Stuff We've Messed Up (and Learned From)

Designing Tomorrow: Creative Strategies for Social Impact

To wrap Season 3, Eric and Jonathan are doing something different — and a little vulnerable.

In this raw and unfiltered finale, they look back on the leadership decisions, strategic misfires, hiring blunders, and marketing missteps that didn’t go according to plan. No spin. No gloss. Just two founders owning their hardest lessons out loud.

Why end the season like this? Because mistakes aren’t just part of leadership — they are leadership. If we want a social impact sector that embraces failure as fuel for growth, we have to start by telling the truth about what we've gotten wrong.

So here it is.

Episode Highlights:

[00:00] Opening: “Today we're going to talk about all the shit we've messed up.”

[01:35] Why talk about mistakes at all?

[02:23] Jonathan’s board breakup

[05:34] Eric’s accidental leadership path

[08:04] Burnout and showing up as a leader

[10:26] When design isn’t enough

[13:28] Strategic blindspots

[18:17] “I blind copied them.”

[20:48] Firing with (or without) dignity

[27:07] Going too wide in marketing

[28:53] The cost of not marketing

[33:30] When vision stalls

Resources:

• Podcast - Rethinking Failure in Social Impact
• Podcast - How to Stop Planning and Start Doing - Discussion of MVS framework
• Podcast - Designing a Purpose and Strategy with Eric Ressler
• Article - Test Your Niche to Develop Your Organization’s Superpower
• Article - 8 Key Ingredients to Defining Your Social Impact Niche
• Article - How to Build a Next-level Content Strategy
• Article - A Guide to Social Impact Marketing Through Brand-building

Listeners, now you can text us your comments or questions by clicking this link.

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Thank you for all that you do for your cause and for being part of the movement to move humanity and the planet forward.

فصل ها

1. Stuff We've Messed Up (and Learned From) (00:00:00)

2. Introducing Our Mistakes (00:00:14)

3. Jonathan's Board Disbanding Blunder (00:04:04)

4. Eric's Leadership Learning Curve (00:05:34)

5. Team and Hiring Mistakes (00:13:17)

6. Marketing Missteps and Lessons (00:26:58)

7. Finding Balance and Avoiding Coasting (00:32:17)

8. Final Thoughts on Normalizing Failure (00:36:12)