Finding Your Way

What to Do When You're Unsure About Your Career Path

Author: Mike Scaletti

It starts as a whisper: a creeping doubt during your morning commute, a sigh while scanning job listings, or the numbing dread of Monday mornings. "Is this really what I want to do with my life?" That quiet unease can grow louder over time, becoming a constant background hum to your daily routine. Maybe you’re excelling in your current role but feel strangely disconnected. Perhaps you pursued a path you thought you "should" follow, only to realize it doesn’t fulfill you. Or maybe you're paralyzed by choice, with so many directions to go that none of them feels right.

If you feel stuck, uncertain, or overwhelmed by your career path, know this: you're not alone. Many professionals, from fresh college graduates to seasoned veterans with decades of experience, wrestle with the same question. Career paths today are rarely linear. In an age of rapid technological change, shifting job markets, and evolving definitions of success, it's no surprise that people often feel lost or misaligned.

The good news? Uncertainty isn't a dead-end. It's a signpost, an invitation to pause, reflect, and recalibrate. In fact, questioning your path can be one of the most constructive things you do for your future. Rather than a crisis, think of it as an inflection point, a moment where you can choose a new trajectory with more intention.

At The Job Shop, we work with people every day who are navigating career crossroads. Some are questioning whether their current role aligns with their values. Others are trying to reinvent themselves after a layoff, burnout, or life transition like parenthood or relocation. We see engineers becoming teachers, marketers becoming therapists, and longtime professionals finding new meaning in startups, nonprofits, or passion projects. Whatever your situation, this guide is designed to help you slow down the overwhelm, explore your unique skills and values, clarify your goals, and begin building a path that feels right for you, not for your parents, not for your peers, but for you. Let's begin.

Begin with You - Self-Assessment Techniques to Clarify Your Direction

Before you change course, it's essential to understand who you are today, your strengths, values, motivations, and blind spots. This process of self-discovery isn’t just a box to check off; it’s the bedrock upon which meaningful career decisions are built. The more clearly you understand what drives you, what excites you, and what you want to avoid, the better equipped you'll be to steer yourself toward a satisfying and sustainable path.

Self-assessment isn't about boxing yourself in or assigning yourself a permanent label. Rather, it’s about shining a light on what matters most to you. It allows you to zoom out from the daily grind and gain a holistic view of your internal compass. What fuels your energy? What makes you feel proud at the end of the day? What activities leave you feeling drained or disengaged? These questions are key to understanding where you might want to go next.

Think of this phase like building a detailed map before setting out on a journey. You need to know where you are, what terrain you're best suited to travel, and where you might run into challenges. It also helps you recognize patterns, the throughlines that have followed you from job to job, project to project, even in hobbies or volunteer work. Noticing these themes can offer powerful clues about your ideal direction.

In addition to clarifying your present-day self, self-assessment provides language and confidence for communicating your goals to others, employers, mentors, peers, and even yourself. It's much easier to update your resume, build your network, or explore new roles when you can articulate not just what you do, but who you are and why it matters.

Ultimately, this foundational step ensures that your future choices aren’t reactive or based on guesswork. Instead, they’re anchored in deep self-awareness and intentionality, two qualities that can significantly increase your chances of finding meaningful, long-term satisfaction in your work.

Identify Your Skills (Hard and Soft)

Think beyond your resume. Skills aren't limited to your formal job description. They are cultivated through life experiences, hobbies, side projects, and even challenges you've overcome. Consider:

• Hard skills: coding, copywriting, budgeting, foreign languages, data analysis, graphic design, project management, spreadsheet modeling, marketing analytics, CRM platforms.

• Soft skills: empathy, communication, leadership, problem-solving, time management, conflict resolution, adaptability, active listening, emotional intelligence, and strategic thinking.

Hard skills are teachable and measurable. They're what you typically list on a resume or learn in a course. Soft skills, on the other hand, are often what make the difference between a good employee and a great one. They're developed through experience, reflection, and feedback.

Exercise: Start by listing 10 skills you use regularly at work, and then another 10 that you genuinely enjoy using, even if they aren't part of your job description. Next, try to identify 5 aspirational skills you'd like to develop. Use a Venn diagram to visualize which ones overlap, which ones are exclusive to either list, and which aspirational skills connect to your existing strengths.

Reflection Prompt: Ask yourself, "Which of these skills energize me when I use them? Which ones feel draining, even if I’m good at them?" This helps you differentiate between competency and alignment.

Bonus Tip: Ask colleagues, mentors, or trusted friends for input on your skills. What do they consistently come to you for help with? Their responses might reveal strengths you’ve taken for granted.

Discover Your Core Values

Work that aligns with your values tends to feel more fulfilling, even when it’s challenging. When there’s a mismatch between your work and your values, it often manifests as dissatisfaction, stress, or a sense of disconnection from your purpose.

Ask yourself:

• What causes or ideas do I feel passionate about supporting?

• When have I felt the most proud or satisfied in my work?

• What ethical or personal boundaries do I refuse to cross?

• What kind of workplace culture makes me feel safe and motivated?

Exercise: Select your top 10 values from a comprehensive list (e.g., creativity, autonomy, integrity, service, achievement, collaboration, recognition, stability, innovation, flexibility). Narrow it down to your top 5. Then, write one sentence describing why each value matters to you.

Deeper Dive: Compare your current or previous job against those top 5 values. How well did your environment align with each one? Where were the greatest misalignments, and how did they impact your performance and well-being?

Optional Prompt: Describe a professional moment where your values were honored, and one where they were challenged. What did those experiences teach you about what you need in a career?

Understand Your Personality Type

Your personality shapes how you approach challenges, interact with others, and recharge. Understanding your personality preferences can help you determine the types of roles, work styles, and team dynamics that will feel most natural and rewarding.

Common tools to explore include:

• Myers-Briggs Type Indicator (MBTI): Helps identify preferences for introversion/extraversion, sensing/intuition, thinking/feeling, and judging/perceiving.

• Enneagram: Focuses on core motivations and personal growth paths across 9 distinct types.

• DISC Assessment: Measures communication style and behavioral tendencies in workplace environments.

• Big Five Personality Traits: Offers insight into your levels of openness, conscientiousness, extraversion, agreeableness, and neuroticism.

These tools aren’t prescriptive, but they offer valuable clues. For instance, someone high in conscientiousness might thrive in detail-oriented, structured environments, while someone high in openness might prefer innovative, fast-changing fields.

Tip: Try taking two different assessments and compare your results. Where do they reinforce each other? Where do they diverge? Use this insight to clarify your preferences for team dynamics, leadership roles, and ideal tasks.

Integration Exercise: Once you know your type, explore what kinds of roles or industries are commonly associated with your results. Don’t use it as a constraint, use it as a compass.

Reflect on Your Interests

It might sound simple, but interests are often the most overlooked ingredient in career fulfillment. While skills and personality determine how well you can do something, interests often determine how long you’ll enjoy doing it.

Think about:

• What podcasts, books, or blogs do you follow religiously?

• What kinds of conversations excite you?

• When you procrastinate productively, what are you doing?

• What issues or topics do you find yourself getting passionate about, even if they don’t relate to your current job?

Exercise: Keep a curiosity journal for a week. Log any topic, article, video, or conversation that captures your attention. At the end of the week, look for patterns. Are you drawn to certain themes, problems, or communities?

Follow-Up Activity: Choose one recurring topic from your curiosity journal and go deeper. Read a white paper, watch a documentary, or take an online micro-course. How does it feel to immerse yourself in it? If your energy grows, that’s a strong signal.

Pro Insight: Combining interests with your values and skills often points to deeply aligned career paths. For example, if you’re skilled in communication, value justice, and have a passion for social change, you might explore public interest advocacy or nonprofit leadership.

By expanding your awareness in these four areas, skills, values, personality, and interests, you’ll build a clearer picture of the kind of work that will energize and sustain you over the long term.

Narrow the Field - Practical Exercises to Explore Options

Once you’ve clarified your internal landscape, it’s time to connect that self-awareness to external possibilities. This next phase is where the introspective work you’ve done begins to bear fruit. By exploring what's out there, testing ideas, and engaging with new perspectives, you'll transition from feeling lost to feeling curious, and eventually, from curious to confident.

This part is about moving from "I don’t know what I want" to "I have some ideas worth exploring." It’s a journey of exploration, not instant certainty. You don’t need a perfect plan, you need a starting point, an open mind, and a willingness to experiment. Think of it like shopping for a house: you might not find the perfect one on your first tour, but each visit teaches you something new about what you value, what you’re willing to compromise on, and what truly matters.

Exploring possibilities also helps you expand your mental model of what a career can be. So often, we limit ourselves to job titles we've seen or roles we've already held. But the modern workforce is full of hybrid jobs, portfolio careers, and paths that didn’t exist five years ago. With a little research and conversation, you may discover roles that combine your skills and passions in ways you never imagined.

In the sections that follow, you’ll find creative and practical strategies to begin this outward-looking process. You’ll brainstorm freely, talk to professionals in the field, experiment with small projects, and even dip a toe into industries that pique your interest. Whether you end up changing industries, shifting roles, or simply adjusting your focus within your current field, these tools will give you clarity and direction.

Above all, remember: this is a process. You’re not committing to anything yet. You’re exploring, testing, learning, and refining. Give yourself permission to be curious and imperfect. The goal is progress, not perfection.

Create a Career Brainstorming Map

Create a mind map that starts with you in the center. From there, branch out into categories like:

• Skills I want to use

• Values I want to uphold

• Topics I enjoy

• Industries I’m curious about

• Work environments I prefer

• Causes or missions I care about

• Ideal lifestyle goals (e.g., travel, flexibility, stability)

Spend time fleshing out each branch, jotting down any roles, companies, or ideas that come to mind, even the unconventional ones. This exercise is about generating options, not filtering them (yet). Let your imagination roam. No idea is too wild or too small.

Then look for intersections. For example, if you love writing, value justice, and are curious about healthcare, medical communications could be a fit. If you enjoy public speaking, prioritize innovation, and have a background in tech, a role in startup fundraising might be worth exploring. This method helps uncover possibilities that match multiple aspects of who you are.

Extra Tip: Turn your brainstorming map into a visual board using tools like Miro, Canva, or a simple whiteboard. Visualizing connections can spark new ideas and clarify priorities.

Conduct Informational Interviews

Talking to real people doing real jobs can be far more enlightening than reading job descriptions. Online resources can only go so far. Hearing first-hand accounts of a job’s realities helps you cut through the fluff and get a real sense of what the work entails.

Steps:

• Identify 3–5 industries or roles you want to learn more about.

• Use LinkedIn, alumni networks, Meetup groups, or industry-specific forums to find professionals in those areas.

• Reach out with a brief, respectful message requesting a short 15–20 minute informational interview.

Conversation Prompts:

• What does a typical day look like in your role?

• What do you love most, and least, about your work?

• How did you get started in this field?

• What qualities make someone successful in this role or industry?

• If you could go back in time, what would you have done differently when starting out?

Pro Tip: Don’t ask for a job, ask for their story and insight. Express genuine curiosity and gratitude. Most people are flattered to be asked and willing to help. Follow up with a thank-you message afterward.

Optional Step: Keep a spreadsheet to track who you spoke with, their role, what you learned, and any next steps. Patterns will start to emerge that guide your decision-making.

Try Job Shadowing or Volunteering

Reading about a job is one thing. Observing it in real-time is something else entirely. If possible, spend a day or week shadowing someone in a role you’re considering. Even just a few hours can offer valuable insight into workplace culture, communication dynamics, and job expectations.

Volunteering is another low-stakes, high-impact way to test the waters in a new industry. It shows initiative, builds your resume, and expands your network, all while helping a cause. Try volunteering:

• At a nonprofit related to your field of interest

• At events or conferences in your desired industry

• On short-term consulting projects through platforms like Catchafire or Taproot

Alternative: If shadowing isn’t possible, try conducting a “day in the life” simulation. Plan a day where you perform tasks related to the job you’re exploring. Track your energy levels, enthusiasm, and frustrations throughout the day.

Experiment Through Side Projects

Not ready to commit to a career change? That’s okay. Start a side project that lets you experiment and build new competencies at your own pace. Side projects offer a safe space to play, grow, and refine your interests without high stakes.

Examples include:

• Launching a blog, podcast, or YouTube channel about a topic you’re passionate about

• Freelancing part-time in a new field (writing, design, coaching, etc.)

• Enrolling in a course and building a project to showcase your new skills

• Starting a small business or nonprofit initiative to test entrepreneurial ideas

• Participating in a hackathon, creative challenge, or innovation lab

Reflection Prompt: After each project or milestone, ask yourself: Did I enjoy this? What did I learn? What would I do differently? Would I want to do this full-time?

Side projects often turn into full-time opportunities, or just as importantly, they clarify what you don’t want. Either way, you’ll gain confidence, insight, and experience.

Move Forward - Action Steps to Build Momentum

Now that you've done the inner and outer work, it's time to translate reflection into results. This is the phase where clarity meets action, where you begin to experiment with the insights you've gathered, test your hypotheses, and actively shape the next chapter of your professional life. Momentum doesn’t require a giant leap; it begins with a simple shift from thinking to doing.

Building momentum doesn’t mean rushing forward blindly, it means taking intentional, informed steps that help you test ideas, build confidence, and maintain your motivation. These steps are often small and iterative. You don’t need to have every answer before taking action. In fact, action often generates clarity. You might try a course and realize you love it. Or you may take on a side project and decide it’s not for you. That’s not failure, that’s progress.

This stage is about gathering feedback from the real world and staying flexible as you learn more. It's also about embracing the idea that your career path is a living, evolving thing, not a rigid plan carved in stone. Your sense of purpose and preferences may shift as you grow, and that’s natural. The more agile and open-minded you are, the better equipped you’ll be to adapt and thrive.

Momentum also builds emotional resilience. Taking concrete steps reduces anxiety and builds self-trust. Each small win, completing a course, updating your resume, reaching out to a new connection, reinforces your sense of agency. And when you encounter obstacles, as you inevitably will, you’ll have a growing toolkit of reflection, self-awareness, and action to draw upon.

In this section, we’ll outline practical strategies to help you move forward with intention, focus, and courage. Whether you're ready to apply for a new job, pivot to a different industry, or simply take the first steps toward something new, the path ahead begins here, with momentum fueled by clarity, courage, and commitment.

Set Short-Term SMART Goals

Big career shifts are made up of small, actionable steps. The SMART framework helps you move from vague aspirations to concrete, trackable actions:

• Specific: Clarify what you want to achieve. Avoid generalities like "network more" and opt for specifics like "connect with five UX designers on LinkedIn."

• Measurable: Define how you'll track progress. Set metrics: how many applications, how many pages written, how many hours studied.

• Achievable: Make sure it's realistic. You don’t need to redesign your life overnight.

• Relevant: Align it with your long-term vision. Choose goals that connect to your values and aspirations.

• Time-bound: Set a deadline. Without time constraints, goals tend to drift.

Examples:

• "I will schedule three informational interviews within the next two weeks."

• "I will complete a 10-hour beginner’s course in digital marketing this month."

• "I will update my resume and submit applications to five roles by next Friday."

Bonus Tip: Write your goals down and post them somewhere visible. Accountability breeds action.

Refresh Your Resume and LinkedIn

Your resume and LinkedIn profile are more than summaries of your past, they’re storytelling tools that highlight who you are becoming. As you shift direction, these tools should reflect your evolving brand.

Action Steps:

• Reframe experience in terms of transferable skills (e.g., team leadership, project coordination, communication).

• Use your headline and summary sections to reflect your current goals, not just past roles.

• Tailor each resume to the job description, emphasizing alignment with the employer’s values and mission.

• Add side projects, certifications, volunteer work, or freelance gigs relevant to your new direction.

Extra Credit: Ask a friend or mentor to review your resume and LinkedIn with fresh eyes. A second perspective can spot clarity gaps or opportunities for improvement.

Invest in Continued Learning

Identify gaps between where you are now and where you want to go. Upskilling doesn't need to be expensive or time-consuming, it just needs to be intentional. Even dedicating an hour a week can make a significant difference.

Learning Options:

• Enroll in online courses (Coursera, LinkedIn Learning, edX, Skillshare, etc.)

• Attend local or virtual workshops and industry panels

• Subscribe to newsletters or YouTube channels in your desired field

• Read blogs, whitepapers, or books by thought leaders in the industry

Pro Tip: Set a recurring calendar reminder for a weekly “Learning Hour.” Make it a habit.

Additional Ideas:

• Join book clubs or discussion groups related to your professional interests.

• Start a study group with peers also navigating transitions.

• Share your learning on social media or in a personal blog to solidify understanding and showcase growth.

Seek Guidance from a Career Coach

Sometimes, a neutral third party can accelerate your clarity and progress. Career coaches are trained to help you:

• Clarify goals and set strategy

• Identify limiting beliefs and blind spots

• Prepare for interviews and negotiate offers

• Improve personal branding materials (resumes, portfolios, online presence)

How to Find a Good Coach:

• Ask for referrals from peers or mentors

• Use coaching directories (e.g., International Coaching Federation)

• Attend a free discovery call to assess fit

Alternatives: If coaching isn’t feasible, look for mentorship opportunities through your network or professional associations. A trusted mentor can provide similar value and support.

Final Thought: Progress doesn’t require perfection. It requires consistent, purpose-driven action. Start where you are, use what you have, and trust that every small step is part of a larger shift toward alignment and fulfillment.

Uncertainty is the Beginning of Possibility

Feeling unsure about your career isn’t a flaw, it’s a signal. A sign that you’re ready to stop drifting and start designing. It’s okay not to have it all figured out. The truth is, most people don’t. Careers are no longer linear, one-size-fits-all journeys; they’re complex, evolving narratives filled with pivots, experiments, and growth. Embracing that complexity is not only wise, it’s empowering.

Uncertainty, when met with curiosity and courage, becomes one of the most valuable tools in your professional development toolkit. It prompts reflection, fuels reinvention, and challenges you to define success on your own terms. Even if the path ahead still feels unclear, know that every step you take to understand yourself, every conversation you initiate, and every risk you explore builds momentum. Over time, those efforts compound into a career that feels purposeful, sustainable, and uniquely yours.

At The Job Shop, we believe every professional journey is unique, and we're here to support you at every turn. We understand the challenges of modern work, and we know how powerful it can be to have the right resources, encouragement, and opportunities along the way. Whether you're exploring new fields, preparing for a transition, or just need a sounding board, we’re ready to help you navigate uncertainty and discover what’s possible.

Call to Action: Ready to start designing a career that fits who you truly are? Check out our Career Resources, explore open positions, or schedule a conversation with one of our expert advisors today. You don’t have to walk this path alone, we’re here to walk it with you.