Strategize to Win

The New Way to Start Out, Step Up, or Start Over in Your Career

Charting Your Course to the Ideal Career

When we contemplate a job change, it’s often shrouded in negativity. Perhaps you were dismissed, the company folded, or you simply couldn’t stand the environment.

But what if we reframe this? What if a job change is actually a stepping stone to your ultimate career goal?

Consider this – the job market today is a labyrinth of career paths. This translates to a multitude of opportunities to acquire the skills needed to secure your dream job. Why not explore as many as possible?

So, let’s kick off this Summary with a golden rule: to optimize your career progression, envision your career as six to eight modules, each spanning five years.

In essence, switch jobs every five years! Ideally, assume diverse yet complementary roles at various companies.

Gone are the days when a 30-year tenure at a single company was the norm. The contemporary workplace demands individuals with a broad skill set, adaptability, and a constant drive to excel.

So, how do you cherry-pick the right jobs at the right companies throughout your career? That’s precisely what you’ll discover in this Summary.

We’ll also navigate you through the skills and experiences required to secure a job, how to extract maximum value from it, and most importantly, how to transition successfully. Let’s dive in!


Cultivate Skills and Experiences for a Lifetime

The cornerstone of a rewarding career lies in identifying activities that you genuinely enjoy. These activities form the crux of what the author refers to as, “the content page of your career.” So, discard job titles, and choose what truly piques your interest. Not only will this keep you engaged, but it will also pave the way to your ultimate dream job.

Begin by compiling a list of activities that excite you. Once you’ve done that, it’s time to research jobs that encompass these activities and combinations. Take Gregory, a 20-year-old sophomore, unsure about his career trajectory. He was an exceptional basketball player in high school but was frequently injured. After discussing his background and his interest in technology with the author, Carla A. Harris, he discovered that he could leverage these to work in sports medicine, orthopedics, or engineering.

Transferring strong interests into skills is often straightforward. If you’re accustomed to a particular activity, you already have some experience in it. Suppose you had a previous job in telemarketing. You perhaps enjoyed the communication aspect but disliked the remote nature. You’d have a strong case to convince your next employer that your skills could be extended to face-to-face sales instead.

Even if you’ve never tried an activity before but it interests you, that could translate as well. So, include the specific job titles that encompass your favorite tasks on your job list. Allocate 100 hours every month to converse with seasoned professionals in that field about their roles and the skills they acquired to get there. Don’t hesitate to invite experienced connections for a coffee chat to pick their brains. Request friends and mentors to introduce you to individuals in their networks who possess the skills and knowledge you seek.

The responses to your queries will significantly aid you in making informed decisions about the roles that align with your skills. If you can’t meet people, research their profiles on the internet.

Only after thorough research should you begin hunting for jobs that match your activities list. Again, research and network to secure interviews. What matters most in an interview is your ability to market your skills to your prospective employer. Marketing your skills means emphasizing those aspects of your education and experience that the recruiter is most likely to value, and how you would leverage them to enhance their business.

We’ll delve into this in more detail in the next section.


Become a Magnet for Recruiters

As the sole architect of your career, you must morph into the star employee everyone desires.

First, you need to secure an interview. To gain an advantage, blend online methods of making contact with traditional ways of approaching employers. This is a surefire way to get noticed. Instead of emailing your résumé and cover letter, consider mailing them to the recruitment manager.

Research recruiters online and then identify if you have contacts and mentors who can introduce you to them. This way, you’re entering the scene with a recommendation. If you’re still in school, attend job fairs on campus. Request your mentors to introduce you to hiring managers for a chat.

These chats, tours, or informational interviews will help you learn more about the company. You’ll get the opportunity to market yourself even before deciding to apply.

So, suppose you now have your career trajectory mapped out, the necessary skills and experiences locked in, and your interview secured. How do you go about landing the job?

It’s crucial to note here that you might not possess everything the recruiter wants. But the key to success is your ability to market yourself. And when it comes to the interview, weave your story in a way that showcases your ability to perform your job and fit into the company’s culture.

Considering that this job is merely a stepping stone to the next one in your career trajectory, study how it will prepare you for that advancement.

At the end of the day, three things matter in the job interview: what you can do, what you will do, and whether you’ll fit into the culture of the organization.

If you lack some of the necessary skills or education, don’t panic. First, you might actually have performed work that demonstrates these skills elsewhere. You just didn’t perceive it that way initially. For instance, a mortgage restructurer with an English degree, sound judgment, excellent analytical skills, and proven community engagement could likely find work in corporate philanthropy. It all boils down to marketing your skills. Bring in everything you’ve learned, both formally and informally.

Beyond that, the company would like to know if you possess the drive and tenacity to perform the job and fit into the organization’s culture. Your fit depends on your personality, motivations, and work style. Your success on the job will largely depend on how you relate within the company, so present your authentic self.

Finally, to secure the job that propels you forward in your career, do your homework on the employer to determine if you’ll genuinely enjoy working for them. Ideally, apply for jobs that you enjoy, as well as ones that will sharpen the skills you’ll need for your next job.


Seize the reins of your career journey.

To truly excel in your professional life, it’s crucial to comprehend the established norms of advancement within your organization. Don’t fall into the trap of believing you’ll be the outlier to a system that has been in place long before your arrival.

Ideally, this understanding should be in place before you even step foot in the company. However, if you’ve missed that boat, it’s never too late to grasp the intricacies of the promotion structure within your organization.

Remember, a job isn’t just a paycheck; it’s a stepping stone in your career path. The only exception to this rule is if you’re a novice and the company is taking a gamble on you. In such a scenario, you’re investing in yourself, and it’s crucial to set a timeline for when you’ll ask for the raise or position you desire. Failing to secure appropriate compensation can hamper your future prospects, casting a shadow on your capabilities.

Furthermore, prioritize learning. Cultivating fundamental strategic skills such as selling, analysis, organization, and management will equip you for leadership roles. If your workplace doesn’t offer learning opportunities, seek them elsewhere. Volunteer, enroll in online courses, do whatever it takes to hone these skills.

Lastly, seek out and engage in rotational programs within the company. These programs not only enhance your skillset but also help you forge new relationships. Investing in relationships can elevate your status within the team and potentially open doors to career-transforming opportunities in the future.

Harness the power of performance and relationship currency.

As you climb the career ladder, you’ll naturally crave more stimulating work that offers influence and commensurate compensation.

The most effective way to achieve this is to consistently deliver exceptional work. Everyone wants to collaborate with a high performer. It not only offers the opportunity to work on challenging tasks but also reflects positively on them. Your sponsors within the organization will take pride in your work and advocate for you.

Producing admirable work also cushions you when you stumble. This influence, built on the back of strong performance, is your performance currency. It’s a form of capital that can be exchanged for new opportunities. However, it can diminish over time. To bring about significant change within a company, you need to tap into the power of your relationships. Relationship currency is the strength of your personal relationships within your organization and how you can leverage them to gain influence.

Some relationship currency is earned through collaborative projects, but most of it hinges on the frequency of your interactions, both within and outside the workplace.

Make a conscious effort to connect with individuals in the organization who would be delighted to see you progress. Forge meaningful relationships that foster trust. Over time, these connections can help you secure favors, find sponsors, and recover from missteps.

Your professional standing will be a reflection of your performance currency and your likability.

In your quest to support your teammates and partners, you might find that you’ve given more than you’ve received. Don’t fret; this imbalance can be repaid in the future. Even if they don’t remember their debt, they’ll likely be more than willing to return a favor when asked.

Regrettably, many women neglect to invest in relationship currency, often to their detriment. While women excel at building relationships outside of work, they tend to focus on performance currency at work. Women should not hesitate to cultivate and leverage their relationship currency as well.


Master the art of communication for career advancement.

Effective communication is a universally acknowledged key to success. To optimize your communication, devise a personal communication plan that considers your audience, how to disagree with them, provide feedback, and interpret nonverbal cues.

Strive to articulate your ideas with clarity and proper grammar, whether spoken or written. Be mindful of generational communication preferences. Traditionalists and baby boomers often favor face-to-face interactions, while Generation X and millennials lean towards text messages and emails.

When someone is speaking to you, give them your undivided attention. Avoid distractions like fidgeting or checking your phone. If a colleague is nearby and you have a concern, consider walking over to their office for a chat, if they’re available.

When raising an issue, be clear and concise. Follow up to ensure your requests are addressed or rescheduled.

Bring your authentic self to work, but refrain from displaying excessive emotion that could detract from your main message. If you find yourself in disagreement, express your viewpoint politely and effectively.

Disagreements are inevitable, especially when providing feedback or performance reviews. Those who have nurtured relationships through effective communication often find it easier to deliver negative feedback. If someone has performed exceptionally, acknowledge their efforts both privately and publicly.

The most crucial aspect of communication is deciphering the unsaid. Sometimes, people may drop hints or ask certain questions without revealing the full picture. For instance, the company might be subtly nudging you towards the exit by consistently leaving you out of key assignments. If you find yourself perpetually passed over for promotions, it’s time to dig deeper and understand the underlying reasons.

Effective communication isn’t just about broadcasting your message; it’s also about active listening and keen observation. Read the room, pick up on the unspoken cues. The insights you glean from these interactions will inform your decision-making process. It’s through this feedback loop that you’ll know when it’s time to explore other roles within the company – or perhaps even consider charting a new course elsewhere.


Cultivate a Sponsor, Not Just a Mentor.

In your professional journey, you’ll encounter many individuals who’ll offer advice and guidance. While mentors are invaluable, what you really need to propel your career forward is a sponsor.

A mentor can provide you with wisdom, share their experiences, and guide you through challenges. However, a sponsor goes a step further. They advocate for you within the organization, champion your cause, and actively help you climb the corporate ladder.

Sponsors are typically higher-ups who have the power to influence decisions that can shape your career trajectory. They can open doors to opportunities that might otherwise remain closed. They can vouch for your skills and abilities, making it easier for you to secure coveted assignments or promotions.

To attract a sponsor, you need to demonstrate your worth. Show them that you’re a high performer who’s committed to the organization’s success. Make your ambitions known and prove that you’re ready to take on more responsibilities.

Remember, sponsorship is a two-way street. While your sponsor helps you advance your career, you need to deliver results that reflect positively on them. It’s a symbiotic relationship where both parties stand to gain.

Unfortunately, many professionals, particularly women, often overlook the importance of having a sponsor. They focus on building strong performance records but neglect to cultivate relationships with influential individuals who can help them advance. It’s crucial to balance your performance currency with relationship currency to truly excel in your career.


Embrace the Power of Authenticity.

In the corporate world, authenticity is a powerful tool. It’s about being true to yourself, your values, and your beliefs, even in a professional setting. Authenticity fosters trust and respect, making it easier for you to build strong relationships with your colleagues and superiors.

However, being authentic doesn’t mean sharing every aspect of your personal life at work. It’s about striking a balance between professionalism and personal expression. Share your thoughts and ideas, but do so in a way that respects the boundaries of the workplace.

Authenticity also means standing up for what you believe in. If you disagree with a decision or a policy, voice your concerns respectfully. Your colleagues will appreciate your honesty and courage, even if they don’t always agree with you.

Remember, authenticity is not a license to be rude or disrespectful. It’s about being genuine and honest, while still maintaining a level of professionalism. It’s about showing your colleagues that you’re not just a cog in the machine, but a unique individual with your own thoughts, ideas, and values.

In conclusion, the path to career success is not a straight line. It’s a journey filled with twists and turns, challenges and opportunities. By understanding the dynamics of your workplace, cultivating strong relationships, communicating effectively, securing a sponsor, and being authentic, you can navigate this journey with confidence and grace. Remember, you’re not just building a career; you’re crafting a legacy. Make it one that truly reflects your unique talents and aspirations.


Recognizing the Call for Transformation

There comes a moment, perhaps after a three or four-year tenure with an organization, when you sense the need to elevate your career game. Ideally, this is a sign that your career blueprint is unfolding as envisioned, and you’re transitioning into the next phase.

Occasionally, this realization may dawn prematurely due to a mismatch in fit, an absence of fresh roles, or the departure of your primary advocate.

Alternatively, you might simply have outgrown your current role and are seeking to amplify your career in a different setting. In such instances, your next move should be towards a position that offers increased responsibility, superior remuneration, and enhanced influence. Prior to embarking on a new venture, it’s crucial that you and your superior have a shared understanding of what success entails. By this stage, your accumulated skills, experiences, and connections should pave the way for superior opportunities.

For those contemplating a sabbatical, it’s crucial to articulate how this interlude enriched your narrative. Did you dedicate this time to acquiring new competencies, or perhaps embarked on a journey to master a foreign language? Or maybe you volunteered for a charity, sparking a newfound passion for corporate philanthropy?

The road to your ideal job is multifaceted. All it requires is weaving these experiences into a captivating narrative.



Set the stage for triumph by cultivating and strategizing your career journey. Initiate this process even before you secure the job and persist as you navigate through the organization, forging alliances and steering change.

As you evolve into new roles or transition jobs, demand remuneration that reflects your augmented responsibilities, expertise, and influence.

Concentrate on the substance of your career to equip yourself with a diverse array of skills and experiences that will afford you multiple career paths throughout your professional life. Maintain the agility to seize opportunities as they surface. Technological disruptions will inevitably give rise to roles you couldn’t have previously imagined, so stay vigilant and take the reins.

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