Pivot Summary

When you hit a wall in your career, that’s not the signal to stop—it’s the signal to pivot.

1. Career shifts are normal, not something to fear.

Gone are the days when people stayed at one company until retirement. Today, changing jobs or even industries has become the norm, with the average American staying in one position for just four to five years. It’s natural to feel stuck or unsatisfied in a role, but that dissatisfaction can serve as a nudge to explore new directions.

Adam Chaloeicheep’s journey illustrates this. He quit his job as a creative director to recharge in Thailand, where meditation helped him gain clarity on his values and passions. Eventually, he launched his business, ABC Design Lab, which aligned with his interests in technology and entrepreneurship. His bold move paid off both professionally and personally.

Similarly, career pivots don’t have to mean leaving your company. Amy Schonberger transitioned from senior creative strategist to director of digital entertainment just by redefining her role. She took over social media activities others disregarded, and her expertise grew into a new career path.

Examples

• Adam Chaloeicheep left his job, redefined his focus, and built a thriving design business around his passions.
• Amy Schonberger used social media responsibilities as a stepping stone to a new role within her firm.
• A Gallup poll revealed that up to 90% of employees feel unfulfilled in their jobs, pushing them to rethink their paths.

2. Define your personal values to guide your next steps.

Before you dive into any career change, it's wise to step back and assess what truly matters to you. This clarity helps you align your vision for the future with your core values, making each decision purposeful instead of random.

For instance, Justin, a real estate professional unhappy in his family business, identified his health, environment, relationships, and financial security as top priorities. With this clarity, he pursued an opportunity in a healthier, inspiring environment—getting a scholarship to a business school in San Diego.

Similarly, Gillian felt unfulfilled in her trajectory as an attorney. By connecting her values—flexibility, an active lifestyle, and community—she transitioned from law to a yoga teaching career, eventually securing a managerial role in the yoga business. This alignment gave her fulfillment and stability.

Examples

• Justin switched from real estate into business school when his values signaled a needed change.
• Gillian left a secure legal job to build a career around her passion for yoga and health.
• Values-driven shifts steer decisions and keep long-term direction intact.

3. Embrace your strengths before making the leap.

When considering a change, take stock of your strengths and financial circumstances. Starting over completely isn’t necessary—you can build upon your existing skills and position yourself to succeed in a new arena.

Jason Shen tapped into his lifelong interest in computers when transitioning from content marketing to product management. A rediscovered kindergarten evaluation affirmed his confidence, showing how his talents could translate into this new role.

Similarly, Andrew Deffley prepared financially when pursuing acting after eight years in production management. He layered his move with part-time work leveraging his existing production skills, ensuring security while he transitioned into his dream job.

Examples

• Jason Shen reconnected with childhood skills to validate his pivot into product management.
• Andrew Deffley bankrolled his acting aspirations with a financial safety net and part-time work.
• Building on existing talents eliminates the fear of starting over from scratch.

4. Build relationships to assist your career change.

Your connections are invaluable when transitioning. Instead of hunting for a single long-term mentor, consult a variety of advisors and assemble a support network to guide you with diverse perspectives.

Jenny Blake, the author, reached out to expert Susan Biali for a one-off career consultation. This evolved into an enduring mentorship that helped guide her further. Similarly, Luke Schrotberger sought advice from a peer within his company when trying to transition roles.

Online communities and networks can also play a vital role. Lora Koenig found a group through the author’s program that supported her leap from product management to volunteering with the Peace Corps in Ethiopia.

Examples

• Jenny invited advice from different mentors, including long-term guidance from Susan Biali.
• Luke Schrotberger consulted an experienced colleague for an internal pivot.
• Lora Koenig’s online network supported her jump to a meaningful life abroad.

5. Actively seek new opportunities.

Instead of waiting for opportunities to come to you, actively seek—or create—them. Pivoting requires proactivity and leveraging your strengths to uncover hidden chances.

Shawn Henry at the FBI successfully transitioned to a supervisory role by applying the investigative skills he already had to a new area—cybercrime—instead of waiting on conventional opportunities. Similarly, Daniel Kelleghan turned his love for photography into a rich new career by using Instagram to showcase and market his talent.

Examples

• Shawn Henry secured a leadership role by spotting potential in an emerging industry: cybersecurity.
• Daniel Kelleghan leveraged social media to build a dream career in photography.
• Opportunity arises when you’re proactive and intentional about your goals.

6. Use small experiments to test the waters.

Great changes don’t have to start with an all-or-nothing gamble. By piloting your ideas with minimal risk, you can figure out what works and make adjustments.

Christian Roberts and Bill Connelly tested their comedy show format through initial small-scale performances. When attendance flagged, they shifted efforts toward networking and building an online presence. Likewise, consultant Bob Gower ran pilots for his bondage course idea anonymously, realizing the project wouldn’t scale but still learning lessons he applied elsewhere.

Examples

• Christian and Bill grew their comedy show by adapting after each trial run.
• Bob Gower tested an unconventional project under a pseudonym to limit exposure.
• Piloting allows you to experiment without high stakes.

7. Set clear markers to overcome launch anxiety.

Fear of failure stalls many pivots. Combat this by setting concrete launch criteria—whether it’s a financial benchmark, a specific date, or external validation—so you know when to move forward confidently.

Tom Meitner chose a financial goal of earning $2,500 as a freelancer before quitting his job. He hit his target and over time built a six-figure income. Meanwhile, John and Christian transitioned through multiple pivots, learning to adapt plans rather than viewing adjustments as failures.

Examples

• Tom Meitner launched his copywriting business after reaching set financial goals.
• John and Christian learned adaptation is a core part of any pivot.
• Launch criteria transform uncertainty into measurable action plans.

8. Pivoting benefits companies when managers support mobility.

Employees feeling stuck often see quitting as their only choice. Managers can tackle this by fostering workplace mobility and encouraging open discussions about career growth.

Courtney John-Reader left her job because she felt undervalued despite liking her work. Instead, managers can follow Whole Foods’ example, which helps employees grow through certification programs. Continuous learning ensures employees grow without leaving.

Examples

• Open dialogues at work could retain employees like Courtney John-Reader.
• Whole Foods provides job-specific training to encourage internal shifts.
• Proactively supporting career goals leads to loyalty and engagement.

9. Pivoting is a repeated process.

Career shifts aren’t one-time decisions but an ongoing process. Moments of stagnation in your career are just opportunities to go back to the pivot method: plant, scan, pilot, and launch.

Christian and John, who left corporate trading for urban farming, pivoted back into new technology careers after realizing farming wouldn’t secure their future. Similarly, failure isn’t the opposite of success—it’s a natural part of adapting and emerging stronger.

Examples

• Christian and John tackled multiple pivots until they landed fulfilling roles.
• Restarting a pivot process ensures continual growth and discovery.
• Viewing change as cyclical makes each pivot less intimidating.

Takeaways

1. Identify your long-term values and let them guide short-term goals before undertaking any change.
2. Run low-risk experiments to validate your ideas and steer clear of unnecessary, big leaps all at once.
3. Build multiple connections, both informal and formal, to support and inspire steps toward your next career move.