Overcoming Imposter Syndrome in a Coaching Business

How Kendra pivoted her coaching business.

Kendra is a former multiple six figure functional health coach, but now she’s an online business strategist for health and wellness coaches and practitioners. I really can’t wait to dive into her story, how and why she pivoted her coaching business, and what she’s doing now that’s working for her and her clients.

Kendra, I would love for you to give yourself a more thorough introduction, and then I’m going to ask you a million questions.

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How Kendra Pivoted Her Coaching Business

Thank you for having me, Alison. I really appreciate it.

I’m an online business mentor and strategist for health and wellness coaches. The reason why I help health coaches is because, like you said, I used to be one. That’s how I got started in my business in 2014 – as a health coach.

The reason I ended up in that industry is because I was having a lot of my own health issues in my early 20s. I started to get cystic acne after taking this birth control pill. And for anyone who’s had acne, they know that it’s rough. It really crushes your self esteem. I was super obsessed with trying to get rid of it. The doctor essentially offered me more birth control pills, antibiotics, and Accutane. None of that appealed to me.

So, I started kind of looking into alternative health, and that was my gateway into it. Later on in my 20s, after years of partying and doing drugs and being crazy and not taking care of myself and hating myself and all of that, I ended up having a pretty severe health crash that led to an eight-year struggle with chronic fatigue, chronic insomnia, undiagnosed Lyme disease, that sort of thing.

So I pursued a career as a health coach, with two purposes: to help myself, but also to start a new career.

At the time, I was working in forestry, and forestry is a very physical job. I just really didn’t have the energy for it anymore. Plus I’d injured my knee – I just couldn’t really keep up with that anymore.

So that’s what started me into a health coaching business. Eventually in 2019, I transitioned to business coaching. I got really burnt out with health. I was obsessing over it. Obsessed for myself and for my clients, both. This was during my struggle with my health; I was researching constantly trying to figure out what was wrong with me, and then trying to figure out what was wrong with my clients. I just needed to take a step back.

So, I transitioned over to business coaching, and then ended up hiring my own health coach so I could fully just let go of all that. I’ve been doing business coaching for health coaching since 2019.

So, you’re a classic example of someone who had the struggle, got over the struggle, taught others how to get over the struggle, and then did that 2.0 when you hit the second wall.

It’s very much like in Russell Brunson’s book, Expert Secrets, where every entrepreneur kind of has a story where they have the success and they help others with success, but they hit another wall before they kind of get to their real thing.

Breath Work

So, you’ve used a lot of different tools in your health coaching journey. Some of the reasons why you and I connect specifically is that I have an interest in breath work. I’ve been dealing with the issue that I’ve got all the practical stuff down. I’ve been business and marketing coaching for a long time, and blogging for a long time. Then I hit an income wall, and there’s no more strategies to learn.

Breath work to me is an introduction into the deeper level of mindset, not just saying affirmations, but really tuning into my nervous system.

I’m not sure where to start, because I want to know your process for how you help your clients get sales. And I also want to know how the breath work plays a part in this deeper leveling up that you’re doing. So I’m just going to put that out there and I’ll let you start. 

The breath work was a result of my own health journey.

I’m very science minded and I’m very analytical. In my head, I like to analyze the shit out of things. So, with my own health, that’s what I was doing. I ended up doing a certification in functional lab testing. I was running tests, analyzing, and looking at data.

For my entire health journey, I was just focused on the physical and physiological side of things. I didn’t even look into emotional, spiritual, that sort of thing. I’m someone who, I mean, like a lot of people, I was raised to not express my emotions, right?

  • “You’re a drama queen.”
  • “Don’t freak out.”
  • “Calm down.”
  • “You’re fine.”

All of those sorts of things, which I think a lot of us were raised hearing.

So I was really pushing everything down, and I believe that that played a huge role in what I ended up experiencing with my health.

But, I was very resistant to looking at it. Because it felt hard, I didn’t get it.

I thought it was stupid; I was very atheist, I guess, in terms of spirituality. Growing up, we went to an Anglican church, but we gave that up when I was like 10, and just had no connection to God or spirit. Just was not into that. It was later on in my health journey that I started to work with a mentor and started to recognize that this could be playing a huge role in what I’m going through with my health.

I actually started doing breath work after this same mentor turned me onto it, and I was blown away by it. I was just like, “Holy crap.”

One of the first sessions I did, I just bawled my eyes out. I can be a very apathetic and stone cold bitch. So I was just like, “Whoa, where did that emotion come from? That was crazy. Wow, that was really powerful.”

So I ended up doing a facilitator training, and then started to realize how powerful this could be in helping my students. I tell them about the mindset stuff. I’m like, “Oh yeah, watch out for imposter syndrome,” etc., but now I’m like, “How do we actually move it out of the body?”

At that point, I’d been doing counseling for years and talk therapy, which is valuable. It’s good to become aware of things, I guess, but then what do you do with that?

And that’s where I was getting stuck. What do we do with it?

We can determine that you have imposter syndrome, but what do we do with it? That energy is in your body.

So I did the facilitator training, because I just thought it would be a great way to help my students clear energy and actually move some of the stuff out of their body and out of the cellular structure of their body.

From a Health Coaching Business to Helping Health Coaches

You have quite a journey – the forestry gig, and then moving into the health coaching, and then moving into the business coaching. Can you talk to me a little bit about the pivot between being a health coach to helping health coaches? How did you launch that? How did you move out of the health coaching? I want to talk about that briefly.

I was on unemployment insurance when I started my business. I’d been working in forestry, which is seasonal. So you get laid off at the end of the season, and you collect unemployment. I would ski in the winters.

And so I was in this situation where I was like, “Okay. I’m making like $1,600 a month from the government. How do I just start making that my own business?”

The certification program that I went through, I did really well in the program. They ended up offering me a position as a course mentor, which was great. It paid me part-time was more than what I was making full-time in forestry.

I ended up working for this organization about 20 hours a week for the first three years of my business, which was great. I was mentoring students as they went through the course. And then, eventually, I ended up developing their graduate membership. In that membership, I was delivering a lot of the business training. At that point, I was a few years into my business, and they needed business help. I was answering a lot of business questions and leading some trainings.

And I was noticing that I was getting really excited about that sort of thing. I was like, “Oh, I really like this.”

Then, when my business got to the point where I ended up leaving that job, because my business was taking off, I really missed working with the practitioners and the coaches.

I was doing business consulting on the side, because people had been reaching out to me from that community.  Then, the big moment for me was interesting: there was a woman who I follow online, she was a health coach. She actually made the transition into business coaching.

I watched her go through that transition and I felt so jealous. I was like, “What am I feeling? Oh my gosh, I’m jealous because I want to be doing that. I want to make that transition too.”

So that was actually a really big wake up call. Then I simultaneously was realizing how burnt out I was becoming, that second wall, like you said, and just like, “I’m so exhausted. I don’t want to talk about health anymore, because I’m doing this 24/7.”

So, I just made the transition to a coaching business helping health coaches.

It was a pretty smooth transition, because I already had a lot of coaches following me just from the organization that I was associated with. And then there was maybe six months where I was doing both. I was doing health coaching and business coaching, and I dedicated certain platforms to health coaching, certain platforms to business coaching. But for anyone who’s ever had two niches with a really small team, it was exhausting. I was like, “This is f*****.” I can’t do this. It was just too much. So I had to decide: which one do I want to do? And I went for the business coaching.

So, then you pivoted, and then eventually, you ended up hiring your own coach.

Coaching Business Burnout

You burned out from talking about health. How did that show up when you were helping other health coaches? How did your experience in burning out help you help them?

A lot of health coaches are doing it because they’ve had their own health issues. That is one of the most common reasons why someone in that space becomes a coach like that. And there’s definitely a lot of imposter syndrome mental shit there, because a lot of times, they’re not fully healed.

They feel like, well, who am I to help other people when I haven’t fully healed myself? That was a big thing for me, because I was niching in energy. I was helping women with chronic fatigue – while I had chronic fatigue.

I was so hard on myself, and it pushed me to maybe obsess over it a little bit more, because I felt like I have to heal this before I can be fully credible. Right?

I try to teach my students that being an expert in something is just really blazing the trail a few steps ahead of the person behind you.

I think that helps, because we want to be this perfect version of ourselves before we think we can help people. That can cause a lot of exhaustion, because we’re striving for this perfectionism. Really, I think having the same issue as your clients can actually be a really powerful tool.

People want to know that you’ve been through it.

I just tried to be really transparent, and I would talk about my struggles with fatigue. A lot of people really respected that I was still dealing with it. A lot of people worked with me because of it. It’s important to have your own coach, so you have this third party who is not emotionally connected to the problem help you.

But also don’t be so hard on yourself, and understand that your intimate experience with the issue that you might be trying to help people solve is actually a super power.

I think it’s really important if you are coaching, that you often or always have a coach. You need the accountability the same way that your clients do. That’s a really important point to highlight.

How Kendra Gets Clients

So, now, how do you get clients now for your coaching business?

My primary program is Health Coach Accelerator.

We have a few different ways, but I mostly sell through webinars and in certain live events.

So for example, right now, we have an automated webinar. We run ads to what’s called a self-liquidating offer. We run ads to a low-priced product, which is essentially something that I pulled out of my program. The intention is to pay for your ads.

So when people buy a low-price offer, it liquidates the cost of your ads and it gets maybe what you’d call a higher quality lead – someone who’s just a little bit more interested in investing. Then we invite them onto an automated webinar, which invites them into the program.

Now, we don’t get everyone that way.

But then what I do is, typically every couple of months, I do a live workshop. I do one on sales, and we then invite people in there.

A lot of people come in through the live event. They weren’t necessarily ready, coming right off of Facebook ads into a webinar. We get some people that way, but then we tend to close more of them after the live event, once they can kind of get that experience of working with me in real time, experience my energy, that sort of thing.

There are so many different funnels these days, and people are saying, “Webinars don’t work anymore. Everyone’s doing this, everyone’s doing that.”

I think everything works as long as it feels good to you. And so, just so I understand, you’re doing an SLO, self liquidating offer, which is a low-cost offer that pays for itself. And then that leads them to eventually get an invite to a live event. Is that right?

Yes. So first, they’ll get on the confirmation or the thank you page for the offer. We invite them into the automated webinar. If they don’t join, then we invite them again at the end of the nurture sequence.

And then if they don’t sign up then, then they actually go into a year-long nurture sequence where we continue to warm them up. Then we will also invite them onto these live events, which is typically like a low-priced paid workshop.

Once or twice a year, I’ll do a bigger free event.

For example, in February, I did a five-day challenge to help them build their signature offer.

You’re starting your funnel with the paid offer. I love that. And do you teach your clients to do the same thing?

No, because my clients are brand new. They don’t even have a niche, or have their business and servcies set up. This is definitely a more advanced strategy, and I’m helping people who are way before this sort of strategy.

Yeah. Yeah. I’m sure you and I are on the same page where you just shouldn’t be doing the low-cost offer before you’ve figured out your main offers.

I don’t think you should even be doing paid traffic until you actually know your ideal client and you understand messaging and communication, and content creation. I see a lot of people who are trying to do these things without having any of those foundational pieces in place.

Yeah. Yep. Yeah. So for you, in your business, having a funnel like this takes a lot of optimization and time and probably a team. You’re probably not running them on your own anymore.

I’m taking a break from ads, because when I started, I realized that once I started tuning into how I was feeling, when I was turning on ads and testing stuff, I was kind of triggering myself. I’m not good at tracking or optimization left to my own devices.

It was like my nervous system wasn’t right. I was going outside of my window of tolerance.

Breath Work and Resilience in a Coaching Business

I’m wondering about how you as a business owner use the breath work and resilience, and other work that you’ve done, to continually stretch yourself. How does that show up in your business?

Yeah. So are you familiar with Human Design?

A little bit.

Yeah. So I’m a projector.

Human Design, for the listeners, is essentially a combination. I think it’s astrology, I` Ching, Kabbalah system, Chakra system.

It’s a bunch of these things, combined in one for the ultimate personality test. And I’m a projector, which is maybe 15% of the population. A projector is someone who doesn’t have access to their own consistent source of energy. So I get my energy from other people. I have to be really intentional with my energy. Projectors, they’re not really meant to be the workhorses. They’re meant to sort of lead and guide and be coaches, but kind of essentially show other people how to do the work.

And I dove into that about a year, maybe two years ago, year and a half ago. And I’ve really, really started to run my business like a projector, and it’s been a game changer. A big part of that was actually building a decent-size team.

I have a lot of contractors. I really only try to focus on doing the things that I like in my business.

Obviously, I’ve gotten my business to a point where I can do that, but I have someone who does operations, the virtual assistant, someone who does the Facebook ads, graphic design, a creative director. I have all those things, because I just want to focus on supporting students and improving my programs, creating content, that sort of thing. That’s been a really big piece.

So yeah, I do have higher expenses, but to me, that’s worth it for the time to just spend doing the things that I’m good at.

And then, with breath work – we get ourselves into kind of like a tizzy throughout the day in different ways. It’s like, something is not working, and then we make it mean something about us.

Like my Facebook ads aren’t converting. I suck. What the hell? Or stuff like that. Or you get a mean comment on Facebook and we’re like, “I suck.” Or a student wants a refund or whatever. All these things, little problems that happen throughout the day. Over time, you develop resiliency towards that because you just realize that problems are just these neutral things that actually are good for the business, because they make the business better.

But when I get myself into a tizzy, I love to do what’s called integrative breath work.

It’s a short breath work session, because you can do breath work for so long.

I love to do a nice 30, 40 minute breath work session where I go through space and go to another planet. I love that. But doing just a five-minute session to get yourself out of your head and back in your body, I have just found so effective. When we’re dealing with all that stuff, like the I suck, I’m not good enough, what the hell, it’s not working – that’s because we’re in our head. Where we need to be is in our body, and we rarely go there, especially throughout the day.

I have to take these little breath work breaks throughout the day, especially when those things happen, just to kind of get back to where everything is fine, everything is calm, and nothing has a story behind it.

The Resetting Power of Breath Work

Breath work has definitely been one of the biggest resets for me. When I discovered it, I had gotten these new coaches in November. At first conversation together, I was so emotional, because I had such a bad year and I was just really upset.

And then, of course, I make this big investment, which seems insane because I had such a bad year. Why would I make this big investment? So on our first coaching call, I’m just crying and upset. And they’re like, “Yeah. We can’t even really talk about business right now, because you just need to get out of your shit.”

And so they just told me. They didn’t tell me why, or how it worked, or why it worked. But they just said, “We need to build up your resilience and your window of tolerance, and give you a good reset.” They just gave me a beginner breath work exercise, and they gave me another exercise that had to do with movement.

And they just said, “Do these every day.” It was an 11-minute breath work exercise by Wim Hof, who you might have heard of. Yeah. I just remember the first time I did one, it was so much more powerful. I don’t know if powerful is the right word.

But when I try to meditate, I have a really hard time just relaxing, but breath work was the first thing I’ve ever done where I was really able to get 100% out of my head.

I felt I just had never had that feeling before. And that was the beginning of my journey now.

I’m a business and marketing coach, but what I’ve realized is that a lot of my clients get stuck where a lot of your clients get stuck, which is the mindset stuff.

They need the strategy, and eventually, they figure out the strategy and they get the sales, but then, then they start freaking out again. That’s all mindset, nervous system. I’m getting a certification now where I can help people tie into that more. But yeah, breath work, crazy stuff.

Well, it’s interesting that you said you did Wim Hof, because my intro into breath work was Marcel Hof, Wim Hof’s brother, who also has his own breath work thing. Did you know that?

I did not. That is so interesting. I have no idea.

Yeah. It seems like Wim Hof does his breath work in extreme environments in Europe, whereas Marcel Hof is in Bali.

You can find all these guys on YouTube. There’s another one I really like, and you should try this out too. It’s called Breath Work Beats on YouTube. Oh my gosh, I love it so much.

Sounds good.

It’s exactly what it sounds like, like deep, intensive breath work stuff to really good music, and so I get really into it.

What are you working on now?

Right now, I’m in crazy optimization mode.

I’m looking for all the holes, figuring out everything that’s wrong in the business and just optimizing.

It’s crazy when you actually look at certain things, you’re like, “Oh, I haven’t even looked at that in a year. And that’s actually kind of f*****. I have to deal with that.”

Awesome. Very exciting. And where can people find you?

People can find me on Instagram. That’s where I typically hang out. My handle is @kendraperryinc. I answer all my DMs. If you have any questions, want to connect with me, you can chat with me there. I also have my own podcast, which I think Alison is going to be a guest on soon, right?

Should we do that? Yes. Perfect. It’s called The Wealthy Coach. So we talk about strategy, mindset, tools, anything that you need to get started and grow your business to six figures. And my website is kendraperry.net.

Kendra, this conversation has been amazing. I’m going to go follow you. I can’t wait to stay in touch, and thanks again.


If you’d like some help growing your business, let’s chat: AlisonReeves.Co/strategy-call

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