Super Shadows | When Strengths Limit Growth

In this episode, I’m joined by my co-host Carly Malatskey, a former software engineer turned entrepreneur and host of She Leads. We tackle a listener’s career dilemma: feeling stuck and unsure how to adapt to shifting expectations. Using a structured approach, we break down when to make a change, how to advocate for yourself, and how to evolve without losing what makes you successful. Whether you’re navigating subtle shifts or considering a big move, this episode helps you own your superpower—and the shadow that comes with it.–Key topicsThe unseen influence of Super ShadowsWhy past success won’t fuel future growthBreaking free from career stagnationThe power of self-advocacyHow top leaders seek feedbackIdentifying what actually needs to changeMuch more–Where to find Carly:LinkedInShe Leads PodcastTwitter/X–Where to find Nikhyl:Twitter/XLinkedIn–Find The Skip:WebsiteSubstackYouTubeSpotifyApple Podcasts–Don't forget to subscribe to The Skip to hear me coach you through timely career lessons. If you’re interested in joining me on a future call, send me a note on LinkedIn, Threads, or Twitter. You can also email me at [email protected]–Timestamps(00:00) How your superpower can stall career growth(01:11) Show format(02:45) Listener question: Navigating a quiet career crisis(06:40) How to break free from feeling stuck at work(11:35) The case for self-advocacy in your career(16:36) Why past success won’t fuel future growth(19:48) Super Shadows: What they are and why they matter(30:46) When it’s time to confront your shadow(37:53) The risks of ignoring your shadow(40:56) How great leaders seek feedback(47:07) Pinpointing what actually needs to change(55:57) A strategy for sustainable career growth(57:04) Why change has to happen on the job(58:19) A real-world example from Nikhyl’s offsite(61:28) Key takeaways and final thoughts This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit theskip.substack.com

In this episode, I’m joined by my co-host Carly Malatskey, a former software engineer turned investor and podcast host of She Leads. We tackle a listener’s question about whether to stay in their current job or take a new one. Using a 5-factor framework, we break down how to evaluate career decisions based on compensation, skills, lifestyle, long-term success, and work environment. Whether you’re considering a career move now or just want a structured way to assess future opportunities, this episode offers a practical guide to making confident job decisions.–Key topics:The Stay vs. Go framework for career decisionsHow to assess if your job is career additiveBalancing comp, skills, and lifestyle in job choicesThe probability of success matters in career movesHow long you should stay before making a switchAnd much more–Where to find Carly:LinkedInShe Leads PodcastTwitter/X–Where to find Nikhyl:Twitter/XLinkedIn–Find The Skip:WebsiteSubstackYouTubeSpotifyApple Podcasts–Don't forget to subscribe to The Skip to hear me coach you through timely career lessons. If you’re interested in joining me on a future call, send me a note on LinkedIn, Threads, or Twitter. You can also email me at [email protected]–Timestamps(00:00) The 5-factor framework(01:20) Mailbag question: “Should I stay or go?”(03:38) Is your job career additive?(09:52) Why tenure matters less for some people(15:51) Framework overview(17:21) How to think about compensation(21:28) Fishing for outlier comp offers(23:54) Don’t just optimize for comp(25:46) What skills are you picking up(30:09) How esoteric are your skills(32:37) Weighing up lifestyle(36:56) What’s the probability you will succeed?(42:03) Think about the environment you thrive in(44:54) Final advice This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit theskip.substack.com

In this episode, I’m joined by my co-host Carly Malatskey, a former software engineer turned investor and podcast host of She Leads. We dive into a listener's question about multiple tech job offers, and compare three compensation packages. We break down tactics for negotiating comp while exploring how to pick a role that aligns with your superpower. Whether you're actively job hunting or looking to understand tech compensation better, this episode offers practical insights for making informed career decisions.–Key topics:Why chasing comp early hurts career growthComparing job offersBreaking down key components of total compEnsuring you can exercise your sharesWhen and how to discuss salary expectationsMuch more–Referenced:Tech compensation: Beyond the offer letter–Where to find Carly:LinkedInShe Leads PodcastTwitter/X–Where to find Nikhyl:Twitter/XLinkedIn–Find The Skip:WebsiteSubstackYouTubeSpotifyApple PodcastsTikTok–Don't forget to subscribe to The Skip to hear me coach you through timely career lessons. If you’re interested in joining me on a future call, send me a note on LinkedIn, Threads, or Twitter. You can also email me at [email protected]–Timestamps(00:00) Tactic for negotiating comp(01:54) Unpacking the mailbag format(03:09) Three job offers: which one should I take?(06:02) Understanding bonus structures(09:32) Why equity still matters today(17:38) Breaking the equity exit trap(25:29) Equity versus your market rate(30:37) Don't chase comp early on(34:12) Aligning the role to your superpower(37:47) Negotiating comp: Start with what matters most(47:30) When to discuss salary(51:49) Problems with averaged comp This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit theskip.substack.com

In this episode, I’m joined by Carly Malatskey, an engineer-turned-investor and podcast host of She Leads. We dive into one of the most important career questions in tech today: Should you work in big tech or small tech, or found your own company? With the rise of AI and new economic conditions, these choices have never been more different. We break down how industry dynamics have changed, the tradeoffs associated with each path, and some exercises for determining the best fit for you.-Key topics:How AI is reshaping the tech job marketThe (under-appreciated) differences between big tech and small techHow PM and engineering roles have changedHow to assess your potential as a founderWhat your worries reveal about your ideal work environment-Referenced:Carly’s podcast: https://www.sheleadspod.com/Ready to start a startup?: https://www.skip.show/ready-to-start-a-startup-shreyas-doshi-former-pm-leader-at-stripe-twitter-google/-Where to find Carly:LinkedInShe Leads PodcastTwitter/X-Where to find Nikhyl:LinkedInTwitter/XThreads-Where to find The Skip:WebsiteSubstackYouTubeSpotifyApple PodcastsTikTok-Don't forget to subscribe to The Skip to hear me coach you through timely career lessons. If you’re interested in joining me on a future call, send me a note on LinkedIn, Threads, or Twitter.-Timestamps:(00:00) Teaser: Big tech vs small tech: Should you do both?(00:35) Intro(03:15) Why this discussion matters(05:06) The biggest change in tech during 2024(08:20) Why everyone should consider being a founder(10:14) How to assess your potential as a founder(14:44) How PM & engineering changed in 2024(23:06) The all-important differences between big and small tech(28:55) Assessing your fit for big vs small tech(36:18) The challenges and benefits of working at both scales(42:31) Do the best PMs work in big tech?(52:17) Who this advice doesn't apply to(54:56) Key takeaways(56:33) Get in touch with Nikhyl This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit theskip.substack.com

I'm joined by product leader turned founder Shreyas Doshi to discuss the founder's journey and when starting a company might be the right move for you. We challenge common startup wisdom and explore why traditional career advice often misses the mark for aspiring founders.Key topics:Which PMs are secretly great founder materialRed flags: when founding isn't for youThe right time to start your companyKey skills that set you up for successThriving in ambiguityDebunking the "venture scale or bust" mindsetThe counterintuitive way to avoid burnoutMuch moreReferenced:4 questions Shreyas wished he’d asked himself sooner: https://www.youtube.com/watch?v=atS060bNpE0&t=698sAvoiding burnout for high achievers: https://www.youtube.com/watch?v=5Iwymgai-ZMCrafting a compelling career story: https://www.youtube.com/watch?v=0Reh9wTUIYc&t=928sImproving your product sense: https://maven.com/shreyas-doshi/product-senseIs my next job at a startup or big tech?: https://www.youtube.com/watch?v=H59CRHQ6va0&t=2053sManaging your PM career in 2025 and beyond: https://maven.com/shreyas-doshi/product-management-career?utm_source=lennyNikhyl’s career advice highlights at Lenny’s Summit: https://www.youtube.com/watch?v=rujK7HvD6es&t=124sStage of Company: https://www.youtube.com/watch?v=H59CRHQ6va0&t=2053sWhere to find Shreyas:Twitter/XLinkedInYouTubeWhere to find Nikhyl:Twitter/XLinkedInFind The Skip:WebsiteSubstackYouTubeSpotifyApple PodcastsTikTokDon't forget to subscribe to The Skip to hear me coach you through timely career lessons. If you’re interested in joining me on a future call, send me a note on LinkedIn, Threads, or Twitter. You can also email me at [email protected](00:00) Teaser: Why average PMs can make great founders(01:17) Introduction(02:34) The essential first step before founding(06:21) Successful founder traits(10:48) Managing at scale vs managing uncertainty(18:25) Thriving in ambiguity(21:29) Red flags: when founding isn't for you(23:34) The surprising link between average PMs and founding success(25:51) Building better product sense(29:35) The right time to start your company(37:03) Beyond venture scale: rethinking startup success(44:26) A guide to avoiding burnout(49:23) The real truth about big tech working hours(52:27) Why taking a "demotion" might be a good move(58:45) Learn more: Shreyas' Product Sense course(63:15) Key takeaways(65:22) Get in touch with Nikhyl This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit theskip.substack.com

Welcome to a special episode featuring key moments from my presentation at the very first Lenny and Friends Summit in San Francisco. In this talk, I've distilled the most valuable career insights I've gained from coaching product managers and creating PM content over the past 12 months. In this highlight reel of career advice, I discuss:Rethinking retirementThe career-defining question every leader should askPower years versus foundational yearsLeveraging career storiesFinding peak rolesUnderstanding the shadow of your superpowerThe relationship between personal brand and reputationBreaking down burnoutBuilding your support network through Skip Community–Referenced:Mastering your 30s career resume4 secrets of career boosting companiesAvoiding burnout for high achieversBattling job search anxietyBill Campbell: https://en.wikipedia.org/wiki/Bill_Campbell_(business_executive)Crafting a compelling career storyJZ: https://www.linkedin.com/in/jiaona/Shadows of your superpowers (Part 1)Shadows of your superpowers (Part 2)Shedding perceptions: Moving from lone wolf to team playerSix superpowers of product managersStage of company: A career unlockThe art of building your personal brand–Where to find Nikhyl:TwitterLinkedIn–Find The Skip:WebsiteSubstackYouTubeSpotifyApple PodcastsTikTok–Don't forget to subscribe to The Skip to hear me coach you through timely career lessons. If you’re interested in joining me on a future call, send me a note on LinkedIn, Threads, or Twitter. You can also email me at [email protected]–Timestamps:(00:00) How to help the Skip community(01:37) Lenny’s Summit(04:10) Breaking your career into levels(07:33) Crafting a compelling career story(10:26) All elite PMs find “peak roles”(12:15) “The reputation you build today is the brand you’ll have tomorrow”(13:17) Avoiding burnout(16:13) Knowing the shadow of your superpower(18:13) Don’t build a career alone(18:53) Summary of advice(20:19) Special announcement This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit theskip.substack.com

A great career story can accelerate growth, yet most struggle to craft one. Even top performers fall short, telling stories that are overly detailed, abstract, jargon-filled, or poorly structured – all of which can lose a listener's interest.The first 30 seconds are crucial; you need to hook your audience quickly. Think of the beginning of your story as a movie trailer: highlight the most engaging aspects rather than chronologically detailing every event.This episode focuses on crafting a captivating 30-second introduction to your career story that engages listeners and enhances your professional profile. We've taken a unique approach by inviting Skip community members to submit their career stories for a live workshop. You'll hear real examples of me coaching engineering and product leaders, demonstrating the transformation from initial attempts to polished and punchy narratives.We also discuss:Common storytelling mistakes that everybody makesTechniques for weaving a theme into your storyEffective strategies that will hook listenersAdapting your story for various audiences and situationsBalancing between brevity and showcasing your unique valueReferenced:Crafting a compelling career storyFounder Mode, done right with Shreyas DoshiWhere to find Nikhyl:TwitterLinkedInFind The Skip:WebsiteSubstackYouTubeSpotifyApple PodcastsTikTokDon't forget to subscribe to The Skip to hear me coach you through timely career lessons. If you’re interested in joining me on a future call, send me a note on LinkedIn, Threads, or Twitter. You can also email me at [email protected](00:00) Episode teaser: Mastering your 30s resume(01:15) Common mistakes everybody makes(09:42) Why you need a 30s and 2m career story(12:21) Showing the trailer, not the movie(16:44) Example 1(17:28) Thinking about story sequencing(19:04) Example 2(19:44) Avoiding detail(21:21) Example 3 (before)(21:54) Avoid abstract stories(23:52) Example 3 (after)(24:41) The art of thematic narratives(28:29) Example 4 (before)(29:18) Crafting a theme(29:51) Example 4 (after)(31:24) Avoiding jargon(34:51) Tailoring communication tempo(36:19) Example 5 (before and after)(39:04) Example of a strong 30s resume(41:13) Preparing multiple versions(45:20) Nikhyl’s strong but generic resume(47:50) Nikhyl’s deeper version(50:57) How to submit your career story(52:50) Get in touch with Nikhyl This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit theskip.substack.com

In this episode, I’m joined by product and leadership expert Shreyas Doshi to dissect Founder Mode, why it’s appealing, and how to activate it. We dive deep into Paul Graham's recent essay which struck a chord in the tech community and resonated strongly with many founders and leaders.We also discuss:Why founder mode is a mindset, not a titleWhether founder mode is good or badBalancing detail and delegationThe importance of product sense and good judgmentMastering founder mode as a product leaderOperational insights from Meta and StripeReferenced:Crafting a compelling career story: https://www.youtube.com/watch?v=0Reh9wTUIYc&t=928sPaul Graham’s "Founder Mode": https://paulgraham.com/foundermode.htmlShreyas’ Tweet on founder mode’: https://x.com/shreyas/status/1830767630917214318Six superpowers of product managers: https://www.youtube.com/watch?v=OnsSwHP3d-cShreyas’ previous appearance on the podcast: https://www.youtube.com/watch?v=y_TnXtnY3QM&t=23sThe 3 types of product leaders: https://x.com/shreyas/status/1375491623308550144Where to find Shreyas:Twitter/XLinkedInYouTubeWhere to find Nikhyl:Twitter/XLinkedInFind The Skip:WebsiteSubstackYouTubeSpotifyApple PodcastsTikTokDon't forget to subscribe to The Skip to hear me coach you through timely career lessons. If you’re interested in joining me on a future call, send me a note on LinkedIn, Threads, or Twitter. You can also email me at [email protected](00:00) Teaser: Unpacking founder mode(02:47) What Shreyas has been up to(04:04) Shreyas’ take on founder mode(08:59) Why judgment and product sense is critical(13:04) Balancing detail and delegation(20:57) The key question for founders about ownership(23:01) Not every company needs a CPO or Head of Product(28:07) When product people should prioritize detail(31:32) What everyone gets wrong about Steve Jobs(34:22) Shreyas’ observation about John and Patrick Collison(38:17) Nikhyl’s observation about Mark Zuckerberg(40:05) Founder vs manager mode(43:40) Should leaders avoid manager mode?(48:17) Chase impact, not optics(57:00) The 3 types of product leaders(60:46) Aligning your environment, opinion, and superpower(63:10) Shreyas’ non-consensus view on building product(67:52) Mastering founder mode as a PM(72:58) Getting in touch with Shreyas(74:49) How to find Nikhyl This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit theskip.substack.com

Not all successful companies can supercharge your career. And not all companies that struggle are bad for your career. How can you tell if your company, or one that you are consider, will supercharge your career? In this episode, we'll explore four key characteristics of career-accelerating companies: speed, market position, quality of talent, and development culture. Whether you're job hunting or evaluating your current role, these insights will help you identify environments that truly foster career growth.–We also discuss:Strong signals of a supercharged companyWhy shipping velocity is crucialLearning opportunities at immature companiesLooking for companies with strong talentWhat makes an excellent development culture–Referenced:Crafting a compelling career story: https://www.youtube.com/watch?v=0Reh9wTUIYc&t=913sGreatest hits on career advice with Peter Yang: https://www.youtube.com/watch?v=-BcCHEXAVVkIs my next job at a startup or big tech?: https://www.youtube.com/watch?v=MiELOo4_XGg&t=9sShould I join or leave an ex-hypergrowth company: https://www.youtube.com/watch?v=5-rr1cYYfEUSix superpowers of product managers: https://www.youtube.com/watch?v=OnsSwHP3d-cStage of Company: A career unlock: https://www.youtube.com/watch?v=H59CRHQ6va0&t=2053s–Where to find Nikhyl:LinkedInTwitter/XThreadsFind The Skip:WebsiteSubstackYouTubeSpotifyApple PodcastsTikTokDon't forget to subscribe to The Skip to hear me coach you through timely career lessons. If you’re interested in joining me on a future call, send me a note on LinkedIn, Threads, Twitter or email me at: [email protected]–Timestamps(00:00) Episode Teaser: How to 10x your career(01:10) Introducing the framework(03:41) The caller’s question(05:00) 1: Speed and execution(08:43) 2: Market position(11:47) 3: Quality of talent(15:27) 4: Development culture(20:22) How to get in touch This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit theskip.substack.com

In this short and sharp "peacast" episode of The Skip, I share insights from a conversation with a pregnant Product Executive facing a career dilemma. She was convinced she needed to leave her current company, but while searching for a job, she got pregnant. And now she's been offered a new role at her company due to a reorganization. We discuss her options: accept the role, take a less senior role post-maternity leave, or seek opportunities elsewhere.–We also discuss:Maximizing career potential without sacrificing familyReframing career decisions in the context of long-term growthHow to have it all, just not at onceThe value of wartime leadership experienceOvercoming job search anxiety–Referenced:Avoiding burnout for high achievers–Where to find Nikhyl:LinkedInTwitter/XThreads–Find The Skip:WebsiteSubstackYouTubeSpotifyApple PodcastsTikTokDon't forget to subscribe to The Skip to hear me coach you through timely career lessons. If you’re interested in joining me on a future call, send me a note on LinkedIn, Threads, Twitter or email me at: [email protected]–Timestamps(00:07) Applying my career framework to the caller’s case(02:13) Caller context(02:52) Why one option is a “no-brainer”(03:58) The value of wartime leadership experience(07:43) Why you won’t regret choosing family > career(09:53) The wisdom in “playing it safe”(11:11) Key takeaways(11:44) How to get in touch This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit theskip.substack.com