0:00–1:15 – Introduction & Setup

• The episode opens with a lighthearted tone and a metaphorical “walked off into the mist” visual.

• Douglas and Eric introduce the topic: working with former clients again after a breakup—good or bad.

1:16–4:45 – Personal Example: Client Returns After Break

• Eric shares a real-life scenario: a former SEO client’s contract was dissolved, and they’ve now shown signs of interest in re-engaging.

• He notes their site traffic dropped, which may be why they’re reconsidering.

• The dilemma: do they want to return for genuine partnership or just to fix declining SEO?

4:46–7:30 – Classifying Past Clients & Emotional Factors

• Douglas reflects on clients in “tiers”:

  • Ones he’d ignore if they returned

  • Ones where he’d consider it

  • Ones he’d happily take back

• He compares it to personal relationships—some breakups are final, others might work again if day-to-day interactions were good.

7:31–10:00 – Caution, Patterns, and Guardrails

• They explore how some clients “let you down easy” with false promises to return.

• They caution against repeating cycles and recommend setting clear terms and contracts if re-engaging.

• They use metaphors like “the same dance” or “bike with no momentum” to describe these risky returns.

10:01–12:30 – Negotiation & Detachment

• There’s value in revisiting clients when it comes from a place of strength—not desperation.

• If revenue is stable without them, you’re in a better place to negotiate stronger terms and create clear boundaries.

• Detachment from outcome is key: if they walk, you’re still fine.

12:31–14:40 – Relationship Analogies

• They revisit the personal relationship metaphor:

  • Initial excitement may fade.

  • If neither party has done personal/professional work to grow, old problems will return.

• However, businesses can change more than individuals—new hires, different culture, etc.

14:41–17:30 – Practical Considerations

• Bringing a past client back could be easier with an intermediary buffer (e.g., working through a PR firm instead of directly with a problematic stakeholder).

• Having that distance could neutralize personality conflicts.

17:31–20:00 – Defining Guiding Principles

• Eric realizes they may need clearer internal criteria:

  • What types of clients align with their values?

  • What makes an account a good fit?

• Recommends using past experiences to create a values-based decision framework.

20:01–22:30 – Upcoming Travel & Sidebar Chat

• Eric talks about an upcoming trip to Omaha for a contractor summit and new gear setup.

• Casual conversation about travel logistics and College World Series.

22:31–24:30 – F1 Chat & Episode Wrap

• Brief Formula 1 update: Mercedes, Verstappen, Lando Norris.

• Final sign-off with podcast info and business plugs.