Capítulo 4
Confronting the Worst-Case Scenario
When facing major decisions about starting something new, I've held onto a simple mantra: What's the worst thing that could happen? The saying "no risk, no reward" doesn't withstand logical scrutiny. You don't need to assume risk in direct proportion to your desired reward-some risks are just plain stupid, and some of life's greatest rewards require little to no risk.
Instead of focusing on risk, I ask: "What is the worst thing that can happen?" followed by "Do I have a plan for dealing with the worst if it does happen?" If I can plan for disaster, everything short of disaster becomes manageable. If I can't handle the worst-case scenario, I probably shouldn't proceed.
This approach isn't about dwelling on catastrophe; it's about acknowledging possibilities and creating contingency plans. The worst-case scenario rarely materializes, but when properly anticipated, even the worst outcomes aren't catastrophic.
This worst-case-scenario decision-making first appeared when I was seventeen. After being rejected for a singing role in the church choir, I was cast as "the rebellious boy." As our choir tour approached, we needed to bring bagged lunches. With my parents out of town and sisters unwilling to help, I faced a dilemma. Standing with my buddies, we were staring at Terri Elizabeth Dillard-imagine Helen of Troy with a radiant smile and effervescent personality. She had never noticed any of us.
"I think I am going to ask Terri Dillard to make my lunch for me," I announced. My friends laughed, saying she didn't know I existed. My response was simple: "What's the worst thing that can happen?" Just rejection-and since we were at church, even a "no" would likely be delivered kindly. Miraculously, she said yes. The risk of private humiliation among teenage boys paled compared to the reward-thirty-two years of marriage to Terri Dillard. The reward exponentially outpaced any perceived risk.
"What's the worst that can happen?" isn't just devil-may-care thinking-it's acknowledging fear while seeking security. It means thoroughly analyzing potential consequences: Will this decision endanger my family? Can I recover from failure? What are the financial implications? Have I developed backup plans?
Don't wait for complete certainty-even our legal system only requires "beyond reasonable doubt," not absolute certainty. If "firmly convinced" is sufficient for capital murder trials, it should be enough for starting a master's program or launching your dream business.
Starting something new means looking past the comfortable status quo to see the end scene you desire. Sometimes the worst thing that could happen is not pursuing an opportunity. Dreams and aspirations are powerful forces, and ignoring them may mean missing what makes life worth living.
Capítulo 5
When Dreams Pull You Forward
Every decision you make has a unique balance sheet of facts, and you alone are positioned to interpret that balance sheet. When weighing risks and rewards, pros and cons, passions and obligations, we often discover a dream pulling us in a direction others might consider imprudent.
From 1994 to 2000, I had what I considered my dream job: federal prosecutor. Nothing professionally compares to standing before a judge or jury and saying, "I am here on behalf of the United States of America." The work initially seemed perfect: challenging cases, a noble purpose, and the best client possible-my fellow citizens.
Yet reality didn't fully align with my dream. What began as exciting eventually became routine. Most cases involved firearms possession or drug distribution-after ten narcotics cases, they become monotonous. I began questioning the proportionality when drug offenders received longer sentences than those convicted of possessing child pornography. This disproportionality struck me powerfully after a drug trial where the defendant received life without parole, while Susan Smith-who murdered her two young sons-would be eligible for parole after thirty years.
Once I acknowledged my dream had shifted, I needed to decide whether to leave the U.S. Attorney's Office to pursue becoming a state prosecutor. I created a pros and cons list. The pros included more variety in workload beyond just drug and firearm cases, more purpose in prosecuting violent crimes, and more possibilities for career advancement. The cons were significant: I'd have to run for office against a popular incumbent, risk failure, lose job security, fundraise with limited connections, and struggle to find endorsements.
Logically, the risks far outweighed the rewards. During countless walks on golf course paths-my personal therapy sessions-I repeatedly concluded staying was most prudent. Yet I found no peace in that decision. Sometimes one pro can outweigh all the cons when it aligns with your metric of success. Using my mantra "What's the worst that could happen?", I built mental safety nets for potential defeat and realized failure wouldn't be unbearable.
I ultimately decided my revised dream of becoming a circuit solicitor aligned with my desired closing argument in life and my definition of success. The pro of purpose and meaning outweighed all arguments for security and familiarity.
I left my job as a federal prosecutor in February 2000 and announced my run for circuit solicitor. At a wedding reception, John B. White Jr., a prominent figure supporting my opponent, approached me with devastating news: their polling showed me losing 80% to 20%. Stunned and ready to drop out, I called Dr. Dave Woodard, who revealed I'd actually improved from 2% to 20% in a month! This perspective completely changed my outlook. I ultimately won with 55% of the vote. Even if I'd lost, running was the right decision-not running would have been the ultimate failure.
Capítulo 6
Balancing Logic, Intuition, and Emotion
When considering starting something new, fear and emotions inevitably arise. While I've long favored logic-centered decision making, I've learned to appreciate how fact and feelings work together in making sound decisions.
Everyone naturally leans toward making decisions with their head (logic), heart (emotions), or gut (intuition). Like our government's three branches, these provide essential checks and balances. Logic should drive decision-making, with intuition navigating and emotions providing the soundtrack. Logic keeps us on course, but relying solely on it makes for a lonely journey.
Often, our intuition manifests as fear. I've lived with fear my entire life-from childhood fears of abandonment to professional fears of appearing unprepared. The key is making fear a passenger rather than letting it drive. Fear can be valuable when it makes us pause, encourages caution, or prevents rash decisions. When tamed, fear transforms into useful intuition.
When confronting fears, separate possibilities from probabilities. Apply reason through numbers and develop worst-case-scenario plans while recognizing you'll likely never need them. Consider all possible outcomes, but don't live in fear of the one percent. Defuse fear with facts.
We can also fight fear by focusing on others. We're often most courageous when defending someone or something we care about. My fear of being alone vanishes when anyone else is present-even an infant-because I shift focus from my fears to protecting them. My wife exemplifies this approach during the pandemic-while I analyzed mortality graphs, she focused on helping her students, writing encouraging cards, and checking on others. When we focus on others through compassion, fear becomes a companion rather than a controller.
When starting something new, you'll cycle through countless emotions-anxiety, excitement, hesitation, hope. These powerful feelings can override rational thought. Rather than letting emotions dictate decisions, let them punctuate them. Treat emotions as witnesses, not judges. Cross-examine their testimony for inconsistencies. Your emotions provide valuable information-enthusiasm confirms good choices, uncertainty warns of ignored problems-but they should inform, not control your decisions.
Capítulo 7
The Power of Perseverance
Deciding to stay isn't merely declining a different path-it's about taking inventory of your current position, investing effort to build toward better goals, and giving your initial decisions the gift of time and patience.
I once eagerly signed up for what I thought was a bowling class ("BL") in college-perfect timing, convenient location, and seemingly an easy grade to boost my struggling GPA. On the first day, I arrived at the Student Union Building's empty bowling alley only to discover "BL" stood for ballet. Despite my embarrassment walking into a room of leotard-clad dancers, the instructor Rudy convinced me to stay with the promise of an "A." Staying taught me about commitment, challenging myself, and not fleeing when things don't turn out as expected. The class gave me lifelong memories, friends, and important life lessons about perseverance.
While life offers plenty of opportunities to change course, there's no guarantee the next option will meet your expectations either. Persevering often yields unexpected rewards. Staying builds the invaluable gift of experience-something you can't acquire by wishing for it. When hiring others, I was always wary of applicants who bounced between positions frequently. Consistency signals dependability-a fantastic character trait.
In 2016, when Sheria Clarke, an experienced investigative attorney, asked my advice about joining our team investigating Russian election interference, I advised against it despite wanting her help. D.C. politics is brutal, and contentious investigations doubly so. I told her to "look at the film" of her career, not just the snapshot of a potential promotion. Her reputation for fairness, respect and faith was too valuable to risk in another political fight. When you face "once-in-a-lifetime" opportunities, consider what's best for your long-term aspirations rather than short-term gains.
Staying put isn't merely defensive-it often enables building your future with greater freedom. Before leaving any situation, have an honest conversation with yourself: Are you really escaping external problems, or avoiding deeper internal changes? Have you become addicted to the excitement of starting fresh? Have you given your current circumstances a fair trial?
To make the most of staying, commit to sticking with it for a certain period. Whether it's one month, a semester, or several years, setting a timeframe helps you fully engage rather than keeping one eye on the exit. Look for ways to grow your skill set or challenge your potential. Whether learning to cook, taking on new work responsibilities, or navigating relationship conflicts, uncomfortable challenges provide opportunities to learn. Determine whether there are pieces of your final closing scene present in your current reality. Look for elements of your ultimate goals in your current situation.
Dreams only become reality with perseverance, work, and patience. Stick with them until they've fully run their course or until your main dream changes. Sometimes no change is the best decision; change isn't necessarily progress. Staying may be difficult, boring, and thankless, but you're building something that will live beyond you.
Capítulo 8
Finding Your Trusted Advisors
No matter how thoroughly we analyze our decisions, we're often too close to see the whole picture. That's why we need trusted people who can point us in the right direction or spot obstacles we've missed.
There are two decision-making extremes to avoid: the loner who seeks no counsel, and the waverer who's paralyzed by indecision. The best decision makers know their own minds while consulting others. Wisdom includes knowing who's worth listening to. Everyone needs a Nathan in their life-someone with the courage to speak truth, even uncomfortable truth. In the Bible, Nathan confronted King David after his adultery with Bathsheba and murder of her husband with the powerful words "You are the man!" The best advisers tell us what we need to hear, not what we want to hear.
In 2001, shortly after being elected circuit solicitor, I considered leaving for a U.S. magistrate judge position offering eight years of security. Despite having just asked voters to elect me, I rationalized the move as providing stability for my family. My father visited and was uncharacteristically direct: "You cannot do this. It's not right or fair to those who helped elect you." Unhappy with his response, I sought validation from my risk-taking friend Ben Gramling. But Ben agreed with my father, arguing that while he understood the appeal of security, taking the judgeship would be like putting on handcuffs-limiting my potential.
When seeking Nathans in your life, look for three crucial traits: people who have your best interest in mind, who know you well including your strengths and weaknesses, and who are honest and courageous enough to speak difficult truths. To benefit from these relationships, you must be humble enough to listen without becoming defensive.
Just as important as finding your Nathans is identifying who shouldn't advise you. The opposite of a Nathan isn't necessarily an enemy but someone who only wants your momentary happiness without challenging you. Some people don't want to see you succeed-even those who should have your best interests at heart. Like Elijah Cummings' guidance counselor who told him he'd never be a lawyer (ironically becoming Elijah's first client after law school), these people project their limitations onto you.
In today's world, strangers feel entitled to express opinions about everything, but allowing them to influence our decisions throws us off balance. You're rarely as good or as terrible as others claim. Instead of seeking validation from social media strangers, consult those who truly know you and your motivations. Your Nathans build you up, while strangers often tear you down.
Capítulo 9
Knowing When to Walk Away
Deciding to leave can be simultaneously challenging and liberating-scary, sad, exhilarating, difficult, relieving, necessary, or all of these. Knowing when to leave requires honest assessment of both your current situation and who you want to become next.
By 2009, prosecuting violent crimes had taken a devastating spiritual toll on me. As a prosecutor, I had to immerse myself in the darkest aspects of humanity-domestic violence, child abuse, and homicide cases where victims died terrified and alone. The most effective prosecutors force themselves to experience what victims felt, to be their voice. This meant constantly dwelling on scenes of malice and terror.
One case that haunts me involved an elderly couple murdered in their bed by someone they had helped. The image of the husband's broken body reaching toward his wife in death remains etched in my memory-love trying but failing against depravity. After seeing hundreds of similar crime scenes, I struggled to reconcile these horrors with my faith. Sitting in church hearing about God's love and control, I couldn't square these platitudes with crime scene photographs.
The job was exacting too steep a price on my family. My daughter would sleep on our floor after overhearing conversations about "bad people," and I projected my work-based cynicism onto my son's upbringing. That Mother's Day in 2009, both my wife and mother independently concluded it was time for me to leave-a rare intervention from Terri, who typically trusted my professional decisions.
When considering leaving a position that was once your greatest aspiration, the hesitation often stems from feeling like you're betraying yourself or abandoning a dream. Dreams should liberate, not debilitate. They should make you better, not more cynical. When making healthy decisions, dreams either evolve with us or we retire them for our betterment.
I faced the challenge of how to leave an elected position before my term ended. I couldn't share my spiritual crisis with constituents-my cynicism shouldn't impact them. After much debate, I decided to run for Congress as an honorable exit from a job I could no longer do, hoping the twin themes of fairness and justice could manifest in a different sector of government.
Even a decade removed from the courtroom, my hometown remains a collage of crime scenes. Everywhere I drive, I see reminders of cases-the interstate where a mother was kidnapped and killed, the grocery store where I might run into still-grieving families. While victims and even old cops find their faith sustains them through tragedy, the images that renewed their faith caused me to doubt.
Capítulo 10
Embracing Your Authentic Path
Your decisions determine your success, but first you must decide what success means to you. Define it by what you can control-your words, mindset, and effort. The small daily choices matter: using respectful language during disagreements, maintaining optimism about projects, choosing reading over television, showing care to loved ones.
I'm astonished when people claim to have "no regrets." Such a stance suggests arrogance or lack of introspection. Regrets are natural parts of self-reflection-I regret things done and undone, correct decisions made for wrong reasons, and some things I'd repeat exactly. One regret is not performing better academically in my youth. The question isn't whether we'll have regrets, but what we allow them to become. Regrets can teach us, helping us become better parents, spouses, and friends.
To turn regret into remembrance: be honest about what happened without sugarcoating; reflect on what you learned; and replace "if only" with "next time" or "now that I know." We can't pursue every opportunity, so we shouldn't waste time looking down paths no longer available.
After Trump's 2016 election, Tim Scott called me, emotional about the opportunity for me to serve on the Fourth Circuit Court of Appeals-the very court I once dreamed of joining. All pieces aligned perfectly: Republican president, Republican Senate, supportive home-state senators, and two court openings. But my interest had vanished. I'd finally scaled the toughest mountain-letting go of others' expectations. I stood in my kitchen listening to my most trusted adviser, Terri. Yes, a judgeship meant security, but I'd reached a point where who I worked with meant more than what I did. When White House Counsel Don McGahn called a third time to confirm my disinterest, I was certain: "I do not want this anymore."
Have you ever been asked what advice you'd give your younger self? This question helps us evaluate our life decisions at crucial markers. It helps sort perceived failures from actual ones and distinguishes regrets from remembrances. Understanding your motivation is liberating. About half the world is motivated by success-seeking, the other half by failure-avoidance. I've always been in the latter camp. Fear has influenced my decisions my entire life. But I've reached a peace with fear-letting it look and edit, but not write my life's closing chapter.
I hope your closing argument is a long way off and that you'll make countless decisions between now and then with greater confidence. There are innumerable paths to your final scene-your best closing argument-and your decisions to start, stay, or leave will determine what shape you're in when you arrive. For me, I hope people remember that I tried to be fair. That I advocated effectively for those who couldn't stand up for themselves. I envision a final picture with my closest friends gathered around. I hear someone say, "He was fair." Funny and fair-that's all I need to believe I've made the right decisions.
