How To Stop Struggling With Chaos & Overwhelm with Jennifer Sherwood

Feb 15, 2021

You may feel like everything is disorganized, you just can't find what you should be doing with your days effectively, and you just can't get a handle on time management.

If this sounds like you, then I'd like you to meet Jennifer Sherwood! Jennifer is a certified coach, speaker, and writer who loves working with women who are overwhelmed and helps them find their inner calm. Her goal is to guide them in creating a life on their own terms that they really LOVE and not just tolerate.

Jennifer also happens to be a client of mine and is in my The Content Creator's Mastermind, and we also go over how we mastered setting up her day, so it doesn't feel like a grind and how she was able to make the shift to get things DONE!

I'd love for you to stay and listen to Jennifer's journey in how she was able to stop the overwhelm in her own life and help women feel empowered to make their goals a reality without the stress in theirs.

To connect with Jennifer, you can find her on Facebook and Instagram @JenniferSherwoodCoaching and her website.

Along with her 3 Simple Morning Ritual Freebie so you can start your day grounded: 

Watch The Full Interview! 

Full Transcript: 

Jen: If you struggle with some of other things that many of my clients struggle with, which are time management time, mastery or feeling disorganized, and pretty much every entrepreneur I struggled with this idea of what they should be doing with their days. Especially in this time of people who are shoving this lifestyle down our throats that we be at the beach with our laptops and working four hours a week. Which feels like a bunch of crap. So I am bringing you Jennifer Sherwood today because we are going to about the realities of having and having a life and having time to have both. So Jennifer is a coach I'm going to her tell you about her business. But I'm really honored to have her here today to talk about this idea of what's the right way to organize our time? How does that feel? Does that feel like a good thing to talk about? 

Jennifer: t's like exactly what we should be talking about. So thank you for having me Jen I'm really happy to be here.

Jen: My pleasure, Hello! Before we get started, I want everybody to know, what is your business? What kind of coach are you? Who do you work with? Who do you help?

Jennifer: Yeah, thanks for the opportunity. So I work with women who are just overwhelmed. They feel really pulled between the stresses and demands of work and home. They never make time for themselves and I just imagine her sitting there thinking, "Man is this as good as it gets?"

That's the woman I love to work with. And then what I do with her is I help her create a life on her own terms that she really love not just tolerates. That's who I love to work with.

Jennifer: That's a big differentiator. A life that you love and design versus a that you put up with.

Jennifer: Right it's being carried along by what you think you should do, how you think you should show u,p listening to all of that versus deciding how you want to live your life. And most women don't realize that that's an option. I did not realize that when I was in the thick of early motherhood and running kids to different things and showing up at the PTA that I didn't even want to be in and trying to juggle a career. I didn't realize that I choices. And then once that opened up to me, it felt like... I can't even think of the word. But it just felt like this revolutionary. That's it! It felt really revolutionary to think, "Wait, what I've been doing this for so long? And I could do this?"

And once I figured that out and the relief that came with it, then I to do that for other women. So I had a 20 year career before this that I because this was so life-changing for me.

Jen: So your women wake up in morning what's the first thing that they think?

Jennifer: The first thing that came to mind was the swear word. I know you, Jen. I probably could just say it but...

Jen:  Go ahead!

Jennifer: Normally, you know, the first thing they think of ism, "Ugh!"

That's the first thing, you know?  Can I hit the snooze? How much longer can I stay in bed? And then the mind chatter starts going like who needs this? Where do I to be? What do I to do before I can get out the door? Can I get breakfast? It's just on the go immediately.

Jen: So, the first thing they do is they wake up they're like "Oh, this again?" Like, basically, like Groundhog Day.

Jennifer: Yes.

Jen: Yeah, okay, that makes a of sense. So now the reason that you and I talking specifically, this is you want to talk about the success that you've had in figuring out some of this stuff for you. And you and I have had many conversations.

So, Jen is a client of mine and she is in my matermind program, The Content Creator's Mastermind, and she is talking today about where she was and where is now and the work she's done to get there. Because I think the things that she's learned are really useful to the kind of people she's describing, but almost every entrepreneur struggles with what you struggle with, which is "How am I supposed to set up my day so that it doesn't feel like a grind and I actually get some shit done?" Right?

Jennifer: Yeah, so if I just say that I am enjoying the mastermind so much and working with you and this particular piece has really fallen into place for me. It was definitely improving,there's been massive improvement. I want to clear about that. But something clicked for me recently which I will share and it's just opened things up for me.

So there was a thought in my head for probably most of my life that I don't have enough time. I'm always.... I was always saying "I don't have enough time. I don't have enough time." I bought every planner that you can imagine. I tried every course. Everything. I had a coach one time who was so Type-A herself, and this is not a criticism but this was her method. And so she was saying to me, well, time block and then color code the time blocks. Dude, I couldn't even remember what the colors were for. I had to write every week in the planner. So it just didn't work for me.

And what would happen is when it didn't work for me, then I felt lousy about myself. That there was something wrong with me. How come everybody else... Cause I was hearing that time-block, time- block, time- block. Which is true, but I'll tell you how I got there. 

But the thing that was really rough and I what a of women struggle with is, "Oh I'm not as good as so and so because I can't hold all my crap together." And so that was a piece. I coming to understand the time blocking more. Sort of planning my time out more was helping. Forget the color coding it didn't do any good. Hey, if that works for you, good on you. But it didn't work for me.

And then I started working with you, Jen. And really, what I want to share with your audience is what you told me. And this was super helpful.

So Jen and I went through my whole business. We listed out all the tasks that need to be done and then I went back. I don't remember if we did it together when I went back it doesn't matter, but I what needed to be done weekly, monthly, and then that list is sitting on a clipboard.  That sounds so 80's. It's sitting on a clipboard on my desk where I can look at it and I have put all of those things in my calendar. It feels loose, though because one of the things that Jen said to me, what you said to me was, "You know part of being an entrepreneur is freedom and you are not very free with your freedom."

So I would not get something done and I would beat myself up. So it's been this culmination of trying something different. So, yes, I have blocks in my time. If I need to move them I am okay with that. I just make sure I move it.

And then...So this is all sort of happening, and then I know where this came from. I'm sure I've heard this six bajillion times in my life, right? That my to-do list will never end. But I think what used to happen is that used to feel like, "Shit!"

Like it felt defeating that it would never end. And recently that was the shift. Was it's not defeating it's freeing. If I know that my todo list will never end, then I don't have to get it all done. It just transfers to the next week, like I pick the things that are most important. Cross those off. Move them. Like the to-do list it's free-flowing. It's always on.  It's like the laundry, you finish doing it, you fold it, you put it away and then you put your dirty clothes in the hamper that night. You just keep doing it. 

Jen; That is such a great analogy. 

Jennifer: Thank you,

Jen: Because do you make your bed every single day? Do you brush your teeth every single day?

Jennifer: I do. 

Jen: Twice a day!  Do you make breakfast every day? Do you make dinner every day? This is a huge tip for people because they think that somehow they "should" get to the end of their to-do list. I love this. This is like the laundry. It's just never-ending.

Jennifer: Yeah, and if you are like, I was when you never got to the end of that list, you just felt like crap. Like man, it's never gonna end. Well, duh, cause it's never going to end. I really want to emphasize that instead of feeling defeating, if people can look at this, like, "Oh, yeah it's never going to end. So I have to get it all done."

Jen: So freeing. So can you talk a bit about the strength that you explored in yourself to help you get there?

Jennifer: So it's interesting I did the CliftonStrengths Finders Test. I imagine some people listening to this are familiar, but if not it just, it gives you your top strengths. Well, I did it years ago and the funny thing is when I first did it, I didn't like my strengths. This is just so when I about it just makes me laugh. I wanted some really hardcore strengths to be my top five. I mean, what are those?  Right? I don't know, but I ended up with three out of the five--

So the CliftonStrengths they have different categories. I don't know what they all are, but relationship and executing is really high on my list. And I don't know what I really wants. Like Super Badass? I mean that's not a category.  But whatever it was, I didn't have it and then I came around to, "Oh, wait, relationship building is super important in entrepreneurs, anyway, but for a coach!" So then I started really embracing that.

And as I going through this time journey, if you will. it suddenly occurred to me one day out of my top five strengths number three is adaptability. So I'm not wired to be a color-coded time boxed person. My strength is being able to go with the flow. And so having that list that we created and knowing that I move things and come back to things. I think it was a big "Aha!" moment of just realizing how I'm wired.  So instead of fighting against that, just embracing it.

Jen: I absolutely could not love this more because you're basically saying like, there's no one right way to do it. I have to figure out how it works for me. The other thing is when we are entrepreneurs and we go through a struggle like this and we out a that works for us, the good news is we can share that with our clients and I'm sure many of your clients. Those women who wake up every day, they wake up overwhelmed, right? I mean that sucks it's not even like they're getting to 10:15am and their overwhelmed. They're waking up overwhelmed.


Jen: And that sucks.  So then the whole day yawns ahead of them and they know I'm already set up for failure. Like, you just turn that on its head for them. And now there's an option for them. That is huge.

Jennifer: Yeah, thank you. I hadn't thought about it like that, but, yeah, I was thinking not only does she wake up overwhelmed, but I don't know if you've experienced this, but I definitely did. Waking up in the middle of the night and the thoughts are still going. And then you can't even go back to sleep.

So, yes! Totally!

Jen: Especially women of a certain age who aren't sleeping to begin with.

Jennifer: Oh yes! Which we know well. 

Jen: Yeah.  The mind snowball that is. It's like it just gets worse and worse and worse. 

So let's talk about the things in your business that you really got your hands around. I feel like in the time we've been working together we've done two. We're on our third round of the mastermind and it's an amazing group of women who are really supportive of each other and the growth that all of you have had has been incredibly fun to watch for me.

One of the things you really were trying to wrap your head around was making the time for content creation and marketing. And so can you tell me a little bit about what you were struggling with at the beginning of that specific aspect of your business. Yeah, you know what I really think looking back now... And this might sound a little crazy to people who are listening. But I actually think what was happening was I had so much going on in my head about what I didn't have time for that it was taking up all my time. I mean, yes. But really, it was taking up all my energy.

So instead of being productive, I was racing around in my head about all that I had to do. And it's so interesting that you asked the question in the way you did. I was just noticing yesterday. I have things on my plate which we all do. And in the moment I have a few more things that I would like to get done than I normally do. And it's almost like I'm looking for the overwhelm because I could hear it start to kick up yesterday. "I have this, I have this", and then I just took a breath and I was like, "I'm not going there."

And part of that came from, and I'll share this with your listeners as well. Part of it came from long ago. A friend, a really good friend I still have who I met in my coach training said to me that a shift she had made as if she was starting to feel overwhelmed then spinning about it in her head wasn't helpful. And I didn't get it at the time and that's why I really want to share this because people might not get it yet. But maybe they'll hear it later. That spin you think is inevitable, you think that's just how it has to be. But it's not, We get to decide if we're going to keep spinning. Or if we'll stop and do something about it. So that was sort of the early steps of me noticing it, trying not to spin and then dropping into the spin because it takes a while to change it.

Jen: Can I ask you a question about that?

Jennifer: Absolutely,.

Jen: Is there a relief in the overwhelm? Because you know what to expect with? It's like, the devil that, you know, and you're like, "Oh, the thing that I have to do." Let's talk about marketing or creating content.

"I have to be seen. I have to write something. I have to figure out how to say it. I have to publish it. This is so scary."

Like that's a whole plate load of its own crap, right?

Jennifer: Yeah.

Jen: But then there's this other plate load of crap, which is overwhelm. Of those two plate loads of crap the overwhelm is the one you know how to deal with, right?

Jennifer: Right.

Jen: And so part of me wonders is do we sometimes default to something that we already know how to do even though it's uncomfortable rather than pursuing this thing that's going to be hard to kind of chip through.

Jennifer: Totally, I mean, we do that a lot right. We stay in the job we don't love because it's scary to go out. This is kind of the same thing when you think about it. Just sitting there telling yourself over and over, how you can't get things done. You're not as good as so and so because you can't get things done. Like it's just that mind spin which I totally agree with you is a way to stay back from what it is that you want.

You say you want to do, but it's scary and so kind of bringing that full circle that's what I really think that's what was taking up a huge part of my time when I wasn't making the time to market. And the thing is, we all have the same amount of time. We all do. Nobody has more than anybody else.

So figuring out how to best use it and not sitting in those fears and spins and drama and just getting to work makes a big difference, but it's not easy. I don't want anyone to feel bad. 

Jen: No!

Jennifer: It is not easy. It's a process. It's a process to notice where you're at and shift that. So, yeah, I just don't want anyone to feel like...What we talk about here you can't use that to beat yourself up. We won't let you do that.

Jen: We are not speaking from the pulpit we're really speaking from the crowd because we still struggle with this stuff ourselves.

Jennifer: Absolutely.

Jen: We're not here to judge we're actually here. You and I talk all the time about being a few steps ahead of our clients sometimes. So, yeah we're still dealing with it too.

So can you talk a little bit about what do you think the two or three lessons that have been most helpful to you in regard to content creation, marketing, being visible? What have you taken away?

Jennifer:  Oh, wow. Well, I would say one of the biggest things was what you worked on with us about really getting to know our client. Because I can say what I think makes sense, but if that's not how she thinks about it, if that's not how she talks about it she's going to scroll right by it. Which I think you may have even said in very similar words. That I think was the biggest piece of it. And then also the way, for anybody who's watching, the way Jen teaches breaking down content.

Look, if you haven't got the idea from how much I've spoken on this interview I'm a wordy girl and that's how I write. So the other piece about really distilling down to what is the message people need without all the other stuff that has been super helpful.

Jen: You've gotten really foo at that. You've gotten really concise and to the point.

Jennifer: Thank you. Thank you. 

Jen: Yeah, definitely.

Jennifer: It feels a lot better. And then just some of the formulas you've given us for sort of overarching themes and then breaking the material down within that. Just coming up with ways to make things easier for ourselves, too. Because if we're sitting in overwhelmed because we don't want to do it then having a tool that makes it easier helps to get off the overwhelm bus.

Jen: Right, and then having a group to show up to every other week and knowing that you're not the only one I think that is really...

I mean, I have private clients but the group clients that I have, love each other and they show up for each other. So having to be accountable and say, "I'm going to launch this lead magnet" or "I'm going to launch this nurture series of emails" or whatever it is that you guys are launching to be able to post it and get feedback and then to meet each other's growth, I think that is really powerful.

Jennifer: I think that's really powerful. But I also want to say I used to think that I didn't want to do a group business coaching program because I thought I needed all the attention on me or I wasn't going to be able to grow but as you work with each person in the group, I learned something. And then there is that support from the other women. And Jen attracts amazing women. So it's been this very warm just lovely environment. And if you're scared which we all are to be visible to launch having that behind you is super helpful. And then you've got a group of people who are like, "Oh I'll share that for you. I'll put that out there."

So the whole thing has been spectacular. I have enjoyed it so much, thank you.

Jen: Me too. 

One of the things I want to say for people who are considering doing some kind of group program also is you might fear that you can't give everybody enough attention. But like you were saying, Jen, when you coach one person you're really coaching everyone. If you're somebody who's an entrepreneur who wants to make a bigger impact I want to encourage you to think about doing a group program because you can impact so many more people because time, as we started this conversation talking about time, there's only so much time in the day. So if you are thinking I have to be a one to one  practitioner, this actually opens it up for you. Not just for your own business to scale, but the impact that you can have on people.

Jennifer: Yeah, I totally agree, and I also think you've been very conscious about how many people you have in the group and I never feel cheated of time. I never feel like there wasn't enough. It's been really good. And again, I can't say enough about the whole group experience.

Jen: Thank you I'm so glad you're welcome. That just fills me right up.

Now because time management is a big part of entrepreneurship, content creation and marketing is a huge part of entrepreneurship, is there anything else that you'd like to share? You've given us so much great insight already. Is there anything else you'd love to share with us about, you know, advice that you would have for a woman in business who is either at the beginning stages or kind of in the middle of the beginning who really wants to go to the next level.

Jennifer: I think it's going to go back to what we've been talking about already and that's really about the mind drama. I think it's important for women who are just starting to understand that there may be the outlier people who walk into this super confident and are successful right away. But that's not the norm. Most of us walk in, sort of befuddled about "Where do I go next?" and confused. And so getting clear on that, that it's not because there's anything wrong with you.

Think about it like this. I couldn't walk into an accounting firm and sit down at a desk and start working. It just wouldn't work. And yet somehow I expected myself to be an entrepreneur from day one with not very much training. And so I'm offering that it takes time. Be kind to yourself. Watch out for those crappy thoughts which will just hold you back and keep you in your plate of overwhelm. And just there's so many resources out there. Just educate yourself.

Jen: And take your time.

Jennifer: Exactly.

Jen: I find that when a woman comes in, in fear like, "I have to make money right now!" That's the absolute worst thing that she can do. And I know that some of us do come to and we're like, "Shit, we need to make money right now," but it tends to be a longer journey for that woman than the one who's like, really, like you did, like, figuring out what my strengths are. Where do I to supplement those strengths? Understanding that there is a flow and an ebb, of course. And being kind to ourselves about that.

Thank you for all the insights you share, because, I mean, I that you're very willing to be there and go there about the journey. Tell us if somebody listening happens to be struggling with chaos in their life how can they follow you you're very grounding in. I highly recommend you get on Jen's email if she sends beautiful lovely messages that are very uplifting. They're not fluffy either they're not Bullshitty Fluffy. Like they're really helpful tools. So you can either get on her email list or follow her on the social, but I she also might have a freebie for us too, right?

Jennifer: Yeah, thank you for that about my emails. I appreciate that so if you want to get on my list,  is my website and then Instagram and Facebook @jennifersherwoodcoaching. You can find me there.

You know, we were talking about how the women wakes up already in chaos. And I really firmly believe that the way you start your day impacts the rest of your day. And when you say like a morning ritual, people are like, "Oh, God, I have time to meditate for an hour." Right?

So I created three simple morning ritual. They take less than 30 seconds each. So we're talking if you do all three, less than two minutes a day you can start your day from a place and then just see what that does for you for the rest of the day.

So that's what I love to your audience.

Jen:  Oh, thank you. There is this belief that my morning routine has to be like 20 minutes of this and 20 minutes of this and then you have an hour gone before you even start your day. So I this is a great resource for people.

Jennifer: Thank you.

Jen: I also wanted to say Jennifer Sherwood coaching there's nothing hard to spell there it's very it's a great handle. So, for those of you who are starting with your content make sure your audience can find you.

Jennifer: That's great. Thanks, Jen. 

Jen: Very easy to find Jennifer Sherwood Coaching. Jen, thank you so much for your insights. But also your time today and sharing your growth and for all the lovely things you said about the group and the work that you've done I'm so proud of you. I'm so proud of you.

Jennifer: Thank you. And this was absolutely my pleasure. Thanks for giving me the chance to do it. Because obviously it's fun, I enjoy this.

Jen: It is fun. It's totally fun. I always say I wish I could just interview people all day long. That would be my favorite.

I hope you took away a nugget today that you can implement in your life. Please go to  and find Jennifer's downloadable there. I also have the links for you in the comments and I appreciate you showing up and listening to my content. And I  hope that I bring you quality valuable content that you can use in your own life and business, thanks, everybody.


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