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How to Choose a Career: Key Advice from Bestselling Career Books

Unlock expert-backed career advice for success with insights and strategies inspired by top career development books.


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In 2024, an astounding 95% of workers are either searching for a new job or planning to make the switch. Starting a new career isn't easy, regardless of where you are in life. Whether you're switching careers, expanding your opportunities, or simply looking for personal growth and improvement, the expert tips gathered in this article will help you choose your dream career step by step. I'll show you how to make the most of your skills while being happy at work.

I've drawn on insights from bestselling career books, including 'What Color Is Your Parachute?' and 'So Good They Can't Ignore You,' to offer you actionable steps that are grounded in proven strategies.

Step-by-step guide to choosing your best career

The idea of starting a new career means something different to everyone. For newcomers to the job market, it's a chance to take on a new role or enter a new industry. For seasoned professionals, it could mean refocusing their work on their interests or reconsidering their long-term goals. Whatever your situation, it's an opportunity to take on new challenges, explore new avenues, and discover unexpected possibilities.

1. Start with an in-depth self-assessment

"The person who gets hired is not necessarily the one who can do that job best; but, the one who knows the most about how to get hired." — Richard N. Bolles, 'What Color Is Your Parachute?'

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Whether you're fresh out of school making your first career decision, or you already have full-time work experience and wish to change your profession, there's a strategic approach to help you make a wise decision. But before you jump into creating your LinkedIn profile, polishing your CV, or scrolling through endless job listings — dive into yourself! Knowing your strengths, passions, and what truly drives you is where the search for your dream career starts. One option for determining an employee's personality type is the Myers-Briggs Type Indicator (MBTI).

What is MBTI, and how can I use it?

The MBTI is a personality assessment tool widely used for career guidance, used primarily in recruitment and personnel selection for a given position. It's a test that identifies 16 distinct personality types based on your natural preferences, helping you understand which professions might best align with your strengths and interests for a more informed and satisfying career choice. The assessment is available in three main variations: a standard 93-question version, a more detailed 144-question version, and an expanded 167-question version. You can complete the assessment online or track your answers in a notebook.

The MBTI examines four key areas:

  • How you interact with the world (Introversion vs. Extraversion)

  • How you process information (Sensing vs. Intuition)

  • How you make decisions (Thinking vs. Feeling)

  • How you organize your life (Judging vs. Perceiving)

For example, if you receive an ENFJ result (Extraversion, iNtuition, Feeling, Judgment), you'll likely excel in roles requiring emotional intelligence and leadership. Your natural eloquence and ability to organize ideas help you turn your fantasies and ideas into reality. You are also likely to intuitively make the right decisions in various situations, making you well-suited for positions like teaching, mentoring, or public relations.

"Always define WHAT you want to do with your life and WHAT you have to offer to the world, in terms of your favorite talents/gifts/skills-not in terms of a job-title." – Richard N. Bolles, 'What Color Is Your Parachute?'

2. Step out of your comfort zone: Leap into a fulfilling career

You can find inspiration from Tess Vigeland's story in her work titled 'Leap,' as she shares her journey of change following her successful 20-year radio career. Her story reflects on the risks and benefits of changing careers as a leap, an opportunity, and a breakthrough. 

"Leaving a job with no plan is terrifying. It's also exhilarating. It's where you find out what you're really made of." – Tess Vigeland

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Vigeland worked in national radio during the 1990s, hosting her successful finance show, Marketplace, for 11 years. When she began contemplating quitting her job, she described feeling anxious. She grew tired of performing the same routine weekly and year after year. Realizing it was time to move on, she recognized that a change was necessary. Vigeland emphasizes the importance of evaluating your readiness to change careers. In 'Leap,' she proposes a question for thinking: "How can you understand this moment?" For her, it was a mix of nerves and stress. Her publication discusses how 70% of Americans feel disengaged at work and are dissatisfied with their jobs.

Staying in one role for too long can lead to feelings of stagnation and decreased motivation. While seeking a new career might feel daunting, it offers: 

  1. Fresh challenges that break the monotony

  2. The chance to start anew and to learn new skills

  3. Renewed enthusiasm for life and work

  4. Opportunities to work in diverse environments

  5. Personal development and growth

Vigeland asks her readers to ask themselves:

  • What do I currently do? 

  • Do I genuinely enjoy it? 

  • If I could quit today, what would I want to do instead?

Today, Vigeland works as a freelancer on various projects for prestigious organizations like the New York Times and NPR — a feat she once dreamt of achieving. Although there have been ups and downs, taking that leap without a plan B led her to become a motivational speaker who helps people search for themselves and their careers for a more fulfilled life. 

3. Analyze the job market and choose a promising career path

"It is a great victory if you learn how to survive in today's hard times; it's an even greater victory if you help someone else survive and find meaningful work." ― Richard N. Bolles, 'What Color Is Your Parachute?'

The professional world constantly evolves, creating new opportunities in a rapidly changing environment. Today's workplace focuses more on helping individuals realize their intellectual, creative, and personal potential. As technology continues to reshape the job market, it creates new careers while transforming existing ones.

According to US News & World Report's 2024 rankings, which consider factors like growth potential, salary, and work-life balance, these are the most in-demand fields:

1. Software developer

2. Practicing nurse

3. Manager of medical services and health care

4. Information security analyst

5. Physiotherapist

6. IT manager

top_in_demand_careers_in_2024

The broader job market shows significant growth in these key areas:

  • Information technologies

  • Finances

  • Energy and engineering

  • Health care

  • Natural sciences

  • Industry

IT professionals — including programmers, testers, analysts, cyber security specialists, and web developers — currently dominate the job market. Approximately 36% of global organizations currently use business process management software, while 50% of leaders intend to adopt these processes soon. However, at the same time, many employers complain about the insufficient training of specialists, meaning those with relevant qualifications and expertise often receive the more attractive offers.

4. Land your dream job with a targeted strategy

"The best way to predict your future is to create it." – Cal Newport, 'So Good They Can't Ignore You'

At first glance, finding a dream job seems simple: you write a resume, send it to a dozen vacancies, and await a response. However, like trying to achieve any other goal, looking for a job can be done differently. Strategies include setting a specific goal, being ready to devote more time and effort, and not losing hope and self-esteem after the first rejections. It will consist of understanding the labor market's demand, undergoing training, and improving yourself to offer your talents to potential employers.

​​"The job-hunting process is much like a parachute jump. You need to know where you're going to land before you take the leap." – Richard N. Bolles, 'What Color Is Your Parachute?'

Rather than passively waiting for LinkedIn recruiters to discover your profile, take a proactive search approach. Share your career goals on social media platforms like Facebook, LinkedIn, or Instagram. Networking often reveals hidden opportunities, such as positions that aren't publicly advertised. Plus, these roles typically have far less competition.

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"Don't follow your passion. Instead, develop rare and valuable skills that will make you stand out." – Cal Newport, 'So Good They Can't Ignore You'

Another creative and bold approach is to create your own opportunities. Choose your dream company and create something specifically for them, like a design concept or marketing strategy. Request a chance to present your work or try to arrange an informational interview. Treat it as if you're preparing for your final interview.

5. Be open to all possibilities

If you're starting over, you'll have to start from the lowest rungs, taking contract work or short-term jobs. Do what you can to open the right door, and don't rule out temporary positions, freelance work, or nonprofit organizations. These positions are a good way to build valuable connections, so when permanent positions open up, you'll already have a foot in the door.

"Use this opportunity. Make this not only a hunt for a job, but a hunt for a life. A deeper life, a victorious life, a life you're prouder of." ― Richard Nelson Bolles, 'What Color Is Your Parachute?' 

6. Build career capital

The best way to start a new career is to prepare. Changing careers becomes much easier when you have the right tools, such as a strong desire to succeed, the patience to get through tough moments, and the determination to keep going. Even if you're new to the process, having these qualities can make the journey smoother and help you focus on your goal. 

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 "You don't need to be passionate about your work to be great at it. You need to be great at it to become passionate about it." – Cal Newport, 'So Good They Can't Ignore You'

Why education is essential for career growth 

Due to rapid technological advancements, professional knowledge must be updated every two years. As technology gains momentum, information changes and becomes outdated quickly. This reality makes continuing education essential for every professional, regardless of their field, age, or experience level.

Employers value higher education not just for the professional knowledge it provides but also for the soft skills it develops, such as problem-solving and communication skills. The US Bureau of Labor Statistics 2022 data shows that completing high school and pursuing further education significantly impacts employment prospects.

Certain "classical" professions still require traditional education, such as a bachelor's degree or internships. These include doctors, lawyers, technologists, scientists, psychologists, psychotherapists, engineers, and teachers. These fields rely on fundamental knowledge that has remained unchanged for many years, including human anatomy, laws, formulas, and the physical properties of materials.

"If your goal is to love what you do, you must first build up "career capital" by mastering rare and valuable skills, and then cash in this capital for the traits that define great work." – Cal Newport, 'So Good They Can't Ignore You'

Aim to acquire new skills necessary or valuable for your new career plan. How? Start by taking online courses, attending training sessions or seminars, reading books, or watching videos. You can also turn to experts, mentors, career coaches, and career counselors to get the most out of your studies.

7. Weigh the pros and cons and make a final decision

"Do not pick your career simply because it is expected of you, or because it is the most logical option. Pick it because it excites you and fits your own unique self." – Richard N. Bolles, 'What Color Is Your Parachute?'

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A decision matrix can be your ally when comparing different career options. This method helps reduce the stress and uncertainty of decision-making while making your options more precise and concrete. Creating a simple grid of essential factors to analyze and compare allows you to evaluate each option on a scale of 1 to 5 to make a confident, balanced, and rational decision. This approach gives you a complete picture of your choices in one place, considering all the essential factors influencing your decision.

Common mistakes and how to avoid them

Career choice is a serious and responsible step that many begin contemplating in high school. The job market is evolving rapidly, and this pace will only accelerate. While it may be tempting to follow certain trends, it's more beneficial to focus on work that aligns with your personality and interests. Instead of selecting a specific profession, choose an activity that excites you and offers growth opportunities.

Mistake 1: Chasing money over fulfillment

While a good salary is important, making it your primary focus can lead to regret. It's essential to recognize that, although money is necessary, it should not be your main priority; instead, your peace of mind should come first. You can earn a high salary by gaining knowledge and experience, but if your work doesn't resonate with you, you may feel disconnected and unfulfilled.

Mistake 2: Moving forward without a clear direction

Identifying what you desire from yourself, your life, and your work is essential. The best approach is to start with self-determination. Career counselors, parents, and friends can assist you in gaining a better understanding of yourself, but recognizing your strengths and weaknesses is crucial when making a career change. Personality tests also offer valuable insights into your natural abilities, preferences, and areas for growth.

Mistake 3: Limited understanding of available options

Many people choose careers based on assumptions rather than concrete knowledge. While some professions become obsolete, new and in-demand ones continue to emerge. When exploring your options, research thoroughly and consider future trends. 

Mistake 4: Letting others define your path

While parents and others may pressure you toward specific careers, remember that their valuable perspectives aren't the only truth. Your career choice should ultimately reflect your values and goals.

Discover your career path with expert guidance — start with Headway for deeper insights

Are you motivated to make thoughtful changes and informed decisions? Let personal stories like Tess Vigeland's 'Leap' inspire you as you move gradually toward your dream career.

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Come and explore our library's collection on career development and career change. Headway offers a convenient and effective way to learn on the go with our condensed text and audio versions of top self-development books. Download Headway to master these insights in just 15 minutes — learning and development have become more accessible than ever.


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