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World of Coaching - Interview

What a pleasure it is to feature Stephanie Benedetto today, who joins us to share her experiences in starting and maintaining a successful coaching business that she can manage from wherever she is located at the time. 

Upon asking her to give us some adjectives to describe herself she starts with telling us that she is business coach and marketing specialist, but then goes on to share that she sees herself as a storyteller (check out her Wildspire Podcast), a community catalyst and an adorable geek who loves dragons and deeply probing at seemingly impossible questions. 

She goes on to say that her business services focus on helping coaches, conscious entrepreneurs and teams create the change they wish to see and share their heart’s message with playful marketing techniques-- no hustle, hype of endless social media required.

Q: Most of us feel that inner saboteur voice; those in the coaching and mentoring positions, like yourself, must have a hill to climb re: the inner voice saying they aren't strong enough or equipped to offer a substantial value. When did you get that epiphany that now was the time, that what you have to offer is worthy of sharing?

A: I tricked myself into starting my current coaching business, The Awakened Business. 

I was already running a successful business with my now ex–husband which brought in over $200,000 each year. We were selling an online membership, courses and coaching to help wedding professionals build their businesses.

The business was working, but I’d lost my passion for the market. I wasn’t doing very much coaching at the time, and the coaching I did was more like consulting. We’d come up with great marketing strategies, but either the client wouldn’t implement them, or they wouldn’t be as impactful as I hoped. I wanted to make a real difference with clients, and that just wasn’t happening.

So I started working with my first business coach who introduced me to transformational coaching. This wasn’t just about improving my performance and creating accountability or get stuff done; it was about transforming the way I see the world. It shifted my life dramatically, and I knew this was the impact I wanted to share with others through coaching.

Now, for the story of how I tricked myself into starting a new coaching business…

If I had said, “I’m going to start a new coaching business!” it probably would have freaked me out, so much that I would never have started. I had a vague idea about wanting to work with entrepreneurs who were making a difference beyond the wedding services market, but not much else. I didn’t know who they were or how I could help them.

I had an idea to take on a 100 Conversations Challenge. I would have 100 conversations with inspiring entrepreneurs and see how I could help them. This took the form of an experiment or game, which meant I didn’t have to declare myself as starting a new business, or take it seriously. I was just playing.

The 100 Conversations Challenge got me off my butt and into action. Shortly after beginning, I was invited to participate in an online event for a group of women entrepreneurs. I used that as an excuse to build my first website, and The Awakened Business was born.

So to answer your question directly, if I had waited until I knew that I had an offer worthy of sharing, it never would have happened. If I had waited for a life-shattering, “Now is the time!” epiphany, I’d still be waiting. 

If you want to know what you’re doing and how you can help people, dive in and start helping them. You’ll discover what you do by doing it, and not before.

I’m a huge fan of the “first draft” that Anne Lamont speaks about. Just do it. Just start. Let it be messy and imperfect.

Simply getting started with any action is the best thing you can do to create your business. Don’t wait until you’re ready.

Q: Do you have someone to go to for advice or comfort when you are stressed or depleted after helping others?

I actually don’t feel depleted after helping others, though that wasn’t always the case.

A few years ago, when I switched to primarily 1:1 coaching, I found that I was exhausted by doing more than three coaching sessions in a day. I could push myself and do four, but it was clearly too much. As it was, I needed down time to recover from a full day of coaching.

I scheduled coaching sessions on Mondays, Tuesdays, Thursdays and Fridays. Wednesday was my blessed relief, No-Coaching Day. By Tuesday afternoon I was yearning for it!

Then I attended a weekend Coaching Mastery training with Michael Neill. We didn’t learn any strategy or tactics, but rather focused on the power of presence and deep listening to create impact with clients.

At some point later that week, I noticed that it was Friday and I had tons of energy. I thought it was odd that I hadn’t needed my Wednesday break that week. The trend continued and I realized that not only did I no longer need a break from coaching on Wednesdays, I could fill my day with coaching sessions without feeling depleted. Of course, I still felt tired sometimes after a full day, but not absolutely drained like I used to.

What I realized is that working with clients wasn’t what depleted me, but rather the stress created by overthinking about those client sessions. Are they happy? Am I doing a good job? Is this going well?

I was doing way more work (thinking) than I had to. When I simply showed up present, without a lot on my mind, and just listened to clients, coaching felt relaxing and energizing. Relaxed listening is like meditation. Now I sometimes feel tired before going into a session, but quickly find energy just by dropping in to listen and be with a client, instead of my noisy thinking.

What if the client doesn't appear to be a good fit after all - how do you go about that selective process? ...What emotional conflict resolution tips can you pass on to our audience today?

I rely entirely upon my intuition when it comes to accepting a client. I almost always begin by giving a potential client a free coaching session so they have a real experience of what it’s like to work and play with me. Then, if it feels right, I’ll invite them to a second conversation to explore what they’d like to get out of coaching and what’s on offer, to see if it’s a good match.

We take our time getting to know each other. My intention is to be crystal clear about what they want and what’s available in a coaching experience with me. Then both of us can recognize whether this is a fit or not. This eliminates most of my coaching mismatches, and the conversation is also incredibly valuable for the other person because they get clear about what they’re really looking for. 

However, occasionally a client still doesn’t seem like a good fit. I had one such client last year. I spent extra time getting clear on what they wanted and thought we had a clear agreement about how to proceed, but when it came down to the loving disruption of coaching, they were unwilling to allow me to guide them. Both of us erupted in frustration at one point or another, and I suffered from a lot of doubt and insecurity about whether I was actually helping. 

What helped was to wait until my emotions settled before taking action. Our IQ drops dramatically when stressed and upset, and I know that is not the time to make good decisions. I did the best I could and moved through some very troubling situations with this client. I kept asking myself, “Should I fire them?” and the answer was no. Eventually, they asked to discontinue our agreement for personal reasons (illnesses in the family) and I agreed. 

The best advice I can give is to wait until you’re calm and clear to decide what to do. You’ll have access to your intuitive guidance and creative solutions will come.

Q: Do you feel that a feeling emotion on a deep level helps, or hinders, coaches/mentors?

Feeling emotions deeply is never a problem; it’s a misunderstanding of what it means that can create challenges for coaches and mentors.

As humans, we’re designed to feel what we think. If a client shares a painful story, and it looks like a problem to me, I’m going to feel my painful thinking about it. But when I know the feeling will pass, another thought will come along that’s more helpful. The client is strong. They have what they need to navigate this. It doesn’t have to trigger my own stories about those emotions and what they mean.

Feeling a negative emotion is like feeling physical pain. When I put my hand on a hot stove, it hurts, and that tells me to stop touching the stove. The same is true with thought. When I give my attention to a painful thought, it hurts. That’s a signal for me to stop thinking it. Unfortunately, most people don’t see the role of thought in creating their pain, and they end up blaming it on the person or situation in front of them. That’s when things get messy.

The ability to feel is a great gift. It allows us to connect with others and acts as a guide to help us use thought creatively, rather than to hurt ourselves.

Q: How should clients prepare for working with you?

A: I like to spend some time sharing how to get the most out of the coaching experience before we begin our journey together, and have even written an article about how to get the most ROI out of your coaching.

It comes down to:
  • Be open, honest and willing to be impacted.
  • Have an intention for what you’d like to get, and hold it loosely. Be open to discovering something new you couldn’t have imagined.
  • Be an explorer. Let go of what you think you know, and be curious enough to really look.
  • Listen, without much on your mind. Listen within.
  • Allow yourself the space to reflect and rest. This is often when your biggest insights and breakthroughs will occur.

Q: How do you utilize/manage social networking accounts and things like FaceBook groups to attract or maintain your coaching clientele?

I stopped using social media for my business over two years ago as an experiment. (Experiments are another way I often trick myself into doing things.) At the time, I was spending 4-5 hours each week on Facebook, creating content and commenting in groups. It did create relationships and clients, but I didn’t like the idea of feeding the social media beast. 

I started talking to entrepreneurs who’d quit social media, interviewed a few of them and wrote some articles sharing what I’d learned. I wondered, “Everyone says you HAVE to use social media to have a successful business, but is that true?”

I easily found dozens of entrepreneurs running profitable businesses without using social media, and many others who limited their interactions so they barely spent any time on the platforms. And they still had clients.

When a group owner challenged me for sharing content about not using social media in their Facebook group, I acknowledged the irony and took it as my cue to stop my social media activities. A one month experiment turned into three, then six months. Now it’s been over two years and I haven’t been tempted to go back.

I do share videos on YouTube, but that’s the only social media platform I’m actively using. My income has continued to increase each year. I’m living proof that you can have a thriving, healthy business without promoting on social media.

Now, if you aren’t going to connect with people via the socials, you’ll have to take other actions. What works for me is creating content for my blog, becoming an active member in communities where my ideal clients hang out, and inviting people to conversations for coaching and partnerships. It’s much more fun and better suited to my personality.

Q: I think a lot of people will find that information quite reassuring. So beyond social media, youtube and community groups... How did you go about attracting a customer base? Have you experimented with advertising and if so, where was the best advertising dollar you spent?

The best advertising investment I ever made wasn’t actually spent on advertising! I joined the high-end program of a well-known coaching mentor that gave me personal access to him. Part of the program involved creating different forms of content. He liked two of my stories so much that he shared them on his podcast and in one of his programs. As a result, a dozen people reached out to me and a few of them became long-term clients.

Every time I engage in a coaching community like this as a student and member, it pays for itself in creating clients. I don’t promote my business in these communities at all; I simply show up and share in the group forum and connect with people by being me.

Q: What are your specialties - that sets you apart from others offering similar services? 

I don’t have a process or proven system for people to follow. I help people discover their own path in business by following their inner guidance and engaging in playful experiments. 

I don’t believe hard work, hustle and marketing hype is necessary for success. You can have fun and authentically share to create clients.

My specialty is helping people come alive inside their businesses and fall in love with every part of it, including marketing. Business feels like play when you get to show up as your authentic self, doing what you love, and sharing it in ways that feel good. As a result, you take more actions in business and create more clients and money. And it’s so much more fun!

Q: How do you generate new ideas?

Humans are designed to create and we’re born hooked up to an infinite conveyor belt of Thought filled with ideas just waiting to be conceived. We have great ideas all the time, but usually talk ourselves out of them.

I love to generate new ideas by talking to people and listening, both to their words and beyond them. What can I do to serve? Often, I’ll ask them directly, and the possibilities and ideas for creating new experiences and services come to me.

I don’t usually try to generate ideas. They just happen when I’m enjoying my life and interacting with the people around me. By looking in the direction of creativity and inspiration, ideas are a natural side effect.


  1. Thank you Stephanie for dropping in to share these experiences with us!


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