How to Know if it's Time to Quit

Sep 26, 2022

Finding the right people to work, especially in the last couple of years, has become very tangled. People have started new businesses, closed businesses, changed jobs, juggled an ever-changing job landscape… and so on. While experts in fields have become more scarce, many entrepreneurs have had businesses explode before they are even ready. And thus, they need help but it has been rather chaotic. The frustration of finding enough good people has become very real. Business owners are finding what they’re seeking for their business is no longer matching what those who are skilled want. So does that mean it’s not going to work? Is it time to hang it up? Or is it time to approach and frame things differently?

“First of all, our clarity in how we design roles is critical… I need people who can think about what to do and they can actually do it... I have to hire strategists that also produce.” – Kris Plachy

What You’ll Learn

  • Where have all the experts gone?
  • Segmented help
  • People who actually know how to execute
  • The need to develop expertise
  • Identify potential

Contact Info and Recommended Resources

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Kris Plachy: In the spirit of talking about change and in recognition of the conversations I have been having with so many women, not just my clients, but just so many women running businesses, how do we know if or when it’s just time to quit? Let’s talk about it.

Welcome, welcome to Leadership is Feminine. First off, I want to let you know that the week of October 10th, I’m going to be running what we’re calling a free pass and this free pass will be five days of live advisement with me, your resident CEO expert advisor. And I want to focus on what I’m referring to as my Leadership is Feminine Formula. I want to really help you learn why, who you are as a woman makes you absolutely perfect to be a leader.

But so few women believe that that’s true, so few women believe that leadership is natural. And I really want to help you see that you can actually be more of who you are, not less. You don’t have to become another version of yourself to be successful. Do you have to grow and expand? Of course, but you already have so much available to you that I believe the world in many ways has taught you to be dismissive of.

And so, we’re going to spend that five-day pass working together live. Every morning, I’m going to teach you a concept and idea that relates to my formula, and then I’m going to have live conversations with the women, the female founders, entrepreneurs on that call.

So, if you are a woman who is running her own business, I am inviting you to join me and I would love to invite you to sign up immediately. It is free. This is an incredible way for you to get support, for you to be involved with and learn from other women who are like you, and to really try it on. Like, is this the kind of experience that will support the next version of your business? Because in order to grow the business, you have to grow the woman running it, right? You know that. So, go to, Register, you’ll get all the information, all the details. I can’t wait to see you there.

So, let’s talk about the heavy, let’s talk about the elephant in the room. I don’t know, I know that it’s been several years, we’ve been going through such a grind for many people. Really, for a lot of women, businesses have grown and expanded quite rapidly, unexpectedly, you know, you haven’t been ready necessarily for the growth.

And now, as a client of mine today, right? We probably, maybe in some ways have plateaued. I want to couple that with some observations in general, that I’m making... Now, these are anecdotal, I’m not making a sweeping statement, I just notice things and share them. But I do think there’s some truth to it. I’m not a social researcher, so I don’t have data.

But if you look at what has happened, just because of the pandemic really systemically to the world, but you know, here in the US is obviously worse, majority of my clients are. We had this moment in time where the world stood still, and then we had so many people, and even still to this day, right? A friend of mine just posted on Facebook that every third day—they’ve started school mid-August and she’s already had to have her daughter out of school.

I think it was like five or six times because she’s been exposed to COVID. And she’s like “For employers who haven’t embraced remote work, how are you functioning? Because I wouldn’t be able to go to work this many times already, because I don’t have childcare,” right?

So, we’re not done. There are a lot of implications to people’s lives right now that we can argue with, but there’s just truth to it. And because of all of the challenges that we’ve gone through, there are less childcare options. We have just a really big systemic kind of web that is I hope going to get untangled. It might get just redesigned, I’m not.

But what happened is the world stood still and a lot of people kept working, but a lot of people left. A lot of people have started their own gigs, their own businesses, their own consulting practices, give it another 36 months, right? There are people who want very much to do that, but they’re really not cut out to be entrepreneurs, they’ll be back in the workforce.

But I was at the bank the other day and I was trying to get a wire done—three wires, actually, and nobody in the bank knew what they were doing. And the truth is this bank that I’ve been going to locally here where I am, every time I go in, it’s an entirely new team and that’s been true for the last several years. And so, I sat there just wanting an expert.

And so many of the women that listen to this podcast, you are experts, right? You are the expert in your field, your industry, your space, your town, your community, your whatever. So, we’d like to work with experts, right? I like to work with someone who knows what they’re doing, and that’s what I hope to offer to my client. I know what I’m doing.

I really do believe this. I would not say I really believe. There is nothing a client will bring to a call, ever, that I won’t be able to help them figure out how to solve. Doesn’t mean I’m going to know the answer, but I’m going to know how to help them solve it. And I just want that too. Don’t we all just want that? We want experts, but what I realize sitting there in the bank is, we’re kind of right now surrounded by a lot of novices. There’s a lot of new people in the workforce, and that’s okay, that’s how it works, that’s part of growth, that’s part of life. We’ve had some change. A lot of the experts are no longer in the big companies, they’ve gone off and done their own thing or they’re done, they just are done.

And so, we’re all sort of navigating a world right now that is missing that. And then, we also have a lot of people who—like the more expertise someone has, the more people question them, have you noticed that? Don’t we trust people with experience anymore? Or are we just now going to make that be like a disadvantage to be experienced? I don’t get it. But nonetheless, we have a lot of amateurs.

And so, as a hiring manager, somebody who’s running a company, that’s a lot of what you’re looking at. The people that you would want to hire don’t want to work in a company anymore. They want to be a contractor, they want to have their own gig, they want to have four clients, not just one. They only want to work these many hours; they only can work these days. And we’re in a buyer’s market, is that the way you say that? The employees get to sort of decide right now because there’s not enough.

And so, what’s happening—and these are the conversations that I’m having with friends, colleagues, and clients because I hang out with female entrepreneurs in every part of my life. Good heavens, everybody’s frustrated. We can’t find people. This lack of support for so many people is painful, and it’s nobody’s fault.

It’s not the fault of the people who you do work with, who are amazing because I know we all would say we have great people on our teams, but we don’t have enough, but finding good people right now is challenging, and I don’t know that it’s because they’re not available, I think it’s because there’s a finite amount of experts and what you are looking for is not what they’re looking for.

I just had a client who had to go through that with someone on her team. She needed someone for this kind of coverage and the person was like, “Yeah, I can’t do that even though I said, I could do that.” So, they sort of had to agree that there are at an impasse, like, “Okay, well, I can’t keep you if you can’t meet the expectations of the position. And that doesn’t mean I don’t think you’re amazing, but it’s not going to work,” right?

So, I’ve had a lot of conversations with people who are like, “Is this worth it? What are we doing? When is it time to quit?” Do you quit because you can’t find people? Do you let that be a reason?” Now, of course, my answer is no, even when I have to have that conversation with myself, which I will tell you, I do. I’m frustrated, I’m very frustrated, but I’m also not hopeless and I’m also not helpless, but I have moments where I’m like, “I mean seriously, can we just get someone who’s an expert?” And wants to see the whole pieces and parts.

I think honestly, the part of being an entrepreneur that I’m realizing, that is different, big time different, than being in a corporation. And I’m 10 years into my own business, and I remember having this distinct experience when I was trying to hire an executive admin. This was years ago. And everybody I would talk to or even bring like, and try and work with, they were all supporting other people too, and they all wanted me to fit my business around their systems.

And it was so foreign to me because as a leader in a company, right? You hire people and they learn how we do it, and they do it that way. But in the gig kind of world and the contract kind of world, that’s not how that works. You have to do it their way, or at least they think you do. And that’s never worked for me because I know how I want to run my company and I have proven experience, so I’m not a novice.

And we’re watching that then so much of the support we need is overly segmented. Like I’m really good at this, she’s really good at that, he can really do this, she can really do that. So, then I’ve ended up with seven people to do what normally was one job. Are you guys finding this? Am I losing my mind? So, I’m finding there are massive amounts of very finite limited experts in a little space, but they can’t do anything like that over here, right?

It’s like, I was talking to my Facebook ads gal who I assume is amazing, I love her. She doesn’t know how to do YouTube ads, right? She hasn’t learned it yet, which is fine, that’s her business, it’s her company. But I told her, I’m like, “Could you please learn how to do YouTube?” I need someone who understands and could do ads, not just this ad, right?

That’s a very basic example and I am not disparaging her because she’s incredibly talented, but that to me is a great example. It’s like someone who says, “Well, I know how to type emails, but I don’t know how to write letters. Like, I need someone who can create written communication. I know how to make landing pages, but I don’t know how to write sales emails. I know how to balance this kind of transaction, but I don’t know how to do those parts of the books.” And I think I sound old, I think I’m going to sound old, but I’m going to say it.

In the olden days, you had to learn all of it. If I’m going to be an expert in sales, I have to understand sales, and then there are channels that drive sales. I need an expert who understands the sales process, not just how to do a sales call, not just someone who knows how to post on social media. I need somebody who understands a digital media strategy and oh, by the way, can perform one. Isn’t just going to talk to me about what needs to be done, but can actually do what needs to be done. I don’t know, we’ll see how this one lands for y’all. You’ll have to tell me because you’re either going to say get over yourself, Plachy, or you are going to listen to this and be like, “Hell yes! Preach!” right?

And so, you think you’ve found someone to bring into your company, hire them as a full-time employee to oversee marketing, but really all they know is how to talk about marketing, they don’t actually know how to do marketing. Maybe you hire someone to sell for you, and they really know how to talk about selling and they know how to talk to customers, but they don’t know how to get them. You following me?

And I guess again, I feel like I sound old, but I used to work in sales, I had to know how to do all of it. I had to know how to make outbound calls, I had to know how to take inbound calls, I had to know how to sell through email, I had to know how to book business development meetings, I had to know how to run a business development meeting, I had to know how to do cold calling, I had to know how to generate referrals. It was a discipline sales.

Now, there’s 12 disciplines within a discipline, and you can get really good at one and you can sell that. “Hey, come learn. I know how to do this.” And you think you’re hiring an employee who understands sales, but really all they understand is this part, script writing. They don’t know how to actually use the script.

Operations management, same issue, right? We have people who…I have an office manager, she understands operations, she knows every part of operations. Is she great at all of them? No, nobody is. But she gets how they all go together. So, when we’re talking about putting something together, her brain is like, “Oh,” she sees all the pieces and parts. Now, does she need to do them all? Sometimes because we don’t have enough people, because we can only find people who know how to do the pinky size version of it.

So, into a certain degree I’m venting, you know that, right? But I hope you feel me. But I do believe I’m not hopeless, I really am not because I…But I think the answer is- first of all, our clarity in how we design roles is critical. We have to know what we want. And so, I’ve started really adding the language. I need a strategist producer. I need people who can think about what to do and they can actually do it. Now I’m a small business, so that’s the kind of business I have to have. I don’t have capacity for a team of strategists, and a team of executioners.

That’s funny. I don’t have the bandwidth for that, I don’t have the resources for that. I have to hire strategists who also produce and I think for other businesses like mine, that’s where a lot of us are running into trouble. And that’s not even including all of the other problems that people are having right now in their lives that are preventing them from being as available as they used to be, to take on those kinds of roles.

So as the business owner, my first responsibility is clarity. I have to be honest and clear about what I’m looking for and I have to watch that shiny object thing where I’m like, “Oh! this person’s got so much great experience and they’ve done all this great stuff, but have they?” So now, anybody that we hire, you have to actually demonstrate skill set. I can’t take you at your word, not because I think you’re not telling the truth, but because I need to make sure that your version of what it means to do marketing is the same version of what I think it means to do marketing, or whatever it is.

The second thing is recognizing that in many cases, if it’s your jam, if it’s your wheelhouse, if you’re the accounting guru or if you are the doctor and you’re exceptional, or you are the florist and you’re exceptional, or you are the retail founder of a really cool brand and you are the expert, there is more requirement of us right now to develop expertise.

And so then, what we need to do is hire for attitude, for value alignment, for initiative, for problem solving, all the parts and pieces that are not up to you to teach. But if they don’t quite understand all the facets of something, you might need to hire those people who are really, really eager and really, really invested, but they just need a little more development.

We might have to start to think a little bit about apprenticeships, internships because we have a lot of really, really intelligent, bright talent in the world, but they don’t have the breadth and depth of experience that I know a lot of us wish we could find. Big breath for me. Because otherwise what’s your solution? Otherwise, your solution is to not have support. It’s to be overworking and doing things that you really shouldn’t be doing anymore because you’re not very good at them, and you make mistakes at them and you get in the way.

And for a lot of those women, you feel frustrated, you start to resent your business, you start to resent employees, you start to be mad, and I don’t want that for you, and I know you don’t want that. So, we’re not going to be hopeless and we’re not going to feel helpless, but we are going to make sure that we’re getting way more clear, you’ve got to do it, you’ve got to take a minute—if there’s parts of your business that are not thriving at the level that you would like them to be thriving, the first place you have to start is with yourself. Have I been clear?

Where am I making assumptions? That are interfering with the ability of that person, that team, that part of my business, or for me to get results that I want. Where is that happening? And do I have people on the team who are incredibly eager, incredibly excited, incredibly committed, who have the capacity and the ability to grow, to change and accept new responsibilities and skill.

And I guess I would throw one other thing in there. If you really, really want that expert at that high level, then we have to evaluate, are we willing to pay for it? Because in most cases you can find those experts, but it has to be worth it to them too, right? So hopefully, I’ve given you a little something to think about. Like I said, this might be one that you’re like, “Oh no, Plachy” or you’re like, ding, ding, ding.

So, don’t forget. Go to let’s get you signed up for the five-day free pass that we’re doing because I’m super excited about that, and it’ll be an awesome opportunity for us to work on real issues that you’re really facing as a woman running her own business. Thanks for tuning in today.

Hey, entrepreneur, you started that gorgeous business of yours to do some real good in the world. You probably didn’t start your business to manage people, but here you are, having to figure out how to manage people to get work done, and maybe it’s not going so well. So, head on over to and let’s talk about how we can help you learn how to lead, manage, hire, fire, and all the things so that you can build a team that expands on your amazing dream.

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