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- Yesterday10 min
Starting Over at the Top 😳
This is a free preview of a paid episode. To hear more, visit moonshotmentor.substack.comRobert 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.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.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.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.The Default Move That BackfiresWhen 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.But in new territory, that strategy can work against you.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.Why This HappensYour 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.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.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.None of these responses is what the new territory actually needs from you.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.What Actually Moves the NeedleWhen 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.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.”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.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.What Attitude as Strategy Actually Looks LikeLet me make this concrete, because “show up with a good attitude” is advice that sounds nice and means nothing without specifics.* Ask more questions than you answer. 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.* Name what you don’t know before someone else does. 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 o
- 1 weeks ago9 min
I Know I Should Reach Out 🙈
This is a free preview of a paid episode. To hear more, visit moonshotmentor.substack.comI asked a room full of smart, ambitious professionals to rate how important relationship building is to their careers right now. On a scale of one to ten, the answers came back: Seven. Eight. Nine. Ten.Then I asked a follow-up question: how does that actually show up in your day-to-day? My favorite response: “Actual importance: ten. How I’m treating it: three.” We all laughed. Because we recognized ourselves.It may seem like that gap between knowing relationships matter and actually building them is an issue of will-power, discipline or follow through, but it’s actually more interesting than that.Close the Relationship Gap with TimingHere’s what’s really going on. We build relationships reactively. We reach out when we need something like a referral, an introduction, a favor, a job, an investment, an opportunity to pitch. We fumble the ask, not knowing how assertive to be or we over index on small talk. We feel like imposters despite our knowledge, training and experience.The problem isn't the ask. The problem is your timing.When you reach out before you have an ask the whole dynamic changes. You're not a transaction. You're a person.Ditch Networking. Build the Relationship.Relationship building isn’t networking. Networking implies a transaction with better branding. Relationship building is different. It’s deciding, in advance, who matters to your work and your life, and getting on their radar.That shift in framing makes the energy of the outreach about building rapport. You’re not trying to extract something. You’re trying to meet someone and build a mutually beneficial relationship that doesn’t have an immediate timeline.It’s so simple, right? But why don’t we do it?The Five Things That Actually Stop YouI’ve had versions of this conversation with a lot of clients. And the reasons people stall on relationship building tend to cluster around the same five things. You may recognize a few as your own.1. The fear of doing it wrong. When the fear of a bad outcome feels bigger than the cost of no outcome, doing nothing feels like the safer choice. But silence doesn’t advance your career.One client said, “If I do it the wrong way, I’m going to sabotage a potential relationship before I even have a chance to have one.”It’s paralysis masquerading as caution.You know this: there’s no perfectly worded email that guarantees a response. There’s no flawless DM that removes all risk. There’s no single phone call that converts a stranger into your bestie.Practice courage over perfection.2. Waiting for the right moment. Another person described her pattern as this: “I love sending emails when I feel like I’ve just had a win and I’m like, yeah, let’s go. But on days when I’ve had a setback, I put that off and wait for the magical day to arrive when the sun is shining on me and no one can say no.”If you’re only reaching out from a place of momentum and confidence, you’re leaving most of your calendar year on the table. Relationships get built in the ordinary weeks, the in-between moments, the days when you reach out anyway.3. Never having your ducks in a row. This one is sneaky because it sounds responsible. “I’m just being thorough. I want to have something to offer. I want to be ready.”But ready for what, exactly? A first email isn’t a pitch. It’s an introduction. You don’t need a portfolio, a deck, or a fully formed ask. You need a sentence or two and a genuine reason you thought of this person.Real life example: I got a cold outreach from someone over LinkedIn who wanted to zoom for 15 minutes to swap stories from the front line as grief workers. There was no ask, but we shared enough information that we’ve agreed to chat again down the road.You’re reaching out “early” as part of getting your ducks in a row.4. Believing every reach is secretly transactional. This one hit me hard in a recent conversation. Someone said: “I feel like there’s always an ask, Laverne. I don’t know. It’s eventually… there’s always something.”And they’re not wrong. Eventually, most professional relationships do involve an ask of some kind. That’s how collaboration works. But “eventually” is doing a lot of heavy lifting in that sentence.The goal of early relationship building isn’t to pretend you’ll never need anything from anyone. It’s to build enough of a real connection that when the ask comes, on either side, it lands in a context of mutual trust. That context takes time. Which is exactly why you start before you need it.5. Needing a reason to reach out. Yo
- 1 weeks ago9 min
I Know I Should Reach Out 🙈
I asked a room full of smart, ambitious professionals to rate how important relationship building is to their careers right now. On a scale of one to ten, the answers came back: Seven. Eight. Nine. Ten.Then I asked a follow-up question: how does that actually show up in your day-to-day? My favorite response: “Actual importance: ten. How I’m treating it: three.” We all laughed. Because we recognized ourselves.It may seem like that gap between knowing relationships matter and actually building them is an issue of will-power, discipline, or follow-through, but it’s actually more interesting than that.Close the Relationship Gap with TimingHere’s what’s really going on. We build relationships reactively. We reach out when we need something like a referral, an introduction, a favor, a job, an investment, or an opportunity to pitch. We fumble the ask, not knowing how assertive to be, or we over-index on small talk. We feel like impostors despite our knowledge, training, and experience.The problem isn’t the ask. The problem is your timing.When you reach out before you have an ask, the whole dynamic changes. You’re not a transaction. You’re a person.Ditch Networking. Build the Relationship.Relationship building isn’t networking. Networking implies a transaction with better branding. Relationship building is different. It’s deciding, in advance, who matters to your work and your life, and getting on their radar.That shift in framing makes the energy of the outreach about building rapport. You’re not trying to extract something. You’re trying to meet someone and build a mutually beneficial relationship that doesn’t have an immediate timeline.It’s so simple, right? But why don’t we do it?The Five Things That Actually Stop YouI’ve had versions of this conversation with a lot of clients. And the reasons people stall on relationship building tend to cluster around the same five things. You may recognize a few as your own.1. The fear of doing it wrong. When the fear of a bad outcome feels bigger than the cost of no outcome, doing nothing feels like the safer choice. But silence doesn’t advance your career.One client said, “If I do it the wrong way, I’m going to sabotage a potential relationship before I even have a chance to have one.”It’s paralysis masquerading as caution.You know this: there’s no perfectly worded email that guarantees a response. There’s no flawless DM that removes all risk. There’s no single phone call that converts a stranger into your bestie.Practice courage over perfection.2. Waiting for the right moment. Another person described her pattern as this: “I love sending emails when I feel like I’ve just had a win and I’m like, yeah, let’s go. But on days when I’ve had a setback, I put that off and wait for the magical day to arrive when the sun is shining on me and no one can say no.”If you’re only reaching out from a place of momentum and confidence, you’re leaving most of your calendar year on the table. Relationships get built in the ordinary weeks, the in-between moments, the days when you reach out anyway.3. Never having your ducks in a row. This one is sneaky because it sounds responsible. “I’m just being thorough. I want to have something to offer. I want to be ready.”But ready for what, exactly? A first email isn’t a pitch. It’s an introduction. You don’t need a portfolio, a deck, or a fully formed ask. You need a sentence or two and a genuine reason you thought of this person.Real life example: I got a cold outreach from someone over LinkedIn who wanted to zoom for 15 minutes to swap stories from the front line as grief workers. There was no ask, but we shared enough information that we’ve agreed to chat again down the road.You’re reaching out “early” as part of getting your ducks in a row.4. Believing every reach is secretly transactional. This one hit me hard in a recent conversation. Someone said: “I feel like there’s always an ask, Laverne. I don’t know. It’s eventually… there’s always something.”And they’re not wrong. Eventually, most professional relationships do involve an ask of some kind. That’s how collaboration works. But “eventually” is doing a lot of heavy lifting in that sentence.The goal of early relationship building isn’t to pretend you’ll never need anything from anyone. It’s to build enough of a real connection that when the ask comes, on either side, it lands in a context of mutual trust. That context takes time. Which is exactly why you start before you need it.5. Needing a reason to reach out. You don’t need an excuse. You need a sentence. And that sentence can be easy in the form of a low hanging fruit request.Something like: “We have
- 2 weeks ago9 min
Why Is No One Getting Back to Me? 😩
If you want to know where you stand with someone, don’t listen to what they say. Watch what they do.It’s taking me years to learn this. And I got a great reminder of it a few weeks ago. It was late afternoon in Mammoth Lakes, California, fifty degrees with a little cloud cover, and the trails near our favorite place to stay, Tamarack Lodge, were enticing. I mean, the mountain looked absolutely pristine, birds were chirping like they were auditioning for Pitch Perfect, and there was hardly anyone around. Ideal conditions.So I’m about a quarter of the way up the mountain, and I notice where the snow has melted there’s a line where reality begins. One side looks composed in gorgeous white. The other side is real life.Broken branches. Dry brown scrubs. Rocks. Dirt. Dead trees.It was the perfect metaphor for the disconnect between what someone says they’ll do and what they actually do.And then I thought about all the people I know who are job hunting.The follow-up that never comesHow many times have you refreshed your inbox over and over after a submission or an interview?They said I’ll be in touch by Friday. Or the colleague who said I’d love to read it, send it over. Or the boss who keeps promising you’ll have that conversation next week. And then, crickets.When the follow-up doesn’t come, most of us wonder what we did wrong. We debate whether to send a nudge. We tell ourselves the silence might just mean they’re busy, swamped, or traveling.Hard truth: the silence does mean something. You just haven’t been trained to hear it.The problem with wordsIf I could turn back the clock on my career, one of the things I’d do differently is stop listening so hard to what people say, and start paying attention to what they do.We’re wired to take people at their word. It feels respectful. Optimistic. Generous. And words are data. Just the least reliable kind.Here’s what I’ve come to believe: most people aren’t lying. They’re doing their best, and they’ll often tell us what we want to hear to reduce tension in the moment. Aren’t we all a little bit people-pleasers on some level? Words are easy to give. They cost nothing.Actions, on the other hand, take effort and investment. They reveal someone’s true priorities, capacity, and intentions.Words are the snow on top of the mountain. They look perfect.When the words melt away, you’re left with what’s really there.Part of why we over-index on words is that we don’t want to seem cynical. In professional settings, especially, it’s not cool to challenge someone’s promises. We prize harmony over honesty. We’ve been taught to respect hierarchy and not to question it. So if you’re job hunting, hoping for a promotion, or trying to get funding, the last thing you want to do is treat someone’s words with skepticism.And so we wait. And refresh. And wait some more.What it looks like when you ignore the actionsMy client “Mary” spent 18 months putting a deal together. It had nearly fallen apart half a dozen times, but she always managed to pull it back. Until she was one deal point away, and the investor walked.She was stunned. Then outraged. And when we finally unpacked what had happened, the signs had been there for a long time. The weeks it took him to respond to a single negotiating point. The pouting and obsessing over minor issues. The questions he’d ask during their calls revealed a naivete about how their industry worked.Mary had heard his words — I’m committed to this, let’s make it happen — and held onto them. She’d overridden what the actions were consistently telling her.She missed the signals because she wanted to believe what he said.Four ways to start listening to actions insteadI’ve been there countless times. It even happens to me at home when my teenager says, “Yeah, sure,” when I ask her to pick up her dishes. Every time I choose to listen to the words, and then I’m shocked the next morning when I find a dry, crusted bowl of pasta lying on the living room floor.Inspired by mothering two teenage daughters and a few decades in the entertainment industry, here are four ways to better listen to the actions, not someone’s words. They’ve helped me figure out who my people are and, most importantly, protect my self-esteem.Look for the pattern, not the single miss. One unanswered email? Things happen. A consistent pattern of not following through? That’s your track record. That’s your data. Once you see the pattern, you’re no longer Charlie Brown waiting for Lucy to hold the football. You know how this story ends.Take your emotions out of the analysis. This is hard, but important. Strip the words away entirely
- 3 weeks ago8 min
Waiting for the Axe to Fall 😰
Rebecca, a senior executive at Warner Bros., just wants to know the truth of what’s going on with the Paramount merger and when she’s going to be axed. The uncertainty is “killing her.”She’s not alone. Not even close. 2026 is packed with mergers and consolidations across industries: Devon Energy and Coterra. SpaceX and xAI. Engie and UK Power Networks. Tens of thousands of people going to work every day inside organizations mid-transformation, wondering the same thing Rebecca is wondering.Am I going to be okay?And here’s the thing: she’s not being dramatic. The waiting — that particular brand of not-knowing — is one of the most exhausting places a career can put you.What Rebecca is experiencing has a name: anticipatory grief. It’s the grief we feel before a loss that hasn’t fully landed yet — when the change is coming but hasn’t arrived, when the future feels like it’s being written without you chiming in.And the reason it matters — the reason I’m writing about it — is because of what happens when it goes unrecognized.The Thing That Will Trip You Up If You Let ItMost conversations about job uncertainty focus on the practical stuff. Update your resume. Build your network. Stay visible.All good. All useful. But they skip the thing that’s going to trip you up unless you recognize and take care of it now.When anticipatory grief goes unnamed, it tends to seed apathy. A low-grade helplessness. A “why bother” feeling that creeps into the edges of your days and makes it hard to invest in anything — your work, your relationships, your future — because some part of you has already checked out.This is you protecting yourself from a disappointment that hasn’t happened yet.I see this in high performers especially. They keep showing up. But their spark has gotten a little dim. Their tolerance for staff meetings is zero. The projects they nurtured now feel abandoned.Here’s why: they haven’t named what they’re actually afraid of losing.The Scariest of All Roller Coasters that No One Warned You AboutAnticipatory grief is like riding the Kingda Ka at Six Flags Great Adventure in New Jersey (RIP) — supposedly the scariest roller coaster in the world. You wait for the big drop and it turns out to be a gentle twist. You think you’re entering a flat run and suddenly you’re weightless and upside down. The not-knowing when and how is its own particular torture.And then hope climbs into the car beside you. Maybe you’ll dodge the restructure. Maybe your team won’t be gutted. Maybe it won’t be as bad as you fear.That hope is real. And it makes the lurches harder, not easier — because every time you exhale, the next one catches you off guard again. The stomach drop. The pounding head. The heart beating like a hummingbird.With “typical” grief, we’re reacting to what happened. With anticipatory grief, we’re responding to something that hasn’t happened yet. And might not.Which makes it especially hard to sit with.The question worth asking — gently, with real compassion for yourself — is this:What are you actually afraid of losing?CASE STUDY: WHAT REBECCA WAS REALLY AFRAID OFWhen I finally sat with Rebecca and asked her that question, here’s what came up, which surprised her because it wasn’t really about anticipating the loss of income or title.What Rebecca was actually afraid of losing was the dream of retiring by 60 and sending her two kids to the colleges of their choice.Her job was the how to a future she’d been building for years.Here’s what happened when she named it out loud.She felt relief.The merger news didn’t change. Her job was still uncertain. But dissecting the fear allowed her to question it: is this truly something I need to be worried about right now? And if it is, what can I do now?Once Rebecca saw that she was truly trying to protect a dream, she got clear. She and her husband made an aggressive savings plan that would account for a greatly reduced salary and still keep them on early retirement track. She also had a conversation with her kids to find out if they were aligned on the college dream. Turns out they didn’t want Ivy League, nor did they have the grades.She couldn’t control the merger. But she could tend to the dream.Here’s what I know to be true: naming your fear doesn’t make it worse. It makes it workable. A spiraling thought that lives in your body at 3 am is a lot harder to respond to than something you’ve put words to on a page.The path to
- 4 weeks ago7 min
What Do You Owe a Difficult Boss?
This is a free preview of a paid episode. To hear more, visit moonshotmentor.substack.comI was having lunch on the patio at Kiwami with a long-time colleague — we'd served together on the board of the Coalition of Asian Pacifics in Entertainment — and we were debating whether to order the Kiwami tray or go à la carte. And then, I felt the energy around me shift. I didn’t turn my head, but I could see her outline in my peripheral vision. The boss who fired me. OMG, she was seated close enough to hear us order, and I was close enough I could smell her perfume. My first instinct: pretend she doesn't exist. Keep smiling. Keep chatting. Keep still. But the light-hearted parley about omakase was now nausea inducing and there was a buzzing in my ears.My boss, no, my ex-boss flagged a waiter and asked to move inside. I can't remember anything that happened after that. Here's what I know now that I didn't know then: what happened in my body had a name. My nervous system registered a perceived threat and responded accordingly — heart rate, shallow breath, the works. I was in a fight / flight / freeze / fawn moment — and caught between freezing and fawning. Why not do both when I’m under threat? What's interesting is that the threat wasn't real. I wasn't in danger. But my nervous system treated my ex-boss’ arrival as if something horrible was about to happen and I would be blind-sided all over again. Reader Question: Should I Reach Out to a Former (Not Awesome) Boss for a Job?I was reminded of this Kiwami experience recently when a reader sent me a question I suspect a lot of other people have too. He'd just learned that a former boss had landed a senior role at a new company. This was someone who had been skilled at managing up and promoting himself, but less focused on developing and advocating for his team. Now that this person was back in a leadership position, my reader found himself wondering: does it make sense to reach out? And if they ran into each other at some random place, what exactly should he do?We all know how important it is to maintain business relationships, but what do you do with the professional relationships that were genuinely complicated and triggered you into fight / flight / freeze / fawn mode? Thank you reader for such a powerful, timely question. The Tool: Friendly, Not FriendsEarlier in my career, when I was a “baby” network executive, some of the senior executives I worked with were … well, I just have to say it. They were mean girls. When I would walk on set, they literally turned their backs and formed a circle. It was the kind of thing that makes you feel like you're back in junior high.My first response was to shrink, you know a kind of freezing. I started showing up at the last minute so I wouldn't have to stand on the periphery. I avoided the spaces where they gathered. I got smaller and smaller until one day I realized: their behavior was changing mine. And I hated it.I love having authentic conversations with people. I love collaborating and solving problems together. I love being nice because I know you never know what’s going on behind the scenes with someone. So I made a different choice: treat the mean girls the way I'd treat any stranger.Friendly, but not friends. A few months later, the ringleader pulled me aside and said: I don't know how you did it, but you did it. Everyone likes you now.It was a little crazy to hear that because my goal wasn't to make everyone like me. I just didn't want other people changing my behavior or my values. I didn't like who I was becoming.. Should You Reach Out? My Honest Answer So back to my reader's question: should you reach out to the former boss who wasn't great to you, now that they've landed somewhere new?My honest answer: only you know. What I'd encourage you to do is get clear on which value you're honoring with your choice — whichever way you go. I'll be transparent though: if it were me today, I would not reach out because I now prioritize a flat hierarchy and working with people who are willing to have hard conversations in a grounded manner. But I also don't know what's happening behind the scenes in the reader’s life. Financial pressure, health insurance, a shrinking market — these are real considerations that can make pursuing every opportunity not just reasonable but necessary. There's no shame in that math.
- Apr 13, 20268 min
The Career Wins You Forgot To Count
This is a free preview of a paid episode. To hear more, visit moonshotmentor.substack.comYou know what you’ve lost. But can you name your wins?Most people in a career transition can recite their losses on demand. The VP title. The 401K contribution. The Friday happy hours with the work family. The satisfaction of knowing what the job is and how to do it.Ask them to name their wins? Awkward silence then a short, apologetic list they immediately start walking back. “I mean, it wasn’t that big a deal.” “Anyone could have done that.”This isn’t humility. It’s your brain doing exactly what it was designed to do.Your Brain Thinks It’s Helping - It’s NotYour brain tracks threats and losses with far more energy than it tracks wins. It’s called negativity bias and a lot has been written about it. Essentially, as humans we’re wired to look for what’s not working as a way to protect ourselves.During a career transition, exactly when you need a clear and accurate picture of your professional story, your brain is actively over-indexing on the negative. The losses stay top of mind while the wins get tucked into a bankers box and put into the back of a storage container.Over time, negative bias feels like the truth. And once it does, it starts calling the shots on every decision you make — what you apply for, how you talk about yourself, what you believe you’re capable of next.I learned this the hard way. And what made it worse is that my brain wasn’t the only thing working against me. I was also using the wrong measuring stick.Another Reason Your Wins Go MissingSeveral years ago, when I was pivoting out of independent film and TV producing, I went after three corporate opportunities, hard. Made it to the final round for all three. Got none of them.When I dug into why, the feedback was consistent: the candidates who were hired had more recent, measurable wins. Box office numbers. Emmy nominations. Projects that crossed the finish line in ways the industry recognized.Ouch. I knew how hard I’d been working. And I knew that a lot of the gap wasn’t about effort — it was about circumstance. COVID. The lockdowns. The writers’ and actors’ strikes. An industry that had slowed down so much, we could count the number of greenlit productions on one hand.Turns out my wins weren’t missing. They just didn’t fit the industry’s scoreboard.I’d spent years making sure the people on my projects felt respected. I knew this because they kept wanting to work together on new projects. I took great pride in responding to submissions when most people didn’t bother. Timely passes built relationships with agents, managers and other producers who understood that most of the time, the answer is no. Nobody was measuring those things that fell under the emotional intelligence category. They weren’t measurable in the same way the industry looks at ROI or KPIs. They were about humanity.I wasn’t winless. In fact, I was quite victorious. But me and the industry were using different measuring sticks so I felt less than.Finding The Wins Hiding In Your StoryIf your career story feels heavier on losses right now, here’s an exercise worth sitting with that includes the parts that haven’t made it onto your résumé yet.Start with the most obvious place: external recognition. Awards, nominations, acknowledgments — any moment where someone outside your own head said yes, this. Write them down without editing or qualifying.Then go a little deeper. What do people thank you for, come to you for, refer others to you for? This one matters more than it might seem. When something comes naturally to you, it stops feeling like a win — it just feels like any other day. But the fact that people consistently seek you out for it says a lot about you.Then ask yourself about the goals you hit without fireworks going off. The ones you set, achieved, and moved on from without a big victory dance. Those count too.Now here’s where it gets more interesting. We tend to define victory as coming in first, getting the public recognition, beating the competition. But that’s only one definition — and for many people, it’s not even the one that matters most.Think about a time you made a decision that honored your values, even when it went against what others expected. Or a time you went so far outside your comfort zone to make something happen that it surprised even you — even if the outcome wasn’t perfect, even if it wasn’t work-related at all. The stretch itself is a win. The integrity itself is a win. These moments are the most accurate picture of who you actually are.
- Apr 6, 20265 min
Why Don't My Clothes Feel Like Me Anymore?
This is a free preview of a paid episode. To hear more, visit moonshotmentor.substack.comRemember when lockdown happened and there were all those stories about people showing up to Zoom meetings looking perfectly presentable from the waist up — and if you got a peek below the camera line, you’d find them in their underwear and socks?I loved that. It was so human. So real.It was a great contrast to the pressure to get my wardrobe choices right. All those spoken and unspoken rules: Women wear heels, men keep shirts tucked. Dress for the role you want, not the one you have. First impressions happen instantaneously and last a lifetime — so be careful of what your sweater says about you.When we all worked remotely in 2020, those rules — and a gazillion others — started feeling more like suggestions.But here’s the thing about rules going soft, whether by a global pandemic or a career transition, chosen or not: it’s disorienting. When the pre-approved look comes off, a lot of people don’t know what to put on instead. Because for years, the job dressed them, in every sense of the word. And when the job changes, so does the style guide.When I made the transition out of corporate and into indie filmmaking, my Manolos and Pradas were not only inconvenient on set — they genuinely felt like a costume I’d been wearing for decades.If you’re in the middle of a career change, contemplating one, moving up, or been pushed into one, you may no longer feel confident about what to wear — or even who you’re dressing for anymore. When you open your closet, do you stand there longer than you used to?What Your Wardrobe Is Actually Asking YouHere’s what I’ve come to believe: getting dressed during a career transition isn’t really a fashion problem. It’s a values question.Let me explain what I mean.When I was in an executive gig, I genuinely valued the stability of that world — the sense that I could build something there over decades. Wearing those Manolos was part of that deal. I knew the rules, I understood the culture, and I made a conscious choice to dress for it. It wasn’t always comfortable, but it was mine to choose.My brother Jim is a great counterexample. Jim would sooner show up to a board meeting in a tuxedo than wear a suit to work — and he never has, except on his wedding day. He works in construction because he loves the outdoors, loves working with his hands, and is completely at ease getting grubby. His wardrobe is a direct expression of what he values. He just never had to think about it because his work and his values were two peas in a pod.When you’re in a career transition, you get a chance to ask a question most people never pause long enough to consider: Does what I’m wearing actually reflect what I value? Or have I just been dressing for someone else’s idea of who I should be?.The Difference Between Choosing and DisappearingWhen I dress in a way that feels true to me, I can regulate my nervous system. I stay grounded. I stay clear. In high stakes situations — interviews, pitches, hard conversations — that is an incredible advantage.At the same time, I’m not going to pretend the external piece doesn’t matter. It does. Every industry has a visual language. Every culture has unspoken dress codes. The goal isn’t to ignore that. The goal is to look at it clearly and decide — consciously, on your own terms — how much of it works for you and how much of it doesn’t.That’s the distinction I want you to hold onto: there’s a difference between choosing to dress for a culture and being swallowed by it. One is a decision. The other is erasure.Which brings me to someone I want you to meet.And Then There’s DacyDacy Gillespie is an anti-diet, weight-inclusive personal stylist whose Substack is about letting go of what you’ve been told to wear so you can find what’s actually yours. She also made a significant career pivot herself — from musician to stylist — so she knows firsthand what it feels like to rebuild your identity from the inside out.Where my work lives in the values and identity side of this conversation, Dacy lives in the practical, embodied, what-do-I-actually-put-on-my-body side. Together we cover a lot of ground.I’ve invited her to join me for a live conversation on Wednesday, April 9th at 12pm PST right here on Substack. We’re going to talk about her pivot, what it taught her, and what to wear when you’re job searching, interviewing, or just trying to figure out who you are now.No registration needed. Just show up. And if you have questions you want us to tackle, drop them in the comments below — or bring them live on the 9th.👉 Follow Dacy on Substack <a target="_bl
About Moonshot Mentor with Laverne McKinnon
Stories, tools, and strategies to conquer career setbacks, including grief work, as unresolved loss can lead to diminished resilience—a career challenge faced by everyone at some stage in life. Each podcast is an audio blog post from Laverne McKinnon, a Career Coach and Grief Recovery Specialist, Film and Television Producer, and Northwestern University Professor. Full archive of posts is available for paid subscribers on Substack. moonshotmentor.substack.com
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