“What’s Stopping You?” Working through less obvious resistance rather than pushing through.

Caroline Walsh
4 min readFeb 5, 2024

I’ve been working with a coach to focus on my plans for socializing my Standup Comedy Skills for Leader Development workshop. We talk every few weeks and stay on that specific workshop topic to explore what I’m doing, thinking, feeling, and what way forward continues to evolve. By the third session, we hit the same obstacle that came up in the initial sessions as well.

How do I connect with the corporate world on leader development when my history and network is primatily in the military, government, and academic realms?

We hit this question again as I reported back to my coach that I succeeding in writing up an introductory paragraph for outreach, yet hadn’t nailed down to whom I would send it. I realized, I could make a list. I could just send it out to a few of the more corporate people in my LinkedIn network who were leaders in the executive space. I could push myself to hit send. However, doing that wouldn’t get through what my hesistation was to hit the send button. What was really going on that I didn’t want to even open up an offering? What was beyond the usual introvert excuses such as, “I don’t want to bother people…” or “I prefer to have a close connection before I make any asks…”?

What was happening: Somehow in the conversation, I realized I was leaving out my CIA work experience from the outreach. I was erasing part of my background that gave me legitimacy for understanding how my workshop could support leader development and team dynamics in a mission-driven workspace.

Why was it happening: I didn’t want to be a hack. I saw the reels on Instagram of former CIA officers talking about their “spy experience.” I signed up for a daily email from an “every day spy” newsletter to see what this person was up to and didn’t find it helpful. I sat in the CIA bubble auditorium and listened to a senior leader state clearly that former officers needed to stop writing books. I also already wrote a book that included Agency stories…so maybe I didn’t have much more to lose. I didn’t want to lean on that experience though. I didn’t want to use it to “get my foot in the door.” Even though I think the Agency quietly appreciates stories and glimpses of transparency to support recruitment, I have this resistance to engage too much with my association. I even have videos explaining my dissertation in which I avoid mentioning that the study participants were former CIA officers…even though that’s a key part of the study. I know the mention of the organization piques interest and yet I don’t want to rely on it. It feels like a responsibility not to overuse it.

Photo by Alexander Grey on Unsplash

The problem is that my Agency experience is part of my comedy experience. I took the my comedy class when I was at the Agency and invited all my office and analyst colleagues to join. Our interaction with my comedy set enhanced our relationships. Women who didn’t serve in the military opened up to me about their experiences with harassment int he workplace. Other officemates shared insights into their personal lives or made small jokes about their childcare situation so that we could understanding a little more about their lives. The connection with comedy opened up more Whatsapp communication with the people overseas who asked to see a video of my set. It led us to laughing and brainstorming about comedy and operations on my next TDY. The standup comedy experience opened up people in the office up to using humor to connect on a human level with each other, not just a mission-driven operation level.

The comedy enhanced the creativity we were all working with, which is what helped us be successful at one of the world’s greatest intelligence organizations.

The problem I was facing in my outreach was that I can’t separate my CIA experience from my comedy, research, and career interests going forward.

I could cite probably a hundred articles about:

  • Creativity and play in the workplace
  • The importance of self-awareness
  • Humility in leadership and humble leadership
  • Active engagement with content to support learning, rather than passive
  • etc…etc…

And I would sum up that a 2–3 hour standup comedy workshop focused on leader development touches on all of these aspects and the experience ends up “meeting people where they are at,” naturally individualizing the learning. The workshop gets people connecting at a human-level and listening to each other’s perspectives, talking about identities, upbringing, similarities and differences. It does this without the drag of online mandatory trainings or an accusatory presentation on workplace and identities that leaves some on the defensive. It also is a great primer for further leader development programs because it engages with one’s humility by looking at self and others.

My coaching to-do was to write this out and see what came up in exploring the topic. Basically, I know I don’t want to overuse the association AND I know that the associated experience is relevant. So, I need to balance it and not erase something that helps me communicate the value of the workshop I’m putting on.



Caroline Walsh

Former CIA Analyst and Coastie. PhD Student. Author of Fairly Smooth Operator: My life occasionally at the tip of the spear, available now!