“Bet on Yourself”: Jessica Samuels Offers Practical Tips for Navigating Career Crossroads

In an industry as dynamic as healthcare, it’s not uncommon for individuals who are well-established in their careers to find themselves at a crossroads, not sure of which path to pursue or how to navigate it effectively.

It can be overwhelming, to say the least.

The good news is that most of the time, people already have the answer, according to Jessica Samuels, CEO and Chief Talent Officer at Evolve Career. During a recent Flourish episode, she talked spoke with host Sarah Richardson (President, 229 Executive Development Community) about the importance of listening to your instincts – and trusting them.

Jessica Samuels

“When we start to learn how to trust our gut, and when we start to really get clear on what our values are, decisions actually become much easier,” she said. The challenge, in fact, comes “when we haven’t done that inner work to say, is this role or is this opportunity going to feed my soul, or is it going to drain me?’”

Choosing the right path

And Samuels isn’t just talk; throughout her career, she has made it a point to practice what she preaches. One of those times was last year, when she found herself at a career junction. “I was thinking about pursuing another C-suite role, specifically Chief People and Culture Officer, but it was happening earlier than I had planned,” she recalled. 

The question was whether to remain on that path, or to pursue a different direction that offered more fulfillment, but also came with added risks. Her answer? “I trusted my gut in the moment that I wanted to serve more people outside of one organization,” Samuels stated. “I knew that I was a community builder. I knew that relationships were huge for me,” along with mentoring, coaching, and leading Diversity, Equity, Inclusion and Belonging (DEIB) initiatives.

She also knew that accepting an executive HR position might limit the time and energy she had to focus on these priorities. And so, Samuels chose to scale her business in a way that enabled her to devote more time to executive leadership and career coaching. “Without following my intuition in that decision, I think I would have forced myself to follow the plan that I had laid out, instead of asking what feels right,” she said.

Of course, the ability to lean on instincts and be willing to pivot isn’t necessarily innate in all individuals, including leaders. Samuels – who has held a number of roles during her career, including Chief Learning Officer and Chief Talent and Culture Officer – hopes to change that. 

Below, she shared advice for those who are thinking about making a transition, or who simply want to boost their professional profile.

• Trust but tweak. Although Samuels is a strong proponent of trusting one’s gut, she also believes it’s about more than just intuition. In other words, a strategy is still needed. “You’ll have a bit more peace with the final decision if you create a strategic plan,” she said, which includes short-term and long-term objectives. However, it’s also important to “give yourself permission to tweak the strategy and the plan that you’ve created and look to see if it’s still working.” The key is in achieving a balance of “leading with intuition while also being a strategic thought leader.”
• Be proactive. Any aspiring leader should “know your brand and have an idea of where you want to be in 3-5 years,” but that isn’t enough, she cautioned. “If you’re in a role and you're waiting for someone to approach you with a promotion and thinking, ‘I’ll weigh it when it happens,’ that’s not the right approach.” Instead, Samuels said it’s time to “reverse engineer” and cultivate the skills and experiences that the role might require.
• Create the role. Another option? Don’t wait; create. “Maybe you’re going to design your dream career role within an organization,” or take a page from her book and say, “I’ve been a CEO for 15 years, but I’m going to scale this part-time business into full-time, and you're prepared to do that.”
• Make it fun. It is possible to “connect what you do for fun or outside of work to your main gig,” said Samuels, who has a passion for tech and product development, along with HR and coaching. “I wanted a C-suite role that gave me the ability to do all of those; to get my hands messy in all of those aspects.”
• Expand your vision. When contemplating a career change, she strongly advised candidates to think outside of their current role – or even industry. “Be open to taking roles that may not be traditionally what you’ve had,” she said. It’s also critical to keep in mind that a CHRO role, for example, may look different across organizations. “But if it has bits and pieces around where your superpowers lie, it may be worth taking the risk and gaining skills that may help with your next role.”
• Prioritize self-care. For most, if not all, leaders, finding and maintaining balance can be challenging, noted Samuels, who urged individuals not just to carve out time for self-care, but to put it in writing. That’s precisely what she does in her coaching program, during which leaders are asked on Day 1 to outline their self-care plan and are held accountable to it. And it’s not just clients – Samuels commits to weekly, monthly, quarterly, and annual self-care goals. “You have to block it in your calendar, because if you don’t, you won’t do it.”

For leaders, modeling this type of behavior has become critical, she believes. “If we’re walking around feeling scattered, we’re not going to get the job we want. We’re not going to get the board role we want. We’re not going to make an impact as a leader to our teams. We’re not going to wow our clients. We’re going to be depleted for our family.”

Finally, Samuels encouraged listeners to be their authentic selves and “show up boldly every day,” and not worry about making mistakes or looking less-than-perfect. In fact, “to be a fearless leader is to reject perfectionism,” she said. “It’s being comfortable with risk-taking. It’s taking chances on yourself, betting on yourself, and believing that you are the solution to someone’s problem.”