Graduating Into Uncertainty? How to Actually Land Your First Tech Job

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 [email protected]–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 [email protected]–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 [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