“What Color Is Your Parachute?” by Richard N. Bolles is a job-hunting and career-change guide that has been updated and republished nearly every year since its first edition in 1970. The core argument is simple but counterintuitive: the most effective way to find work is not to send out hundreds of resumes and wait for callbacks, but to figure out exactly what you want to do, identify the organizations where that work happens, and approach the people with hiring power directly. Here is what the book covers and what makes its approach different from conventional job-search advice.
The Book’s Central Premise
Bolles argues that the traditional job hunt, where you post resumes on job boards and respond to listings, has a surprisingly low success rate. He frames job searching as a numbers game that most people play badly because they rely on passive methods. Instead, the book pushes readers toward active strategies: networking, direct outreach, and deep self-assessment before ever writing a cover letter.
The title itself is a metaphor. “What color is your parachute?” is another way of asking: what are your skills, interests, and values, and where do they point you? Bolles believed most job seekers skip this question entirely and start applying before they know what they actually want. The book is structured to fix that, walking readers through self-discovery first and job-hunting tactics second.
The Flower Exercise
The most well-known tool in the book is the “Flower Exercise,” a detailed self-inventory that helps you map out seven dimensions of your ideal job. Each “petal” of the flower represents one factor:
- Transferable skills: What you’re good at and enjoy doing, independent of any specific job title. Bolles distinguishes between skills with people, skills with data/information, and skills with things.
- Fields of interest: The subjects and industries that genuinely fascinate you, not just the ones you’ve happened to work in.
- Preferred working conditions: Physical environment, team size, pace, level of autonomy, and similar factors that affect your daily satisfaction.
- Salary and level of responsibility: What you need to earn and how much authority or oversight you want.
- Preferred geography: Where you want to live, factoring in climate, proximity to family, cost of living, and lifestyle.
- Purpose and values: What matters to you beyond a paycheck, whether that is helping people, creating things, solving problems, or something else.
- Preferred types of people: The kinds of colleagues and workplace cultures where you thrive.
The exercise is designed to produce a single, detailed picture of your ideal work life. Bolles encouraged readers to fill out each petal with specifics, not vague wishes, and then use the completed flower as a filter when evaluating opportunities. The idea is that if you know exactly what you want, you can recognize it when you find it and stop wasting time on jobs that will leave you miserable within a year.
Informational Interviewing
One of the book’s most influential contributions to career strategy is its emphasis on informational interviews. These are short, low-pressure conversations with people who already work in a field or organization you’re interested in. The goal is not to ask for a job. It is to learn what the work is actually like, how people entered the field, and what the organization values.
Bolles recommended a specific protocol: introduce yourself, clearly state that you’re exploring a career direction (not asking for a job opening), and request a brief meeting at their convenience. If someone referred you, mention that person’s name early. The conversations themselves should focus on understanding the day-to-day reality of the role, the skills that matter most, and whether the field matches what you discovered in your self-assessment.
The strategy serves two purposes at once. You gather insider knowledge that job postings never reveal, and you build relationships with people who may later think of you when a position opens. Bolles considered this approach far more effective than cold-applying online because it puts you in front of decision-makers as a real person, not a line item in an applicant tracking system.
How Bolles Thinks About Skills
A significant portion of the book is devoted to reframing how you think about your own abilities. Bolles divided skills into three categories. “Knowledges” are things you’ve studied or learned, like accounting or Spanish. “Traits” are personality characteristics, like being detail-oriented or calm under pressure. “Transferable skills” are the functional abilities you carry from job to job, like analyzing data, managing projects, teaching, or negotiating.
Bolles placed the most emphasis on transferable skills because they are what make career changes possible. Someone who spent ten years in restaurant management may never have worked in logistics, but their skills in scheduling, cost control, team leadership, and problem-solving under time pressure translate directly. The book walks readers through exercises to identify their top transferable skills by examining past accomplishments, volunteer work, hobbies, and everyday tasks they do well without thinking about it.
The Two-Step Job Hunt
Once you’ve completed your self-assessment, Bolles laid out a two-phase approach to actually finding work. The first phase is research: use informational interviews, online exploration, and library resources to build a short list of organizations that match your flower. You are looking for places where your skills, interests, geography, and values overlap with what the organization does and needs.
The second phase is approaching those organizations directly, ideally by identifying the person who has the power to hire you (often not someone in HR) and finding a way to connect with them. Bolles was blunt about this: he believed resumes are a weak tool on their own and that personal connections, even new ones built through informational interviews, dramatically improve your odds. His research suggested that the closer you get to a direct conversation with the hiring manager, the higher your success rate.
Salary Negotiation Advice
Bolles dedicated a section to negotiating pay, with one guiding rule: never be the first to name a number. He advised job seekers to delay salary discussions until after the employer has decided they want to hire you, because that is the moment you have the most leverage. If pressed for a number early in the process, he recommended redirecting the conversation toward understanding the full scope of the role first.
He also encouraged researching salary ranges thoroughly before any negotiation, using industry data, salary surveys, and informational interviews to understand what the market pays for similar work. Knowing the range gives you a factual basis for your counteroffer rather than picking a number based on what you earned at your last job.
Why the Book Keeps Getting Updated
Bolles revised “Parachute” annually for decades, and after his death in 2017, other authors have continued updating it. Each edition adjusts for the current job market, incorporating online tools, remote work, LinkedIn strategies, and shifting hiring practices. But the core philosophy has remained remarkably consistent across more than fifty years of editions: know yourself deeply before you start looking, talk to real people instead of relying on online applications alone, and approach the job search as a structured project rather than a series of hopeful submissions.
The book is often recommended by career counselors and university career centers, and its frameworks, particularly the Flower Exercise and informational interviewing, have become standard tools in career coaching even for people who have never read the book itself.