Do Your Job: Avoid Guilt, Keep Striving | Advice from Alei Shur ft. Rav Dovid Gottlieb

From Shtark Tank with Yaakov Wolff by Yaakov Wolff.

• Published: Mon, 16 Feb 2026 05:10:00 GMT
• Duration: 00:52:13
• Audio: https://anchor.fm/s/e45c8048/podcast/play/115548430/https%3A%2F%2Fd3ctxlq1ktw2nl.cloudfront.net%2Fstaging%2F2026-1-15%2F418160079-44100-2-b0a21cd8facbb.mp3
• Page: https://podcasters.spotify.com/pod/show/yaakov-wolff/episodes/Do-Your-Job-Avoid-Guilt--Keep-Striving--Advice-from-Alei-Shur-ft--Rav-Dovid-Gottlieb-e3f4oqe
• TorahApp: https://torahapp.org/share/p/3P_shtark_tank/e/9ad1a798-a71c-45ca-8151-8049970101b2

What if the most “frum” thing you can do at work… is simply doing your job well?

In this episode, I’m joined by Rav Dovid Gottlieb for a sharp, practical conversation built around a powerful piece from Rav Shlomo Wolbe (Alei Shur)—with guidance that every working Ben Torah needs.

(The short chapter can be found in Alei Shur vol. I pp. 269-271)

Soon after, we take these ideas into one of the hottest and most real-life arenas right now: religious soldiers in the IDF, and the tension of doing what’s right while still missing the beis medrash, the minyan, and the Yom Tov experience. The takeaway applies to soldiers and professionals: avoid guilt, stay honest about what you’re missing, and keep striving.

In this episode:

• The Midrash about Chanuch the cobbler: how “every stitch” can be holy when your goal is to help people

• Rav Wolbe’s big idea: there’s no such thing as truly “secular” work when you bring the right kavana

• The “Do Your Job” principle: why learning/davening at the wrong time can become a mitzvah haba’ah b’aveirah

• The soldier/workforce parallel: no guilt when you’re doing what Hashem needs from you now—while still feeling the loss of what you’re missing

• Balancing the three jobs: family, parnassah, and Torah (and why there’s no one-size-fits-all formula)

• A powerful closing charge from Rav Wolbe: Hashem hasn’t given up on you—keep striving to grow in Torah

• “Latent awareness”: how Torah stays with you even when you’re fully focused on your mission

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