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5 ways women entrepreneurs can leave employee mindsets behind Episode 28 She Breaks The Mold podcast at

FIVE Ways For Women Entrepreneurs To Leave Employee Mindsets Behind

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If you’re an entrepreneur or self-employed woman who was once employed by someone else, this episode is for you!

You may not even realize it, but you might be bringing old employee habits and mindsets to your work and they could be holding you back from achieving everything you dream of in your business.

Think about the last time you said out loud, “I’m really good at (insert skill or ability here)” or “I so wish I was better at (skill you think you suck at)”. Whose voice is saying those words? I’ll bet you anything it a hangover voice – the voice of an old boss or coworker – that convinced you of your value a long time ago.

The great news is, those voices are probably wrong about you in your new job, your new reality. And you can learn to silence those voices and listen to new ones – your own or even those of your satisfied customers! They are the only ones that matter in your new role as CEO/President/Boss of your business.

In this episode you’ll learn FIVE ways to recognize old employee mindsets that are clanking around in your mind, and what to replace them with.

And, I have a FREE worksheet for you so you can start this work right away. Click below to get started once you’ve listened to this episode:

Listen to Episode #28 now:

Episode #28 Transcript:

How to shift from Employee to Boss mindset in your business

This is the start of a series of episodes on mindsets that can be unhelpful or even dangerous to us as women entrepreneurs. In future episodes, we’ll talk about success mindsets, giving vs receiving, and the mama of all the problematic mindsets for self employed women (in my opinion anyway)…money. And since our mindsets help to create our habits, we have a hard time changing those habits, or behaviours, until we can identify the mindset or perspective that’s driving them. Of course, I’m not trying to suggest only women have these issues – far from it. But since I work with women, I’m pulling out some of the most common mindset related issues I see with clients or in conversations with self-employed friends and sharing them here. Every single one of these issues might pertain to you, or maybe only 1 or 2 do. In any case, I hope this episode will help you start seeing your role in your own business differently

All of this coming up in future weeks. Today’s episode is for my listeners who started their business maybe even years into their careers…following significant time being employees. And if that’s you, I’ll ask you to think back to when you started your business. How did you approach or think about your own role in that business? How much work did you do to decide what kind of entrepreneur, leader or boss you wanted to be? Maybe you started with the idea that you would bring your strengths from your past jobs and package them all together to create a base to move forward with. And there’s a lot to be said for that. Certainly, it’s a lot harder to start a business with no experience to fall back on or help you prevent mistakes so to use your strengths and experience is a really great idea – not required, but certainly helpful.

But it can become a little problematic if relying on your old skills as an employee becomes your go-to habit as a CEO or leader in your own business. It’s not your fault and it doesn’t mean you can’t become successful as a self-employed person. It just means you might have to adjust some of the habits you’ve built up around how you think about yourself and your business.

So today we’re going to talk about FIVE ways to drop your old employee mindset and embrace a new one as a boss, owner, self-starter and leader.


Examine how you personally create value in your role as a business owner. In the past, if you were an employee, you got paid for coming to work, executing on your plan (and possibly hitting certain key performance indicators – or KPI’s), showing initiative etc. But unless you were commission based, you could have created massive value for your organization and your salary would NOT have reflected that. Frustrating, to be sure because unless you had an impressive boss who felt it was important to reward that kind of result, you might start to learn that it doesn’t pay to perform. This can either breed mediocrity, or compel other people to overwork because they don’t know where the line is between achieving and burning out. Their compensation is not in line with their output.

Add to that, many employed people derive a sense of security from the idea that someone else is responsible for paying their salary every two weeks and they know exactly what they have to continue doing to earn that salary. This can tend to divorce your sense of your own success from your role because all the work you’re doing seems to have no effect on you personally. But as an entrepreneur, the value you create can be in direct proportion to the money you can earn. And so it’s actually limitless. It becomes clear really quickly that your success is directly tied to the amount of value you create and deliver to your customers or clients. Notice I said the value you create, not how hard you work…there’s a big difference! And this can be both freeing and overwhelming as you learn that true security comes not from being looked after, but from the ability to take care of every single step that creating value in your business requires. There are all kinds of activities in your business that aren’t really revenue generating but that you’ll view as necessary because some expert or guru told you it was. But once you have a handle on the actions that create value for your customers and the impact to your bottom line when that happens, you see very clearly the levers to pull to be more successful, and the actions that can be delegated or even left for another time. But this requires you to leave some old ideas around what to focus on, on the sidelines.

Second way to drop old, employee mindsets:

Start seeing mistakes or failure as information instead of as direct evidence of how much you’re screwing up or how badly you’re doing your job. The only feedback that matters now is your customer’s. There are no annual performance reviews, no justifcations necessary for missed targets, and no bosses to confirm for you what your strengths and weaknesses are. You’ll see the direct results of your action or inaction in your revenue. If you can learn to see the actions that result in lower revenue as feedback…or as something that simply didn’t work and figure out why not, you can learn how to try different things that will work and do more of those. This includes negative feedback you’ve received from previous bosses you’re not strong in one area or another. And so you believe you’re probably just better at something else. These pieces of feedback tend to stick with us and negative feedback in particular stays with us the longest. And so we create stories in our minds, using what we’ve been told to decide how to believe about ourselves…what those comments actually MEAN about us….to say this is what I’m good at/this is what I’m bad at.

I want you to consider whether or not you’ve only checked in on those strengths and weaknesses as they pertained to your previous job as an employee. And so your strengths and weaknesses as a business owner, leader and boss might be (and probably ARE completely different) and are things you’ve learned by just doing and trying that are showing you along the way that maybe you’re better at these things than your previous bosses ever got the opportunity to see. OR maybe that particular skill was seen as a weakness when you were an employee – like not being great at following instructions because you had a mind of your own and like to try unique ways of approaching a problem. Obviously, that’s a behavior that might cause problems in a team where you’re a player, but not necessarily a leader. But this could actually be a point of strength for someone running their own business.

It can also be really tempting to use these beliefs (either I’m really great at this thing, or really terrible at that thing) as a crutch or a way to hide from the work you really should be doing, or that you should be delegating to someone else. Because this work is easy for you to execute on, or completing those tasks feels like you’re ticking off boxes and getting shit done….even though it may not be moving your business forward at all. Maybe you’re not comfortable with having a tough conversation with an employee that desperately needs to be had, so you hide behind cleaning the office kitchen because you’re tired of looking at the mess or waiting for someone else to take the initiative. Or, you lose yourself in creating social media stories because you don’t want to face that financial shortfall you suspect is coming later this month. After all, you’ve always been told numbers aren’t your strength, right?

I want to pause  for a sec before moving onto number 3 to acknowledge that I see you! I see you and I AM you! You aren’t alone in these beliefs, in fact I would say it’s one of the most common things I see holding women back when they start out in their own businesses. Tara Mohr, coach and author of a book I highly recommend called “Playing Big” calls this being hooked on praise and/or criticism….something that women tend to suffer from more than men. Many of us desperately want the positive feedback we’ve been taught all through our school careers means we’re doing a good job, and do everything we can to avoid being criticized because as girls, we haven’t been allowed or encouraged to fail or get dirty. And we somehow believe that the mistakes we make are tattooed to our physical bodies, that everyone else will always know about them, and they’re evidence that we’re going to fail in the future too. Anyone else feel me on this? Read the book….it’s excellent, and this chapter in particular will sing to you if resonated with what I’ve just said.

Third way to drop our old employee mindsets:

As an entrepreneur or self-employed person, until you have a team of employees, you really have no one to rely upon but yourself. In your previous career as an employed person, you probably learned to stay in your lane, not step on another employee’s toes, and just do your job…the one in your job description. The problem with that mindset for entrepreneurs is that your new role requires you to be abundantly resourceful – particularly at first when you just can’t afford to hire out all the work that needs to be done. You’ll need to be a Jill of all trades, and will probably quickly start to feel like a master of none. And you’re so used to excelling within the limited scope of your other roles, that this new reality feels really uncomfortable. Or like you’re spending all your time on activities you don’t like. And lets face it – this sucks! Because aren’t you doing this so you can either follow your passion, do work you love or at least set your own schedule?

I do believe we need to grow to a place where this kind of unsatisfying work can be delegated or outsourced (you’ll see why in mindset shift #4). There’s only so much time in the day, after all. BUT…I also believe that in the early days, there’s so much value in learning to do all the jobs in your business so that you know how to fix them when they break. And even if you don’t know how to fix them, you’ll know how to evaluate the work of the person you hired to fix it! Creating your own website is a great example of this. I’ve spent a lot of time building websites over the years for my two businesses and the various blogs I’ve written. And I’m not going to lie – it was a slog. It was frustrating. And the truth is, the next time I create a site, I’ll probably get some professional help to do so, because hey – time is money. But I consider that time (before I was making money) learning my limited knowledge of html and WordPress to be incredibly valuable. When my website was hacked recently, I knew what to do to get it back online and the questions to ask to prevent it from happening again. And I can make changes to my site on the fly without having to wait for a programmer’s time to become available. I’ve learned a little about the accounting software I use….the design software I use to create freebies and workbooks….enough not to be an expert, but to evaluate offers from other experts and to do small jobs on my own quickly.

All of this leads to the FOURTH way we can drop our employee mindsets:

And that’s getting stuck in execution mode. This is tricky, especially since I’ve just told you to learn to be resourceful and figure things out on your own. I don’t, by any means, suggest that you continue to everything yourself, forever in your business. That will totally prevent you from taking this next step – One of Steven Covey’s Seven Habits of highly effective people is Start with the End in Mind – or start the way you want to finish. But you can do this high level thinking while you’re building the business – the point is, don’t wait to start thinking this way for sometime in the future. Start thinking like a CEO now – think about what the important leadership functions in your business are – those roles that only you can do, like developing the right strategy, hiring and growing a strong, cohesive and collaborative team, managing the finances of the business and deciding what kind of business model you’re trying to create. Your job is different as boss…CEO…leader…than it was as employee. You have to start looking at the skills you need to do this job in a new way and maybe even seek out the right training or assistance to help you get there. Here’s an example, and it’s something I hear a fair bit: It’s a big shift to go from “I’ve always been told I’m great at design and have a great eye so I like to spend a lot of time on the marketing materials and social media visuals in my business” to “I can use the skills and vision I’ve developed over the years to evaluate the work of others really quickly and efficiently and make fast decisions about how to best promote my business now.” Getting stuck working on executional details that don’t connect in a straight line to growth or revenue isn’t really the job of a business leader. And we often start using these activities as crutches to avoid the harder, newer, more unfamiliar jobs we haven’t yet been trained for and that seem scary.

If you start out doing business the way you ideally want it to be run in the future, you’re already part way there. Why start with processes, mindsets or actions you’ll just have to change eventually when you can start with your goals in mind on day 1? Well, because it’s easier. We do this because we don’t think we have time to strategize, don’t have time to determine our specific niche, the WHY of our businesses or what we want to build for the future. And so, we continue to stay stuck in executional details, working in our business instead of on our business. But you get to create your own goals, timelines and structures. So make sure you’re building them to support the business you want down the road. You’re already doing the hard work to build it….it might as well work for you from the outset. Take the time early – it’s important and you’ll thank yourself for doing it. Promise.

And finally – mindset shift #Five:

Waiting for permission to start. This one is probably self-explanatory, although so many of us continue to do it. No one is coming to save us, my fellow amazing women bosses. It’s all up to us. Which includes the day you start, the way you start and the decisions you make along the way. It can feel scary and lonely to be out here on the tightrope by yourself, but also completely exhilarating. There’s never been a better time to start a business. The internet and social media have killed almost all the gatekeepers who told you this life and this work isn’t for you. But somewhere along the way, you might have forgotten to let yourself in on the secret that it’s all completely up to you. And so you wait for the perfect timing, the perfect idea, the perfect solution to offer to your customers – or for them to tell you when they’re ready to buy. Meanwhile, someone else started early, quite possibly with an inferior product, but they were there and available and you were stuck waiting for perfection and permission to start. I will admit I struggle with this one personally – a LOT. I’m learning to hear myself when I say things like “I wish I could build this/offer this great program/design that cool product…” and then to ask myself why I can’t? What am I wishing for? And who is this magic fairy who’s going to grant me my wish? It’s all up to me. And to circle back to Step 2, if it “fails”, I have tons of new information about why my potential customers really want so I can build something better next time.

I see this in facebook groups and on forums all the time. Entrepreneurs who want to hand over decision making to a guru because they paid for their course, so that means they need to listen to them and get their blessing on every step they take. But you don’t! By all means be inspired, learn from others’ mistakes and successes where possible but lose the idea that someone else knows how to create value for YOUR customers better than you do, just because they’ve done it for their own – this is actually reverting back to behaving like an employee. You can make the best decisions for your business.

You are the person you, and your ideal customers, have been waiting for. And you no longer have an overbearing boss to tell you your idea doesn’t fit into the plan for this year.  One of the most inspiring things I hear on other entrepreneur’s podcasts and in their writing is that they spent a ton of time creating a plan that they thought would work, until they realized the feedback from their customers said they needed something entirely different. As entrepreneurs, we have the ability to change our model, or our offerings (especially for service based businesses) and our timing to suit that customer need. Their ask is the only thing that matters. We don’t need anyone else’s permission to toss out the original plan and move forward with a new one that will work even better. If you still feel like you do? Time to look in the mirror my friend. Why are you still waiting?

OK…so I’ve mentioned several ways to think differently about being a boss, but there are also a few constructive things you can do to start overcoming the employee mindset and getting clarity about the truth of our own strengths and weaknesses as a self-employed woman

One of the ways I do this with my clients, is to take them through a personal SWOT analysis. For anyone who doesn’t know what I mean by that, SWOT stands for strengths, weaknesses, opportunities and threats. But instead of doing this for your business, we analyze your personal characteristics. You may have done this already for your business if you’ve done the work of building a business plan (which I hope you have and highly recommend). For yourself as a leader and as a person, it’s great to check in honestly and with a new lens on some things you might be good at but have never thought about or been told you’re good at but you don’t really believe yet. Or you never analyzed how some of the weaknesses you believe you have (maybe they showed up on an old performance review?) could actually be strengths in the process of building your business.

If you’d like to try this on your own, I have a FREE worksheet available for you on my website at (You can go there directly or find the link in the shownotes for this episode). Download that PDF and do this exercise yourself to see where you need to lean into your strengths a little more, what perceived “weaknesses” might not even be weaknesses in your self-employed world, and what opportunities can you see in yourself now that you’ve really analyzed all of this with a new perspective.

Any moms listening will get this, but it’s similar to acknowledging that some of the really annoying habits your kids have – like not listening to you, being really stubborn and headstrong, seemingly having to learn everything the hard way (which is really courageous when you think about it), will probably be strengths for them as adults and they’re not behaviours you want to totally discourage! You have to start looking at your own behaviour through that kind of lens – what is actually serving you, and by the same token, what were you getting praise for as an employee that is no longer serving you as a business owner.

The second part of this is writing a job description for your own role as leader, President, CEO or however you refer to yourself, in your business. This will help you to see yourself and your role in a whole new light. In the spirit of starting the way you want to finish, define your role now. And keep checking back with your definition as your business grows and as your role changes so you’re not sliding back into this co-worker or employee mindset. If you have employees, this is so important. Figure out what kind of leader you want to be…what the WHY of your business is, and how your role supports that. If you’re a true CEO with employees, and possibly a board of directors, you probably want to see yourself as leading strategy, finances and people. And of course there are all kinds of roles that fall under those categories that you’ll be responsible for. But it’s likely that a lot of the busy work you’re doing day to day should instead fall within the job descriptions of your employees as you grow into the more expansive leadership role in your business. OR, they’re activities that can be done more cost effectively by a freelancer who excels and specializes in that kind of work.

The point is, take the time to truly evaluate the strengths and weaknesses you bring to your current role, and stop relying on the opinions of past critics or supporters back when you were doing an entirely different job. Do this analysis with an honest, open mind and heart because not being true to yourself could be worse than not looking at these issues in the first place. Enlist the help of trusted people in your circle who know your current job AND your abilities well enough to provide constructive acknowledgement or feedback. Or hire a business coach whose job it is to help you identify your blind spots and move past them. Many of my clients, if they were here right now, would tell you we spend a good amount of time on this kind of work, AND that it’s some of the most important work they do.

Mindset truly is everything. You can overcome so much, see barriers that were previously invisible, gain new perspectives on what you thought was going to hold you back, and build your business from a new perspective of strength and possibility when you are honest with yourself about unhelpful mindsets like these.

Do yourself a favour….download the worksheet at and let me know if it helps you. If you have questions, or even suggestions about what’s worked for you, email me at or reach out on social media. I’m @beambitiousforher on pretty much all the platforms, and I would love to talk more with you about this!

As always, thank you for joining me for this episode of the She Breaks The Mold podcast. I’ll be back more regularly from now on…hoping for no more unplanned breaks! If you’d like to be notified of new episodes as soon as they’re posted, subscribe on Apple podcasts – or wherever you listen to podcasts – or go to and you’ll receive updates straight to your inbox.

Have a wonderful day, ambitious bosses!

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