Three Career Lessons from Being on “Jeopardy!” (and Meeting Alex Trebek)
On November 8, 2020, America lost Alex Trebek, the host of the long-running quiz show “Jeopardy!”and a cultural icon. For 36 seasons “Jeopardy!” stimulated our minds and competitive spirts, when virtually everything else on TV put us on autopilot. In recent years, when famous figures questioned science and knowledge and attacked the truth, millions of us found comfort in Alex Trebek’s attention to detail and accuracy. On “Jeopardy”, facts matter and truth prevails.
“Jeopardy!” has been nightly appointment viewing for me since childhood, 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. Recent events made me reflect on my own experience preparing and auditioning for the show, and then taping it, which includes meeting the legendary Alex Trebek. Here are three lessons that helped me reach success on “Jeopardy!” These served me well for my subsequent 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 my responses, especially the incorrect ones. Next: training. I beefed up on my shakiest subjects by studying 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 strongest 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 one). 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 still 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 would tape two days later. But a new day brought a much different game. My opponents this time were young, sharp and quick on the buzzer. Categories I liked came up, but the other players kept ringing in faster than I could. I fell further and further into a hole, which reached $8,000 at one point. Like the proverbial boxer who gets punched in the mouth, I had to make a new plan. I recognized that my competitors’ advantage was their buzzer speed. I realized I couldn’t do better here, though, because improving your buzzer timing takes a lot of practice. I decided to avoid going head-to-head and instead searched for clues that I hoped I alone could answer. I scanned the board and saw the category “Hide & Sikh”. As it happened, I knew a fair bit about Sikhism because my brother had just spent months with a Sikh community 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 shying 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, which were environments enabling me to succeed with ease. But these didn’t last long. They were disrupted by reorganizations: new managers and team additions and departures. My initial handlings of these changes were passive acceptance. These resulted in bad outcomes, though; at best I languished, at worst I got bounced out. Later I took an active role in responding to change. I learned to assess my fit within the new environment and recognized my comparative advantage. I formed a plan to capitalize on my strengths. As a result, I notched up successes and built up a strong reputation within the new organizations.
3. Make it a true Daily Double
Getting back to game two, my change in strategy helped to chip away at the lead. Still I was still trailing by $5,000 with in Double Jeopardy with half a board to go. Then I hit a Daily Double. This is one of two opportunities in the round when you can bet anything — or everything — you have. How much should I bet? I was lukewarm about the category, Literary Terms, and if I gambled big and missed, I thought, there wouldn’t be enough time to come back into the game. But before dwelling too long on the downside, Alex Trebek spelled out the upside. “If you made this a true Daily Double”, a maximum wager, “and were correct, you’d be in the lead!” One of the common mistakes of Jeopardy! players who trail far behind is making a small bet — playing scared. “You’re a good salesman, Alex,” I grinned. “True Daily Double.” Alex read the clue. He mentioned the poet Edmund Spenser and the term prothalamion. I cringed. I hadn’t heard of either. Alex asked for the name of the event tied to these topics. I shook my head and blurted out the first thing that came to mind. “What is a… what is a wedding?”. Trebek waited a beat. “Yes.” I breathed a huge sigh of relief. Game on! 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 risk-averse but once in a while an intriguing opportunity arises. These initially seem like risky gambles, but I took the time to examine the potential payoff and then steeled myself to take the plunge. Some didn’t pan out, but some rewarded me splendidly. And, 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. I’ll never forget Alex Trebek’s words of advice: make it a true Daily Double, bet big for you may not have this opportunity again. I hope Trebek’s wisdom rings true for you, too.
