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What Is Your Definition of Success?

by | Last updated: Apr 14, 2022 | Podcast

What does it mean to have success on your terms? For many, it looks like being your own boss, on your own schedule, and making as much money as you want. Then you see the success of entrepreneurial influencers online, start to feel like you’re doing things wrong, and try to change the way you operate, only to realize you’ve just created another 9-to-5 job for yourself.

To help you discover your own definition of success, I’ve created a workbook covering five areas of life. In this episode, I walk you through this workbook so you can transform life and business to align with your real desires in 2022.

On this episode of Promote Yourself to CEO:

3:15 – I remember when I started realizing that our definition of success as women entrepreneurs had massively changed.

6:22 – Why can you still feel disappointed when you hit a revenue goal? Having clarity on your definition of success gives you a decision-making filter.

8:02 – What does your ideal regular day look like for you? I walk you through the first part of the workbook I’ve created.

13:19 – Keep these questions in mind as you think about your relationships with family and friends.

17:35 – This is an area where I often put myself last, especially when I’m feeling stressed. It goes back to when I was a teenager.

22:44 – Discover the biggest benefit of having creative outlets outside of your business and how I avoid the temptation to turn every hobby into a business.

26:16 – Fulfilling your definition of success in this area will have you feeling more empowered and grounded in your life and business.

29:23 – To wrap up the episode, I quickly recap the five areas you want to think about to define your success.

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Racheal Cook: When I talk to many women entrepreneurs about why they started their business, they tell me, “Racheal, I started my business because I wanted to create success on my terms.” When we drill down a little bit into what that actually means, when we start, we have this vision of success meaning owning our own schedule, being the boss, calling the shots, being able to make as much money, as much income as you want so that you can have real financial security and financial independence. But something happens along the way to a lot of us. We find ourselves looking at all of the celebrity entrepreneurs in our space and it starts to feel like the only way to have a successful business is to do things everyone else's way. It just becomes another version of the traditional nine to five success trap of climbing that corporate ladder where instead of doing the nine to five to climb that corporate ladder for the corner office, now we're working 24/7 in order to have the beachfront property and the fleet of Teslas. What is going on? In this episode, I want to bring us back to our own definition of success, whatever that actually looks like for you so that when we look ahead to 2022, we can make sure that our business is aligned with our actual desire and real definition of success.

Are you ready to grow from solopreneur to CEO? You're in the right place. I'm your host, Racheal Cook. I've spent the last decade helping women entrepreneurs start and scale service-based businesses. If you're serious about building a sustainable business, it's time to put the strategy, systems, and support in place to make it happen. Join me each week for candid conversations about stepping into your role as CEO, the hard lessons learned along the way, and practical profitable strategies to grow a sustainable business without the hustle and burnout.

Hey there, CEOs, I wanted to have this conversation with you today because you might be experiencing the same things that I have, and having the same conflicting feelings as I have had, looking at what success is supposed to mean for us. Like most children of the 80s and 90s, I'm right there as either a late Gen X or elder millennial. I was raised with the generation girls who were told that we could grow up to have it all. We could go to college, we could break through the glass ceilings in corporate America and go to that corner office. We could bring home the bacon and fry it up in the pan. We could achieve anything, so we did. More women than ever before are graduating college, scooping up master's degrees, and becoming doctors, lawyers, and professionals. We have incredible women in powerful positions sharing how we can lean in to become leaders, executives, and CEOs in our industries. Despite all of the progress that we have made in the workplace over the last few decades, it's still not enough. We're still struggling to close the wage gap. We're still fighting for our rights to paid maternity leave. And women are massively underrepresented as CEOs, executives, and leaders in every single industry. This explains why more and more women are breaking free from this old paradigm of success, climbing the corporate ladder to find their own path through entrepreneurship. After all, if the rules of the game aren't working, isn't it just time to change the rules?

I started realizing what was going on here and how the definition of success has massively changed in 2014 because I was invited to speak in the U.S. Chamber of Commerce Center for Women in Business in Washington, DC. It was absolutely incredible to be speaking in this ballroom in front of hundreds of amazing women. Afterwards, I spent nearly two hours with women grabbing me just as I was trying to leave the room. They wanted to talk with me about creating their own version of success. I realized after my talk that these amazing women entrepreneurs from around the world had gotten caught up in the only measure of success that we tend to focus on, the dollar, dollar bills, the revenue level.

While over 88% of women entrepreneurs never break the six-figure mark in their business—and this is something we really have to address if we're going to talk about true financial security, and success for women business owners—the honest truth is money is only one metric of success. Don't get me wrong here. A profitable business is an absolute must for long-term success. Unless you are having an expensive hobby, your business needs to do more than just barely pay the bills. But when we're only focused on the money, instead of creating a business that loves us back, a business that we adore waking up for on Monday morning, we find ourselves in this relationship with our business that is so unhealthy. Our business is demanding 100% of our time, of our energy, of our mental bandwidth, leaving us with zero time or energy to actually enjoy our life. Too many entrepreneurs are finding themselves in this place where they are on their fast track to burnout. Too often, research is showing 80% of new businesses crash and burn within the first few years. How can we better set ourselves up for long-term success, for sustainable success other than a dollar figure? What if we looked at what we really wanted in our lives and in our business?

You have to define what success truly means to you. I have found over and over again that many of us haven't stopped to truly define our version of success. We tend to default to whatever we were conditioned with. When we don't spend the time to answer this crucial question when we're going out there to plan the year ahead, when we're setting these big goals for our business, we still find ourselves disappointed when we hit that revenue goal but we realized that it didn't allow us the freedom or the lifestyle or the relationships we thought we would have as entrepreneurs. We didn't leave the nine to five work 24/7. We don't want to be over working for our business at the expense of everything else in our life. This is so crucially important, that's why I wanted to release this episode before we officially kick off the Plan Your Best Year Ever Challenge, coming up next week in November. Hint, hint, if you haven't signed up for it, I encourage you to go sign up for it now at, because we find that when we have clarity here. When we have clarity around your definition of success, you have a filter for decision making. You're more quickly able to assess if an opportunity is a shiny object or a gold mine. It helps you to make space for what matters in your life and becomes a tool that you can use to strategically plan your business trajectory.

I've created a workbook for you. I want to walk you through multiple parts of this workbook to ask you some important questions. If you want the workbook, head over to the show notes, but these questions I find if we don't answer them early on in our business or as we're going through major growth times in our business, we get distracted by things that might seem like they are important but are actually pulling us off track and out of alignment with what is actually deeply most important to ourselves. Go grab the Definition of Success workbook from the show notes and let's walk through some of these sections together.

The first part I want you to think about is your life and your desired lifestyle. Now, this might sound so backwards. I know so often when you sit down to do business related planning, we tend to not think about how our life is a part of it at all, but this is such a huge value for us at The CEO Collective. It is on our list of values, this is the first one that comes up, is life before business. That's because I found over and over again, if you don't make space for what matters most in your life, you will struggle to find space at all. If you've ever found yourself struggling to find an hour to yourself every day, then we need to press pause and re-evaluate. We need to re-evaluate how we can have it all. I want you to ask yourself, if you were to plan an ideal regular day, what would that look like for you? What does a regular day in your life look like? If you are living your best life, your best highest most successful version of your life, what does it look like? You can break the “rules” on how this is going to look like.

I know I had a really hard time breaking free from the idea that I needed to be at my desk by nine o'clock and not leave until five o'clock but I found that I actually love having a really slow early morning. I love having time in the morning between waking up and sitting down at my desk to take care of myself. That is my personal self-care time. Then I like to show up at my office around ten o'clock, work until about two o'clock, then I check out for the day, head home, and enjoy time with my family. What does an ideal regular day look like for you from the time you wake up until the time you go to sleep? Then if you were to extrapolate that across an entire week, are there any other things you want to be making time for through that week? Maybe you want to make sure that you're having quality time with your partner, going on a date night or having an inside date night since some of us are still in lockdown, maybe you want to have one-on-one time with your kids, maybe there's other relationships that are important. Is there anything else that you want to make space for? Is there a class you love showing up for? Is there something you want to do just for yourself once a week?

How much time do you actually want to spend working? I think this is one of the hardest things for us to de-program if everyone in the US, Canada, we have this Puritan work ethic that tells us we have to work so many hours in order to deserve rest, but the truth is you deserve rest regardless of how much you work. Rest is a right. You want to be thinking how much time do you want to spend working where you're spending just enough time working. Enough time to get the results that you want but not so much that you are burning yourself out or sacrificing any time in your life. What are your top three lifestyle non-negotiables? What are the things you must have in order to feel happy, fulfilled, and in alignment? These non-negotiables can be incredibly, incredibly simple. They could be my lifestyle non-negotiable is having my quiet morning routine and not having to get to the office until 10 o'clock. It could be saying, “I have nothing on my calendar past six o'clock. I don't say yes to anything past six o'clock. That's my time.” It might be that I need to make sure my living space is set up in a way that feels warm, inviting, and cozy to me. Here's what that looks like.”

Then I want you to think about if you could upgrade three things in your current lifestyle in the next 90 days, what would you upgrade? These could be so simple. It could be restructuring your calendar so that you have more time for yourself. It could be planning to go on a solo vacation. I know I have one booked this coming weekend where I'm going to have three days in a hotel room all by myself. That is a huge upgrade for me. What are some things that you would like to upgrade in your lifestyle that will make you feel like you are taking amazing care of yourself, like you are living your absolute best life?

Once you've answered some of these questions, I want you to also think about the next section here, which is family and friends. I find that women are relationship-connection driven. Relationships are so important to us but sometimes, we get wrapped up in our business, then we struggle with quality time or we struggle with boundaries with our family, our friends, and our loved ones. What do you want your relationships to look like with your family and friends? Who are your most important relationships in your life right now? Who are the people that you want to connect with the most? This could be your children, this could be your partner, this could be your best friend, this could be your sister. Who are those people for you? How often do you want to have quality time with those people in your life? This is going to vary by person. I want to have quality time with my kids every single day in some way but as much as I love my mom, I really only need to see her once or twice a month, then I have to ask myself, what does quality time with these people look like for me?

Quality time with your kids could be—this is one thing I love to do—I give them each a date with me. They get a couple hours, we go out, and go somewhere they want to go. Usually, they like to go to the bookstore or the library. We're big readers. We'll go get a Starbucks and a cookie, and have some one-on-one time with them. They love that. How often do you want to have that quality time and how often do you want to have a date night or a getaway with your partner? I know this is something that if you have small children, this can be really hard to figure out, especially now, you can make these at-home date nights but you can get creative here. We decided that once a year, at least we want to have time off from the kids, so we contacted my in-laws and said, “Hey, will you all take the kids for a week in the summer?” Every summer, the kids go to what we now call GG camp where they get dropped off with their grandparents and Jameson and I get a whole week together to do whatever it is that we want to do, which usually involves a lot of sleeping in and going out to dinner.

Then finally, when can you make more time for friends? This is a hard thing for me, especially because I'm super introverted. I have to set a goal for myself because these are relationships that I want to nurture. I want these women to be in my life for a long time, so I've got to be there for them and connect with them. How can I do that? It could be as simple as I want to schedule one or two lunches a month with a friend or I want to reach out to so and so, and have a phone call. I want to make sure that I'm thinking about these things because at the end of the day, the relationships are truly what help get through any tough situations. They're the people who will be there when things get tough in life and in business. You want to invest in them. Don't wait until too late.

It's official, we are fast approaching the final stretch of 2021. It’s that time of the year when we’re starting to look ahead for what we want to accomplish in 2022. I know you’re a high-achieving entrepreneur who loves the fresh start of the New Year. And you’re ready to have a real plan to yes to strategic action steps and say no to shiny objects that keep you spinning your wheels in your business. That’s why I’m so excited to announce the 100% free 5-day Plan Your Best Year Ever challenge starting on November 1st. In five days, I’m going to walk you through a strategic planning process that will help you to map out your business and marketing strategy for 2022, month-by-month, so you’ll have a real profit plan that helps you to stay focused on your goals. All you have to do is head over to and join us.

The next part here is your health and well-being. I'm going to raise my hand right here because this is the area that I often put last. This has been a 20-year journey for me, learning how to take care of myself instead of berating myself or talking down to myself or punishing my body basically. I know that when I'm in stress, this is one of the first things that gets put on the back burner because when I'm in stress, I tend to go into head down, work, work, work mode. I feel like I can work through any possible challenge but really what I need to do is lean into taking great care of myself. Having a clear picture of what you'd like to experience in your health and your well-being, in your body, it truly is essential to taking care of yourself. I want you to think about this. Ask yourself, are you happy? Are you satisfied with your current state of health and well-being? Do you know your current state of health and well-being?

Three or four years ago, I went and I hired a functional medicine doctor. There's an amazing practice here called WellcomeMD in Richmond, Virginia. They are a concierge practice, so I pay a subscription to them every year to have access to them but they do these executive level physicals. It was the first time I'd actually had somebody go through all of the different parts of my health with me and help me look objectively at what's going great, what's not going great. I discovered that it wasn't just in my head that I was tired. I had some severe vitamin deficiencies. I had a thyroid problem I wasn't aware of. I had things that weren't just in my head. They were actual things that we could improve now that we had done the testing. For me, that was so huge. It helped me to start thinking about, what does a healthy body look and feel like to me?

Now, for me, this is a big one because when I was in my teens, I had an eating disorder and I was very harsh on myself about what I looked like, so I have adopted the Health at Every Size mentality. For me, a healthy body isn't as much about what size my genes are because I can be healthier at a size 12-14 than I ever was at a size 4-6 because at a size 12-14, I am taking great care of myself, I am not depriving myself, I am moving my body, I am not in pain, I am loving myself, and accepting myself. What does that look like for you? What does a healthy body look like for you? Is it about being able to keep up with your kids or are you the athlete type and you know a healthy body is about being strong or about being fast? Whatever it looks like, it's all okay. It's all up to you.

How would you like your self-care to look like every day, week, and month? This is not just physical health too, this could be mental health, emotional health. These things are just as important and a huge part of your health, and well-being. What does your self-care need to look like? Are you making time each day to move your body? I like the language move your body over exercise. Again, some of us get triggered by those types of things but move my body makes me think, “Oh yeah, I don't just need to sit at my desk all day. I can get up and walk around the block, and pick up a coffee or I can make sure that I'm parking in the parking lot a couple blocks away, so I can get some extra movement in since I am sitting for several hours every day. I can make sure that I'm going on the family walk every evening, making sure that I'm actually making it a priority to move my body.”

How do you nourish your body each day? Again, nourish is the word I'm choosing. You're learning a lot about me today but this is part of me deprogramming some of the diet mentality. It becomes more of how am I taking care of myself so that I can have the energy and mental clarity to show up for you, to show up for my clients, to show up for my family. It's so simple. It's like eating enough vegetables, trying to eat as healthy as I can, making home-cooked meals as often as I can, and drinking a ton of water. How am I nourishing my body every day? For me, it's all about feeling good, having energy. Having the mental clarity that comes when I'm eating whole foods, when I'm drinking a lot of water, when I'm getting enough movement, when I'm getting enough sleep, suddenly, I have the energy to sit down and get these podcasts out for you. I have the energy to talk to all of my clients and to create new things. If I'm not prioritizing this, then that all slows down.

We talked about so far your life and your lifestyle, your family, your friends, your health, and your well-being. Let's go on to part four out of five here. This is your creativity and self-expression. Entrepreneurs, I find, are a pretty creative bunch. We like to learn, we like to grow, we like to try new things, we like new hobbies. In fact, it can become a challenge because we'll try to turn every new hobby into a business but I really encourage people to have interests and creative outlets outside of your business because it has been shown over, and over again that these will help you show up being more refreshed and creative in your actual business. It's so important to have that mental white space. Those different connections can show up when you're doing something that's completely unrelated to your business. Ask yourself, what do you like to do for fun? I know for fun we can have fun. What is it that's fun for you? Is it doing adult coloring books? Is it working on a puzzle? Is it reading a book? I sound so boring but those are some things that I absolutely love doing. Those are some things that I do to relax. They're really fun for me. Do you have any other interests you'd like to explore, any classes you wish you could take, something you wish you knew how to do even better?

Have you always been interested in painting and you've just never had an art class? Have you always wished that you could sew your own clothing but you never picked up a sewing machine? What hobbies do you wish you had time to pursue? Maybe you bought a really nice camera once and took a couple pictures but you didn't really know how all the settings worked, so it's been sitting in the cabinet for a while. What are some hobbies that would totally light you up? I think this is something that for me also, a lot of my hobbies can get into business too easily if I'm not careful, so I'm looking for things that my inner child would love. I'm looking for things that allow me to be silly and practice being a beginner, practice being imperfect. Earlier this year, I picked up cross stitching. My daughter and I went to the craft store. I think this was back in March, they had a bunch of cross stitch patterns that were feminist for women's history month. I was just working on these little cross stitches. It was the first time I'd ever done it. It isn't perfect at all. I made a lot of mistakes. I didn't match all the colors correctly but you know what, it was so fun to be a beginner again and try something new.

I think that's something we need to remind ourselves of to do. What's something new would be fun for you? My husband is a huge board game person—I'm not talking about monopoly. I'm talking about crazy strategic board games that for me, they're a little too complicated—but he makes it a priority to get these and to organize little game nights with some of his friends. They have so much fun doing it because it's another outlet to explore and to have fun with. What are you doing for fun? What will make your inner child happy? What are you doing for creativity?

Finally, part five here. Your personal growth and spirituality. When you're investing energy into filling your own love tank every day, you will feel more grounded and you will feel more empowered in your life, in your business. Often, you hear the saying, “You don't want to pour from an empty cup.” The key is not that you're pouring from an empty cup. It's that you are constantly refilling the cup and what you're giving to everyone else is the overflow. Remember, if you were to pour water, let's say you put a cup under a faucet and you turn that faucet on, at some point, the cup fills all the way, then water starts spilling off the sides, that's what you want to be giving to other people. How can you do this? How can you make sure you're filling your own cup? I like to ask myself these things. What mindfulness practices would you like to cultivate? This could be meditation, journaling, yoga. There's so many mindfulness practices you could check out and adopt.

How much quiet time do you need every day to sit with your thoughts? These are the times when I'm really just not doing anything in particular but I'm letting my thoughts marinate in there. What helps you stay inspired and focused in your life and your business? What helps you stay excited and inspired? Do you look at your mission? Do you look at your vision? Do you have a picture, a painted picture, a vision board, something in front of you that helps you remember why you're doing all this? How often do you need to fill your soul and your spirit each week? For some of us, this could be quiet meditation practice at home or morning routines. For some of us, this is going to a church or a synagogue or some other religious gathering being filled by the community. For some people, this could be connecting with a trusted spiritual teacher. What do you need to fill your soul and your spirit each week?

What are your uplifting books or blogs or podcasts content that you love that helps lift you up, that helps keep you inspired, that helps you be motivated? Make a list of those. Have them ready to go. I really encourage everyone to make space for these things. This is something that does not come naturally to me. But I found the more that I give myself this quiet time and I allow my thoughts to wander, and I can think deeply about my spiritual practice and connecting to myself, the more I have the overflow to give to everyone in my life.

There you have it. These are the five areas I want you to think about when it comes to your definition of success. First, your life and lifestyle. How do you want to be spending your time and energy? Where's it going? What does it look like? Actually sit down and journal on this, and create a model calendar. Two, your family and friends. Who do you want to spend your time with? What does that look like? How often is it? What types of things are you doing together? Three, your health and well-being. Again, this is not about losing weight, diet mentality, this isn't about beating yourself up. This is saying, “How am I taking care of myself so that I can show up present with energy, with focus, with mental clarity, and be able to do the types of things I want to do in my life? Four, your creativity and self-expression. How do you have fun? How do you express yourself? How do you become a beginner again? These things are so incredibly important for us entrepreneurs. Five, your personal growth and spirituality. How do you fill that inspiration tank? What do you need there to stay inspired and to stay excited about what you're building?

I hope that this helps you to start thinking about what success on your terms really could look like. Even if you're not 100% in alignment with your definition of success right now, I hope that you're seeing opportunities to move towards it.

If you love this conversation today, I encourage you to join us for the Plan Your Best Year Ever Challenge. This free five-day challenge is designed to help you design a 12-month action plan, 100% around creating success on your terms. We are dropping all of the hyphy definitions of success we feel like we should have and instead stepping into what actually feels authentic and aligned to each of us individually. Find out more at

Write Your Definition of Success!

Yes - you CAN have it all!

But first, you've gotta define what it all means to you!

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