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.

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Key topics:

• The Stay vs. Go framework for career decisions
• How to assess if your job is career additive
• Balancing comp, skills, and lifestyle in job choices
• The probability of success matters in career moves
• How long you should stay before making a switch
• And much more

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Where to find Carly:

• LinkedIn
• She Leads Podcast
• Twitter/X

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Where to find Nikhyl:

• Twitter/X
• LinkedIn

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Find The Skip:

• Website
• Substack
• YouTube
• Spotify
• Apple Podcasts

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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 nikhyl@skip.community

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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