Three Career Lessons from Being on “Jeopardy!” (and Meeting Alex Trebek)

America’s favorite TV quiz show “Jeopardy!” made headlines in 2019, its 35th season. First, there was host Alex Trebek’s announcement that he was battling stage 4 cancer. Then came James Holzhauer’s revolutionary $2 million run. I followed these stories eagerly, because I’ve been a fan for virtually all of my life. The show has been nightly appointment viewing since the first grade, when it was on TV at dinnertime. After two decades of playing along from home, I tried out for the show — and made it. I appeared on three episodes and was champion twice. The events of this year caused me to reflect on my own experience training, auditioning and appearing, as well as meeting the legendary Alex Trebek. Here are three lessons that helped me reach success on “Jeopardy!” — and then served well for my career.

1. Find your flow

Like many “Jeopardy!” fans, I had thought about trying out for many years. Finally I decided to get serious about it. My preparation model: the SAT. First I took a diagnostic test, which was watching and playing from home for a week. I kept track of each category and and my responses, especially the incorrect ones. Next: training. I beefed up on my shakiest subjects by perusing Wikipedia articles, and I made flash cards out of key concepts, names and facts. I set aside a couple of hours after work each day to read, write and drill. To most people this sounds like monastic drudgery, but to me the process of exploring new topics and diligently gaining mastery of them was trancelike. This was my flow state. After several months, I felt ready to audition. I passed on the first try.

I was able to align a natural interest (general knowledge) with a goal (becoming a “Jeopardy!” contestant), and I created a structure to make continuous progress (2+ hours of daily practice). All kinds of professionals can attest to the power of the flow state, from musicians to surgeons. Ironically, in those days I wasn’t experiencing flow in my day job as a software engineer; in fact, when I was at work I couldn’t wait to get home. But later in my career I found a passion I could harness professionally: connecting with customers. Meeting them, understanding their needs and building products for them energized me more than solving technical challenges for their own sake. This inspiration enabled me to get absorbed in my job. I eventually pivoted my career to product management so that this part-time interest could blossom into a full-time pursuit.

2. When the game changes, change your game

If merely making it onto “Jeopardy!” was a dream come true, the first game surpassed my wildest imagination. My best categories came up, I rang in first on most of the clues, and I landed on all of the Daily Doubles (and correctly answered each). The only misstep was ignoring Alex Trebek’s advice before Final Jeopardy. He asked rhetorically, “what’s the maximum wager William could make and still not lose this game?” I did the math, but I bet thousands less than the host suggested. (He playfully chided me for it after the show.)

I went back to my hotel with sky-high confidence for the second episode, which was to be taped two days later. But on a new day arrived a drastically different game. Both of my opponents were young, sharp and quick. Favorable categories appeared, but the other players kept ringing in faster than I could. I felt helpless as they steadily built a lead, which peaked at $8,000 over me. Like the proverbial boxer who gets punched in the mouth, I had to form a new plan. I realized that my competitors’ advantage was their buzzer speed. I couldn’t improve my signaling skills during the game, however, because this takes a lot of practice. I decided to avoid going head-to-head and instead went for clues that I hoped I alone could answer. First, there was “Hide & Sikh”. As it happened, my brother had just spent months with a Sikh community for a project and shared his experiences with me. I went for the most valuable clues there and managed to answer them correctly. Next was “Entertainers”. Pop culture was up my alley, and my opponents were staying away from this one. I dove in and got three questions.

I’ll step back from the game for a moment to reflect on my career. It has had a few periods resembling my first “Jeopardy!” game: settings enabling me to succeed with ease. But these didn’t last long; they were disrupted by reorganizations, new managers and team additions and departures. The first of these times I passively accepted my changed role. At best I languished, at worst I got bounced out. Subsequently I learned to assess my fit with the new environment, and I recognized my comparative advantage. I formed a plan to capitalize on my strengths. As a result, I notched up successes and built up a reputation with the new organization.

3. Make it a true Daily Double

Getting back to game two, my strategy change helped to chip away at the lead, but midway through Double Jeopardy I was still trailing by $5,000. Then I hit a Daily Double, one of two clues in the round where you can bet anything you have. How much should I bet? I was lukewarm about the category, Literary Terms, and if I gambled big and lost, there wouldn’t be enough time to come back into the game. But before I dwelled too long on the downside, Alex Trebek pointed out the bright side. “If you made this a true Daily Double” — a maximum wager — “and were correct, you’d be in the lead!” Trebek reminded me that I wasn’t like the many timid contestants I had watched before, who lagged far behind but placed a small bet anyway. “You’re a good salesman, Alex,” I smiled. “True Daily Double.” The clue mentioned the poet Edmund Spenser, the term prothalamion, and asked what event it celebrated. I cringed. I hadn’t heard of any of these before. I shook my head and blurted out the first word that came to mind (wedding). Trebek waited a beat. “Yes.” I breathed a huge sigh of relief; it was a game again. I rallied to finish the round with a small lead and correctly answered Final Jeopardy to win.

I took two things away from this comeback victory. First, listen to the old hands around you. They want to help, and their experience makes their advice very good. Second, find the Daily Doubles in your career — and then bet big. I’m naturally inclined toward avoiding risk but occasionally intriguing opportunities have popped up. They initially seemed like daunting gambles, but after I examined the potential payoff I steeled myself to take the plunge. Some didn’t pan out, but some rewarded me splendidly. If you have a safety net, bet the farm. On “Jeopardy!” I could afford a true Daily Double because I was playing with house money.

“Jeopardy!” was essential to my life. Early on it entertained and educated me. Then it became a goal to strive for. Finally it gave me a template for attaining success in my career. When Alex Trebek made his medical announcement early this year, his fans began preparing for the end of an era. But last month the TV legend shared news that he is in “near remission”. I hope that he will pull through, and that his show will inspire thousands more for years to come.

Technologist, traveler, photographer

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