5 min read

Pivot #12: Strategic Serendipity

Pivot #12: Strategic Serendipity

PayPal Mafia member and LinkedIn Founder, Reid Hoffman, helped author, The Startup of You, a fascinating book that takes a more unorthodox perspective on career building, clearly influenced by his Silicon Valley experience and start-up background. The mental model he uses to describe the way people should think about their careers is helpful. Careers are not linear, but rather punctuated by breakout opportunities that lead to exponential career growth. Temporal opportunities, if capitalized on, can help you level up in your career and life. It’s critical to expose yourself to as many breakout opportunities as possible by creating serendipity. Serendipity is a great word. Many people might chalk up other’s success to good luck, but opportunities don’t just fall in our lap. We need to actively engineer the connections, projects, and experiences that will lead to exponential career opportunities. We’ll call this strategic serendipity. 

The point is to take deliberate action to court randomness into your life. Get involved. It’s likely you don’t even know the opportunities you’re intending to cultivate, but the point is to expose yourself to opportunities, nonetheless. Especially opportunities that leverage a skillset that you’ve honed for a period of time. 

George Clooney

An example right out of the book, The Startup of You, George Clooney moved from Kentucky to Hollywood with the cliche dream of making it big as an actor. He spent much of the late 80s and early 90s scraping by as a small part actor, until his friend sent him a script for a new television series. The script was for a medical drama called ER. Clooney immediately jumped at the opportunity recognizing the potential the series had. He even called the producer to say he wasn’t going to allow anyone else to get the lead role but him. ER was a smash hit and we all know how things turned out for George. It was a lucky Hollywood break by some accounts, but Clooney cultivated his own serendipity in a few important ways: 1) Years and years, reps and reps of reading script after script. Honing his discernment skills to recognize a good opportunity when he sees one. He invested significant time learning the industry inside and out. The boring minutia of building skills and learning often goes unappreciated 2) Cultivating a vast web of relationships - the ER opportunity did not come to him through traditional means (agent), but through a friend; a script he never should’ve seen in the first placet 3) Proactive - George took immediate action to call and show strong interest. He didn’t take ‘no’ for an answer. When in doubt be your own best advocate and error on the side of aggressiveness. 

Philippe Dauman

This week legendary Wall Street dealmaker Steve Volk passed away at the age of 87. The M&A titan was famous for being a trusted confidant of CEOs everywhere. Everyone from Jack Welch at GE to John Mack at Morgan Stanley. One of the more notable dealings was Volk’s relationship with Summer Redstone, founder and former Chairman of CBSViacom (which is now Paramount Global). Redstone was a local theater owner in Boston when he called Volk to help him make a run at acquiring Viacom. Volk assigned the transaction work to his most trusted associate, Philippe Dauman. This innocuous opportunity for Dauman, led him to a multi-decade career at CBS Viacom, culminating in his ten year tenure as CEO. Right place, right time for sure. High performance, keeping close to Volk, and earning his mentor’s trust put Dauman  in position to head down the Viacom career path. 

Derek Block 

Recall our good friend Derek Block from last week’s newsletter on TJ Oshie’s Warroad Hockey. Derek was a college hockey player at Miami-Ohio before founding his company Touchstone, a leader in the merchandise retail branding space. I came across a 20 minute podcast interview from 2108 where Block expanded upon his career. At the 8:58 mark, Derek used the word “serendipitous” to describe his start in the merchandise business. To paraphrase, he wanted to just get started on something and head down a path that was exciting and different. Without expectations, the journey transpired into a multi-decade run at the helm of his own company. Derek took the first few steps down a path he knew was in a positive direction. He embraced the unknown and built skills in a niche area, while heading on a positive trajectory. 

So how can hockey players create strategic serendipity?

If you are a NHL player, creating strategic serendipity is one of the easiest things you can do for yourself, namely because you’re leveraging your status and platform at its peak. If anything, players should be more selective with the opportunities that come their way. Easy example for NHL players to execute: attend a team corporate sponsorship event or charitable function. Find the biggest baller in the room. Clues as to who the possible ballers are: thick framed glasses, white teeth, tailored pants, silver fox hair, sharp, reserved, talks slow, sharp as a tack. Link up with said person. Exchange numbers. Meet periodically and soak up everything they know. Rinse and repeat with more ballers. Another easy tactic is to link up with other NHL players. If you know of another player involved in something interesting, reach out. The NHL is a small fraternity and everyone is one mutual teammate away. 

If you're a former player climbing the career ladder in another profession, I have hope for you as well. The greatest career arbitrage in the history of modern economic times is occuring. Imagine if you tried out for a hockey team over the course of a week and the other players only showed up to skate in three of the five tryouts. You would have a significant advantage making the team by showing up to all five tryout sessions.

Since the pandemic, HR Departments everywhere have concocted guidelines (not rules) for workers to adhere to. Employees gained the flexibility at some firms to only show up to the office two, three, four days a week. While others are enjoying sleeping-in on Fridays, shuffling across the bedroom in slippers to their laptop, you could see this as an opportunity to show up to the office. Because you know who are still going into the office? Senior leaders. C-Suite. Your manager’s manager’s manager. Literally, the entire competition is being “told” to stay home, giving you undisturbed access to senior leaders and an opportunity to create serendipity for yourself. I’m not saying you have to go ‘Game 7’ every week at work, but showing up to the office on the occasional work-from-home day may be worthwhile.You could be the next Chris Volk associate who gets the call to work on something interesting that catapults your career. All because you showed up. Go in on Fridays too. The big boss is probably more likely to take you for coffee or maybe even a drink.

Moral of the story, always be moving. Find ways to be involved in things you’re interested in. Keep solid relationships. Reach out to interesting people on social media. Attend events and conferences. Work on side projects and tell people. Express your interest to help with projects in a different area of the company. Never let your calendar get too blank. All these small efforts can cultivate the serendipity you need to level up in life.

Game Notes

  • Netflix to stream WWE Raw in $5 billion bet on live events - Reuters
    • And the sports and entertainment only keeps getting more competitive
  • Highest Paid Athletes of 2023 - Forbes
    • Today, the average salary in the NBA-$8.3mm, MLB $4.0mm, NFL $3.3mm, & NHL $2.7mm
  • I think Martha Stewart is fascinating - WSJgram
  • Jamie Dimon, JP Morgan CEO, makes good points on Trump and MAGA critics - Instagram
  • The No. 1 challenge Fortune 500 execs say they’re facing with employees - CNBC ...job cuts will only continue
  • Does Negative Advertising Pay Off for Consumer Brands? hint: stay positive - WSJ
  • Apple could have an electric vehicle by 2028 - eGadget
  • After 50 years how did we manage to make refrigerators less useful? - X
    • After watching, this guy has a point
  • The 20-Year-Old Amateur Who Just Eclipsed Tiger Woods and Phil Mickelson - WSJ ... "Pressure is a privilege - Billie Jean King" - Nick Dunlap
  • Great story from Ariel Helwani. Who's fired up to get in that office on Friday and ask for what you want! lol - X