How to Choose a Career Path: The 5 Parachute Steps

This article is an excerpt from the Shortform book guide to "What Color Is Your Parachute?" by Richard N. Bolles. Shortform has the world's best summaries and analyses of books you should be reading.

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Do you know how to choose a career path? What are the suggestions from What Color Is Your Parachute?

What Color Is Your Parachute? offers a 5-step process for how to choose a career path. These 5 Parachute steps can help guide you.

Read on for the 5 Parachute steps for how to choose a career path.

How to Choose a Career Path: The 5-Step Process

Step #1: Determine Possible Career Paths

There are a few steps to using your flower to direct you on how to choose a career path:

  • Write your top three knowledges from Petal #5 on a sheet of paper.
  • Write your top five skills from Petal #3 on the same sheet of paper. Consider whether your skills point toward working with people, information, or things.
  • Show the sheet of paper to at least five people you know and ask them what jobs they think of when they look at the items on the list. The skills usually cue a job title and the knowledges usually cue a field. The goal is to combine a few of your knowledges into a specialty. 
    • For example, if your top three knowledges are music, crafts, and counseling, what jobs involve all three?
  • Find people who are experts in your knowledge fields. Determine which person needed the most training (because this person likely has general knowledge in many fields) and set up an informational interview. Ask them how to combine your three knowledges.
    • For example, meet with a counselor. She might tell you about the existence of art and music therapy, which combine two of your knowledges.
  • Don’t worry if your three knowledges seem so disparate you’ll never find a job in which you can use them. You may not be able to find something that perfectly matches right away, but you can get close.
  • After a week of talking to people, evaluate your notes. Circle the most useful suggestions, and if nothing seems useful, go talk to more people.

Step #2: Research Possible Careers 

The careers you came up with in step 1 might sound perfect, but you won’t know for sure until you try them. As a result, the next step is to talk to people who are already doing the job and find out what it’s really like via informational interviews.

In an informational interview, ask the interviewees the following:

  • How they got into the field.
  • What they like about the job.
  • What they don’t like about the job.
  • Who else you could talk to who does the same job.
  • What other types of careers use the same knowledge and skills as the type of job you’re discussing, and who else you might talk to about those other careers
  • How much education or training the job requires. Most of the time, it will be a lot, but there are almost always exceptions, so ask about those too.

Keep in mind that not everyone will see the job or field the same way. You may have a different experience in a job than your interviewee did.

If you learn that a career requires a lot of training, consider shadow professions. Shadow professions are jobs that require less training than a professional specialty but are in the same field. For example, a paralegal is a shadow profession of a lawyer. 

Step #3: Figure Out What Kinds of Organizations Hire for the Types of Jobs You Want

Brainstorm the kinds of places that hire for the job you’re interested in. For example, if you want to be a teacher, you’ll think of schools, but also consider things like corporate training, military bases, ESL associations, and so on. Consider places that hire both full-time and temporary employees.

Step #4: Figure Out What Specific Companies Hire for the Types of Jobs You Want 

It doesn’t matter if companies have open positions at this point; you just need to make a list of organizations that you think look interesting. It’s important to keep an open mind if you want to know how to choose a career path. You’ll likely want to focus on smaller companies (fewer than 100 employees) and newer companies.

  • You might stumble upon this information during your informational interviewing. 
  • Keep talking to your friends, family, and network and ask them if they know of particular companies you could look into.
  • Search online using LinkedIn and search engines.
  • If you end up with too many companies (more than ten), use your petals to narrow down the options.
    • For example, if you want to work for a company that hires receptionists, you’ll find companies that meet this criterion in many industries all over the world. If your location petal indicates that the place you’d most like to live is Maui, and your working conditions petal indicates you want to work for a company with fewer than ten employees, then this will help you narrow down the search.
  • If you end up with too few companies (fewer than ten):
    • Look at, local business directories, or newsletters.
    • Go to your local library and ask the librarian to help you find resources.

Step #5: Research Specific Companies 

Researching companies is very important. You do this for two reasons: 1) to learn about an organization’s culture, working style, mission, and how you can be an asset to them, and 2) to determine if you would like working for that company. (Most people don’t find out if they like a workplace until after they’ve already started working there when it’s too late to turn back.) Here’s how to conduct your research:

  • Interview people who work at the organizations you’re interested in. A bridge-person is the best way to find people to talk to, but you can also:
    • Use LinkedIn to find people who work at the organization and email them directly. This only sometimes works; people are busy.
    • Go to the organization and ask questions. This works best for small organizations (fewer than 50 employees) who don’t have security guards. Don’t ask any questions you could have figured out on your own, for example, information you could have read on their website. Talk to the gateway people, such as the receptionist, before approaching others who are higher in the organization, talk to subordinates rather than the boss, and don’t try to get yourself hired. You’re simply gathering information.
  • Research online. Some companies will put information about their culture on their company website. Additionally, you can explore sites such as Glassdoor, on which employees review companies they currently work for or have worked for in the past.
  • Read company materials. The CEO of a company might have given talks you can get a copy of, and many companies put out brochures and annual reports. You might even find a company file at a public library.
  • Test-run companies by signing up with a temp agency. Temp agencies send you to different employers that need your specific skills and knowledges. Even if you don’t get sent to the company you wanted, sometimes you can develop contacts temping for a different company that works in the same industry.
  • Test-run organizations and causes by volunteering. Volunteering allows you to learn about an organization and gives you an opportunity to feel helpful (which is important, if you haven’t been working in a while).

What If I’m Offered a Job During the Five-Step Process?

It’s unlikely that you’ll be offered a job while you’re working through the five-step process, but it’s good to be prepared in case it does happen. If you’re desperate for a job, take the job. If you’re not desperate, it’s best to wait until you’ve completed the whole process. Remember that the goal of the flower exercise and parachute approach isn’t just to get yourself any job, it’s to find your dream job. It’s about how to choose a career path.

Tell whoever’s offered you the job that you’re still in the researching phase and want to finish the whole process before making a decision. Explain that you want to be sure you’ve found a place where you can be the most helpful, which any potential employer should appreciate. Say that your initial impression of their company is that you’d like to work there and promise to get back to the employer once you’ve finished your research.

How to Choose a Career Path: 5-Step Process Post-Assessment

Ideally, after going through the five-step process you’ll have discovered the existence of a job that meets the criteria of multiple petals. If your job matches only one of your petals, at best, you’ll be bored. If it matches all seven petals, it’s a dream job. When choosing which petals to prioritize, consider survival (in which case you’d choose the money petal) and your stage of life (if you’re older, you might prioritize the purpose petal).


Jobs are two-headed entities; they represent both what you do and what field you do it in. If your flower leads you to a dream job that’s different from both what you do and the field you do it in, it will be hard to get that job because you don’t have any experience. You might be able to network yourself into moving directly, but it’s easier to change one thing at a time.

For example, if you’re an architect and you want to become a music teacher, you’ll have trouble going directly to the music teacher role because if an interviewer asks you if you have any experience working as a teacher, or in the field of music, you’ll have to say no to both. If, however, you find a stepping stone job such as designing soundproof practice rooms, then you’ll be able to acquire some experience in the field.

How to Choose a Career Path: The 5 Parachute Steps

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Like what you just read? Read the rest of the world's best book summary and analysis of Richard N. Bolles's "What Color Is Your Parachute?" at Shortform .

Here's what you'll find in our full What Color Is Your Parachute? summary :

  • How to not just find a job, but find a job you love
  • Why traditional resumes don’t find you the right job
  • The 7 steps to identifying your ideal career

Rina Shah

An avid reader for as long as she can remember, Rina’s love for books began with The Boxcar Children. Her penchant for always having a book nearby has never faded, though her reading tastes have since evolved. Rina reads around 100 books every year, with a fairly even split between fiction and non-fiction. Her favorite genres are memoirs, public health, and locked room mysteries. As an attorney, Rina can’t help analyzing and deconstructing arguments in any book she reads.

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