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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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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.
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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
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Where to find Nikhyl:
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Where to find Carly:
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Join The Skip:
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Find The Skip:
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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]
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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
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