Stop Climbing Ladders. Start ZigZagging.
How job-hopping went from being a liability into a strategic asset for career growth.
The traditional career ladder is dead. What replaced it is the career “zigzag” and it can be the key to future-proofing your career.
We asked our network of executives to share advice with their younger selves, specifically related to career moves and job changes, and how they view people today that they’re looking to hire/promote who have changed jobs every 2-3 years.
What we learned isn’t just career advice – it’s career intelligence.
THE GREAT CAREER NARRATIVE SHIFT
Remember when changing jobs every few years looked bad on your resume? Those days are over. What used to be called "job hopping" is now recognized as strategic career building but only if you can tell the right story and flip the narrative.
Dave Trifiletti, who went from the Army to agency account management to COO, explains his perspective: "I would never assume immediately that changing a job every 2-3 years is job hopping. In order to gain a breadth of experience, sometimes it requires you to move to different companies or different roles."
What matters now isn't tenure—it's the story you tell about intentional growth. Debbie Kemp, who started on the floor at Goldman Sachs and is now a global CHRO at a FinTech company, looks for candidates who can "articulate how each move enabled them to grow, add value, and bring those insights to our team."
The key question isn't "Why did you leave?" but "What did you learn?"
WHY ZIGZAGGING BEATS LADDER CLIMBING
Not all executives rise to senior levels by following a straight path. They got there by being curious, taking calculated risks, and building what we call a "transferable skills portfolio."
My own pivot from agency life to consulting was a lateral move that many called "foolish." Instead, it became the catalyst that leapfrogged me over my peers and even some former managers. What started as a lateral move ended up being the best decision for my career growth.
Diversity of experience is now more valuable than depth of tenure. Companies need leaders who can translate across functions, understand different perspectives, and adapt quickly to change. You can't get that by staying in one lane.
Our co-Founder Julie Davis, recalls filling two product manager roles with marketing professionals instead of traditional engineers. "They learned how to engage with engineers and translate their language of tech speak and understood the impact of our product on customers vs marketing metrics." That experience changed their career trajectory and pay because they were able to leverage their marketing skills in a new job family.
THE SKILLS THAT ACTUALLY TRANSFER
Our executives consistently highlighted the same capabilities that made their zigzags successful. These aren't technical skills (although those are important to learn), they're the leadership attributes that become more valuable as you advance:
Communication and relationship building remain foundational, but it's more nuanced now. The ability to navigate people, collaborate with empathy, and maintain transparency across generational differences is becoming essential as workforces become more diverse.
Problem-solving and adaptability compounds with each role. When you've solved similar challenges in different contexts, you develop pattern recognition that makes you invaluable.
Operational excellence and project management are increasingly critical. The ability to streamline processes, manage complex timelines, and coordinate across multiple stakeholders becomes essential as you advance to senior levels where you're orchestrating rather than executing.
Carly Feinstein learned more about "client service, project management, operational excellence, and setting boundaries in one year at Accenture than I did in the 17 years prior combined in Marketing roles." Her zigzag helped her build her portfolio of transferable skills that she was able to apply when she started her own consulting firm.
MAKING YOUR ZIGZAG STRATEGIC
The difference between successful career zigzagging and random job hopping comes down to intentionality. Here's how we recommend approaching it:
Lead with future outcomes. Before making any move, ask yourself: How does this help me get to where I want to be in 1, 3 or 5 years? Is this role the stepping stone to the future role I want? Every job is temporary anyway so be strategic.
Think portfolio, not position. Instead of optimizing for title or salary alone, consider how each role adds to your overall capability set. The most successful zigzaggers develop a portfolio of transferable skills that transcend industries and functions.
Connect the dots for others. Don't assume people will see how your diverse background creates value. As one executive stated, "If they have changed industries and they can articulate how each move enabled them to grow, add value, and bring those insights to our team, I view that positively."
THE FUTURE-PROOFING FACTOR
Whether you want to become the head of the company where you work or build your own, career zig-zagging helps you build more than skills – it builds resilience. In a world where AI is reshaping every industry, the professionals who survive and thrive will be those who can adapt, learn, and apply knowledge across contexts.
YOUR ZIGZAG ACTION PLAN
Ready to make your career moves more strategic? Start here:
Audit your current skills portfolio. What capabilities do you have? What gaps exist for where you want to go?
Identify your next learning edge. What skills or experiences would make you more valuable? What industries or functions intrigue you?
Activate your network strategically. Don't just network for your next job—network to understand where industries are heading and what skills will be valuable.
Practice your narrative. Can you clearly articulate how your diverse experiences create unique value? Practice until it feels natural.
Kimberly King, who started her career in music promotions, followed by editorial/content, transitioned to integrated marketing and now drives Inclusion in media, shared her mantra:
"Remain curious. If the advice I give myself is to remain curious, the advice I would give to someone who is early in their career is to remain curious."
The traditional career ladder promised predictable progress. The career zigzag promises something better: the skills, perspective, and adaptability to thrive in an unpredictable world. It’s not whether you should, but whether you’re being strategic about the direction of your zigs and zags.
You’ve got this. We’ve got you.
Your Career Wingwoman
The Inner Circle shares career intelligence from our network of senior executives who've committed to sharing practical guidance for career advancement. If you need more frequent and personalized intelligence, sign up for a paid subscription and a 1:1 with one of the executives in our network.