The Skip Podcast

Career ladders aren't just changing—they're being demolished and rebuilt in real-time. In this emergency "weather report," Carly and I decode four career dilemmas that have completely flipped in the last six months. We explain why directors are taking IC roles (and thriving), why your Big Tech salary might be a golden trap, when to finally leave that stalled growth company, and why founding is suddenly on everyone's radar. If you're making any career move in 2025, your old playbook will hurt more than help.The New Career Math:• Why senior IC roles now trump management positions—and when stepping down is stepping up• The Big Tech paradox: 3x market comp but career stagnation (what's your breaking point?)• Ex-growth company reality: Why staying another month makes things worse• The founding surge: Why 8x more product leaders are starting companiesWhat's Actually Happening:• How AI and flat orgs killed the traditional ladder (and what replaced it)• What elite companies want now: hands-on builders, not ivory tower managers• The talent gravity effect: Why your coworkers matter more than your title• The "elite middle" strategy: Which companies offer both growth and stabilityYour Action Plan:• How to evaluate if you're becoming obsolete (and what to do about it)• The unnatural acts worth taking (hint: it involves a pay cut)• Six-month forecast: Where the opportunities will be and who will winTimestamps:(03:45) The rise of Super ICs(07:59) Why IC roles are considered premium(18:56) “I work at Google: should I stay, or should I go?”(27:05) How Nikhyl gives career advice to tech leaders(31:12) What are startups hiring for?(37:10) Why are more people leaving ex-growth companies?(42:21) Advice for choosing the right company to join(46:24) You need to work with great talent(48:21) How to navigate the wealth of career options(52:37) The career trap you need to avoid(56:29) Should you found a company?(59:09) Nikhyl’s forecast for the next six monthsWhere to find Nikhyl:• Twitter/X• LinkedInWhere to find Carly:• LinkedIn• She Leads Podcast• Twitter/XJoin The Skip:• Skip Coach• Skip CommunityFind The Skip:• Website• Substack• YouTube• Spotify• Apple PodcastsDon'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 nikhyl@skip.community 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 to share the early-career playbook most people wish they had at 21. Whether you're fresh out of college, navigating your first job, or advising someone who is — this episode is for you.–Key topics• Why your first job should feel like a sprint, not a stroll• How to tell if your job is setting you up — or holding you back• The truth about internships (they matter more than your degree)• How to stand out when applying — and why “spray and pray” fails• Why it’s okay (even smart) to view your first job as a stepping stone• Red flags and green flags once you’re hired• How to network in a way that doesn’t feel transactional• The mindset shift that separates top performers early in career• Why working in-person still gives you an edge• How to take real risks when you have the least to lose–Where to find Nikhyl:Twitter/XLinkedIn–Where to find Carly:LinkedInShe Leads PodcastTwitter/X–Join The Skip:Skip CoachSkip Community–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 nikhyl@skip.community–Timestamps(00:00) Why most grads feel lost — and what to do about it(01:44) How to navigate the 2025 job market(03:29) Why hustle still wins (yes, even now)(08:24) What to really look for in your first job(15:03) Why seeking feedback is a career unlock(17:30) Choose your boss — not the logo(20:02) Why taking risks early pays off later(28:35) How to tell a compelling career story(32:15) Job hunting that actually works(37:38) Making the leap from college to career(42:18) Why you should work while studying(46:13) How to maintain a network(55:10) Green flags and red flags once you’re hired(58:55) Your first job is a launchpad — not a life sentence(63:12) Final advice we wish we heard at 21 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 entrepreneur and host of She Leads. Through 6 listener questions, we break down how mentors spot patterns others miss, and how you can use that insight to unlock your next move. Whether you're leading a team, switching paths, or just feeling off, this episode is packed with tactical advice for unlocking your career.–Key topics6 common patterns holding leaders backHow mentors can spot them, and what advice to giveBreaking through organizational barriersWhy smart people still get stuckNavigating change vs. waiting it outThriving in early-stage chaosWhy strong reviews don’t always lead to promotionTaking leadership roles before you feel readyFinding—and becoming—a great mentorHow to ask better questions and get better advice–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 nikhyl@skip.community–Timestamps(00:00) How to spot patterns(01:08) How to find and then become a mentor(10:57) Scaling mentorship(15:09) How to heat seek around patterns(21:47) Question 1: How can I break through organizational barriers?(22:29) Pattern 1: Are you actually stuck?(30:05) Question 2: How can busy leaders stay technically up to date?(30:28) Pattern 2: If you know what you should do, why aren’t you doing it?(42:48) Question 3: How to navigate change?(40:56) Pattern 3: Do you need to work on this problem, or just wait it out?(52:23) Question 4: How normal is chaos in early stage companies?(52:54) Pattern 4: Broken might be normal, and you were hired to solve problems(61:07) Question 5: My performance reviews are excellent, but why am I not being promoted?(61:41) Pattern 5: Are you growing faster than the company?(67:35) Question 6: Should I take a leadership role that I don’t feel ready for?(68:29) Pattern 6: Are you too humble or negative?(73:23) Key takeaways and summary(77:57) How to 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 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 nikhyl@skip.community–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 nikhyl@skip.community–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 nikhyl@skip.community–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 nikhyl@skip.communityTimestamps(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 nikhyl@skip.community–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 nikhyl@skip.communityTimestamps(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 nikhyl@skip.communityTimestamps(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: nikhyl@skip.community–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: nikhyl@skip.community–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

Many product managers focus on brand names or job titles, overlooking a crucial factor: company growth stage.This episode reveals how a company's phase - from startup to market leader - shapes your work and career path. We explore the four key growth stages, how product management evolves, and how to align your strengths with the right stage.Featuring insights from seasoned product leaders, learn to identify your ideal company stage and navigate transitions. This episode is your guide to making strategic career moves in product management by leveraging the often-overlooked power of company growth stages.We also discuss:The 4 stages of company growth: drunken walk, product market fit, hypergrowth, and established market leaderHow PM roles evolve across stagesMatching your skills to each stageIntentionally choosing your company stageThe value of diverse stage experience for successful PMsStrategies to gain multi-stage experienceReferenced:Stage of company, not name of company: https://theskip.substack.com/p/stage-of-company-not-name-of-companyShadows of your superpowers (Part 1): https://www.youtube.com/watch?v=XZbjvymjabA&t=912sShadows of your superpowers (Part 2): https://www.youtube.com/watch?v=lcdb5enbDLEWhere 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, or Twitter.Timestamps(00:00) Intentionally choosing your company stage (episode teaser)(01:25) The importance of company stage(02:47) 3 common questions from PMs(05:383) The link between PM and company stages(07:48) The 4 company stages(13:45) What’s unique about early-stage PMs(15:24) How PM evolves when there’s customer traction(18:00) Product management at a hypergrowth company(21:50) One example of what changes between the first three stages(24:49) PM at an established leader(30:04) How to know which stage is right for you(37:03) Spotting when it’s time for something new(38:36) Choose your stage of company wisely(41:38) Why top product people have multi-stage experience(43:28) 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

Personal branding is a crucial yet often misunderstood aspect of career development. Many professionals mistake personal brand for self-promotion or social media showmanship.This episode debunks these myths and reveals the true power of strategic personal branding. Featuring insights from two tech executives, Annie Pearl of Microsoft and Iska Saric of Meta, we pull back the curtain on how industry leaders craft and wield their personal brands to open doors, land dream roles, and shape their legacies.The episode provides actionable strategies to build an authentic and compelling brand that catapults your career forward.We also discuss:The critical distinction between reputation and brandWhy you don’t need to become an influencerThe power of ‘peak roles’ in accelerating your careerTailoring your brand story to specific audiencesStrategies for expanding your professional networkNavigating gender dynamics in personal brandingThe 30-minute per week method to brand-buildingReferenced:Annie Pearl, CVP at Microsoft: https://www.linkedin.com/in/anniepearl/Iska Saric, VP of Communications at Meta: https://www.linkedin.com/in/iska-saric-97210212/Crafting a compelling career story: https://www.youtube.com/watch?v=0Reh9wTUIYc&t=1078sWhere 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, or Twitter.Timestamps(00:00) Episode format(02:14) Why brand matters(04:47) Building a brand ≠ becoming an influence(08:14) Reputation versus brand(10:28) How to establish a reputation(13:55) Leveraging professional connections(18:08) The role that will transform your career(24:12) Crafting and communicating your brand(30:09) The "30-minute per week" method(30:49) Navigating(35:36) Key takeaways from this episode(35:56) 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

Navigating job transitions in today's competitive tech landscape is difficult. Many people get stuck between roles, and an extended job search can dent your confidence. You might doubt your past achievements, question your current skills, and worry about what's next.In today’s episode, we tackle job hunting in today’s tough market. I share insights from a real coaching session with a design leader who's struggling after being out of work for a few months.The episode is packed with concrete tools, useful tips, and proven strategies to help you navigate a job transition.–We also discuss:The mindset needed when in between jobsRebuilding your confidence from the ground upThe role of grit and hustle in an extended job searchHow to run an effective job searchMaking the most of your time between jobsTransforming your mental, physical, and social game–Referenced:Avoiding burnout for high achieversSteve Jobs 2005 Commencement speech–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, or Twitter.–Timestamps(00:00) Episode teaser(01:45) Navigating a job transition(04:34) The caller’s crisis of confidence(10:22) Nikhyl’s advice(16:24) Several strategies for effective job searches(17:53) Pro Tip 1: Set realistic expectations(21:41) Pro Tip 2: Work on yourself(28:04) Pro Tip 3: Treat your craft like an athlete(30:40) Pro Tip 4: Don’t cut your search short(34:50) Pro Tip 5: Run the process with grit and hustle(41:33) Pro Tip 6: Take advantage of the US calendar(43:55) Pro Tip 7: Don’t try to find the ‘perfect role’(47:55) Pro Tip 8: Bet on yourself(48:59) Key takeaways from this episode(51:02) 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

Around 10-20% of my coaching calls tackle burnout. Despite being a deeply personal experience, burnout frequently affects high achievers, who often don't have the time to develop effective coping strategies.In today's episode, we dissect several paraphrased conversations, drawing from years of career coaching experience, offering insights and practical advice to help you manage burnout, set healthy boundaries, and cultivate a resilient mindset.–In today's episode, we discuss:Why burnout is a deeply personal experienceInsights on burnout from real-world examplesWhy burnout is a side effect of successAdopting a long-term career viewThe importance of finding a hobbyAvoiding low-energy work–Referenced:Balancing Work and Life: Insights from Nikhyl and the Skip CPO group–Where to find Nikhyl:Twitter/XLinkedIn–Find The Skip:WebsiteSubstackYouTubeSpotifyApple PodcastsTikTokThis episode on YouTubeDon'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/X.–Timestamps(00:00) Why you resent your company(01:35) People experience burnout differently(04:52) Today’s episode format(05:36) The mindset needed to enforce boundaries(07:25) Observation 1: High performing companies will always push their best people(11:45) Observation 2: Family planning will require you to rework the timing of your career plan(17:23) Observation 3: Ambitious, overworked people will eventually resent their job(23:21) Pro tip 1: Changing your mindset toward burnout(24:58) Pro tip 2: Finding a hobby forces joy on your calendar(29:00) Pro tip 3: Recognizing what drives low energy at work(31:04) Key takeaways from this episode(32:39) 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

After a three-month hiatus, The Skip returns with exciting news: April marked my departure from Meta, and I'm now fully focused on The Skip.Though leaving was a difficult choice, the decision highlighted something important: effectively telling your career story matters more than ever in today’s job market. Companies are concerned that some people may have been spectators to growth rather than contributors. Or worse yet, compelling successes at work are ignored or misunderstood due to an articulation skill gap.In today's episode, learn to craft a compelling two-minute career story you can use for interviews, personal assessments, networking events, and LinkedIn. Good stories ensure clarity, showcasing your achievements and authenticity. We dissect a typical PM career story and walk through how to make it compelling.—In today's episode we discuss the 6 steps of career storytelling:Describe the projectDefine your roleFrame the challengeOutline what you built and whyHighlight what worked and what didn’tConclude—Referenced:Shedding perceptions: Moving from a lone wolf to a team playerIs my next job at a startup or big tech?Coaching grit, patience, and tenureWhere to find Nikhyl:TwitterLinkedInFind 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) Why your career story is more important than ever(01:25) Leaving Meta(04:09) Episode format(11:38) The case study(15:04) The 6 steps(16:44) Step 1: Project context(16:40) Nikhyl’s commentary(18:09) Step 2: Role context(18:43) Nikhyl’s commentary(21:12) Step 3: Frame the challenge(22:15) Nikhyl’s commentary(25:14) Step 4: What you built and why(25:19) Implementing step 4(32:05) Step 5: What worked and what didn’t(31:58) Nikhyl’s commentary(37:08) Step 6: Conclusion(37:30) Nikhyl’s commentary(38:39) Key takeaways from today’s episode(39:42) How to work on your career story 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 my fourth live coaching session, this caller felt like they had earned an unfair reputation as someone who struggles with collaboration in the workplace. The caller wanted guidance on transforming past perceptions into a new reality.The caller reveals both their superpower and its shadow. They are an opinionated product manager, blessed with exceptional taste and intuition. However, these traits also lead them to resist compromise. We confront the caller’s shadow, and explore frameworks and strategies essential for effective collaboration.Privacy is paramount for these calls, so we have anonymized the content and received permission from the caller to ensure no personal or sensitive information is disclosed.—In today's episode, we discuss:How to shed poor perceptions in the workplaceNavigating organizational power dynamicsThe up/down/across model of collaborationWhen and how to compromiseWhy 0 to 1 doesn’t exist in big techHow to use the founder mindset in a large org—Timestamps:(00:00) Introduction(01:56) Caller context(05:02) Caller’s reputation as a “rebel leader”(07:11) How can I change people’s perception of me?(08:37) Nikhyl’s response(12:05) What the caller wants to avoid(13:09) Nikhyl outlines two choices(15:12) Should I optimize for short or long-term career wins?[00:15:41] Nikhyl’s advice on risk and reward(17:38) Should I leave big tech and become a founder?(19:25) Nikhyl’s notes on compromise(20:57) Should I play organizational Game of Thrones?(21:45) Nikhyl’s recommendation(25:39) Key takeaways from today’s episode(33:03) Key links for this podcast—Where to find Nikhyl:TwitterLinkedIn—Where to find The Skip Podcast:WebsiteYouTubeTikTokSpotifyApple Podcasts—Don't forget to subscribe to The Skip to hear Nikhyl teach unique and timely career lessons. If you’re interested in joining me on a future call, send me a note on LinkedIn, Threads, or Twitter. 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 my third episode of live coaching sessions, this caller was feeling dissatisfied with their narrow scope of role and lack of cultural fit in their current company. The caller wanted guidance on what their next role should be, given their personal situation and professional ambition. Their situation captures a difficult choice facing many superstars: seeking a sizable impact rarely found outside of startups, while also craving the compensation only late-stage companies can afford. We discuss the frameworks and strategies required to approach this career choice wisely. Privacy is paramount for these calls, so we have anonymized the content and received permission from the caller to ensure no personal or sensitive information is disclosed.—In today's episode, we discuss: Aligning the stage of company to your specific situationCompensation expectationsRisk tolerance in making career movesThe risks and benefits of joining big techWhy top product executives do tour duties at big companiesHow to break a big tech tenure into two rolesWhy some big tech projects are more data-driven than othersWhy experienced managers should consider IC roles—Where to find Nikhyl:TwitterLinkedInWhere to find The Skip Podcast:WebsiteYouTubeTikTokSpotifyApple Podcasts—Don't forget to subscribe to The Skip to hear Nikhyl and other executives teach unique and timely career lessons. If you’re interested in joining me on a future call, send me a note on LinkedIn, Threads, or Twitter. —Timestamps: [00:00:00] Introduction and caller context [00:02:17] Caller’s question[00:07:40] Nikhyl’s follow-up questions [00:10:15] Matching the stage of company to the caller’s situation[00:11:03] Nikhyl’s recommendation[00:16:56] Should I join a big tech company?[00:18:03] Nikhyl’s response [00:22:08] How do big tech product teams operate?[00:22:55] Nikhyl’s response[00:25:58] Why managers should consider IC roles at late-stage companies[00:29:44] Key takeaways from today’s episode[00:32:27] Key links for this podcast 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