Career Pivots

Career Pivots and Starting Your Own Business

A career pivot can mean many things: a new job title, a new industry, moving from employment to freelancing, or starting up a new business. These are big decisions, but putting some focused work into self-reflection will help you to be more strategic about your next steps.

Ask Yourself These Questions

Interests and Values

  • Do I really want a new career, or do I just want to get away from a stale job, bad boss, or bad culture?
  • What are the jobs or careers of people I find fascinating, interesting, or successful?
  • Am I willing to start at a lower level and take a pay cut to enter a new career?
  • What's a project I've worked on that I am the  most proud of?
  • What things do I like most about my current/past job(s)?
  • What things do I dislike most about my current/past job(s)?
  • What are the jobs or careers of people I find boring and uninteresting?
  • What organizational cultures resonate with me, because they fit with my own values, style, and preferences?

Skills and Experience

  • What career capital (skills and experience) can I leverage?
  • What skills or qualities am I known for? How do my colleagues/bosses describe me?
  • What skills and credentials do I need to compete for a new job or career?
  • Am I willing to do what it takes to develop new skills and earn credentials?
  • What distinctive skills do people see in me, and what specific indicator(s) makes people see them (credentials, behaviors, experience, etc.)?
  • What are the most impressive elements of my resume? (Focus on unique and difficult accomplishments.)
  • What skills would I love to have acquired in three to five years’ time?
  • What new jobs or careers exist that require my skills and interests?
  • If I could have three different careers between now and retirement, which ones would I pick (if there were no obstacles or limits, and if I were a great fit)?

 

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Use Design Thinking 

Design Thinking is a creative, iterative approach to problem-solving that’s especially useful when making a career pivot. It emphasizes experimentation over perfection, which reduces pressure and helps you explore new directions with purpose and curiosity.

Empathize: Understand Your Needs

The assessment process helped you to identify what matters most to you: interests, values, skills you enjoy using, and environments where you thrive. 

On the Assess Your Next Steps page, we've included links to a wide range of assessments that may be helpful, including one that will help you decide if you are ready for entrepreneurship.

Take it a step further by conducting informal interviews with people in roles you’re curious about. Gather insight into what different careers actually look and feel like.

Define: Narrow Your Focus

Analyze the themes in your reflections and conversations. What problems do you want to solve? Who do you want to serve? Define a few career areas that align with your evolving sense of purpose and strengths. These don’t need to be perfect—they’re hypotheses.

Ideate: Brainstorm Possibilities

Generate a wide list of career directions. Include realistic and unconventional ideas. Think about roles, industries, or work formats (freelance, nonprofit, startup) you haven’t considered. Quantity matters—aim for range, not refinement. Don’t filter out ideas prematurely.

Prototype: Test Career Concepts Quickly

Prototypes are low-risk ways to explore a direction without a long-term commitment. Try job shadowing, volunteer projects, short-term gigs, informational interviews, online courses, or side projects. Create experiences that give you real insight into the day-to-day.

Evaluate and Iterate

After each prototype, ask: What did I like? What drained me? What surprised me? Use this feedback to refine your direction or try something new. This approach keeps you moving forward while reducing the pressure to get it right the first time.

Design Thinking reframes a career pivot as an experiment, not a leap. It helps you stay flexible, action-oriented, and focused on building a career that actually fits.

 

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Commit to Your Pivot

Once you’ve chosen your new direction, own it. Whether you’re moving into a new industry, function, or both, clarity is essential. Define the roles you’re targeting and the skills those roles require. Understand what’s realistic based on your experience and where you’ll need to build new credibility.

Network to Bridge the Gap

Because your background may not be a perfect match on paper, referrals and warm introductions are key. Conversations often lead to interviews that cold applications won’t. Be transparent about your pivot, curious about their experience, and clear about what you’re hoping to do next.

Update Your Resume

Your resume should showcase transferable skills and downplay experience that doesn’t support your pivot. Start by analyzing job postings to identify core skills for your new path. Reframe past accomplishments to emphasize adaptability, leadership, results, and any relevant tools or domains.

Use a headline and/or summary at the top of your resume that reflects your new direction, not your past. Move relevant experience to the top, even if it’s from volunteer work, side projects, or certifications. Remove or condense roles and tasks that distract from your pivot.

Position Yourself on LinkedIn

Your LinkedIn headline should immediately signal your new focus, as this is what shows up in search results. Use terms aligned with your target role, not your old title.

Revise your About section to tell a clear, future-facing story: who you are, why you’re making the pivot, and what value you bring. Use language that conveys enthusiasm, transferable strengths, and recent steps you’ve taken (e.g., courses, projects, mentorships) to build credibility in your new space.

Edit your Skills section to highlight relevant skills (move them to the top, get endorsements for them, add them to relevant Experiences). 

Own Your Pivot in Interviews

Expect to be asked: “Tell me about yourself.” Use this as your pivot moment. Briefly explain where you’ve been, then clearly state what drew you to your new direction, what you’ve done to prepare, and what strengths you bring.

Throughout the interview, tie your answers back to the role’s needs. Show you’ve done your homework, that you’re confident in the value you bring, and that you’re not just exploring, you’re ready to contribute.

 

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Tools and Resources to Help You

Tools

LinkedIn Resources

Design Thinking Resources

Other

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