The Context Gap: Why Athletes Struggle to Be Fairly Evaluated After Career Transition

I recently read a LinkedIn post from former LA Galaxy and U.S. Men's National Team player AJ Delagarza that really resonated with me. He spoke about the often difficult transition for athletes from their athletic career to the corporate world. Confusion around how "experience" actually translates, and what value athletes bring to their potential new environment, often provides a dark cloud during this athlete transition.

One of the most under-discussed challenges athletes face after their playing careers end has nothing to do with work ethic, intelligence, or ambition. It has everything to do with context, opportunity, and fair evaluation.

For many athletes, the transition out of sport is not a lack-of-direction problem—it is a translation problem. Skills honed over decades are suddenly judged through hiring frameworks and professional lenses that were not designed to evaluate them properly. The result is a frustrating and often disorienting roadblock that countless former athletes encounter: “You don’t have enough experience.”

This statement is usually delivered without malice. But it is almost always incomplete.

The Context Problem: Experience That Doesn’t Fit the Template

Most professional evaluation systems are built around linear career paths. Internships lead to entry-level roles. Entry-level roles lead to management. Management leads to leadership. Years in seat often matter more than depth of responsibility.

Athletes do not follow this model.

By the time an athlete finishes their playing career, they may have:

• Managed intense performance pressure on public stages

• Worked under constant evaluation with short feedback loops

• Operated in high-accountability environments where results are binary

• Learned rapidly from failure because adaptation was not optional

• Navigated leadership dynamics without formal authority

Yet none of this fits neatly into a résumé section labeled “Relevant Experience.”

The issue is not that athletes lack experience. It is that their experience is contextualized differently—and most evaluators are not trained to translate it.

This creates a gap where athletes are overqualified in reality but under-credentialed on paper.

The Opportunity Gap: Being Locked Out of the Starting Line

Even when athletes understand how their skills translate, they still face an opportunity bottleneck.

Hiring systems tend to reward:

• Familiar titles

• Recognizable employers

• Predictable career arcs

Athletes often enter the post-playing world without any of those markers, regardless of how capable they are.

This leads to a paradox:

• Athletes are told to “start at the bottom”

• But the bottom often assumes a lack of maturity, leadership, or real-world pressure

• Which is rarely true

As a result, many former athletes are either:

• Passed over entirely, or

• Placed into roles that dramatically underutilize their capabilities

Neither outcome creates momentum. And without momentum, it becomes difficult to prove what you already know you can do.

The Fair Evaluation Problem: When “Lack of Experience” Is a Proxy for Uncertainty

When someone says an athlete lacks experience, what they often mean is this:

“I don’t know how to assess you.”

This is not an indictment of the athlete—it is a limitation of the evaluator.

Fair evaluation requires:

• Understanding non-traditional paths

• Valuing transferable competencies over titles

• Separating time served from value created

Athletes are frequently assessed using tools that were never designed to measure them. The result is a default rejection based on uncertainty, not capability.

This is why athletes can ace conversations, impress in interviews, and still be told they are “not quite the right fit.”

The system is uncomfortable making a bet without familiar reference points.

How Athletes Can Overcome These Career Transition Barriers

While these challenges are systemic, there are practical ways athletes can regain leverage in the transition process.

1. Control the Narrative Through Context

Athletes must proactively frame their experience in terms decision-makers understand:

• Outcomes over roles

• Accountability over tenure

• Learning speed over years

Do not assume people will make the connection for you. Most will not.

2. Seek Environments That Value Asymmetry

Some industries—entrepreneurship, investing, sales, operations, performance-driven roles—are better at valuing non-linear backgrounds. These spaces are more comfortable with unconventional profiles because results matter more than pedigree.

3. Build Proof, Not Permission

Short-term projects, advisory roles, writing, investing, operating, or consulting can create evidence faster than traditional job ladders. Proof compresses time and reduces perceived risk.

4. Align With Translators

Mentors, sponsors, and operators who understand both sport and business can bridge the gap. They help validate capability in rooms where athletes might otherwise be misunderstood.

A Shared Roadblock—And a Shared Responsibility

This roadblock is not unique. It is experienced by athletes across sports, levels, and geographies. It is not a failure of effort or ambition. It is a structural mismatch between how athletes develop and how professional systems evaluate.

But there is shared responsibility.

Athletes must learn to articulate their value in new languages. Organizations must evolve how they assess talent beyond traditional heuristics. The opportunity cost of failing to do so is enormous—not just for athletes, but for industries that benefit from leadership, resilience, and performance under pressure.

The question should not be whether athletes are “experienced enough.”

The better question is:

Experienced enough for what—and by whose definition?

Until that question changes, the transition will remain harder than it needs to be.

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