Challenges Faced by Solo Entrepreneurs in Building and Managing Teams

You can calm chaos at work, but it starts with a reality check from Charlie Gilkey, delivered with his signature wit and generosity: You might not have a team problem, you have a you problem.

It’s time to stop catering to air sandwiches, Crisco watermelons, broken printers, ghost plans, and other corrosive practices, and start implementing Charlie’s finely-tuned, road-tested systems instead.

Today we’re talking about his new book Team Habits: How Small Actions Lead to Extraordinary Results. We also talk about scaling from maker to manager (and sometimes back again), accounting for those who don’t want the added social overhead of that (often due to some combination of hoarding control, people-pleasing, introversion, and empathy).

More About Charlie: Charlie Gilkey has advised hundreds of teams, from Fortune 100 companies to tiny nonprofits, through Productive Flourishing, the coaching and training company he founded. Charlie is a former Army logistics officer and near-PhD in philosophy living in Portland, Oregon. He is the author of Start Finishing: How to Go from Idea to Done, and today we’re talking about his new book, Team Habits: How Small Actions Lead to Extraordinary Results.

🌟 4 Key Takeaways

• VUCA: Volatile, Uncertain, Complex and Ambiguous. Operating in VUCA environments can be frustrating for free timers with a “thing for control.” At the same time, the status quo “broken printers” get thrown out too—it forces us to reimagine how we work.
• Shrink the scope of your world enough so that you don’t have to fix everything, everywhere, all at once. What small team habit can you examine and improve this month? i.e. Leaving five minutes at the end of meetings to capture action items and next steps.
• The $300,000 speed bump: If you’re stuck getting over this revenue hump, you may need to decide whether you want to scale or not. Bigger teams have social overhead and hidden costs at work that aren’t dollarized.
• DRIP: Decision, recommendation, intention, and/or plan. Take off the Chief Question Answerer hat by asking team members to come back to you with a DRIP before punting a “thoughts?” question onto your plate.

📝 Permission

Center your needs and wants into how you build your business and your teams. Build so that you want to show up and do the work.

✅ Do (or Delegate) This Next

If you’re getting overwhelmed by uncertainty, pause and ask: What are the gifts of not knowing? What constraints are you willing to accept? What permission slip do you need to give yourself to build a business that meets your needs in a sustainable way as the owner?

🔗 Resources Mentioned

• Charlie on the web, IG , Twitter, LinkedIn, Substack
• Articles: Better Team Habits—Share your guide to working with me and What are your team’s broken printers?, Paul Graham—Maker’s Schedule, Manager’s Schedule
• Video: Office Space—Printer Scene

📚 Books Mentioned

• Team Habits: How Small Actions Lead to Extraordinary Results
• Company of One by Paul Jarvis
• The Dollarization Discipline by Jeffrey Fox and Richard Gregory
• Free Time: Lose the Busywork, Love Your Business
• Pivot: The Only Move That Matters Is Your Next One
• Life After College

🎧 Related Episodes

• Charlie’s podcast: Productive Flourishing
• Pivot: 136: Start Finishing—Pricing, Projects, and Momentum Planning with Charlie Gilkey
• Free Time: 052: Perceived Capacity vs. Actual Capacity
• 091: Quarterly Planning with Charlie Gilkey
• 141: Process, Permission Slips, and Business Pivots with Tara McMullin
• 143: Exploring Time, Money, and Energy Capacity with Tara McMullin and Charlie Gilkey
• 016: IP Licensing with Lee LeFever, author of Big Enough
• 228: The Burdensome B’s—Four Red Flags Signaling it’s Time to Make The Big (Delegation) Leap

📝 Check out full show notes and share with friends: https://itsfreetime.com/episodes/235

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