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Executive Search for Intimacy

by Subomi Plumptre

I watched a clip from the TV show, Billions. The character Taylor Mason, a brilliant portfolio manager, hires a professional hugger to help them connect with and understand intimacy.

In the chat group where the clip was shared, I remarked how cuddling-for-hire is a real phenomenon, especially in the US and Asia. Escort services for the wealthy are also popular. Some executives prefer hiring an escort over a prostitute to enjoy conversation and dinner before intimacy. It reflects a desire for connection on a convenient schedule.

I used to wonder why these executives couldn’t simply strike up a conversation with another human. But I can hazard three guesses:

  1. Relationships are messy. Conversations take time. They are not as efficient as a transaction.
  2. Vulnerability is scary. Real connection is unpredictable and requires a level of openness that assumes weakness and a need for something money cannot buy.
  3. Paying for a service ensures discretion. Professionals are bound by confidentiality.

Executives are among the loneliest people on earth. Very few treat them as humans. Instead, they are often viewed through the lens of their roles or what they can provide. Success attracts many “friends.”

Additionally, executives struggle with intellectual connection. Their minds are typically buzzing with ideas and grand visions, making it rare to find someone who truly understands them.

Then there’s the inevitable low that follows the high of achievement. In those moments, they want to talk about the dragons they’ve slain or the mountains they’ve climbed and be appreciated for those feats. They crave someone to offer a fresh perspective on their challenges—one they haven’t already considered.

Because executives are naturally guarded —having been used or betrayed before — love often needs to come to them. They rarely seek it out.

This pattern is especially true for men. Women approach them, not the other way around. For instance, you’ll notice that some of the world’s most successful men fall in love with unlikely partners. These are often women who entered their lives uninvited, without guile or demands and proved themselves loyal and genuine over time.

Loneliness is difficult for everyone, but it has particularly sad implications for leaders:

  1. Intense work thrives in joy. Loneliness drains happiness and stifles creativity.
  2. Diversity of perspectives is lost. Loneliness makes leaders insular, causing them to rely on their knowledge.
  3. Loneliness fosters authoritarianism. Without someone to challenge or question their decisions, leaders may become rigid.
  4. Seeking validation at work. When leaders lack approval at home or from loved ones, they often overcompensate by taking on more projects.

If you have an executive in your life, give them a hug and ask how they’re doing—really. Buy them a gift to lift their spirits and to show appreciation for the unseen efforts they make every day.

Love on a leader today. You might be the only one who has done so in a very long time.

Thanks for reading.