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3 Good Questions

About a month ago I did something that’s been on my to-do list for about five years: I signed up for professional life coaching certification. Ever since I started the regular practice of meeting with a coach of my own, I’ve let the thought simmer on the back burner what it might look like to do the same for others.

For a good part of this year, I’ll be in class, learning from professionals. For the second half of the year, I’ll be logging practicum hours, learning what it’s like to coach in real time. I’m nervous and I’m thrilled.

I don’t yet know what my practice will look like once I’m certified, because my priority will remain writing — more books, in particular. But I’m pretty sure it’ll have something to do with the marriage of travel and introspection; my purpose for the relatively newly christened trips I lead is to host meaningful conversations in meaningful places. That feels like the type of coaching I want to embody.

Who knows really where this will lead, at this point, but I love the idea of holding space for others to find their answers as we let meaningful places around the world speak to us in new ways. And doing this in small groups is where it’s at, I think — just enough people to tap into a hive mind of thoughtful wisdom, but small enough for those conversations to truly have purpose and meaning.

For me this year, it looks like leading a small group of brave women for a week in London and its surroundings, using the filter of its literary greats to explore, learn, and move forward in wisdom.

And it looks like this fall, where a small group of brave women patrons will gather with me for a weekend right in Georgetown, my delightful small town just outside Austin, where they’ll be my guinea pigs as I practice the fine art of life coaching in a small group weekend setting. More gatherings will most likely follow, since there’s already a waiting list the size of two more small group workshop weekends.

It feels good to learn and try something new. It feels good to have finally started something I’ve wanted to do for half a decade. It feels good to feel vulnerably like a beginner, to not know what lays ahead, to risk going beyond the safety of screens and delight in face-to-face connection.

As I continue to learn what it means to coach well, here are three small questions my coach has asked me over the years. These three questions almost embody all the introspective questions we ask ourselves.

1. Where am I right now?

This question asks us to name the present, to acknowledge where we are today, and to notice the little things. No judgment, no panic, no stress. It just asks us to name the place where we stand right now.

2. Where do I want to go?

Asking this question summons the possibilities, gives us permission to dream big or be honest about the small, and to get clear on what’s just beyond the fog in front of us. It’s an invitation to be honest with ourselves and give a name to the thing we want — again, without judgment. We’re simply being honest with what’s already inside us, asking to come alive.

3. What’s getting in the way?

This is The Question, right? Because by parking here, we invite honest feedback and a gentle reality check. Again, this question doesn’t hold judgment, but it does ask us to get real about the thing behind the thing — what’s behind the curtain, after the bend in the road, or hiding under the clutter.

None of these three questions are easy, but they are simple — and they can be asked again and again, about all sorts of things. You can be macro about the whole thing, and ask these three things about Your Life As It Stands. Or, you can zoom to micro level, and ask the trio on repeat about your health, your work, your relationships, and beyond.

These three questions hold so much power, and yet I see them simply as envelopes to open, one at a time, with invitations to ask what’s really going on. They remind me a little of what I ask myself in my Think Days. But these can be asked as I sit in traffic, stir the soup, or brainstorm the book outline. I can mull over them in real time, in real life.

They’re the keys to unlock what’s really going on.

Sometime this week, consider asking yourself these three questions. Perhaps you’ll find a “enroll in life coaching certification” of your own, patiently waiting inside your soul, asking if it can come out and play. Or maybe you’ll simply find the measure of contentment you’ve been looking for, to help you remember you’re doing the right things you need to be doing at the moment.

Either way, let these three questions be invitations you give yourself. What do you think some of your answers will be?

Reading Time:

3 minutes





  1. Devi

    Funnily enough, I think the first question is the trickiest to answer. One thing I learned in 2018 is that there are layers of truth, and we (I) can often not even see the realities of my own life clearly. Maybe this is the problem of our message driven world, we are so used to packaging our lives for the consumption of others that we miss what’s really going on. I’ve discovered that it takes a ton of time, silence and radical acceptance of myself, my thoughts and my ideas that leads to the ability to just SEE my life truthfully.

    • Tsh Oxenreider

      That’s a great point, Devi… Acknowledging where you actually are requires silence, stillness, and honesty. Those can be really hard to do.

  2. Angel Weiskopf


    I’ve been a fan for a few years but wanted to say I’m loving your new blog and podcast format. I get a lot more out of the podcast and appreciate the continuity of having the weekly blog and podcast episodes connected. Thanks again for being such a positive voice, sharing your wealth of knowledge and being a bit of a kindred spirit to those of us out in the world listening.

    • Tsh Oxenreider

      You’re too kind, Angel! Thank you for your encouraging words here… I so agree with you. Heck, as the creator of all of it, I’m getting a lot more of out both these mediums, too! 🙂 Really appreciate you sharing this, and thank you for both reading and listening. xoxo

  3. Jessica Robinson Gemm

    Doing the coaching training is a great development, and I LOVE how you’re talking about integrating that with travel. Gave me chills, actually. After doing Like Your Life last year, I could see you already have the coaching skills and instincts. One encouragement from when I went through my coach training program – on the first day, they had us write on the first page of our journal “I am a beginner” – and then on the next, “I am a great coach” – so even as you see yourself as a beginner, remember you already have great instincts and experience. 🙂 Can’t wait to see your progress!

  4. Kimberly

    Thought of you this week as I read Rediscovering Travel: a Guide for the Globally Curious by Seth Kugel. I really had no idea how the travel industry worked.

    I think “life coach” is an awesome fit for you.

  5. Peggy

    Hello Tsh –
    Obtaining a professional life coaching certification is something I’ve pondered for several years but I’ve struggled determining the best training source. Would you be willing to share the name of agency your using?

  6. Irene

    Hi Tsh, these are awesome….I think I’m gonna post them somewhere… I wish I had an ‘own’ room/space…lol
    Bless you…

  7. April

    Thanks so much for sharing these questions. Sometimes you need the right questions to think well about your own life and these resonate so deeply!

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