Coach Interview Series: Jennifer Sherwood

by Brandon

Jennifer Sherwood

Certified Coach, Writer, and Speaker

Our main objective here at the National Coach Academy is to enable aspiring coaches to reach their full professional potential. One of the most effective ways to educate students about the world of coaching is by offering them a window into the world of real, practicing coaches and showing them all the different ways coaches make a difference in the lives of their clients.

We hope today’s interview adds another insightful glimpse into the dynamic world of coaching.

Today we are interviewing Jennifer Sherwood. Jen is a Certified Coach, Writer, and Speaker based in San Leandro, California.

NCA: Can you describe your coaching practice and the kinds of clients you typically work with?

Jennifer: I love to work with women. I know that men have their own issues, but I’m really fascinated by and interested in women.

I love to work with a woman who feels like she has to be everything to everyone. She is the person who will give and give and give and never take time for herself. If she does, she feels guilty or will often cancel because somebody else needs her. Often, they don’t know this but they’re over-giving because they just don’t feel good enough and they’re trying to prove who they are. They’re trying to prove they’re worthy or they think it’s what they should do or what they’re expected to do.

I love to help them see that they matter. It’s a huge part of what I do. What really matters is that they like themselves. People are often trying to prove themselves so they can be seen a certain way or so that people will like them and think positively of them. But what really matters is whether they like themselves.

I also help them to see that self-care isn’t selfish. That’s such a destructive belief in our society. I show them that if they actually take care of themselves, then they get to show up in the world the way that they want to. It actually benefits everybody around them.

I guess you could say I’m on a mission these days. I want women to understand that we don’t have to live up to other people’s expectations. Not the media, not our mothers, not our mothers-in-law. Women can really create a life that they love, on their terms.

I’m never suggesting that you become a jerk, obviously. People don’t have to abandon their families or leave their jobs. I typically think about it as restructuring your beliefs and how you show up. You can be a really good person and still take care of yourself.

NCA: In working with your clients, what would you say is the most rewarding part of that process and on the flip side of that, what is the most challenging aspect of the work that you do?

Jennifer: I have this big grin on my face as I’m thinking about it. The most rewarding thing for me is when I’m working with someone and they just get it. They can see how they are getting in their own way and how maybe they were putting the blame on themselves or looking for that outside reward. The light bulb goes on and they have that A-ha moment. They just get it. That, to me, is the most rewarding.

Then you watch them put that shift into action. Maybe they are now having a hard conversation they’ve been avoiding for a long time, or they went for the promotion, or their relationship shifts. It’s seeing someone get how they can show up for themselves and then put it into action.

That’s the most rewarding thing about this career. I sometimes will finish the coaching session and I’ll think, “Oh, I just love this” because it is so gratifying to help someone shift their life like that.

The most challenging part for me — and this won’t be true for everybody — is working as a solopreneur. I didn’t realize how much I would miss that interaction with coworkers in the office — that quick cup of coffee and chat with someone else. Not being able to bounce ideas off of other people. I have found that to be the most challenging.

I have been putting a lot more effort into growing a network of fellow entrepreneurs to fill that void. But it took me a little while to see that that’s what I was missing.

People are often trying to prove themselves so they can be seen a certain way or so that people will like them and think positively of them. But what really matters is whether they like themselves.

NCA: Can you think of a mentor or a coach in your own career who was the most vital to your success and in what ways did this mentor help you thrive in your career?

Jennifer: The reason why I went into coaching was my own personal experience with a coach.

When I had my kids, it woke up this “perfectionist dictator” in me. (I know that sounds dramatic.) My inner critic, perfectionist dictator — however you want to call it — came alive and was so harsh to me and was driving me to believe I had to be the best. I had to be perfect at this. I really wanted to be seen like I had it all together — the perfect mom, the perfect career, the perfect home, and I balanced it all perfectly. Every aspect that you could think of in life, I was getting hammered about that. I didn’t know it at the time, but I knew that I was feeling pretty lousy.

At some point in my life, I got sick and tired of being sick and tired, so I looked for support. Coaching came into my awareness and really piqued my interest as a possible new career path for myself. Because of those reasons, I hired a coach and she really rocked my world. She helped me to see where I was actually creating all of these unrealistic expectations that I could never live up to and that’s why I was feeling so lousy. That’s what really drove me to leave a 20-year career as a pediatric audiologist to become a coach. I was so impacted and changed by coaching.

The first coach that I had had such an impact on me as a person, how I was showing up for myself, for my kids, for my life, for my career, for everything and then also mentored me early in my career. That was a huge impact for me.

To build on that, I completed the Martha Beck life coach training. The tools in that program were so fantastic for me to work with my clients, but also to continue my own personal growth. Martha Beck was also a huge influence.

Finally, I also love, love, love The Work of Byron Katie. The idea that we can dive in and question our thoughts, and that we don’t have to believe everything we think was absolutely revolutionary for me.

NCA: One of the most common challenges new coaches face is self-doubt. Some coaches call it Imposter Syndrome, where early on they feel somehow inadequate to take on the role of coach. What is one piece of advice that you would give to somebody who is in the beginning stage of their coaching career and dealing with these doubts in their mind?

Jennifer: The first thing I want to say to someone coming into this is that that’s fear coming up and it’s so normal. I would bet a huge percentage of coaches can relate to that.

Know that it’s normal and then that’s your work to do — to get into that fear and work through it. That’s where you have to coach yourself or hire a coach and really work on those thoughts because feeling like a fraud makes it very, very difficult to move forward and go after the life you want or your dream business. But if someone is drawn to coaching, if you really feel like this is where you belong, then you have to follow your heart because it makes such a huge, amazing difference for people. We do the work on ourselves, walk our talk, and then go make a difference.

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