Aspire with Emma Grede

Episode: Plan Your Life Like a Business
Host: Emma Grede
Date: September 23, 2025

Episode Overview

In this episode, “Plan Your Life Like a Business,” Emma Grede—acclaimed entrepreneur, founding partner of SKIMS, and CEO of Good American—shares her personal framework for intentional life planning. Using her own birthday as a trigger for reinvention and goal-setting, Emma encourages listeners to approach their lives with the same vision, precision, and strategy that's reserved for building successful companies. The episode unpacks the step-by-step process Emma uses each year to map out her ambitions in health, career, learning, and relationships, emphasizing radical honesty, habit formation, accountability, and realistic action plans.

Key Discussion Points and Insights

The Power and Necessity of Planning (03:40)

• Emma reveals that detailed planning has been the real game-changer in her journey from ambitious dreamer to high-achieving entrepreneur.
• She recounts how vision boards and hustle alone led to frustration until she started mapping out clear, actionable roadmaps for her life.
• Quote: "I really believe that my life deserves that level of detail, and I think yours does, too..." (05:14)

Sense of Urgency: Life Measured in Moments (09:02)

• Emma steps beyond years and dates, urging listeners to think about “moments” (e.g., limited summers with her children).
• Inspired by Jesse Itzler's framework, she shares how this concept changed her view of time and priorities.
• Quote: "...we don't have the rest of his life or my life. We have another five or six summer moments where all four of my kids are together..." (10:05)

Ritualizing Fresh Starts (12:58)

• Explains her choice to start planning each year on her birthday, capitalizing on Katherine Milkman's “Fresh Start Effect.”
• Suggests listeners pick a meaningful personal landmark to launch their own plans, not just the typical New Year, for increased motivation and separation from past failures.

Science of Focus and Repetition (15:58)

• Emma emphasizes focusing on a few key categories with tightly defined, complementary goals.
• Cites habit research: 66 days on average to form a new habit. Broad, unfocused lists lead to overwhelm and failure.

Five Radical Questions for Annual Planning (21:42)

1. What goals have you had that you didn’t achieve—and why?
   Radical self-scrutiny, no external blame.
2. What are three things you wish you did more of last year?
   Identify sources of personal joy and fulfillment, not just achievement.
3. What are you avoiding or scared of?
   Acknowledge true ambitions and the “work you’re avoiding.”
4. What do you want to learn in the year to come?
   Focus on learning as a gateway to joy, mental sharpness, and opportunity.
5. What habits and boundaries do you want to create?
   Specify new routines and limits that align with your goals and protect what matters most.

• Quote: "Goal setting isn't just about productivity or achievement. It has to include joy." (24:46)
• Memorable Advice: "You can't ChatGPT this stuff... it takes radical honesty." (33:40)

The Trade-Offs: What Gives? (35:34)

• Accepting you can’t have it all at once—intentional sacrifices are necessary.
• Encourages listeners to explicitly name what they're willing to give up for their key goals.
• Quote: "To get something you've never had, you're going to need to do something you've never done." (36:25)

Setting and Structuring Your Goals (38:02)

• Limit major goals to around 6-10, sorted by broad categories (personal, professional, health, finances, learning, etc.)
• Make each goal actionable, bulleted, and clear.
• Tip: Write them in a way that's as useful and direct as a business to-do list.

Breaking Down the Goals: Micro-Steps and Habit Stacking (41:10)

• Use friction-reducing systems and anchor new habits to existing routines ("habit stacking").
• Example: Emma learned to swim only at 43 by piggybacking her lessons onto her children’s regular lessons.
• Quote: "The big changes you want in your life rarely come from big, dramatic moves. They come from small, consistent actions that build over time." (43:15)

Practical Example in Action: Launching the Podcast (49:47)

• Emma describes launching this very podcast using her business-like planning formula: research, networking, information gathering, micro-actions, and realistic timelines.
• She reminds listeners that even her most public successes come from incremental, consistent progress, not overnight leaps.

Navigating Setbacks: If/Then Planning (56:45)

• Introduces psychology research (Peter Gollwitzer) on “if/then planning”—pre-planning for obstacles to double your odds of success.
• Quote: "With all the best plans, they likely will fuck up... so plan for the fuck-ups." (57:16)
• Example: If you miss a workout, plan to make it up in another context.

Measuring Progress and Reflection (1:01:26)

• Track goals in a way that suits you—digital checklists, habit trackers, journals, physical calendars.
• Tips: Visual reminders are key, but don't get hung up on perfection—what matters is forward momentum, not flawless achievement.
• Quote: "Are you in forward motion or not? That is all that matters, I promise you." (1:02:34)

Notable Quotes & Memorable Moments

• On radical honesty:
  “Radical honesty from where you can take responsibility doesn’t happen overnight. So give it a moment and consider what you’re willing to give to make your goals a reality.” (37:14)

• On compounding habits:
  “Small habits compound like interest in a bank account. Over time, the results are massive.” (45:28)

• On failure and pattern recognition:
  “The important part is to be reflective when we fail. Ask ourselves what inside of me is stopping this from happening?” (1:00:12)

• On accountability:
  “Tell people. Accountability adds gentle pressure. If you’re anything like me, a little bit of pressure can go a long way.” (48:32)

• On no overnight success:
  “There is no such thing as an overnight success.” (54:38)

Timestamps for Key Segments

| Timestamp | Topic/Segment | |--------------|-----------------------------------------------------------| | 03:40 | The necessity of planning; where Emma’s system started | | 09:02 | Measuring life in moments, not just years | | 12:58 | Why (and when) to start your plan; the Fresh Start Effect | | 15:58 | Limiting goals and the science of repetition | | 21:42 | Five annual reflection questions | | 35:34 | Trade-offs and radical honesty about sacrifices | | 38:02 | Actionable, categorized goal-setting | | 41:10 | The secret: micro-steps & habit stacking | | 49:47 | Real-world example: launching this podcast | | 56:45 | If/then planning for setbacks | | 1:01:26 | Tracking progress; reflection and iteration | | 1:03:10 | Full recap & 10-point summary |

Emma Grede’s 10-Point Life Planning Blueprint (Recap at 1:03:10)

1. Start on a meaningful day (capitalize on emotional momentum)
2. Ask radically honest questions about past failures and real desires
3. Limit the number of goals for clarity and focus
4. Write specific, actionable goals and find an accountability partner
5. Break goals into micro-actions scheduled daily or weekly
6. Accept trade-offs—what will you say no to in order to say yes?
7. Habit stack to make formation easier
8. Plan for setbacks with if/then scenarios
9. Track progress visually and frequently
10. Review and reflect weekly to adapt and keep growing

Final Takeaways

• Your life's ambitions require the same rigor and revision as a business plan.
• Consistency and clarity are more powerful than sheer hustle.
• Radical honesty, structured micro-goals, visual progress tracking, and planning for setbacks are the pillars of Emma’s approach.
• It’s not about what you can do in a year—it’s about building habits and momentum that transform the next decade.
• "The life you want won't happen by accident. It happens by design." (1:02:59)

For more, connect with Emma at Aspire with Emma Grede on Instagram, or visit EmmaGrede.me. And—per Emma’s challenge—find an accountability partner, walk through the five reflection questions together, and see how it transforms your year.