A CONVERSATION WITH JUDY JOSEPH MCSWEEN · PART TWO OF THREE

She Went to the Retreat Alone

On leaving a secure life, draining your savings, and what happens when you show up even when everyone else cancel

There is a moment in most vocations — if you are paying attention — where the path you have been building and the path you are being called toward stop running parallel and begin to diverge. The question is not whether you will notice. The question is what you do when you do.

Judy Joseph McSween noticed in Maine.

She had traveled to Bethel, Maine for an introspective program — not yet sure what she was looking for, only aware that something was pulling her toward stillness. It was there that she encountered meditation for the first time. And in that stillness, a clarity arrived that she had not been able to manufacture through ambition or analysis: she was called to help people find themselves.

Not to fix them. Not to train them. Not to plan their strategies or optimize their processes — though she had done all of those things and done them well. To help them find themselves. To create the conditions in which something true and buried could surface. To ask the question that went one level deeper than the question they came with.

“My superpower is listening to my inner voice and to the other — and crafting questions that stimulate inner transformation.”

To understand how she arrived in Maine, you have to understand the arc that preceded it. Industrial Chemist. MBA. On-the-road post with the Industrial Development Corporation, meeting manufacturers, foreign investors, high commissioners, government ministers across Trinidad — a whirlwind that let her do what she loved most, which was connect with diverse people. A stint in finance that ended with retrenchment. A role in a Syrian conglomerate where the chairman gave her random projects across the business and she later said was the period of “really finding myself.” A represented role with a European technical assistance firm that required her to travel to Belgium. And eventually, the position that would bring her closest to the edge of her calling: Lead Strategic Planning Consultant at her cousin’s OD firm.

She was good at all of it. That is the thing that makes this kind of story complicated. She was not leaving failure. She was leaving competence — which is, in many ways, harder. Competence has its own gravity. It offers security, identity, the esteem of people who depend on you. Leaving competence requires a different kind of courage than leaving difficulty. It requires you to trust what you feel more than what you have built.

She noticed, in that consulting role, that clients needed something the firm was not designed to offer. They needed to pause. They needed someone to help them go inward, not just outward. The strategic plans were technically excellent. They were not producing sustainable change. And Judy knew why: because the people making the plans had not yet done the interior work that would allow them to carry the plans through.

She left impulsively. At the end of a month, she heard a presentation about taking the leap — about the moment when you stop waiting for conditions to be perfect and simply go. She turned to the woman next to her and said: “My plan is, if I don’t do it now, I’ll never do it.” She handed in her notice.

She took the leap at the same moment she was sending her daughter to university in Canada. She drained her savings. She entered what she describes plainly as a financial pit. Every time the discomfort became acute enough that she considered returning to corporate life, she felt a clear inner no. Not a feeling of peace, necessarily. Just a no. Sixteen years later, she is still in this vocation.

Every time she considered going back, the inner voice said no. Not with fanfare. Not with a vision. Just: no. And she listened.

The first Time Out Retreat she scheduled, all the participants cancelled. Any reasonable person would have rescheduled. She heard an inner voice — which she now names without hesitation as the Holy Spirit — that said: go anyway. She drove to the 22-acre retreat facility alone, on a Friday evening, and arrived as the only person who had registered to be there.

She became both the facilitator and the participant. She asked herself the questions she had prepared for others. She listened. She went inward. She let the silence work on her the way she had learned to let silence work on others. And in that solitude, insights arrived that shaped every programmed design she uses to this day — the architecture of what it means to help a person pause long enough to hear what truly matters.

The second retreat brought executives, staff, and an ordained person. Within twenty-four hours, the feedback was already that the depth of her questions had surfaced more value than the cost of the retreat. She had not manufactured that depth in the intervening weeks. She had received it in an empty room in Maine, alone on a Friday evening, because she trusted a voice that told her to go even when there was no one waiting for her.

This is the pattern that the contemplative tradition names and the Enneagram illuminates and the Six Seconds EQ model grounds in research: the people who help others go inward are almost always people who have learned to go there themselves. Not once, dramatically, but repeatedly, quietly, in the ordinary discipline of listening before speaking, of pausing before acting, of trusting what arrives in stillness over what can be engineered in noise.

She describes her superpower as listening to her inner voice and to the other — and even in the middle of a facilitated session with executives or clergy, she is constantly going inward: asking herself what the stirring is, what the question beneath the question is, what the participant most needs and least expects. She frequently surprises herself with what emerges. Her clients feel it. They do not always know what to call it. She knows exactly what it is.

“Your first response,” she tells the people she works with, “is the superficial response. Let’s go a little deeper.”

She has been saying that for sixteen years, in corporate boardrooms and clergy retreats and prison ministry circles and coaching sessions with executives who have more power than peace. She says it with the calm of someone who has already gone to the depth she is inviting others toward. That is not technique. That is formation.

In our third conversation, we will go into the interior life itself — the masks she wore, the divorce she filed because of five Rottweilers, the Archbishop who called her out of the blue to lead a retreat for sixty priests, and what she wants to say to the person who is still, even now, circling the block because they are afraid of being seen doing the thing they are called to do.

But here, in this middle movement, I want to name what I see when I look at her arc whole: a woman who left competence for calling, who showed up to an empty room because a voice told her to, and who has been helping others find their inner voice ever since by first learning to trust her own.

If this reflection stirred something in you, we invite you to explore what a Time Out might open in your own life — at spiritofeq.com.

Peace and every good.