

In a squiggly career, you might not regularly exchange feedback with your team members face-to-face, so it’s crucial to incorporate it into your meetings when you do interact. When giving feedback, try using the “what went well/even better if” technique. Start with a positive comment, like “Your presentation was engaging and held everyone’s attention.” Then, offer your suggestions for improvement, like “It would be even better if you provided more concrete examples to support your claims.”

Lastly, natural talent isn’t everything. In fact, grit – the effort you put into something – is often a better predictor of success. There are four main ways to cultivate your grit.

First, identify what fascinates you and delve into it. Second, use deliberate practice daily to hone your skills. This involves deciding what skill to improve, how to improve it, and then training extensively. Third, find a greater purpose for your goals to articulate what you aim to contribute to your organization, industry, or the world at large. Fourth, adopt a growth mindset. Simply having an attitude geared towards constant growth and development of your mind and skills relies on your grit as fuel.

By nurturing your curiosity, honing your feedback skills, and developing your grit, you can ensure a smooth career transition when the time comes.


A thorough analysis of your career choices can guide you towards the most fulfilling trajectory.

Does the allure of the unknown always seem more enticing? Every job has its moments of doubt, where you find yourself pondering, “Should I stick around or venture elsewhere?” In a non-linear career, this question will surface time and again – and the answer may not always be black or white.

The crux of the matter is: A thorough analysis of your career choices can guide you towards the most fulfilling trajectory.

If you find joy in your current role and you’re continually expanding your knowledge, reconsider the idea of leaving. To determine if a new role would be a good fit, ask yourself about the fresh opportunities it presents. Will the role leverage your unique strengths and align with your values, or is the paycheck the main attraction? Research by psychologist Daniel Kahneman and economist Angus Deaton revealed that beyond a certain point – roughly $75,000 – income ceases to impact levels of happiness.

Maybe your company doesn’t prioritize employee development. IBM’s research indicates that individuals are twelve times more likely to resign if they’re not enhancing their skills and experience. While some firms lack the necessary funds, others fail to see the value in investing in something with indirect returns.

The silver lining is, you have alternatives. You can seek grants or awards to finance your learning, or even create your own curriculum based on your learning objectives. By championing learning, you can also drive change within your organization. This is an excellent way to engage others and gather their insights on articles, issues, and events.

Side projects can also offer invaluable experience and a platform to delve into something that piques your interest. It could be a passion project, or perhaps it’s a problem-solving initiative that addresses a market need. Forty-two percent of startups attribute their failure to inadequate demand for their product or service – underscoring the importance of validating your idea before diving in.

So, the next time you feel trapped in a job, try to identify the root cause, explore your alternatives, and then devise a strategy to keep your non-linear career on track.



The core insights from this Summary:

As non-linear careers become increasingly prevalent, they also present us with fresh opportunities to steer our professional journey. We can learn to recognize and utilize our strengths, cultivate beneficial networks, enhance our confidence, incorporate our values, and master the art of providing and receiving constructive feedback. Through these actions, an unconventional career path will seem less daunting – and pave the way for a more thrilling, satisfying future.

Practical advice: Record your weekly achievements.

Maintain a record of your accomplishments for a week or two by noting down one each day. Alternatively, consider each day in terms of “progress” and “setbacks.” An achievement is progress, and anything that doesn’t go as planned is a setback. After a couple of weeks, review your list. If there’s more progress than setbacks, fantastic! If not, try to glean insights by scrutinizing the setbacks.

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