May 18, 2026
Starting Over at the Top 😳
This is a free preview of a paid episode. To hear more, visit <a href="https://moonshotmentor.substack.com?utm_medium=podcast&utm_campaign=CTA_7">moonshotmentor.substack.com</a><br/><br/><p>Robert got the call on a Friday afternoon. After trying to find a job in his industry for eighteen months, he faced the hard truth that for someone at his level, there were no viable openings. So he pivoted to Pharma doing sales. A far cry from Vice-President of Marketing at a film studio. He would start the new gig in two weeks.</p><p>Robert was elated to have a gig, but he was dejected because his degree, his experience, and his wins didn’t translate to the new role. He would be starting in a sales training program with a “bunch of 20 year olds.” He confessed he was embarrassed and anxious to be a newbie.</p><p>If you’re mid-career or later, and you’re stepping into something unfamiliar, you may feel horribly destabilized. Because knowing your stuff has always been your anchor. And now it’s not enough.</p><p>Here’s what I want you to know: your credentials are not meaningless. But they’re not the whole story either. In new territory, something else takes the wheel. And most high achievers are the last to figure out what that something else actually is.</p><p><strong>The Default Move That Backfires</strong></p><p>When accomplished people step into unfamiliar terrain, they almost always do the same thing: they double down on what got them here. More preparation. More credentials. More proof that they belong. It’s the only playbook they know, and it’s worked for a long time.</p><p>But in new territory, that strategy can work against you.</p><p>The pressure to perform expertise you don’t yet have when you’re someone who typically hits it out of the ballpark can be debilitating. Instead of projecting competence, you end up projecting effort, which reads very differently in a room.</p><p><strong>Why This Happens</strong></p><p>Your identity has been wrapped up in being the expert for a long time. It’s what happens when you’re good at something and build a career around it. You’re rightly proud of those achievements.</p><p>But when you’re no longer the expert, your nervous system reads that as danger. So you over-prepare. You over-explain. You puff up with overcompensation.</p><p>Or you go the other direction and withdraw, waiting until you feel ready enough to show up. Observing the situation, taking notes, plotting and planning.</p><p>None of these responses is what the new territory actually needs from you.</p><p>The expert identity that protected you in your old lane becomes a kind of armor that keeps you from learning what you need to learn in order to succeed again.</p><p><strong>What Actually Moves the Needle</strong></p><p>When Robert completed his sales training, he told me he almost blew it. He was irritated with the pace of the program, he already knew what he was being told, and he was being trained by someone 15 years younger than him. After the second day, he went home and vented over dinner.</p><p>Now, Robert’s a terrific dad, and his parental wisdom came back to him at the right moment. His 16-year-old son said to him in mid-vent, “Dad, I thought you said attitude is the best strategy.” Those words stopped Robert in his tracks. He knew he was impatient and didn’t “suffer fools.”</p><p>But he also knew that attitude was the difference between a door opening or closing, a brief stint or a place to grow, and his own mental well-being.</p><p>Robert thanked his son, told his family to throw marshmallows at him if he started complaining again, and course corrected his attitude. He started the third day of training with a beginner’s mind and brought cookies.</p><p><strong>What Attitude as Strategy Actually Looks Like</strong></p><p>Let me make this concrete, because “show up with a good attitude” is advice that sounds nice and means nothing without specifics.</p><p>* <strong>Ask more questions than you answer.</strong> A friend of mine struggled with this early in her career. She had so many thoughts she wanted to share in every meeting that she started keeping a notebook just to get them out of her head. What she discovered was that writing things down calmed her nervous system. It freed her to actually listen. She stopped needing to show she knew everything and started learning more by asking. The relationships she built that way turned out to be some of the most valuable of her career.</p><p>* <strong>Name what you don’t know before someone else does.</strong> Early in my time as an executive overseeing primetime programming at CBS, I was given a role that was a significant stretch. On my first set visit to a show that had already been on the air for two years, I said to the production team: you know more than I do. I’m here to learn and be a fan. The room shifted immediately. People who had been braced for a network executive to come in and assert authority instead opened doors they typically kept the suits out of. Naming a gap honestly is a form of leadership.</p><p>* <strong>Let your enthusiasm be visible, and be specific about it.</strong> This one is genuinely underrated. Enthusiasm that is vague feels performative. Enthusiasm that is specific feels real. Show up on time or early. When something impresses you, say exactly what impressed you. Look people in the eye. Say hello. Say thank you in a way that names the thing you are grateful for. None of this is complicated, but it lands differently than people expect.</p><p>* <strong>Protect your energy from the things that spiral you. </strong>Robert deleted social media during a stretch when he noticed he was using it when he felt bored. That was an important strategic decision because boredom for Robert meant he believed he knew everything he needed to know. Your attitude is an asset. Anything that drains it is worth taking seriously.</p><p><strong>The Nuance Worth Naming</strong></p><p>Focusing on attitude is not an argument against skill. You need a baseline. You need to be able to do the work at a competent level before any of this matters.</p><p>But past that threshold, what differentiates you in new territory is relational and energetic, not just technical. The people who are deciding whether to bring you along, collaborate with you, or invest in you are asking a very human question: Do I want this person in the room when things get hard?</p><p>That question is answered by how it feels to be around you.</p><p><strong>Bottom Line</strong></p><p>Robert finished his sales training. Turns out he didn’t know everything. But with his son’s reminder, he showed up curious, asked questions, and let people teach him. And that attitude shift made the training a pleasant experience.</p><p>Your expertise is real. Your accomplishments are real. But in new territory, the thing that earns trust is how you show up with grace and interest.</p><p>Ask more than you answer. Name the gap before someone else does. Let your enthusiasm be specific and visible. Those aren’t soft skills. They’re the strategy.</p><p><p><strong>If someone came to mind while you were reading this, please send it their way. You never know the impact a well-timed message can have.</strong></p></p><p><strong>This Week</strong></p><p>One of the many things I respect about Courtney Romano is that she is not asking for permission in her career. She wears many hats: writer, director, producer, strategist, consultant and is a champion for Non-Dependent Filmmaking. </p><p>Let’s find out how she does it.</p><p><strong>Journal Prompts</strong></p><p>Here are four journal prompts for paid Moonshot Mentor subscribers. These questions are designed to help you examine the role attitude has played in your career and what it might look like to lean into it more deliberately in a pivot.</p>
