Navigating the Job Market: Strategies for the Rising Generation

Finding a job is hard. Finding a career is harder. And finding work you genuinely enjoy is the ultimate challenge.

The job market today can be overwhelming. With countless options and the false sense of progress that comes from applying to dozens of LinkedIn postings—where 400 applicants are vying for a single role, most never even reviewed (or are reviewed by AI) —it’s easy to feel stuck and discouraged.

Tom Jackson’s book Guerrilla Tactics in the Job Market cuts through the noise with a powerful message: (1) Understanding your goals and skills is the most important place to start and can supercharge your search, and (2) the best opportunities often exist in the hidden job market, where roles may never be publicly posted. Jackson’s approach emphasizes uncovering these opportunities by connecting with decision-makers, meeting new people, and exploring professions that make you excited to show up on Monday mornings.

The following insights provide a glimpse into Jackson’s wisdom and offer actionable strategies to help you prepare for and find a job that truly aligns with your goals and passions.

A. Discovering Your Path: Guerrilla Tactics to Sharpen Your Focus

This book, written in 1978 which I discovered at a yard sale for just $1, has proven to be priceless for friends seeking to uncover their true career paths.

By working through these tactics, you’ll gain a better understanding of your skills, interests, and the types of roles that truly resonate with you. This process not only helps you identify potential career paths but also equips you with a sense of alignment between who you are and the work you pursue.

Here are 5 actionable tactics to get you on track. Pull out a notebook and pen.

Tactic 1: Clarify Your Preferences and Interests

• Start by creating a clear picture of your likes, dislikes, and priorities in work.
  • List at least 25 activities you enjoy (work-related or not).
  • Now, shift to thinking specifically about work. List the things you enjoy about work and the things you specifically dislike.
  • Define five key criteria for job satisfaction, such as location, workplace culture, or salary.

Tactic 2: Identify Problems You Care About Solving

• Focus on meaningful work by identifying problems that need to be solved and aligning them with your passions.
  • List 10 real-world problems or needs you have observed.
  • Pinpoint three tasks or activities you love doing and brainstorm jobs that incorporate them.
  • Dream big—list three dream jobs and note the themes or challenges that excite you.

Tactic 3: Reflect on Your Past and Role Models

• Learn from experience and inspiration.
  • Reflect on past roles or projects, listing the duties you enjoyed and disliked and analyze why.
  • Identify five people with jobs you admire and describe what appeals to you about their roles.

Tactic 4: Clarify Your Preferences and Interests

• Highlight and Align Your Skills
  • List 25 things you can do, problems you can solve, or results you can deliver.
  • Match your top five skills with your top five interests to explore overlapping roles.

Tactic 5: Synthesize Your Skills and Passions

• Create a roadmap by combining your skills and interests.
  • Use a grid to connect your top five skills and interests, brainstorming potential job ideas for each intersection.
  • Aim for 20-30 role ideas that integrate both your strengths and passions.

B. Build Relationships, Not Just Applications

Effective job hunting requires more than just applying to jobs posted on LinkedIn. Start now by creating relationships with people in companies or industries of interest.

Networking through LinkedIn, reaching out via email, or attending industry events can open doors to hidden opportunities. Aim for a 1–3-month timeline to allow yourself enough time to connect, build rapport, and identify opportunities that aren’t posted publicly.

Remember, companies are searching for great talent just as much as you are searching for the right job. Think of yourself as a first-round draft pick: a prospective all-star ready to add immense value to any team.

This confidence will not only help you evaluate whether a company is a fit for you but will also create a sense of mutual respect during interviews. When you see yourself as an asset, the process becomes less daunting and more collaborative.

The best jobs don’t always go to the most qualified candidates but to those most skilled at job hunting, and best at building relationships.

Building Bridges: Tactics for Meaningful Networking

Tactic 1: Build a Personal Elevator Pitch

• Craft a concise and compelling summary of who you are, what you are enthusiastic about, and what you are looking for.
  • Example: "I’m a University of _____ student with experience in [specific co-op or internship]. I’ve developed [key skills or accomplishments] and am eager to learn more about [specific field or industry]."
  • Keep it conversational and adaptable, allowing room to tailor it to the person you are speaking with.
  • Tip: Say this aloud to yourself so you have the tone and cadence down. It should be able to flow easily.

Tactic 2: Craft a Personalized LinkedIn Message

• When reaching out on LinkedIn, be specific and authentic. Show genuine interest in the person’s work or experiences.
  • Example Message: "Hi [Name], I noticed [something specific about their work, such as a project, post, or role]. I am currently exploring opportunities in [industry/field] and am interested in learning more about your career path. Would you be open to connecting for a quick coffee or call in the next week or two? I’d greatly appreciate your insights."
  • Keep it brief, respectful of their time, and easy for them to say yes with a Call to Action (CTA) at the end.

Tactic 3: Book and Prepare for Coffee Meetings

• Once someone agrees to meet, prepare thoughtfully:
  • Research their background, company, and industry.
  • Have a list of genuine, open-ended questions ready (e.g., "What led you to your current role?" or "What do you find most rewarding about your work?").
  • Approach the meeting with curiosity—remember two ears, one mouth. Listen attentively and let them share their story.

Tactic 4: Share Your Story and Goals

• After listening, take the opportunity to share your elevator pitch.
  • List briefly highlight your background, what excites you about their field, and your goals for learning or growing in the industry.
  • Be honest, enthusiastic, and confident. Your aim is to leave a positive impression, not to ask for a job outright.

Tactic 5: Find Ways to Add Value

• Networking is a two-way street. Look for opportunities to give back, even in small ways.
  • If they mention a challenge, recommend a resource, article, or contact that might help.
  • If you meet others in your networking efforts, consider making introductions where it makes sense.
  • Simple follow-ups like sending a thank-you note or sharing a relevant article can go a long way in building a stronger connection. Surprisingly few people do this so it will help you stand out from the crowd.

Timeless Wisdom: Work and Fulfillment

Tom Jackson was the inspiration for this article and his book captures truths that are as relevant today as they were in 1978. Now more than ever, we are dominated by instant gratification. If your phone takes 10 seconds to load something, it feels like it is time for a new one. The same sentiment often applies to how we approach our careers and measure success. We crave quick results, immediate recognition, and tangible rewards, often overlooking the deeper, slower-growing satisfaction that comes from our work and our values.

Below are two of my favorite quotes from Tom Jackson:

The book challenges the traditional notion of success, pointing out its fleeting nature, and confronting the allure of chasing future achievements with a powerful truth:

"Success is the promise which is never kept. Satisfaction happens only in the present time: Now. Now. Now. Now. Moment by moment. You can’t satisfy appetites with future bread. You can’t experience future joy."

Tom also offers a practical strategy for uncovering job and career opportunities:

“You can create an important advantage for yourself in your job target fields if you are willing to identify prospective employers, not on the basis of employment ads, but from the premise that if you contact enough of the right people in the right firms you will uncover opportunities that are not public knowledge and may never be."

Finding a fulfilling job today goes beyond submitting applications or waiting for luck—it requires preparation, persistence, and genuine connection. We are in a hyper competitive market, which AI will likely make even more competitive, and brute force no longer works the way it may have in the past. Rather than hammering away at volume applications, the best way to set yourself up for success is do work upfront to figure out areas in which you will truly shine. Quality over quantity. This effort toward self exploration will ensure you are talking to the people and employers that see your value as clearly as you do.

Approach the process with curiosity and confidence, treating each interaction as a chance to learn and grow. Take the first step today, stay committed, and trust that the right opportunities will come your way.

When I was joining Northwood, it was clear they valued people as their greatest asset. We couldn’t serve as objective, independent, and integrated advisors—helping families navigate the complexities of wealth—without a talented and dedicated team.

They take the hiring process seriously, prioritizing relationships with candidates and carefully selecting for both skills and emotional intelligence (EQ). There is a focus on passionate individuals who bring not only expertise but also the ability to build meaningful connections. Most of the best employers follow this.

I’m early in my career and have been fortunate to have great mentors so far. I hope this article helps you take the first steps toward standing out and finding a career that truly excites you.