FIELD NOTES // Episode 7 Field Notes on Careers: Did You Choose Your Job—or Did It Choose You? DATE: September 2026 LOCATION: Somewhere between the career plan and planned happenstance OBSERVATIONS • Very few careers unfold according to plan. More often, one opportunity, relationship, skill, or accidental turn leads to the next. • The most durable career assets aren’t necessarily job titles—they’re transferable skills like communication, project management, relationship building, staying calm under pressure, and consistently showing up. • Finding what you don’t want to do can be just as valuable as discovering what you do. Experimentation gives you permission to move toward the things that fit—and away from the things that don’t. • Career, job, identity, and calling aren’t necessarily the same thing. As we get older, the question may shift from “How do I become successful?” to “What do I want to do with everything I’ve learned?” DISCUSSION Jarad, Brandon, and Travis look back at their careers and ask a deceptively simple question: How much of this did we actually plan? From caddying, cooking, car washes, and teenage side hustles to engineering, consulting, finance, startups, Google, and Silicon Valley, the conversation explores the skills picked up along the way—and how seemingly unrelated experiences can eventually form a coherent through-line. The guys discuss the value of choosing a North Star without needing to know the exact destination, “planned happenstance,” experimenting with different roles, knowing what to say no to, and putting yourself in situations where unexpected opportunities can find you. The conversation also turns toward the second half of a career. After decades spent building skills, financial security, and professional credibility, does the definition of success change? Maybe the next chapter isn’t simply about climbing higher. Maybe it’s about aligning your skills, interests, relationships, and resources with something that feels more meaningful. KEY TAKEAWAYS → Don’t obsess over planning the perfect career. Pick a direction, start moving, and recalibrate along the way. → Build transferable skills. The ability to communicate, organize, execute, build relationships, and stay calm travels with you regardless of title or industry. → Experiment aggressively enough to discover both what you’re good at and what actually gives you energy. Those aren’t always the same thing. → Create opportunities for “planned happenstance” by meeting people, trying new things, volunteering, taking on projects, and putting yourself where unexpected opportunities can emerge. → Your career doesn’t have to define your identity. Over time, success may become less about accumulating titles, money, or status and more about using what you’ve built to contribute to something bigger than yourself. FOR FURTHER STUDY Ask yourself: What is my current North Star—and does the work I’m doing today move me closer to it, even if I don’t know exactly where I’ll ultimately end up? WHERE TO FIND US Brandon - https://www.linkedin.com/in/brmiddle/ Travis - https://www.linkedin.com/in/tlzimbelman/ Jarad - https://www.linkedin.com/in/jaradbacklund/ Jarad’s Writing - www.myoldnotebooks.com END OF NOTES