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HomeProperty InsuranceAre You a Contender or a Pretender?

Are You a Contender or a Pretender?


I am in San Francisco racing in the Rolex Big Boat Series with my seventy-foot sailboat. Rolex sponsored a dinner where tennis star and commentator Jim Courier spoke, offering a presentation that was both enlightening and inspirational. He made a statement that, as I recall, went something like this:

Success comes from the investment in the vision of long-term improvement and is built on the follow-up of short-term action.

Courier’s statement is a testament to what I have spoken about in many of my recent speeches about the Contender Mentality. It is about doing the hard work now while keeping your eyes on a larger horizon. It is about discipline, integrity, and commitment to mastery.

The difference between a contender and a pretender shows up everywhere, from the docks at a sailing regatta to the claims handling in the aftermath of a hurricane. Pretenders live in the shallow water of appearances. They build glossy websites, hire marketing teams, and speak in polished sound bites. They can look impressive from a distance, but they lack the ballast to stay upright.

A contender, on the other hand, has put in the miles. They know their craft because they have done the work, failed and learned, and then done the work again. They invest in skills that are real, not just projected. Their credibility is built over time and under pressure.

I have written before about this distinction in the insurance world. After disasters, contractors and public adjusters descend on devastated neighborhoods. Some arrive with deep experience, solid ethics, and a clear purpose to help. Others come only with slick brochures and promises of quick results.

The true professionals are the ones who take pride in doing it right, even when no one is watching. They understand that cutting corners may win a job today but will cost dearly in reputation tomorrow. The same principle applies in law, business, sports, and nearly every profession. Being a contender means stepping up when things get hard, preparing for that hard work, and not just when the spotlight is on.

I am reminded of stories like that of the “hero contractor,” the one who stayed late on job sites, checked every detail against building codes, and treated each home as if it were his own. That is a contender in action, as I wrote about in The Hero Contractor: Being a Contender and Not a Pretender, or of Austin Merlin Meyers, whom I wrote about in Austin Merlin Meyers Is a Contender. She managed to graduate from law school with honors while balancing motherhood and still earning the respect of her professors and peers. She didn’t rely on appearances or luck; she put in the work, day after day, with quiet determination. These examples show what happens when commitment meets competence. They prove that real success is born of substance, not style.

Mistaking pretenders for contenders carries heavy costs. It can mean lost money, wasted time, and emotional strain. A botched insurance claim, a shoddy restoration, or bad legal advice can ripple for years. Pretenders often overpromise and underdeliver. They disappear when results are due, leaving clients to pick up the pieces.

Contenders, in contrast, are steady even when storms hit. They stay accountable, adapt, and make things right because they care about more than just the transaction. They understand that trust is earned over the long haul.

Choosing between the two begins with careful observation. Look for depth, not just polish. Ask how someone has handled challenges similar to yours. Seek verifiable history, not vague claims. Pay attention to whether their words and actions align, and whether they speak with clarity about risks as well as rewards.

People who do not shy away from hard truths and who can explain complicated matters in plain language often have the kind of quiet confidence that real expertise brings. Contenders have no need to inflate themselves; their work speaks for them.

The path to becoming a contender is often not glamorous, but it is fulfilling. It calls for persistent learning, honesty about strengths and limits, and a dedication to delivering value even when no one is keeping score. It demands that you honor commitments, keep your word, and resist the temptation to sell easy answers. In the long term, substance will always outlast spin. The investment in your craft, coupled with consistent short-term effort, is what shapes a reputation that endures.

The modern landscape makes this distinction more urgent than ever. Technology and artificial intelligence have made it effortless to polish an image. Anyone can publish convincing copy or fabricate testimonials. But when lives, livelihoods, or property are at stake, only the real thing will do. Consumers must look past the gloss to find people who are anchored in knowledge and character. Professionals must choose whether to be driven by the need to seem impressive or by the commitment to truly be competent. I have warned about this in Hire Contenders Not Pretenders—Why Policyholders Have to be Careful Choosing Professionals In an Artificial Intelligence World.

Are you a contender who shows up and delivers, or a pretender living an illusion? The good news is that the probability of you being a contender is pretty high because only contenders would read this deep into a blog post about this topic. The habit of daily study into one’s profession is a sign of attempting mastery.

Thought For The Day 

“True mastery of any skill takes a lifetime.”
— J.R.R. Tolkien