What If the Bigger Career Risk Is Never Trying?

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What If the Bigger Career Risk Is Never Trying?

Career decisions are often framed around the possibility of failure. What if the new role does not work? What if leaving a familiar organization proves to be a mistake? What if a professional gives up stability and later wishes they had stayed?

But those questions only capture one side of risk.

In this episode, Jennifer Simpson Carr speaks with Eva Wisnik, founder and president of Wisnik Career Enterprises, about a different question: What happens when the greater career risk is never giving yourself the opportunity to discover what you are capable of?

For Eva, the question became personal when she left her role as director of recruitment and training at Cadwalader at age 33 to start her own company. Looking ahead 20 years, she asked herself which decision she would be more likely to regret. Her conclusion became a philosophy she continues to share with professionals navigating career uncertainty: “The bigger risk is not trying than risking failure.”

That perspective does not mean every uncomfortable moment requires a career change. Nor does it mean uncertainty should be ignored. Instead, Eva argues for a more thoughtful way of evaluating professional risk; one grounded in growth, values, relationships, evidence of past capability, and enough self-awareness to distinguish genuine intuition from fear.

For law firm leaders, legal marketers, business development professionals, and others navigating a profession experiencing significant change, that distinction matters. Leadership is not only about knowing how to respond to change once it arrives. It is also about developing the perspective, confidence, and relationships that allow professionals to continue contributing when certainty is unavailable.

Is Staying Put Always the Safer Career Decision?

People naturally seek certainty, Eva explains. When an opportunity introduces unfamiliarity, the mind can quickly generate reasons to remain where things feel known.

The problem is that familiarity and security are not necessarily the same thing.

Eva encourages professionals to think of themselves as their own “career portfolio.” Skills, knowledge, experience, relationships, and exposure to new challenges build that portfolio over time. A familiar job may feel secure, but if a professional has stopped learning, growing, contributing at a higher level, or developing new capabilities, staying may eventually create a different kind of vulnerability.

Her question to professionals considering whether to remain in a role is straightforward: If you stay for another year, how much more will you have learned or grown?

That reframes the career decision. Instead of evaluating only what someone might lose by leaving, it also asks what they may lose by remaining stagnant.

Organizations change. Leadership changes. A trusted boss may leave. Firms may merge or evolve in ways an individual professional cannot control. Eva’s view is that the most reliable form of career security, therefore, comes from continuing to increase what an individual can contribute.

For law firm leaders, the same concept has an organizational implication. Talented professionals are assessing whether their roles enable them to grow, influence decisions, develop new capabilities, and contribute meaningfully. A title or compensation may matter, but they are not the only measures professionals use when determining whether an environment still supports their success.

Creating meaningful opportunities for talented people to grow can therefore become part of how firms retain capability, not simply how they fill roles.

How Can Professionals Tell the Difference Between Thoughtful Risk and Escape?

Career dissatisfaction can make almost any alternative look attractive. Eva cautions against making the next decision primarily as a reaction to the current one.

When candidates repeatedly describe what they no longer want, she redirects the conversation. “You have to tell me what you do want, not what you don’t want.”

Trying only to escape discomfort can lead to impulsive decisions because the professional evaluates opportunities based on their distance from the current problem rather than on alignment with the future they want.

The more useful question is whether the source of dissatisfaction is temporary or fundamental.

Organizations can experience periods of turmoil. Leadership structures can change. Mergers, new bosses, and internal disruption can create difficult stretches. Those conditions do not automatically mean leaving is the right decision.

Values misalignment is different.

Eva describes professionals who once felt involved in strategy but later found themselves excluded from important conversations, unable to contribute ideas on the same level, or operating under leadership whose values no longer aligned with their own. When that shift appears unlikely to change, the issue becomes deeper than temporary frustration.

This is where thoughtful career evaluation requires clarity.

• What kind of work does the professional want to be doing?
• Which skills do they want to use?
• What kind of environment allows them to perform at their best?
• Which values are essential to feeling that their work matters?

For leaders, these questions work in reverse as well. When high-performing people appear disengaged, the underlying issue may not simply be workload or compensation. It may be whether they still believe their abilities are being used, their ideas matter, and their values fit the organization around them.

What Does Career Success Actually Look Like?

Titles and compensation are visible markers of career progress. Eva does not dismiss them. But she believes sustainable career success requires something more fundamental. “The way I define success in terms of making good career decisions is when the skills and values fit.”

That framework begins with understanding the skills a person naturally enjoys using.

Eva encourages professionals to look backward for evidence. The skills they rely on today may be more sophisticated than they were earlier in life, but the underlying patterns often remain recognizable. Someone may consistently have been the person asked to organize, plan, analyze, build relationships, solve problems, sell an idea, implement a system, or bring people together.

Those patterns matter because professionals can easily discount skills that feel ordinary to them precisely because they use them so naturally.

Jennifer connects this to imposter syndrome. In the legal profession, capable professionals may diminish their own achievements by telling themselves they have “only” managed a particular initiative or have “only” used a skill for a short period. Yet that capability may be extremely valuable in an organization where it does not already exist.

Eva offers a useful reframing of that uncertainty: instead of assuming that not knowing how to do something means you are unqualified, treat it as something you do not yet know how to do.

The evidence for future capability often exists in past growth.

Her practical recommendation is to keep track of accomplishments, particularly moments when something once felt unfamiliar but eventually became part of your skill set. That record becomes valuable when a new opportunity creates doubt. It provides concrete evidence that uncertainty has preceded growth before.

For leaders, this is also a reminder that professionals may not always recognize their own readiness. Managers, mentors, recruiters, and trusted colleagues can help people see progression that has become difficult to recognize within their day-to-day work.

Sometimes leadership means helping someone understand that the evidence of readiness already exists.

Can Uncertainty Become a Source of Opportunity?

Fear does not disappear simply because someone becomes experienced.

Eva describes fear of failure, perfectionism, and imposter syndrome as recurring issues in her work with law firm professionals at different levels of seniority. What changes is not necessarily the presence of uncertainty but the lens through which someone interprets it.

Is the situation a threat, or is there an opportunity inside it?

Eva has applied that question throughout her own career. She speaks about living through six recessions, significant financial uncertainty in her business, and now another period of change driven in part by artificial intelligence.

Her response is not to deny disruption. It is to ask what can be built because of it.

She sees the possibility that AI tools could take over more mundane, repetitive work, creating additional capacity for strategic initiatives, relationship-building, best-practice development, and other areas that professionals consistently say they need more time to address.

Jennifer connects that perspective to leadership. Headlines about AI, jobs, and instability can create a climate dominated by perceived threats. Leaders have an opportunity to introduce a different question: What can we learn from this, and how can we position ourselves and our colleagues to thrive within changes that are unlikely to disappear?

That shift from passive concern to active participation is central to Eva’s approach.

Later in the conversation, she explains how she responds when the environment feels overwhelming: she talks to clients. She asks what they are seeing and hearing. When similar themes begin emerging repeatedly, she looks for ways she can contribute to the solution.

A colleague once described her as a futurist. Eva’s response was simpler: “All I’m doing is listening.”

That is an important leadership insight. Anticipating change does not always require predicting the future. Sometimes it begins with listening closely enough to recognize recurring problems before they fully crystallize.

Professionals have more agency when they see themselves as contributors to whatever comes next rather than people waiting for change to happen to them.

Why Are Relationships Becoming Even More Valuable?

Skills and knowledge form part of a career portfolio. Eva believes relationships are just as important.

Neither individuals nor organizations can predict every change that will affect their careers. What professionals can build are networks of people they trust; people they can call when they need perspective, information, advice, encouragement, or a clearer understanding of what is happening elsewhere in the profession.

For Eva, those relationships represent one of the strongest forms of career certainty available.

Jennifer describes the same dynamic in her own career. Her definition of success includes being happy, thriving, and working in a culture and environment that fits. Relationships throughout the legal industry helped her reach that point.

The conversation also highlights the particular value of in-person interaction.

Eva argues that trusted professional relationships require investment and can be difficult to build entirely at a distance. Jennifer adds that conversations over coffee, body language, pauses, eye contact, and other human signals carry information that technology cannot reproduce in the same way.

Rather than making relationships less important, the growing presence of AI may make deeply human professional connections more valuable.

This has direct implications for legal marketing and business development leaders. Their work already requires them to identify opportunities, create relationships, interpret what clients and colleagues are experiencing, and persuade others to consider possibilities that may not yet be obvious.

Technical capabilities will continue to matter. But the ability to listen, connect, interpret, advise, and earn trust remains central to how professionals create value.

How Can Professionals Learn to Trust Their Own Judgment?

Knowing that growth requires some degree of risk does not automatically make the next decision easier.

Eva recommends making career progress visible.

One exercise is to return to the job description associated with your role and update it based on what you actually do today.

• What responsibilities have expanded?
• What work are you performing that was never part of the original role?
• What new capabilities have you developed?
• Are you still growing—or are you doing less of the work you expected to do?

Putting that progression on paper helps replace an abstract feeling with evidence.

Eva also recommends journaling, particularly during periods of significant change. Writing down fears can help separate realistic concerns from the stream of hypothetical outcomes that otherwise continues circulating in the mind.

That distinction eventually leads to another: fear versus intuition.

Looking back on the decision to start Wisnik Career Enterprises, Eva remembers being deeply concerned about financial security. But she also remembers having a clear internal sense that starting the company was the right move.

Her advice today is simple: “Trust your gut.”

But she immediately adds an important qualification. Gut instinct and fear are not the same thing.

Fear often generates imagined problems and future scenarios. Intuition, in her description, feels different. Developing enough awareness to tell one from the other makes self-trust possible.

Mentors can help with that process, too.

When a professional is struggling to believe they are capable of taking the next step, someone who knows their work, character, and abilities may see the situation more clearly. As Eva explains, there are moments when mentors believe in us more than we believe in ourselves.

That belief can become the bridge between readiness and action.

The Takeaway for Law Firm Leaders

Career risk is not limited to making the wrong move. There is also risk in remaining somewhere that no longer creates growth, uses a professional’s strongest abilities, or aligns with their values.

For individuals, navigating that tension requires evidence, perspective, relationships, and self-trust. Professionals can build security by continually expanding their career portfolios rather than relying entirely on the stability of any particular organization.

For law firm leaders, the episode raises a parallel responsibility. People are more likely to thrive where their skills are valued, their voices are heard, their development continues, and trusted relationships are actively built. In periods of uncertainty, leadership means helping people see not only the threats around them, but also the opportunities they may be capable of creating.

Sometimes the most consequential career question is not, “What if I fail?” It is, “What happens if I never find out?”

Resources

• Eva Wisnik, Founder and President, Wisnik Career Enterprises: https://www.wisnik.com/about-us/
• Jacob Wisnik, Recruiting Specialist, Wisnik Career Enterprises: https://www.linkedin.com/in/jacobwisnik/
• Your Fairy Job Mentors: Secrets for Success, Eva Wisnik: https://yourfairyjobmentor.com/
• Legal Marketing Association: https://www.legalmarketing.org/
• Dawn Longfield, Former Chief Marketing Officer at Davis & Gilbert: https://www.linkedin.com/in/dawn-longfield-b130325/
• Jennifer Manton, Client Director, US at Herber Smith Freehills Kramer: https://www.linkedin.com/in/jennifermanton/
• Greg Fleishmann, Director of Client Development at WilmerHale, and Advisory Council on Furia Rubel’s International Faculty: https://www.furiarubel.com/our-team/members/gregory-fleischmann/
• Why Law Firm Leadership Starts With Trust, Self-Awareness and Influence, On Record PR: https://www.furiarubel.com/podcasts/why-law-firm-leadership-starts-with-trust-self-awareness-and-influence/
• AI, Value, and the Hard Conversations Law Firms Can’t Avoid, On Record PR: https://www.furiarubel.com/podcasts/ai-value-and-the-hard-conversations-law-firms-cant-avoid/
• From Information to Experience: How Law Firms Can Deliver Real Value in a Saturated Content Market, On Record PR: https://www.furiarubel.com/podcasts/from-information-to-experience-how-law-firms-can-deliver-real-value-in-a-saturated-content-market/
• What Comes Next for Law Firm Leaders in 2026, On Record PR: https://www.furiarubel.com/podcasts/what-comes-next-for-law-firm-leaders-in-2026/