E82: These Two “Whys” Fuel Your Business

Your Why is your North Star, it's your home base and the place that you will always come back to when times get tough"

- Asha Wilkerson, Esq.

Episode Summary:

Are you getting lost in the how without spending time on your why? In this episode, I’m covering the importance of knowing your big “why” and your “why this way” so that you can gain a better understanding of what is fueling your business and personal decisions. Even if you think you already know your why, this episode will help you go deeper in your understanding.

In this episode, we cover:

  • How essential it is to define your two “whys” when venturing into entrepreneurship.
  • Detect the early signals of misalignment and its role in causing eventual burnout.
  • Why it’s so important to make sure the way you’re going about pursuing your purpose feels in alignment
  • How prioritizing your whys can make you more resilient in though times.
When you connect with the deep core reason under it all, you’ll be much more likely to continue on your mission. – Asha Wilkerson


What You’ll Learn On This Episode:

  • 00:00:03 – Introduction,

    Asha Wilkerson introduces herself as a business coach helping service-based entrepreneurs align their business goals with their personal goals. She believes that it’s important to understand both the why and how of your business to build a successful and fulfilling career.

  • 00:01:12 – Knowing Your Why,

    Understanding your motivation and why you are doing what you do is crucial to building a business that aligns with your financial goals, life goals, and mission. Knowing your why helps you stay focused and motivated, measure your impact and accomplishments, and choose the right programs and methods that align with your purpose.

  • 00:03:37 – Why You’re Doing It Like This,

    Why you’re doing it like this refers to how you engage with your business in a way that highlights your skills and passions. It’s important to build a business that you can stand behind and that aligns with your innate talents and gifts. Knowing your why and why you’re doing it like this helps you build a fulfilling and sustainable career.

  • 00:08:55 – The Consequences of Not Knowing Your Why,

    Not understanding your why can lead to getting off track, delaying progress, and wasting time and money on programs and methods that don’t align with your purpose. Knowing your why helps you stay motivated, focused, and fulfilled in your career.2

Resources Mentioned:

  • Get clarity on your “why” and your “why this way” with your Re-Alignment Roadmap (formerly the Money-Making Roadmap). CLICK here to learn more.

Connect With Us: 


You’re listening to Transcend the podcast. I’m Asha Wilkerson, a business coach helping service based entrepreneurs align their business goals with their personal goals to create a life they want to show up for. I will show you how to drop the expectations, thoughts, and beliefs that weigh you down as a woman of color entrepreneur so that you can create and walk your own path with success, confidence, and joy.


Hi, everyone. Welcome back to another episode of Transcend the podcast, and I am thrilled to have you here to listen to this episode, because this week we’re going to be talking about why. You need to know your why before you know your how, because oftentimes we start out trying to figure out the how, and we don’t get into the why like we should. So people say all the time that you need to understand your why in business so you can keep going when times get tough. But my take on understanding your why is a little different.


I believe you need to know both your why, why you’re motivated, what change you’re trying to make, and also why you’re doing it like this. You need to know both of these so you can build a business that supports your financial goals, your life goals, and your mission, and so that you can do what you want to do in a way that is giving and supportive and easy and natural for you. There are a lot of different businesses that you can start or career paths that you can go down to reach a specific why. However, it’s important to intentionally choose the way that you want to reach your why. You need to have a clear answer to why am I doing this and why am I doing it like this?


Both of those things need to feel like they’re in alignment because often we’re chasing a why, but the way that we’re doing it is out of alignment, and then we just get confused, frustrated, and sometimes even stop our progress. So I’m going to break down these two whys and share how you can start to gain clarity around both. And not to surprise you, but again, I’m going to tell you a story from back in my attorney days. I call myself the accidental Attorney, not because I really wanted to go to law school, but because I applied and thought I would see what would happen. I happened to get into UC Hastings on early decision, which meant that I had committed, but of course, I still wanted to weigh the decision in my mind.


I was planning on being a high school English teacher so that I could help kids. And I love teaching English. I like to read, I like to write. But when I really thought about going to law school, I thought that it would give me the best platform or the greatest opportunity to be able to help people in many different ways, whether it’s by going to court. It could be by writing policy, by negotiating a contract, being a voice for the voiceless, all of those things I can do with my law degree.


And then I ended up in a law firm and got very well acquainted with law firm culture, where the biggest driver was how much money we could make and our effort or our impact was measured in time. So every six minutes we needed to be billing a client for some service that we were doing. We couldn’t just do something out of the goodness of our heart because we needed to pay the bills. And so even though the why was to help people and to represent folks who needed help in litigation, the how was really uncomfortable for me. And it didn’t allow me to really flex my skills and show up the way that I wanted to.


And eventually it became really challenging. That led me to starting my own law practice in which I actually recreated the same system that I was coming from. And again, I got burnt out. I didn’t want to be in court, didn’t want to be on a deadline, didn’t want to be so worried about billing for every minute of my day. So before I took my first break from law, I realized that I still had some interest in law.


My why for being in law was still intact, it was still relevant. I wanted to help people. But the why I was doing it like that in terms of running a litigation practice was no longer in alignment. And it made it really hard to focus on my first why because it just didn’t align and didn’t resonate with who I was at that time. So in the beginning, it was okay, in the middle, less okay.


And in the end, it was just so painful that it made it actually hard to show up for my clients in the way that I wanted to. Because how I was carrying out the why or why I was doing it like this just didn’t serve anymore. Over the years, the delivery of my why has changed. My why is that I still want to represent underrepresented people. But how I’m doing that now is through business coaching.


And why I’m doing it like this in terms of providing information, a lot of it for free to my community, is because I get to show up and use my skills in a way that aligns with my just innate talents and gifts. So my why is to help people of color build businesses and leave legacies. And why am I doing it like this through business coaching? It’s so that I can show up and represent myself and the knowledge that I have to share in the best way. It’s not going to be in a courtroom anymore.


It may or may not be in a classroom, but certainly in the one to one coaching container I can show up, teach, learn, share, support, and make sure that my client gets everything that I’m able to give them after that encounter. So now let me explain the two whys a little bit more deeply. First, it’s important to understand your motivation, and you need to go deeper, more than just, I want to make a million dollars, unless that really is your deep, deep motivation, it’s not for me. I was never motivated by money. I wish I was a little bit more motivated by money, but my drive has always been to help and to be of service.


But why? Why do you want to do that? You got to ask yourself why multiple times. You can get down, really to the root of it, because these surface level answers, it’s the right thing to do. It’s fun.


It’ll make me money. Those surface level answers aren’t going to keep you motivated and moving forward when things get tough. My motivation, my why is to make knowledge and information easily accessible to black and brown communities in the United States. Because I want to see us build businesses and leave financial legacies. That gives me a sense of purpose.


So it doesn’t necessarily matter the method that I’m delivering it, but because I’m attached to my why, I know that I’m going to keep going. I’m going to keep showing up, because it’s my purpose right now. It also gives me something else to measure for a sense of accomplishment. The accomplishments that we can measure aren’t always how many courses sold, how many clients you have, how much money you’ve made, but what kind of impact did you make, how many communities did you reach? How much information did you put out there?


It’s a great way to be able to measure impact without just looking at the finances. Answering the second why? Why am I building a business like this? Or why am I doing it like this? Allows you to think critically about how you’re building your business so you can engage with your business in a way that highlights your skills and your passions.


There are things that come really easily and naturally for you. For me, it’s teaching. So when I was showing up in court, I was doing a good job, but I do a much better job at teaching and sharing information because it’s a natural, innate talent that I have. So for me, having a business that allows me to teach and deliver content is much clearer why am I doing it like this? And helps me to stay focused and feel successful.


And thinking about how you want to actually engage in your business or why you want to do it in this particular way helps you to build a business that you can actually stand behind. And it may mean that you end up saying, because I want to, because I want to do it like this. Because it feels good to do it like this. This is how you know you’re actually engaging in your why or carrying out your business like this. I keep saying like this in quotes, but in this particular way because it actually works and aligns with you and who you are.


But here’s the thing. I know a lot of you probably think that you don’t need to go deep and understand your why or who cares. You’re focused on structure and strategy and that you’re just going to get it done right. But let me tell you what happens when you don’t really truly know, understand and embody your why. It’s easy, really easy to get off track.


There are so many programs and methods and strategies and things that sound good. And if you don’t remember your why or truly understand why you want to do it in this particular way, it’s easy to sign up for any group program, any quick method, anything that feels like it’s just going to make it easier. And I’m not telling you not to sign up for programs, but you need to make sure that they are in alignment with your why and why you want to do your business in the particular way that you’ve chosen to do it. If you don’t know your whys, it also can delay progress. You spend so much time trying to figure out, is this thing I want to do?


Is that the thing I want to do? Who are the people I want to help? How is it that I want to do it? So and so has an online business that works for them. Maybe you’re not an online person and you need to have a brick and mortar.


So there is some amount of time that you are just going to figure it out. But it is super helpful to be able to understand your why and your method or why you want to deliver the way that you’re thinking. So then you don’t waste unnecessary amounts of time just trying any old thing that might work. And not only does it waste time, but it also wastes money. I can’t tell you how many programs or things I’ve signed up for that sounded good in the moment.


But if I would have thought a little bit deeper about it, is this what I want to do? Is it actually going to help me get the thing done that I want? Or is it just a shiny program that’s actually marketing to somebody else? I could have saved a lot of money. So when you’re not quite sure what your grounding is, when you’re not sure who your why is or why you want to build a business in the way that you have chosen to do it, you end up wasting time and valuable money.


And lastly, maybe most importantly, is that it’s really, really easy to lose steam if you’re not seeing the progress that you want. If you’re lost in trying to fit anybody’s business structure or model on top of yours. Or if you are seeing slow growth, then it is really easy to get sidetracked, to quit or to get discouraged because your business isn’t filled with your purpose and passion and it’s not being delivered in a way that is in alignment with you. So if you want to dive deeper and make sure you avoid these pitfalls inside the Money Making Roadmap course, I take you through exercises to help you discover or rediscover your two whys. If you’re just starting out, you may not know what your purpose is, or maybe entrepreneurship just sounds cool and you decided to do it.


Or maybe you’ve been in business for a little while and you’ve forgotten your purpose or strayed away from it and you need to take some time to come back. This exercise that I have provided inside the Money Making Roadmap called The Power of Seven Whys will help you to go deeper and to truly understand why you are working towards the goals you’ve set for yourself. It’s all too easy to lose track of your goals or to lose steam when working towards it. But when you connect with the deep core reason under it all, you’ll be much more likely to continue on your mission. So don’t let yourself get lost.


Join the money-making roadmap course and discover or rediscover your why? This is actually the step that gets you closer to learning your how more than any other quote “make a million dollar course.” End quote. Because your Why is your North Star, it’s your home base and the place that you will always come back to when times get tough. Join the course today using the link in the Show Notes.


See you all next week. Thank you so much for listening. If you want to hear more on how you can align your business and your life with me as a coach, head to the Show Notes and sign up for the email list. See you next week.

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