Jocko Podcast Underground #202: Making The Mental Shift Upward

Date: February 23, 2026
Hosts: Jocko Willink & Echo Charles

Episode Overview

In this episode, Jocko Willink and Echo Charles engage with a listener question about making the crucial mental and practical transition from being a solo entrepreneur to building and leading a team. The conversation focuses on leadership development, mindset shifts, and actionable strategies for scaling a business—blending pragmatic SEAL wisdom with personal anecdotes and a grounded, sometimes humorous tone.

Key Discussion Points & Insights

1. The Core Challenge: Leading People

• Main idea: Scaling a business isn’t just about products or markets—it’s about people and leadership.
• Quote: “The most challenging thing about a business, it’s not the market, it’s not the product... it’s the people. People are always the biggest challenge. And… that’s why it pays the biggest reward.” — Jocko (01:26)

2. Leadership Is a Skill, Not an Instinct

• Learning leadership: Jocko stresses that leadership is not instinctual or inborn; it requires study and daily deliberate practice.
• Book recommendations:
  • Leadership Strategy and Tactics Field Manual (specifically pp. 157–158 first; then the whole book)
  • Extreme Ownership
  • The Dichotomy of Leadership
• Quote: “Leadership is counterintuitive, right? So you have to kind of constantly force yourself back on track…” — Jocko (04:02)
• Practical tip: Take abstract leadership principles from these books and overlay them onto your real-world, daily situations—review and reflect on them multiple times a day.
• Quote: “You got to take it out of the abstract and out of the theoretical… and you got to put it into the situation that you’re in.” — Jocko (03:23)

3. Context and Specificity Matter

• There’s no universal leadership “hack” or shortcut—it depends on individual strengths, weaknesses, and the specifics of your goals and situation.
• Analogy: learning leadership is harder and broader than writing a report on the Civil War or learning to play guitar.
• Quote: “Leadership is a bigger subject than either of those.” — Jocko (05:15)

4. Vision and Goals Come First

• Before tactics, define the destination: Where do you want to go with your business and life?
• Echo shares personal training wisdom: Always ask what the client’s goals are before prescribing any plan.
• Quote: “What are your goals for this thing?... What are we trying to do?” — Echo (07:10)
• Encourage conscious goal-setting for both daily wins (“What do I have to get done today to make this a win?”) and longer time horizons.
• Quote: “Gotta look up, gotta have a plan. You gotta know where you’re going.” — Jocko (08:48)

5. Growth Happens Iteratively

• Don’t rush hiring—grow your team step by step, which gives you time to learn and adapt as a leader.
• Quote: “You’re not hiring 100 people… You’re going to hire two or three… then four or five… then you’re going to have ten and twelve…” — Jocko (01:53)

6. Building the Team: Relationships and Trust

• When hiring, focus on building genuine relationships—“Trust, listen, respect, influence, and care.”
• Take care of your people, and they’ll take care of you.
• Quote: “You build a good relationship with people and you’re going to build a solid team.” — Jocko (06:12)

7. Feedback and Adjustments

• Regularly evaluate progress against your goals and make changes as needed.
• Think iteratively: weekly adjustments and constant reassessment.

8. Avoiding One-Size-Fits-All Advice

• Jocko emphasizes that everyone’s path is different: if you already plan well, maybe your focus should be relationships, or vice versa.
• Quote: “Maybe you’re a type of person that builds great relationships with people… but then you get buddy-buddy with everyone and no one knows who’s in charge…” — Jocko (10:20)

Notable Quotes & Memorable Moments

• Jocko (01:42):
  “The people are always the biggest challenge… it’s how we accomplish great things is through leadership.”
• Jocko (03:23):
  “You got to take it out of the abstract and out of the theoretical… and you got to put it into the situation that you’re in.”
• Echo (07:10):
  “Always have to ask them, what are your goals for this thing? Because…”
• Jocko (08:48):
  “Gotta look up, gotta have a plan. You gotta know where you’re going.”

Timestamps for Key Segments

• 00:15 – Listener question: Transitioning from solo operator to team leader
• 01:23 – The challenge of people & leadership
• 02:20 – Book recommendations & learning leadership
• 03:23 – Applying principles to real life
• 06:31 – Importance of knowing your destination
• 08:48 – The need for planning and reflection
• 09:07 – The pitfalls of one-size-fits-all advice

Actionable Takeaways

• Study leadership deliberately—read, practice, review daily.
• Define your vision—be clear on where you want to take your business and life.
• Grow gradually—hire slowly, learn continually.
• Build relationships—trust and care are foundational to a strong team.
• Check progress frequently—adjust your plan as you learn.

Tone and Style

Jocko brings his trademark directness, blending SEAL-level discipline with real empathy. The answers are frank but supportive, mixing depth with accessible analogies. Echo provides relatable anecdotes and reframes lessons through a personal and slightly self-deprecating lens, making the advice actionable and human.

Summary

This episode offers a playbook for anyone stepping up from working solo to leading others, grounding every tip in lived experience and the unvarnished realities of scaling a business. The essence: Leadership is hard but learnable; know where you’re headed, grow step by step, invest in your people, and review and adjust constantly. And above all: “Gotta look up, gotta have a plan.”