Why executives are pushed to build side careers

multidimensional career – As layoffs mount and jobs face structural disruption, executives are increasingly turning their “side hustle” into a deliberate career strategy—built alongside a full-time role, not in place of it. The push is less about fame than about transferable skills, or
Nearly 20 years ago, an MBA class ended one evening, and a marketing professor pulled a student aside—me. The question was simple: had I ever thought about teaching a course?
At the time. I was director of training at a large regional bank and juggling a full-time role with an infant at home. I wasn’t sure teaching fit into a life that already ran on tight schedules and an exhausting childcare bill. But the conversation landed anyway, especially because I could see it working around me. Two coworkers were already adjunct professors. Others consulted on the side, spoke at conferences, or ran small businesses.
So I brought the idea to my employer. I didn’t sell it as personal ambition. I framed it as a win for the bank, too—community involvement, my employer’s stated value. My students, I said, would be a strong match for retail bank branches, strengthening a talent pipeline. By teaching management courses, I could sharpen leadership and strategic planning frameworks that would carry back into my role. They agreed.
That decision became, in hindsight, the start of what I now call a multidimensional career—skills, purpose, and income streams that extend beyond a single corporate position.
The timing matters now more than ever. In 2025 alone, 1.1 million Americans were laid off, 54% more than the year before. The World Economic Forum projects that 22% of all jobs will be structurally disrupted by 2030.
The natural instinct in disruption is to “job hug”—to double down on the current role and make yourself indispensable within the four walls of your organization. But the leaders who navigate the next decade. the argument goes. will need career dimension: transferable skills and options when unexpected organizational changes arrive.
A multidimensional career is not the same as fractional work. where a leader leaves full-time employment to split their time as an executive across multiple organizations. It’s also different from a portfolio career that focuses on building experience inside an organization. A multidimensional career. instead. is built alongside a full-time position—outside a primary employer—making a leader more creative. connected. and skilled inside their day job.
In coaching executives. the claim is practical rather than theoretical: those who build multidimensional careers bring back broader networks. cross-industry pattern recognition. and fresh creative energy. That intentional expansion, the framing insists, isn’t quiet quitting and isn’t moonlighting on company time. It’s positioned as a way to become more valuable in a primary role.
And for many executives, it starts with one question: if you’re going to add something to your professional life, what’s the best place to aim it?
Vetting the “investment” is the first test. Many clients gravitate to the recognition that comes with a multidimensional career—leaders speaking on stages. serving on boards. or running a small side business. But what gets missed behind polished success stories. in this account. is the self-doubt. the calendar jockeying. and the critique that can come with starting a visible new role.
Casey, a senior director in agricultural financing, wanted to build a speaking career not for money or visibility. Her goal was to inspire young women to take leadership roles in agribusiness. As her speaking profile grew. her presence on stage increased brand awareness and positioned her company as a thought leader in its industry. Her CEO began shifting more corporate speaking and thought leadership off his plate and onto hers. Her purpose amplified the company’s profile in the marketplace and aligned with her personal mission.
That’s the kind of outcome an executive is asked to design before committing limited time and energy: what outcomes are you hoping to create, what problem will you solve, who benefits, and how the work will stay sustainable once initial excitement fades.
Then comes the other reality check: the skills you already rely on may be your most bankable edge. With AI automating more tasks every day, the argument is that distinctly human skills carry forward no matter where a career goes.
Jennifer. a technical project leader at one of the world’s largest delivery and supply chain companies. thought her skills were too niche to monetize outside her day job. She started a vending machine side venture for passive income anyway. Her project management instincts took over. She analyzed customer demographics, purchase patterns, and restock rates so effectively that she built innovative new product distribution methods. The vending ownership company hired her as a part-time consultant to train other operators on her approach. The result. in this telling. was a new dimension she didn’t expect—and perspectives she brought back into her corporate role around operations and customer analytics.
The recommended method is straightforward: reflect on where coworkers or peers repeatedly ask for help. Track the tasks that feel effortless for you and hard for others. Watch for the moments when your energy surges and you lose track of time. Those signs point to transferable advantages—then you map where they create value outside the organization and where they can return to your nine-to-five role with a fresh perspective.
Even then, there’s a conversation executives have to face head-on: how to ask permission—or at least present the plan—in a way managers can support.
It can feel risky to tell a manager. “I want to do something outside this role.” But the leaders coached in this account were surprised by how well their proposition landed when the value was clearly communicated. The broader business logic is tied to workforce development. The World Economic Forum’s Future of Jobs Report says 77% of employers globally plan to develop new skills in their workforce by 2030. Organizations. the story suggests. are already investing in continuous development—so the executive’s growth has to connect to what the company cares about.
When I first spoke about teaching at the university, the pitch focused on talent pipeline gains, community involvement alignment, and strategic leadership tools that would return to the workplace. Framed this way, the employer could say yes.
Melanie’s example is used to show how it can play out at the highest level. While she was a CFO. her speaking at conferences drove leads from clients interested in hiring her company and produced a record number of applications from potential employees. The organization responded with a dedicated marketing budget for her speaking efforts and made speaking a key business strategy.
But if executives are going to build something alongside their job, the hardest part may be the rule that contradicts common advice: subtract before adding.
Many pieces tell leaders to “find more time. ” “maximize your mornings. ” or “leverage AI to free up bandwidth.” This account argues the opposite: building a multidimensional career requires establishing structural capacity first. And it cautions executives against assuming AI will create that capacity.
A study by researchers at UC Berkeley’s Haas School of Business. published in the Harvard Business Review. tracked AI adoption at a 200-person tech company. The finding was stark: rather than reducing workloads, AI tools intensified them. Employees took on broader task scope, blurred the line between work and recovery time, and juggled more tasks simultaneously. The message is that system rigor—and real support—matters if you want bandwidth to be sustainable.
Casey’s needs reflected that. She needed childcare coverage for travel days and recovery time to catch up on day job responsibilities after returning. She needed boundaries and work systems so the strategy could last without sacrificing health or family.
For executives leading large teams, subtraction is framed as an organizational task as well as a personal one. The starting point suggested here is a two-week audit of where time actually goes—meetings. tasks. and decisions that could be delegated. The guidance is to be honest about which responsibilities leaders are holding onto because it brings a “helper’s high” from fixing and solving. Household responsibilities also count in identifying what can be shared or outsourced.
The leaders who build the most successful multidimensional careers, this account says, master delegation and boundary setting—skills that align with executive leadership itself.
By now. the story circles back to the first question that triggered all of this: what if teaching could become part of a fuller professional life?. Twenty years later, I’ve built a career with multiple dimensions, including coaching, speaking, writing, and teaching. Some of those dimensions have evolved over time and others have ebbed and flowed depending on client demands.
The payoff described here isn’t just variety. Having multiple ways to serve purpose is portrayed as a way to play the long game as the economy changes. corporate preferences shift. and new trends emerge. It’s also presented as protection from dependence on a single corporate client or industry shift. With broader client perspectives across different settings. the argument concludes. uncertainty continues to reshape executive careers—and leaders who navigate it well will look beyond a single role and add career dimension so expertise and potential aren’t contingent on any one organization’s survival.
executive careers side hustle multidimensional career layoffs job disruption World Economic Forum Future of Jobs Report AI workload UC Berkeley Haas Harvard Business Review delegation leadership