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Answer extracted from the WIRED: Stories of Impactful Women podcast — listen to the full episode below.

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How do you rebuild relationships when switching careers across industries?

September 18, 2026 WIRED: Stories of Impactful Women · Kesi Milligan

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Relationship management is the critical challenge when you transition between roles and industries. The key is reaching back out to past contacts, finding middle ground to reconnect, while presenting your whole self and bringing all your prior experiences forward rather than leaving them behind.

The bridge between worlds: keeping your network intact

Career pivots test more than just your technical skills—they test your ability to maintain trust and relevance across different professional contexts. When you move from one industry to another, the people who knew you in your previous role may not immediately understand how your experience translates. The work of reconnection requires deliberate outreach, not passive hope that relationships will survive the transition.

Kesi Milligan's own journey illustrates this reality. She started in radio at Carter Broadcast Group in 1999, then transitioned to residential real estate with her license in 2004, worked for eleven years at Aflac, returned to school for urban studies, and then moved into commercial brokerage at Select Sites LLC. Each pivot demanded that she show people not just what she was doing next, but how everything she had learned before still mattered. As she explains in the episode, the challenge lies in presenting yourself as a complete person—not someone who abandoned their past, but someone who is building on it.

Finding middle ground: the authentic reconnection

Reconnection is not simply picking up where you left off—it requires you to meet people where they are now, acknowledge the time that has passed, and show them why your evolution benefits them. This is especially true when your new direction seems unrelated to your former role on the surface.

The practical reality, detailed in the WIRED podcast, is that you must articulate the through-line. Why did you move? What did the previous chapter teach you? How does that wisdom apply now? Without this narrative, old contacts may see your career change as a reset rather than a progression, and they are less likely to trust your competence or refer business your way. The emotional labor of this work—the vulnerability required to admit you needed to explore—is part of what makes relationship management such a significant hurdle.

"When it gets right at the difficult moments when you think you just can't take it anymore, that's when the breakthrough comes."

What makes Milligan's insight particularly relevant is her recognition that this podcast explores how career resilience depends not on avoiding difficult moments, but on moving through them while maintaining the relationships that matter. The people who will believe in your pivot are often those who already know your full character and work ethic.

Bringing your whole self forward

The mistake many career-changers make is compartmentalizing—treating your radio background as irrelevant to real estate, or your real estate experience as separate from your community development goals. In reality, each chapter builds credibility and insight that transfers.

When reconnecting with people from your past, the invitation is to show them that you have not abandoned who you were; you have become more of who you are. This requires clarity and honesty, discussed throughout the episode—not defensive explanations, but genuine sharing of your growth. This shift from shame ("I left that industry") to pride ("I learned those skills and now I apply them here") is what transforms relationship management from a burden into an asset.

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