Should you Stay or Go? A 5-factor framework for career-defining decisions

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: www.linkedin.com/in/carlymalatskey
• She Leads Podcast: www.sheleadspod.com/
• Twitter/X: x.com/carlymalatskey
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Where to find Nikhyl:
• Twitter/X: x.com/nikhyl
• LinkedIn:
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Find The Skip:
• Website: www.skip.community/
• Substack: theskip.substack.com/
• YouTube:    / @theskippodcast  
• Spotify: open.spotify.com/show/4oT2rxMsRP64h9NXuA11DJ
• Apple Podcasts: podcasts.apple.com/us/podcast/the-skip-podcast/id1…
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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