A few weeks ago, we went to see Stephen Kellogg’s “Stand Up and Sit Down” show, in which he combines stand-up and musical performances. You are missing out if you have never attended a Stephen Kellogg show; his lyrics are profound, and he seems genuinely lovely. Michael put it best when he said, “He seems like someone you would invite to sit around the fire and drink White Claws with you and Dad.” (We are now White Claw people because our middle-aged stomachs no longer tolerate good craft beers.)
That night was our fifth Stephen Kellogg show. We made a night of it, visiting a local brewery for beer and BBQ before the show. When we arrived, we were overjoyed to see chairs; we would not need to stand all night! At the show’s beginning, SK assured us, “I’ll have you back on your couches, watching Netflix and scrolling your phones before you know it.” His shows begin with a montage of clips, one from a TED Talk he delivered years ago describing his desire to pursue music. During the talk, he quoted The Office: “It’s better to be at the bottom of a ladder you want to climb than at the top of a ladder you don’t.” I could see Michael, who referred to SK as the “lovesick guy with a guitar,” sitting up a little straighter and paying attention.

As always, the show was terrific. Mike and I noted that he played a few of our favorite songs, including “Thanksgiving,” harder than usual. On the ride home, we talked to Michael about the show. Michael, who had made fun of SK’s lyrics about love, is coming around. A few things have changed his mind, including an observation a few weeks earlier:
While driving home from Thanksgiving weekend in Maine, we stopped for gas. Two cars were clearly doing the split custody child hand-off in the corner of the parking lot. Michael has friends whose parents are divorced and is familiar with “at my dad’s” or “at my mom’s,” but this was the first time he witnessed the switch in real life. He sat, speechless. “Are you glad you have parents who still go to Smoochville?” I asked, referring to Michael’s teasing when Mike and I kissed. Michael was affected by witnessing this interaction, mentioning it a few times over the next few days.
This brings us back to the latest show we attended. SK talked about success and family at length. I could see Michael absorbing his words. SK’s words about success and following dreams struck a chord with Michael.
We’ve talked to Michael about high school for the past few months. His district offers several career paths. While Michael’s top dream is to replace Bryce Harper on the Phillies, he is also realistically interested in business. He’s currently taking a business elective and is enjoying every aspect of it. He talks about starting his own business or working in marketing or promotion for a company, preferably in a sports-related field.
I am a teacher. In seventh grade, I knew I wanted to spend my days surrounded by words. I (usually) love my job and cannot imagine doing anything else. I am also aware that if I did not marry an engineer, I would not have enough money to pay for the equipment and lessons that allow Michael to follow his aspirations. After twenty years of teaching, I know I make less money than an engineer fresh out of college.
Mike is an engineer. When he was unsure what he wanted to study, he spoke to a family friend, a bachelor who had all sorts of free time and “toys” (a plane, sports car, etc.). Mike decided on a major based on the projected earnings. He doesn’t dislike his job, but he is not always passionate about it.
While we chose our selected careers for different reasons, both offer stability and safety. We know what our days look like, when we will be working, what our days will look like, how much we will earn, etc. We have spreadsheets mapping out our retirement goals. We plan vacations based on visiting new baseball stadiums each summer. We selected fulfilling but safe pathways and are forever in awe of people who, like Stephen Kellogg, pursued his passions.
So here lies the dilemma as a parent: how much do we support an unrealistic dream? Yes, Michael is a talented player. He’s passionate, hardworking, and blessed with a build that supports hitting dingers. He studies stats and players, genuinely appreciating the art of playing baseball. He joined cross country to get faster, hoping he could progress from leading his team in doubles to leading his team in triples and home runs. At thirteen, he is hitting with the exit velocity of a sixteen-year-old. Do we encourage Michael to take the safe route and focus on business? Or do we encourage him to pursue his dream of being a homerun hitter for the Phillies, knowing the odds are not in his favor?
On the ride home from the show and throughout the rest of the evening, Michael continued to digest the words of the “lovesick guy with a guitar.”
“Did you hear what he said about the ladder?”
“Do you think I can play for a D1 school?”
“Do you think I could play for a collegiate team, even for a summer?”

He’s a talented player in a sea of gifted players. And right now, he’s a talented player who will give his all for the chance to make it to the show… while working on a degree in management or marketing. And, yes, Stephen Kellogg does appear to be someone we’d love to invite over to sit around the fire and drink White Claws; he’s also the person who convinced my son not to play it safe. He convinced Michael to pursue his dreams and climb the ladder he wants to climb. While we try to be realistic, we also entertain his conversations regarding selecting a walk-up song. He is completely confident about this, too. (His choice? Butter, by A Tribe Called Quest, a decision that also brings much pride.)