Here’s how you can find the middle ground that actually grows you because hustle culture and comfort culture can both wreck your momentum 👇

In this episode of The CEO Lounge, Derrick Thompson and co-host Joselyn Flores break down why being “busy” isn’t the goal — progress is. They talk about the difference between profitable, purposeful grind and busy work that burns you out, plus how to spot the red flags when hustle turns unhealthy.

You’ll hear practical leadership insights on:

• Why “I’m busy” can be a warning sign (not a flex)
• How to protect your time and stop saying yes to everything
• Why grinding must be seasonal with a clear end goal
• Systems + people (not chaos) as the real path to scale
• The mindset shift: outlast most people, don’t outwork everyone

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Chapters:

0:00 Busy vs profitable grind
0:30 Hustle vs comfort extremes
3:25 Protect your time (power of “no”)
6:54 Busy work = burnout (no progress)
11:53 When hustle turns unhealthy
14:12 Grind seasons need an end date
22:05 Systems + people (not chaos)
34:04 Outlast mindset + real balance

Everyone talks about running multiple ventures — but almost no one talks about how to do it sustainably without burning out or neglecting the business that pays the bills.

In this episode of The CEO Lounge, Derrick Thompson breaks down the exact calendar system he uses to balance multiple ventures while staying focused, profitable, and sane.

Derrick isn’t sharing theory — this is lived experience from a CEO who runs a digital marketing agency, community initiatives, multiple podcasts, and passion projects without chaos.

In this episode, we cover:

• Why planning your week on Monday means you’re already behind
• How Derrick plans his entire week before Monday (weekend planning strategy)
• His exact weekly structure:

Monday: Client relationship & check-ins

Tuesday & Thursday: Batched meetings

Wednesday: Work on the business (systems, strategy, execution)

Friday: Creative work, vision, and future ventures
• Why your “main thing” must stay the main thing — even with exciting side projects
• How to avoid shiny-object syndrome while still building long-term ventures
• The calendar, systems, and tools that make managing multiple ventures possible

This episode is for entrepreneurs who feel pulled in too many directions and want clarity, structure, and sustainability — not hustle culture.

Chapters:
0:00 When entrepreneurs lose control of their time
0:29 Welcome to The CEO Lounge Podcast
2:18 What it really means to balance multiple ventures
3:19 Why planning your week on Monday puts you behind
9:40 Monday as Client Relationship Day
15:51 Why batching meetings reduces burnout
21:19 Structuring your week to protect energy and focus
27:24 Systems and tools that keep businesses running
38:30 Why your main business must stay the priority
47:10 How new ventures are built sustainably
58:00 Final takeaways + CEO Weekly Operating System

👉 FREE RESOURCE: Download the CEO Weekly Operating System + Calendar Framework
Website - www.theceolounge.net
Direct Resource Link - https://www.theceolounge.net/downloads/ceo-framework

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#BalancingMultipleVentures
#EntrepreneurLife
#CEOSystems
#BusinessLeadership
#TimeManagement
#WorkweekPlanning
#TheCEOLounge

Most entrepreneurs don’t fail from lack of talent — they quit in the middle… right before it starts working.

If you’re building a business and you feel stuck, tired, or unseen, this CEO Lounge episode is for you. Derrick and Joselyn break down the middle season of entrepreneurship — the nights no one claps for, the discipline it takes to keep going, and how to protect your entrepreneur mindset with weekly wins that stack into real momentum.

In this episode, you’ll learn:
✅ How to stay motivated when results are slow
✅ Why “applause” is a trap (and conviction is the fuel)
✅ The 1:00am grind story that built the foundation
✅ How to set weekly goals, celebrate wins, and avoid burnout
✅ How to know if you’re in a breakdown… or on the edge of a breakthrough

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CHAPTERS

00:00 Protect your mindset in the middle
00:55 Welcome + why “the middle” matters
03:55 “Nobody claps for the nights you don’t quit”
06:05 The 1:00am office grind story (what people don’t see)
10:40 Leading without applause (conviction vs attention)
13:15 Why most people quit in the middle
15:35 Weekly wins: how Derrick stayed motivated
17:45 Rewards, discipline, and celebrating progress
20:00 Leading yourself before leading a team
30:05 Applause vs conviction + “breakdown or breakthrough?”
36:25 Someone is always watching (even in the unseen season)
41:35 Fatherhood + “no turning back” mindset
42:40 Redefining success: time, freedom, and peace
44:25 If you feel unseen: what to do next
50:20 Audience Q: What do I focus on first? (and when?)
52:35 Audience Q: Mindset + gratitude in the middle
58:00 When plans take longer than expected (resetting)
1:00:14 Closing encouragement
1:00:38 Bonus: 12:20am “this is what it takes” clip

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#EntrepreneurMindset #StartupLife #BusinessOwner #Leadership #CEO