Steve Young on How to Reinvent Your Career

I’ve written before about Once In a Lifetime opportunities that my membership in EO has afforded me. On October 17th, 2013 I experienced one of the bigger ones – meeting Super Bowl MVP, 2x NFL League MVP and Pro Football Hall of Famer Steve Young. Despite rooting against the 49ers my entire life, it wasn’t that hard to play the part of fanboy that day. I found him to be approachable, down-to-earth, a bit self-effacing and surprise – extremely funny. After that short meetup and quick photo opp, he spoke to our group about football, living in Joe Montana’s shadows, married life and the topic that I’d like to share with you today. At 38 years old, cumulative concussions forced Steve Young out of football and left him to figure out what he was going to do for a career with the 2nd half of his life. The following is Steve’s journey and his advice on how to reinvent your career.

1. Be Humble

Right after winning Super Bowl XXIX, on national TV, Steve shouted the familiar phrase “I’m going to Disneyland.” Little did he know that meant that in addition to actually having to go, he had to go the very next day. As Steve told it, the exhaustion he felt post Super Bowl quickly faded away when the parade started. Riding a float down Disneyland’s Main Street, standing next to Jerry Rice and Mickey Mouse, the applause and adulation was overwhelming. His ego thoroughly stroked, he thought to himself, “I am the man.” That is, until the parade was over. Standing right in front of the float were two young brothers, about 6 and 8. The younger of the two started to run towards the float. At that moment, the older brother grabbed the younger one and said, “You can’t get near him; the two big guys won’t let you.” Just like that, Steve went from being “the man” to Mickey’s bodyguard.

Steve shared that story as a metaphor to what it felt like for him when he was left to ponder his future post football. Outside of football, he was just another big guy. Steve realized that whatever he decided to do next, he had a lot to learn and he was going to have to put in the work. Wisely, he knew that the biggest obstacle he was going to face in starting over was his ego. His advice, “Be prepared to humble yourself.”

2. Surround Yourself with Smarter People.

Once his football career was over, Steve sought out the advice of as many business leaders as he could. “I made it my goal to be the dumbest guy in the room.” Interestingly, Magic Johnson did the exact same thing when he retired from basketball. They both asked as many questions as possible and listened. Both have found tremendous success after retiring from sports.

3. Mt Everest.

Steve’s last piece of advice was to “figure out your Everest and go put your flag on it.” To get there, don’t avoid conflict – “Just go through it.” Reflecting back on his playing career, he shared that he didn’t win the big games until he started throwing the ball “semi-blind”. He would imagine where a receiver should be and throw the ball to that spot even when the lineman in front of him prevented him from seeing the field of play. (Despite being listed at 6’2”, Steve is only 6’.) From his perspective, your professional career should be treated the same way. If you can imagine an opportunity, destination or “Everest”, you sometimes have to pursue it “semi-blind”.

“Figure out your Everest and go put your flag on it.”

The Next Chapter.

True to form, Steve attacked his next chapter with the same obsessive focus, determination and humility that he brought to football. He jumped into venture capital and rose to be the managing partner with 2 different venture firms. Next, he co-founded and is currently a managing partner with the venture capital firm HGGC. With over $2B in capital investments in 46 companies, HGGC is a phenomenal success. This leads us back to Steve’s question. What’s your personal Everest?