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Jan 21, 2022 · 20m · founders-journal

Career Therapy: Mastering a Side Hustle & Full-Time Job

Alex Lieberman · 11m spoken Landon Campbell · 7m spoken
0:00 / 0:00

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Morning Brew co-founder Alex Lieberman launches the Career Therapy series to coach podcaster Landon Campbell on balancing side hustles, employer expectations, and personal brand building alongside a full-time career.

How this conversation actually went

Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Alex holds 60.3% of the talking time here. How this is scored →

Alex as informed peer 4.7 Guest teaching 1.0 Guest disagreement 0.2 Alex pushing back 0.2
05100:0010:0020:000:37–3:41 · Alex as informed peer 2/10 Introducing Landon Campbell and the In Their Twenties Podcast Alex introduces the Career Therapy concept and conducts exploratory background questioning about Landon's 10 internships and podcast origin.3:41–8:21 · Alex as informed peer 6/10 Overcoming Fear of Failure with Daily Micro-Focus Landon reflects on pushing through the fear of failure with small daily goals, prompting Alex to relate his own anxieties and share a brick-by-brick analogy from Will Smith's autobiography.8:22–12:00 · Alex as informed peer 3/10 Redefining Balance as Dynamic Work-Life Harmony Landon gently pushes back against standard notions of work-life balance in favor of dynamic work-life harmony, while Alex probes on maintaining separation between day jobs and side ventures.12:01–16:27 · Alex as informed peer 8/10 Strategic Trade-Offs and the A-Minus Employee Philosophy Alex provides in-depth mentorship on trade-offs, challenging hyper-ambitious instincts by advocating for being an A-minus employee to protect mental bandwidth for entrepreneurial projects.16:28–18:54 · Alex as informed peer 8/10 Three Pillars for Building a Scalable Personal Brand Alex lays out a structured, 3-pillar playbook (Goal, Focus, Community) for building a scalable personal brand while holding a full-time job.18:54–19:18 · Alex as informed peer 1/10 Concluding the Inaugural Career Therapy Session Alex and Landon conclude the session with mutual appreciation and an invitation for future listener submissions.0:37–3:41 · Guest teaching 1/10 Introducing Landon Campbell and the In Their Twenties Podcast Alex introduces the Career Therapy concept and conducts exploratory background questioning about Landon's 10 internships and podcast origin.3:41–8:21 · Guest teaching 2/10 Overcoming Fear of Failure with Daily Micro-Focus Landon reflects on pushing through the fear of failure with small daily goals, prompting Alex to relate his own anxieties and share a brick-by-brick analogy from Will Smith's autobiography.8:22–12:00 · Guest teaching 3/10 Redefining Balance as Dynamic Work-Life Harmony Landon gently pushes back against standard notions of work-life balance in favor of dynamic work-life harmony, while Alex probes on maintaining separation between day jobs and side ventures.12:01–16:27 · Guest teaching 0/10 Strategic Trade-Offs and the A-Minus Employee Philosophy Alex provides in-depth mentorship on trade-offs, challenging hyper-ambitious instincts by advocating for being an A-minus employee to protect mental bandwidth for entrepreneurial projects.16:28–18:54 · Guest teaching 0/10 Three Pillars for Building a Scalable Personal Brand Alex lays out a structured, 3-pillar playbook (Goal, Focus, Community) for building a scalable personal brand while holding a full-time job.18:54–19:18 · Guest teaching 0/10 Concluding the Inaugural Career Therapy Session Alex and Landon conclude the session with mutual appreciation and an invitation for future listener submissions.0:37–3:41 · Guest disagreement 0/10 Introducing Landon Campbell and the In Their Twenties Podcast Alex introduces the Career Therapy concept and conducts exploratory background questioning about Landon's 10 internships and podcast origin.3:41–8:21 · Guest disagreement 0/10 Overcoming Fear of Failure with Daily Micro-Focus Landon reflects on pushing through the fear of failure with small daily goals, prompting Alex to relate his own anxieties and share a brick-by-brick analogy from Will Smith's autobiography.8:22–12:00 · Guest disagreement 1/10 Redefining Balance as Dynamic Work-Life Harmony Landon gently pushes back against standard notions of work-life balance in favor of dynamic work-life harmony, while Alex probes on maintaining separation between day jobs and side ventures.12:01–16:27 · Guest disagreement 0/10 Strategic Trade-Offs and the A-Minus Employee Philosophy Alex provides in-depth mentorship on trade-offs, challenging hyper-ambitious instincts by advocating for being an A-minus employee to protect mental bandwidth for entrepreneurial projects.16:28–18:54 · Guest disagreement 0/10 Three Pillars for Building a Scalable Personal Brand Alex lays out a structured, 3-pillar playbook (Goal, Focus, Community) for building a scalable personal brand while holding a full-time job.18:54–19:18 · Guest disagreement 0/10 Concluding the Inaugural Career Therapy Session Alex and Landon conclude the session with mutual appreciation and an invitation for future listener submissions.0:37–3:41 · Alex pushing back 0/10 Introducing Landon Campbell and the In Their Twenties Podcast Alex introduces the Career Therapy concept and conducts exploratory background questioning about Landon's 10 internships and podcast origin.3:41–8:21 · Alex pushing back 0/10 Overcoming Fear of Failure with Daily Micro-Focus Landon reflects on pushing through the fear of failure with small daily goals, prompting Alex to relate his own anxieties and share a brick-by-brick analogy from Will Smith's autobiography.8:22–12:00 · Alex pushing back 0/10 Redefining Balance as Dynamic Work-Life Harmony Landon gently pushes back against standard notions of work-life balance in favor of dynamic work-life harmony, while Alex probes on maintaining separation between day jobs and side ventures.12:01–16:27 · Alex pushing back 1/10 Strategic Trade-Offs and the A-Minus Employee Philosophy Alex provides in-depth mentorship on trade-offs, challenging hyper-ambitious instincts by advocating for being an A-minus employee to protect mental bandwidth for entrepreneurial projects.16:28–18:54 · Alex pushing back 0/10 Three Pillars for Building a Scalable Personal Brand Alex lays out a structured, 3-pillar playbook (Goal, Focus, Community) for building a scalable personal brand while holding a full-time job.18:54–19:18 · Alex pushing back 0/10 Concluding the Inaugural Career Therapy Session Alex and Landon conclude the session with mutual appreciation and an invitation for future listener submissions.

speaking balance: gold is Alex, purple is the guest (3 minute bins)

0:00 · Alex 65.8% · guest 34.2%0:00 · Alex 65.8% · guest 34.2%3:00 · Alex 41.4% · guest 58.6%3:00 · Alex 41.4% · guest 58.6%6:00 · Alex 65.3% · guest 34.7%6:00 · Alex 65.3% · guest 34.7%9:00 · Alex 16.3% · guest 83.7%9:00 · Alex 16.3% · guest 83.7%12:00 · Alex 68.8% · guest 31.2%12:00 · Alex 68.8% · guest 31.2%15:00 · Alex 83.4% · guest 16.6%15:00 · Alex 83.4% · guest 16.6%18:00 · Alex 90.5% · guest 9.5%18:00 · Alex 90.5% · guest 9.5%
Sharpest disagreement ▶ 8:45 Dismissing traditional work-life balance

Landon rejects the common assumption that work and life can be cleanly bifurcated, insisting that strict cutoffs are unrealistic during early career stages.

 Hardest push from Alex ▶ 13:55 Challenging the perfectionist workplace mindset

Alex challenges the conventional assumption that professionals must strive to be A-plus performers in every role, arguing it drains bandwidth needed for side projects.

 Biggest teaching moment ▶ 5:45 Sharing Ev Williams' principle on micro-focus

Landon teaches a lesson learned directly from Twitter founder Ev Williams about solving small problems for small groups to conquer early venture fears.

 Alex holds their own ▶ 14:15 Alex details the A-minus employee philosophy

Alex demonstrates seasoned business leadership by breaking down the opportunity cost and intellectual property implications of balancing employment with side ventures.
the scores for every segment, with the reasoning behind each
ChapterTopicAlex as informed peerGuest teachingGuest disagreementAlex pushing backWhy
Introducing Landon Campbell and the In Their Twenties Podcast 2100 Alex introduces the Career Therapy concept and conducts exploratory background questioning about Landon's 10 internships and podcast origin.
Overcoming Fear of Failure with Daily Micro-Focus 6200 Landon reflects on pushing through the fear of failure with small daily goals, prompting Alex to relate his own anxieties and share a brick-by-brick analogy from Will Smith's autobiography.
Redefining Balance as Dynamic Work-Life Harmony 3310 Landon gently pushes back against standard notions of work-life balance in favor of dynamic work-life harmony, while Alex probes on maintaining separation between day jobs and side ventures.
Strategic Trade-Offs and the A-Minus Employee Philosophy 8001 Alex provides in-depth mentorship on trade-offs, challenging hyper-ambitious instincts by advocating for being an A-minus employee to protect mental bandwidth for entrepreneurial projects.
Three Pillars for Building a Scalable Personal Brand 8000 Alex lays out a structured, 3-pillar playbook (Goal, Focus, Community) for building a scalable personal brand while holding a full-time job.
Concluding the Inaugural Career Therapy Session 1000 Alex and Landon conclude the session with mutual appreciation and an invitation for future listener submissions.

Statements from this episode (3)

Assertion Supported
Morning Brew co-founders sold a majority stake in an eight-figure deal
“So, my co-founder, Austin Reif, and I have spent the last six years building Morning Brew. That includes raising money, hiring a ton of people, making a ton of mistakes, and ultimately selling a majority stake in the business in an eight-figure deal.”
Alex Lieberman Jan 21, 2022 ▶ 0:37
Disclosure
Alex Lieberman fears the reputational risk of a failed second venture
“Like I have the fear oftentimes about if I was to ever start another business how bad would it look to fail with the second thing after the first thing went well with morning brew?”
Alex Lieberman Jan 21, 2022 ▶ 5:16
Insight
Intentionally be an A-minus employee to scale a side hustle
“There's a world in which actually, like, you really think about the trade-offs of your full-time job and your part-time job, and you may actually be an A-minus employee instead of an A-plus employee in order to give yourself the possibility of doing what you r…”
Alex Lieberman Jan 21, 2022 ▶ 15:10
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