Leadership in Tech
Leadership in Tech
#318 – June 07, 2026
satisfaction in tech often has less to do with titles or money and more to do with managing envy and finding meaning in the work itself
On mid-career satisfaction
3 minutes by Shreyas Doshi
Career satisfaction in tech often has less to do with titles or money and more to do with managing envy and finding meaning in the work itself. The things that impress others, like big roles and high pay, stop bringing happiness almost immediately after starting a new job. What actually keeps people happy are things like good culture fit, work-life balance, and feeling engaged day to day. Your career is not a performance for others, so build it around what matters to you.
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3 constraints before I build anything
3 minutes by Jordan Lord
Good constraints narrow your options and spark better ideas. Before building anything, write a one pager: if you can't fill it without padding, you're not ready. Make sure your core technology can stand alone, separate from the product itself, so your efforts compound over time. Finally, pick one defining constraint that shapes everything users see and do, giving your product a clear identity.
The slide
4 minutes by Michael Lopp
When someone keeps ignoring useful feedback, a story can work better than direct advice. Michael suggests to share a personal experience where you struggled with the same issue and had to learn the hard way. This approach works because most resistance to feedback comes from fear. Sliding in beside that fear with your own story, rather than lecturing, gives people a safe way to finally hear what they need to hear.
What your manager is thinking when you complain
4 minutes by Adler Hsieh
When engineers list blockers in 1-on-1s, managers often hear something different than intended. Pointing to everyone else as the problem can signal weak ownership skills. Strong engineers try to unblock themselves first, give clear context when asking for help, and have direct conversations before escalating. The key question is: what can I do differently before asking others to change?
Suffering isn’t leadership
3 minutes by Aviv Ben-Yosef
Tech leaders often accept years of misery as part of the job, but this mindset is both unnecessary and counterproductive. Aviv argues carrying that daily burden limits creative thinking and speeds up burnout, often with no reward or recognition. Instead, he suggests leaders should treat their own wellbeing as a real priority, challenge their pessimism, and stop reflexively shielding their teams from every difficulty. That last habit actually stunts team growth anyway.
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