1장
The Art of Professional Discomfort: Navigating Work as an Outsider
When Esquire magazine unexpectedly called me in 2005, I felt like an impostor who'd be discovered within a month. Working at Southwest Airlines' in-flight magazine with a degree from the University of North Texas, I was certain I lacked the pedigree for a prestigious Manhattan publication. This "impostor phenomenon," first identified by psychologists in 1978, is remarkably common-even among the most accomplished individuals. Supreme Court Justice Sonia Sotomayor, Kate Winslet, Chuck Lorre, Alexis Ohanian, Tina Fey, and Meryl Streep have all admitted to feeling like frauds. The book that emerged from my experience became an instant hit among professionals struggling with workplace anxiety, even earning a spot on Barack Obama's summer reading list for its honest portrayal of professional insecurity and practical advice for turning that discomfort into strength.
2장
The Outsider's Advantage in Professional Settings
My journey to Esquire began with a random phone call that seemed like a cosmic mistake. Despite being editor-in-chief at Spirit magazine, I felt fundamentally inadequate when the Hearst recruiting director mentioned the position was at Esquire-my professional North Star. My mind immediately cataloged my supposedly second-tier credentials: growing up on the "wrong side" of Dallas, attending a tiny evangelical school, graduating as "acting salutatorian" in a class of eight, attending University of North Texas instead of the more prestigious University of Texas. These self-imposed markers of inadequacy had followed me throughout my career, whispering doubts at every professional milestone.
A week later, I stood nervously at Columbus Circle in New York, reviewing handwritten interview responses and suddenly realizing I'd forgotten a suit jacket-a fashion faux pas that perfectly captured my outsider status at a magazine known for style. The anxiety peaked in the elevator to the thirteenth floor, facing Ewan McGregor's judgmental stare from a framed magazine cover. My palms were sweating, and I could feel the cotton of my dress shirt sticking to my back, a physical manifestation of my imposter syndrome. The gleaming hallways and perfectly curated magazine covers that lined them seemed to mock my small-town background.
But something unexpected happened during those interviews. The editors seemed normal, warm, interested-not elitist or dismissive. They evaluated my personality through casual conversation rather than intense questioning. One editor shared stories about his own humble beginnings in journalism at a small-town paper. Another admitted to being intimidated when he first started at Esquire. This allowed me to relax and be authentic, realizing that perhaps my outsider perspective could be an asset rather than a liability. Even my meeting with the editor-in-chief felt natural, including comfortable profanity and a shared laugh about regional journalism quirks. I left thinking substance mattered more than my missing jacket or pedigree.
Less than forty-five minutes after leaving, I received the job offer by phone, leaving me speechless. Flying home, I gazed at Manhattan from my window, overwhelmed by this unlikely opportunity that would change my life-and eventually lead to writing this book about navigating professional discomfort. The city lights below seemed to mirror the constellation of chances and choices that had led me here. My outsider status, I realized, hadn't been a disadvantage at all - it had given me a unique perspective and authenticity that resonated with the very people I'd feared would reject me. This experience became the foundation for understanding how perceived weaknesses often become our greatest professional strengths.
3장
The Interview: A Match, Not a Prize
While I'm skeptical of overly specific career advice that can make us robotic, some interview guidelines genuinely reduce anxiety and improve outcomes. The classics remain valuable: research the employer thoroughly by studying their website, recent news, and social media presence; practice your answers with a friend or mentor; bring extra copies of your resume and work samples; and prepare thoughtful responses to common questions. The "Tell me about yourself" question deserves special attention - craft a compelling 2-3 minute narrative that highlights relevant experience. For the dreaded "greatest weakness" question, avoid humble-bragging ("I work too hard") and instead discuss a genuine area of growth and specific steps you're taking to improve.
Beyond these basics, focus on providing detailed examples using the STAR method (Situation, Task, Action, Result) to demonstrate your capabilities. Show genuine interest in the company culture and role-specific challenges. Prepare intelligent questions that demonstrate you've done your homework: "I noticed your recent expansion into Asian markets - how does that affect this role?" Don't discuss compensation unless directly asked, and even then, defer detailed discussions until an offer is made. Always send a personalized thank-you note within 24 hours - handwritten shows extra effort but email is acceptable if time is tight.
But what experts rarely address is the critical importance of authenticity. Never pretend to be someone you're not - jobs aren't prizes to be won but matches to be made between compatible parties. The biggest workplace failures I've witnessed involved people who presented an artificial personality during interviews and revealed their true selves once hired. One candidate portrayed themselves as highly collaborative but proved to be territorial and resistant to teamwork. Another oversold their comfort with public speaking only to freeze during their first presentation. Skills can be taught, but personality is permanent - and your future coworkers are stuck with it.
When working with recruiters, understand their broader role in the hiring ecosystem. They're gathering intelligence not just for the current position but to build relationships and collect valuable industry information. Use them strategically to learn about the hiring manager's personality, leadership style, and potential red flags. Share useful information about your workplace trends and market conditions - this builds goodwill and establishes you as a knowledgeable professional. Never use recruiters merely to get a counteroffer from your current employer; this damages relationships and your reputation. Tell your authentic career story, including setbacks and lessons learned. Don't badmouth your current employer, but be honest about your reasons for seeking change. Focus conversations on how you can contribute value rather than what benefits you hope to gain. Discuss nuanced aspects of your experience, including projects that didn't go perfectly but taught valuable lessons.
Consider ending your interview with genuine enthusiasm: "If you throw me out of here right now, this will have been the greatest thing that's ever happened to me." This bold approach works remarkably well - but only if you truly believe it and can deliver it authentically. Your sincerity must shine through.
4장
First Impressions: The Science of Entering Rooms
My interview anxiety centered largely around making a first impression. Research confirms these anxieties aren't unfounded-first impressions form within milliseconds of seeing someone's face and remain highly influential long-term. Studies from Princeton psychologists show that people make judgments about attractiveness, likability, trustworthiness, and competence after seeing a face for just a tenth of a second.
What works in your favor during those crucial moments: gregariousness, friendliness, assertiveness, social skill, verbal ability, eye contact, emotional stability, and agreeableness. Body language experts have found that open posture, genuine smiles, and confident movements signal competence. We form impressions quickly as a survival mechanism, judging not just threats but warmth, trustworthiness, and confidence. This evolutionary trait helped our ancestors quickly determine friend from foe, and these same neural pathways now influence our professional interactions.
The main rule: eye contact. Studies show interview candidates maintaining high eye contact are judged much more favorably, with research indicating optimal eye contact should be maintained 60-70% of the time. Look people in the eye before you even shake hands-it suggests curiosity, the most underrated business virtue. When you're curious about someone, you establish a foundation for the meeting. Harvard Business School research shows that demonstrating genuine interest through appropriate eye contact increases perceived leadership ability by 40%.
My first day at Esquire was preceded by a whirlwind of change-accepting the job, finding a Village apartment above a stripper clothing store, and moving to New York just in time for Gay Pride parade to roll past my window. Nervous and keyed up, I committed the cardinal sin of introducing myself to a stranger at the urinals, even shaking his hand (who turned out to be Bob, the research director). The awkwardness continued with the classic-and ineffective-first-day walk-around, complete with a judgmental once-over from a colleague. These moments perfectly exemplify how anxiety can lead to social missteps that seem catastrophic in the moment.
But here's the truth: first days are anomalies and largely irrelevant. The person walking around isn't really you-it's your representative, operating on high alert and overthinking every interaction. And those aren't your real coworkers either-they're playing parts too, often putting on their own masks of professional distance or feigned interest. People we initially like often turn out to be difficult, while those who seem judgmental become allies. Workplace dynamics research shows that initial impressions are accurate only about 50% of the time in predicting long-term relationships. Everyone's anxious on first days, not just you - studies indicate that 93% of new employees experience significant anxiety during their first week, regardless of seniority level or experience.
5장
The Necessity of Early Mistakes
If you don't screw up when starting a new job, you're probably overqualified. Early mistakes are actually indicators that you've taken a big step into challenging territory. They're how you know you're succeeding.
My checklist of necessary screw-ups includes: shaking hands at inappropriate moments (like in restrooms); pretending to know about something you don't until your ignorance becomes obvious; avoiding eye contact with people you admire; SPEAKING TOO LOUDLY FROM ANXIETY; botching presentations; awkwardly inserting yourself into conversations; using phrases like "first-day jitters"; wanting to metaphorically go home to bed; glaring at your reflection like you want to fight yourself; attributing your accomplishments to luck; and clamming up completely at dinner with new colleagues.
At thirty, I still didn't know how to navigate a dinner with intimidating new colleagues. When someone asked for my thoughts on Werner Herzog (a German director I knew nothing about), I faced the classic dilemma: admit ignorance, barrel through with bullshit, or give vague responses. I chose poorly, saying, "That guy. I think his early work was derivative. But his recent stuff has moved the needle."
With that response, I lost them. I wasn't engaged meaningfully again all night. I should have simply said, "I have no idea who that is." When we don't know something, we should admit it enthusiastically. The problem wasn't my ignorance but my pretending. You cannot be an interesting conversationalist while faking interest.
After dinner, I walked alone in the rain, struggled with my MetroCard, and got on the wrong train. "This isn't going to work," I thought. "Six months, tops."
6장
The Value of Sucking at Your Job (Temporarily)
You suck. I suck. We all suck at something important that we'll eventually master. This must be accepted.
While "failure" is trendy in business literature, what's actually being discussed is making mistakes, not catastrophic failure. Real failure is devastating and teaches nothing. What matters is having a "growth mindset" (as Stanford psychologist Carol Dweck calls it)-embracing challenges because you believe you can improve even when you don't succeed.
My biggest mistake in my early years at Esquire wasn't the work I produced but the shame I felt making mistakes. I acted timidly, staying until midnight perfecting headlines or spending days on single jokes. As a manager now, I tell people to turn in work before they think it's ready. Being fastidious is possibly the worst trait in a young worker-your boss needs options if the work isn't good enough.
Everyone wants you to do bad work initially. Your boss wants you to learn what not to do. Your peers either understand the value of fearlessness or want to feel superior. And you should want to do bad work too, because in every bit of bad work, there's always a kernel of something good-about 2 to 13 percent. Your job is to find that good amid the mess.
During my first year at Esquire, a colleague confronted me at a bar gathering with six words that changed my workplace bearing forever: "Why are you so fucking glum?" I hadn't realized my resting face was vaguely troubled and that I rarely smiled-likely due to stress and feeling overwhelmed in my new environment.
A frown is both demoralizing and contagious. Fortunately, smiling is equally contagious, and science confirms this. The difference between a fake smile and a genuine "Duchenne" smile involves the orbicularis oculi-the muscles that crinkle your eyes, which are difficult to contract voluntarily. To achieve a genuine smile, think of something truly delightful.
7장
The Art of Workplace Communication
At Esquire's weekly production meetings, I initially made the mistake of answering questions truthfully and expansively when asked about project status. I didn't understand that the proper response was simply "It's great" followed by silence.
The rules for talking in meetings are simple:
1. Shh.
2. Shh.
3. Speak.
4. Shh.
In regular meetings, you prove your worth through discretion, not action-saying just what you know clearly and concisely, then shutting up. When asked "How's that coming?" respond with "It's great" and be done. Of course, if it's not great, you'll pay for dishonesty later, so make sure your work actually is great.
Never start sentences with "Well..."-nothing good follows that word. Avoid boring details about who you met with or what "the team" discussed. Apply this test: Are you interested in what you're saying? If not, stop talking, even mid-sentence if necessary. The most underrated workplace tactic is silence.
I'd like to ban the phrase "I think you're overthinking this" from workplace vocabulary. It punishes people for caring and trying to make something great, when the accuser simply doesn't feel like thinking.
Other phrases to avoid in professional settings include: "I'm sorry" (instead, acknowledge the problem and explain how you'll correct it); "...Does that make any sense?" (reveals either lack of confidence or confusion); "It is what it is" (a meaningless mantra for those who've given up thinking); "Everything happens for a reason" (see above); "Let's grab a coffee" (suggests the interaction isn't worth full attention); "I had this dream last night" (boring); "I'm so hungover..." (nobody cares); and "I feel..." (at work, you may think, but you may not feel).
Small talk isn't my natural strength, despite years of practice in New York meeting countless strangers. The first principle of small talk: acknowledge we live in a society with an implicit agreement to speak when silence would be awkward. A 2014 University of Chicago study found that commuters who struck up conversations with strangers reported more enjoyable rides than those sitting quietly. Most people want to connect but wrongly assume others prefer silence-a phenomenon called "pluralistic ignorance."
8장
Professional Style: Beyond Clothing
I'm not a great dresser despite working at a magazine that's a leading authority on men's fashion. I want to look "good" not "great." If you think you don't "care" about fashion, fine, but clothes matter. They change your outlook and represent you-denying this truth means denying yourself a powerful tool.
About a year after starting at Esquire, my boss made me the editorial liaison to the fashion department led by Nick Sullivan. I learned technical things: quarter-inch cuff showing at jacket sleeve, narrow suit silhouette, never buttoning the top button of a three-button suit, and the most important rule-always cut a string, never pull.
I wasn't just learning about clothes but about style, which is more interesting because it's about ideas-particularly confidence. Columbia University researchers call this "enclothed cognition"-the effect of clothing on mental processes. People wearing a doctor's coat showed higher attention to detail than those in street clothes.
After self-deprecating about my fashion sense, a fashion editor offered to help me buy shoes. I bought cap-toe Oxfords with slightly pointy toes that cost more than I'd ever spent on footwear. They immediately made me feel more confident and capable. I still wear them years later after several resolings.
The concept of sprezzatura was introduced by sixteenth-century Italian courtier Baldassare Castiglione in "The Book of the Courtier," a Renaissance etiquette guide. It means practicing "nonchalance so as to conceal all art and make whatever is done or said appear to be without effort." This philosophy revolutionized how I view style. At Esquire, I noticed photos where well-dressed men had something slightly "off"-an askew collar, no belt, a "too short" tie-yet looked fantastic. Sprezzatura endorses whimsy, messiness, and flaws. It's not just about clothes but about work too-your efforts should show wear, indicating you're taking chances. Style follows rules but isn't governed by them. Confidence and clothes build on each other until people see you as someone who knows what they're doing.
9장
Navigating Professional Relationships
"Important" is a complex and multifaceted term in professional contexts. In my career, it's meant notable or famous people, but also those crucial to my career advancement-assistants who control access, peers who become collaborators, direct bosses who guide your path, potential future bosses, PR professionals who shape narratives, and media contacts who amplify stories. Each relationship requires its own careful cultivation and understanding.
When engaging with counterparts at other organizations, strategic transparency often yields better results than maintaining rigid boundaries. Share select information that builds trust without compromising your position. This creates reciprocity and opens channels for future collaboration. When faced with probing or indiscreet questions, master the art of gentle deflection with phrases like "You never know" or "Hard to say" - responses that maintain professionalism while avoiding both confrontation and unwanted disclosure.
Celebrity interviews require particular finesse. Avoid the common trap of limiting discussion to their current "projects," which often yields rehearsed responses. My interview with 50 Cent illustrated the power of authentic engagement. He demonstrated emotional intelligence by saying "This is going to be an interesting interview" at the start-actively disarming potential tension, setting a positive tone, and showing investment in the conversation. During our talk, he would instinctively move my recording device closer when construction noise increased-a subtle gesture that transformed him from subject to collaborator.
The Rihanna interview taught me valuable lessons about preparation versus authenticity. I approached it defensively, immersing myself in Barbados history, exclusively playing her music for weeks, and observing her concert performances. However, the interview only truly came alive when we delved into specific, human moments-discussing her childhood home's details, recounting her career-defining moment at Def Jam while wearing all white. This reinforced a crucial truth: important people have rich histories predating their prominence.
Different types of important people require different approaches. In meetings with peers, practice active listening to ensure people feel both heard and accountable for their commitments. When dealing with top executives, recognize their typically dominant personalities and focus on absorbing their perspective rather than competing for airtime. For new employees, acknowledge their achievement with a warm "Welcome and congratulations"-validating that they've earned their position. When interacting with politicians, show interest in their specific responsibilities rather than general platitudes. With interns, maintain an approachable demeanor-remembering they're tomorrow's leaders and decision-makers.
The fundamental insight remains: successful interactions with "important" people hinge on seeing beyond their current status to connect with their essential humanity. Every important person was once unimportant, and understanding this helps create more meaningful, authentic connections. The most effective professional relationships are built on mutual respect, genuine interest, and recognition of our shared human experience, regardless of current status or position.
10장
Embracing Your Outsider Status
I'll never feel entirely comfortable being on the inside. There will always be someone better, always a better version of me possible. My work will always fall short of what it could have been. This could be crippling, but self-doubt can become fuel when we understand its power.
When I started in New York, I didn't think I belonged. I'd escape to specific benches in Central Park after submitting work, fearing I'd be fired. But feeling inadequate forces you to do your best work-it makes you research more thoroughly, prepare more diligently, try harder. The people I admire most question their abilities even as they succeed, acting as though success wasn't preordained.
As I became comfortable in my job and city, I visited those park benches less frequently. New York became less charged, less cinematic. Now I visit them rarely, to reconnect with that outsider feeling that drives better work. The crucial irony is that outsiders make the inside rich and inspiring. I belonged from the very beginning.
Sometimes you have to insist that you're talented, driven, smart, funny, and wise because no one else will do it for you. The best way to write is to assume authority-to claim knowledge without apology and express yourself clearly without hedging.
For you, writing a book might be a metaphor for the job you don't think you can get, the raise you don't think you deserve, or the promotion you're afraid to compete for. But you must insist to yourself and others that you're ready. You have to tell your boss what you want, confront undermining colleagues, give speeches despite nervousness. With gratitude, self-awareness, perhaps a tiny bit of grounding self-doubt, and a slightly awkward smile, you simply have to act.
