Can I Get Coachy?

I was thanked for not solving the problem.

A dear friend is navigating a hard season: caring for aging parents who live far away, managing her own health challenges, keeping up with a full-time job, and participating in a side hustle she worked hard for and is genuinely proud of.

The side hustle was also ramping up her anxiety. How would she manage it all — the jobs, the travel to her parents, and still be present for her son and young daughter?

She called wanting my advice. She was debating quitting the side hustle but couldn’t make a decision.

Instead of telling her what I thought, I asked if I could “get coachy” with her. (Notice I asked for permission. People — especially friends and family — don’t always want to be coached. Sometimes they need to vent. Sometimes they genuinely want your advice. Ask first.)

She invited me in.

So I asked questions. What was she most afraid of with either decision? What might be possible if she kept it? If she quit? What stories was she telling herself? What was her body saying?

She came to a realization: she wasn’t considering quitting because of her job or her kid. She was considering it because whenever she thought about the side hustle, she felt anxiety. That gave her something real to explore.

When we hung up, she hadn’t made a decision. But she had a lot to think about.

She called earlier this week to thank me. “Thank you for not telling me what to do.”

Her husband and a close friend had both encouraged her to keep the side gig — of course she could handle it all. Well-intended. But what she realized, in her reaction to their answers, was that she wanted someone to tell her it was okay to quit.

Neither of them did. I didn’t either. But my questions opened a pathway to what she actually wanted. And as she put it, she had to “put on my big girl pants and make that decision myself.”

She sent the resignation email the next day.

I asked how she felt. “Like a weight is off my shoulders.”

We are wired to solve, to fix, to find the answer and call it done. But sometimes the most powerful thing we can offer isn’t our wisdom — it’s our curiosity. Curiosity that lets the other person find their own answer, in a way that’s true to them.

The next time someone you care about is struggling with a decision, ask if you can get coachy. Start with “What are you most afraid of?” Listen. Keep asking. And see what happens.

Coaching isn’t reserved for coaches. It’s available to anyone willing to ask a good question and get out of the way.

If you’ve experienced this — on either side of the conversation — I’d love to hear about it.

Hey there! I’m a leadership team whisperer, executive coach, and speaker. I guide leadership teams in high-growth companies to achieve rapid growth in a healthy, sustainable way. I coach senior leaders to discover the path to lead with ease. Let’s talk.