What Color Is Your Parachute 2021

When job markets shift quickly and technology redefines work, waiting for opportunity to find you no longer works. In What Color Is Your Parachute?, Richard N. Bolles argues that the most successful career seekers are those who reverse the usual logic. Instead of asking "Who will hire me?", they first ask "Who am I, and where can I make the best contribution?" His central claim is simple yet revolutionary: you must begin with self-knowledge, not job postings.

Bolles contrasts two models—the Traditional Approach and the Parachute Approach. The former starts with external need, treating the job hunt like a lottery: you send out resumes hoping one lands. The latter starts with internal discovery through a structured self-inventory, then strategically aligns your top strengths with employers who can benefit from them. The rest of the book is both a philosophy and a toolkit for living that philosophy.

From Job Search to Life Design

Bolles treats job seeking not as a desperate scramble but as a design project for your working life. You chart where joy and competence intersect by dissecting your past successes, values, preferred environments, and mission. It’s no coincidence that later editions of Parachute heavily influenced career design and coaching movements (Katharine Brooks’s work in cognitive design and Stanford’s Designing Your Life echo many of these principles).

The process begins with reflective exercises and moves toward concrete strategy—making the book both introspective and tactical. As Bolles says, knowing who you are is half the battle; translating that into meaningful action is the other half.

Why the Old Model Fails

Bolles dissects a core mismatch: job hunters chase convenience, while employers chase certainty. Sending dozens of resumes online saves time but produces little proof of fit. Employers usually prefer hiring someone they know, have seen perform, or who comes recommended. This is why networking and informational interviews outperform online applications despite taking longer. Your task, then, is to transform yourself from a stranger into a known quantity.

Core Principle

“Who precedes what.” Begin with your identity and capabilities before chasing named roles or companies. Employers respond best when they meet a person who knows themself clearly and shows how they can solve problems.

Adapting to Modern Realities

The 21st-century job hunt adds digital complexity: LinkedIn replaces first impressions; AI filters resumes; gig work erodes stability. Bolles acknowledges these realities but insists the human fundamentals remain: curiosity, clarity, and conversation. Your online profile is now part of your résumé. The key is to intentionally curate your presence, not disappear. Nearly half of employers won’t consider candidates they can’t find online. That’s why today, your digital footprint is your new handshake.

From Self-Reflection to Mission

The book ends where it began: with purpose. Bolles invites readers to look beyond employment and consider vocation—work that expresses who you are and what you care about. Through a three-stage model (Being, Doing, and Calling), he connects spiritual reflection to career decision-making. The premise isn’t religious dogma but wholeness: when you align values, gifts, and social needs, work becomes more than wages—it becomes contribution.

How Readers Use the Book

Decades of readers—from graduates to late-career changers—have used Bolles’s worksheets, especially the Flower Exercise, to pivot careers, rediscover joy at work, and even start businesses. The structure of the book mirrors that process: (1) understand your skills through stories, (2) translate findings into your seven-petal Flower Diagram, (3) use that to target organizations and conduct informational interviews, (4) master interviews and negotiation, and (5) if no job fits, build your own path through entrepreneurship.

Viewed as a whole, What Color Is Your Parachute? is not just a job-hunting manual—it’s a practical philosophy of choice, agency, and alignment. It teaches you to work from the inside out, turning uncertainty into experimentation and crisis into discovery. The job hunt becomes a mirror of a larger search: for meaning, mastery, and belonging in the modern world.

Everything in Bolles’s system begins with a simple question: who are you when you’re most alive? To answer that, he introduces the Flower Exercise, a seven-petal map of your professional identity. Each petal captures a vital dimension—skills, knowledges, people, work environment, geography, salary, and mission. Together, they form a visual compass for decision-making.

The Seven Petals

Petal One defines the kinds of people you prefer working with; Petal Two, the conditions in which you thrive (pace, culture, organization size); Petal Three, your favorite transferable skills (the verbs of your working life); Petal Four, the knowledges or interests you enjoy applying (the nouns); Petal Five, your financial and responsibility needs; Petal Six, your ideal geography; and Petal Seven, your life purpose. This one-page diagram distills complexity into usable clarity.

Bolles emphasizes completion and prioritization. He asks you to use a Prioritizing Grid—a tool developed by Beverly Ryle—to compare elements two at a time, revealing your true preferences. This converts vague self-reflection into data you can act on.

Skills Through Stories

The Flower’s power deepens when you add evidence. Bolles’s Seven Stories Exercise asks you to recall seven moments when you felt effective and engaged. Each story reveals repeating skills. These become your top transferable strengths—the foundation for targeting careers. For example, a story about training a shelter dog might expose teaching, empathy, and problem-solving skills that could apply from education to program design.

Why Stories Beat Claims

Employers don’t just want adjectives—they want stories. When you narrate accomplishments with context, actions, and results, you provide proof that you can do the work again.

How the Flower Becomes a Compass

Once you complete your Flower, you hold a personal map that transforms guesswork into strategy. You can test potential roles and industries against how many petals they satisfy. A job rarely fits all seven, but the closer the match, the greater your satisfaction and durability. In Bolles’s workshops, participants have used Flowers as lifelong decision tools—revisiting them before accepting offers or shifting directions.

In short, the Flower Exercise is more than self-assessment. It’s the bridge between reflection and reality—a portable summary of who you are and what you uniquely offer the world.

After defining who you are, Bolles shows you how to find where you belong. The Parachute Approach uses your Flower Diagram to identify ten employers or organizations that genuinely align with your strengths and values. Rather than chasing ads, you become a researcher and networker—someone who investigates where they can make the biggest difference.

Turning a Huge Market into a Small One

If your goal is vague, the job market feels infinite. Bolles asks you to gradually narrow: start with your field, then filter by geography, preferred environment, client type, and values until you have a shortlist. For instance, “financial adviser” becomes “adviser for retirees in small San Jose firms under 50 employees.” Now you have specific names to research.

Too many names? Add filters. Too few? Use directories like Indeed, local chambers, and library databases such as Reference Solutions. At every step, clarity beats volume—the aim is not to apply everywhere but to know deeply where you apply.

Bridge People and Weak Ties

Bolles popularized the term “bridge person” long before LinkedIn made networking mainstream. A bridge person connects you to someone inside your target organization. They give you credibility and context. Sociologist Mark Granovetter’s research backs this up: opportunities often emerge from weak ties—acquaintances outside your close circle—because they expose you to new information.

He advises reaching out respectfully, ideally via alumni networks or mutual contacts, and conducting short informational interviews to explore culture and fit before making any formal ask. Each conversation expands your map, revealing additional leads and understanding.

Action Principle

Treat every informational conversation as both research and rehearsal. The better you understand how a place works, the easier it is to show how you can contribute there.

Targeting transforms you from a reactive applicant into an intentional opportunity creator. Employers often respond with respect—and sometimes create new positions—when they meet a candidate who genuinely understands their work. That’s the essence of the Parachute difference.

Bolles famously insists that you should try careers on like clothing before committing. Informational interviews are the safe and revealing way to do that. Instead of begging for vacancies, you ask for wisdom—short conversations that expose the reality behind job titles.

How and Why to Conduct Them

Begin by researching fields that fit your Flower Diagram. Use tools like O*NET and LinkedIn to find practitioners, then request a brief 19-minute chat. That oddly specific time signals respect for busy people and works surprisingly well. During the conversation, focus on curiosity: “How did you get started? What do you enjoy most? What are the toughest parts? Who else should I talk to?” Always ask for the next contact.

Through these meetings, you may uncover hidden career paths, adjacent roles, or companies you’d never find on a job board. One reader discovered multiple new design job families this way by connecting seemingly unrelated skills—writing, design, and teaching—into hybrid roles.

The Courage to Experiment

Sometimes “trying on” means taking a lower or temporary role to gain exposure. Bolles recounts the story of a sixty-five-year-old executive who took a mail-room job simply to enter a company he admired. Two decades later, he’d risen into senior management again. The lesson: every doorway counts. Temporary work, volunteering, or project-based gigs can all become bridges to something bigger.

Key Practice

Always end informational exchanges with gratitude. Send thank-you notes within a day and capture what you learned in writing. Respect and organization turn short conversations into long-term allies.

By treating the job search as a series of conversations and experiments, you shift from uncertainty to discovery. You no longer wait for approval—you gather data, build confidence, and make informed choices about where to invest your time and learning.

Bolles and Katharine Brooks remind readers that a job search isn’t just logistical—it’s psychological. Prolonged uncertainty breeds discouragement, and mindset often determines persistence. To counter this, the book presents ten ways to win the mind game, a toolkit for emotional resilience grounded in research from positive psychology.

Ten Practices for Emotional Stamina

• Prioritize sleep and physical health to prevent exhaustion from masquerading as depression.
• Use self-compassion to reframe setbacks, drawing on Dr. Chris Germer’s guided exercises.
• Practice learned optimism (Martin Seligman’s method) by tracking and reinterpreting negative thoughts.
• Set small daily goals—crossing them off builds a sense of efficacy.
• Channel frustration physically—walk, stretch, work with your hands—to release emotional residue.
• Imagine and enlist supportive allies; even picturing a friend nearby makes challenges feel smaller.

Each exercise reinforces the idea that you can control behavior even when you can’t control outcomes. Optimism, says Bolles, is not personality—it’s a practice. By nurturing hope daily, you sustain energy for the hard work of networking and storytelling.

Mindset Insight

Research confirms that social support reduces perceived difficulty. Even visualizing a companion softens stress. Don’t isolate—join peer groups or accountability partnerships.

Bolles reframes the search as training not only for employment but for mental agility. Each rejection becomes rehearsal for resilience. This is what allows his readers to stay creative and hopeful throughout the long arc of transformation.

Once you’ve targeted the right employers and built confidence, the practical execution begins: interviewing, negotiating, and sometimes reinventing your career. Bolles provides field-tested methods for each phase so you can manage conversations with assurance and strategy.

Interview as Discovery, Not Defense

Bolles reframes the interview as a two-way fact-finding mission. The employer wants to know five things: why you’re here, what you can do, what kind of person you are, how you differ from others, and whether they can afford you. Your task is to answer each through concise behavioral stories (2-minute examples of real achievements) that prove your value. Remember the 50/50 rule: speak half the time, listen half.

Avoid “mosquitoes”—small irritants like talking over others or ignoring cues—that can sabotage impressions. Virtual interviews require equal care: test your tech, ensure lighting and camera are right, and follow up with personalized thank-you messages.

Negotiating Wisely

When offers arrive, negotiation begins. Bolles’s five secrets boil down to timing, research, and professionalism: research pay ranges (Glassdoor, BLS data), avoid naming your number first, propose researched ranges, and remember benefits are part of the package. Get all terms in writing. He cites creative arrangements like trading lower pay for fewer workdays—proof that flexibility often yields win-win outcomes.

Changing Careers and Starting Again

If you need to switch fields, Bolles recommends two strategies: the two-step career change and the PIE method. Instead of leaping from A to D directly, pivot through intermediate roles (A→B→D) that let you gain experience. And use PIE interviews—Pleasure, Informational, Employment—to gradually build comfort and connections. Tricia Rose Burt’s transformation from corporate PR to storytelling artist illustrates how transferable skills and curiosity can power creative reinvention.

Strategy Reminder

Every interaction—networking, interview, negotiation—is both practice and progress. Treat it as iterative design, not pass/fail testing.

Bolles’s integrated approach empowers you to succeed whether you’re a first-time applicant or reinventing a forty-year career. By combining preparation with adaptability, you not only land work—you shape work that fits who you’ve become.

Every career includes obstacles—ageism, disability, gaps, overqualification, or bias. Bolles’s message is liberating: no single barrier excludes you from every employer. The goal is to find the ones aligned with your strengths and to use the law and advocacy resources to ensure fairness.

Know Your Rights

Federal protections like the ADA, ADEA, and Title VII guard against discrimination. Use the EEOC or local agencies if you suspect violations. For disability accommodations, consult the Job Accommodation Network (askjan.org) for guidance and examples. Timing disclosure strategically (after interviews are scheduled) allows you to focus attention on capability, not limitation.

Translating Experience

Veterans should translate military terms into civilian impact; ex-offenders can use resources like Jails to Jobs and CareerOneStop reentry programs. Older workers should emphasize ongoing learning and vitality, reframing longevity as reliability. Bolles highlights how one barrier often conceals a strength—for instance, those with career interruptions often bring resilience and clarity about their motivations.

Starting Your Own Venture

Sometimes the best solution is independence. Bolles outlines a four-step entrepreneurial model: Write (list your loves and strengths), Read (research the market and avoid scams), Explore (interview business owners and map gaps via the A–B–C method), and Get Feedback (test ideas at small scale). Case examples—Alan the furniture restorer, Beth the genealogist, Maria the career coach—show how side projects can evolve into sustainable businesses.

Empowerment Mindset

Whether you fight bias or create your own job, agency is everything. Once you define what you can control—your clarity, effort, and curiosity—you regain power over your career story.

Final takeaway: there is always a path forward. The tools in Parachute—from Flowers to networks to entrepreneurship—are instruments for regaining authorship over your work life and purpose.