Bold Moves: Transforming from Executive Leadership to Portfolio Mastery

Unlock the path from corporate executive to a thriving portfolio career, showcasing intentional choices and strategic career moves for lasting success.

Today’s guest post is by Merideth Mehlberg, author of YOUR FINEST WORK: Career Fulfillment In A Complicated World (CLICK HERE to get your copy).

Renata, Vice President of Operations for a large fintech company, arrived for coaching ready to leave her role, but fearful of the risks such a shift would include. She had grown fond of the status that came from helping lead a well-known brand. As we began our coaching, Renata sat with two different potential paths: thinking she had “one more big role” in her working at a similar-sized organization, or joining an early-stage company where she could wield greater influence at the C-level.

I recognized this dilemma as one I’d seen many times before when coaching executive clients. I knew that to support Renata best, we needed to help her become her career’s intentional architect, stepping back to clarify her guiding principles. Acting as her compass, they would provide direction from the inside out. To solidify her non-negotiables, I posed questions to distill what she wanted for her next chapter, asking:

What did she value most, and how must those values align with her work?

What did she long to spend her time doing at work?

What type of business problem did she want to help solve?

What type of work environment would bring out her best?

What would make her feel satisfied professionally?

These answers formed a set of criteria that allowed Renata to push past her fears. When we examined what she was afraid of, she recognized that optics felt important. If she moved to a smaller company, she worried that people would think she was wasting her experience. In the future, she wondered whether large companies would consider her for executive roles if she joined a startup now. After strategizing the risks, Renata was able to relax and confirm the intention to join a startup supporting a mission she felt passionate about.

Over time, the conditions at her current employer grew worse. Enduring a tenuous relationship with her boss and pressure to deliver with limited resources, Renata started taking recruiter calls. I coached her to identify and evaluate early-stage opportunities that suited her best. She learned of a startup poised to disrupt an underserved market she cared about. After careful investigation of likely fit, she accepted an offer to join the company as COO and tendered her resignation.

Renata spent the next year leading the startup to implement its operational model. Gradually she grew tired of execution and frustrated as her vision for the company diverged from that of the founder. Although she could have stayed on longer, the desire for freedom was too great, so she decided to leave to pursue a portfolio career.

A portfolio career is one where a professional enjoys multiple income streams, spreading time and effort among different projects, employers, and/or clients. For example, a person might teach at a local university, run a small business, sit on a board, and do fractional work for a company on retainer. The benefits of a portfolio career are many, including diversifying one’s income and gaining a sense of increased control and security.

Renata relished a portfolio career because it allowed her to do the work she loved: engaging customers to understand their needs, defining solutions to meet those requirements, and coaching emerging leaders to develop their professional potential. She could minimize time spent on the tasks she didn’t enjoy: implementing solutions. Shedding the piece that dragged on her energy left Renata feeling delighted in her work.

A key element of Renata’s career portfolio came together when we sketched out her capacity, including the ideal number and types of engagements to carry at one time. This involved solidifying her target client personas. When speaking with a prospective client, she adjusts her approach and pitch to match their needs. She set a cap on the number of engagements she can handle at one time, introducing scarcity that provides her an advantage when negotiating.

Through our coaching, Renata defined her target clients’ needs and what they value in her skillset. We developed her messaging to engage with her network to open doors. Renata now enjoys a variety of projects. The different roles create value in similar ways, AND they allow her to work on disparate business problems. The diversity keeps her interested.

A breakthrough moment came when I observed her penchant for tentative language when discussing her career. Once aware, Renata deliberately shifted her wording to appear resolute, using definitive language with herself and others. For example, she switched from saying “I’m hoping to have…” to “My next phase includes…” when discussing her career transition. That shift helped her embody gravitas and conviction, making her attractive to clients, partners, and employers.

Renata’s portfolio came together over time. She hires herself out as a coach to support individual leaders and companies looking to improve operational excellence. Some clients hired her directly; others she sourced through an agency, trading in some compensation for not having to find and land the business. She engaged in a half-time fractional leadership role with a privately-held fintech company, earning a retainer while accelerating the company’s operational readiness for an acquisition. After a year, she had streamlined the company’s operational model and hired her full-time replacement. She then shifted to an advisory role.

Finally, she also engages with early-stage companies as a retained advisor.

With multiple portfolio components, Renata enjoys a sense of professional detachment. When one engagement ends, she knows that another will take its place. Renata has grown in her confidence as a practitioner and enjoys the lifestyle of her time being her own. Her next move includes investing in startups she believes in, combining compensation and equity to share the upside in companies she is helping to grow.

Merideth Mehlberg, MCC, author of YOUR FINEST WORK: Career Fulfillment In A Complicated World, is CEO of Merideth Mehlberg Group. An ICF-certified Master Coach, she helps executives look forward to Monday mornings. For almost twenty years, she has walked alongside senior and high-potential leaders to define their career priorities, measure the gap with their current opportunities, and close the space between the two. Clients grow their professional satisfaction, impact, and success, transforming their careers and leadership styles from the inside out.

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