E83: Setting Aside Your Pride to Ask for Help

Thinking 'I should be able to figure this out on my own' keeps you stuck.”

- Asha Wilkerson, Esq.

Episode Summary:

If you’re feeling embarrassed and hesitant to ask for help in your entrepreneurial journey, you are not alone! Many women of color entrepreneurs struggle with overcoming the need to do everything on their own. This belief is keeping them from seeking the help they need. However, the truth is that asking for help is a sign of strength and a vehicle for faster personal and entrepreneurial growth. You can go much further in business and life by setting aside your ego, embracing vulnerability, and seeking guidance from mentors, peers, and experts. In this episode, I share my experiences of struggling to ask for help and how finally putting aside my ego opened up many opportunities for me.

In this episode, you will be able to:

  • Understand why overcoming embarrassment in asking for help is crucial in your entrepreneurial journey.
  • Find out how the pervasive “smart enough” mindset can be detrimental to your success.
  • Get a new perspective on the value of seeking professional advice outside your own expertise.
  • Grasp the significance of building a supportive entrepreneurial network and community.
  • Recognize how mentorship can speed up your business success.

What You’ll Learn On This Episode:

  • 00:00:03 – Introduction,

    Asha introduces the podcast and herself as a business coach helping service-based entrepreneurs align their business goals with their personal goals.

  • 00:01:14 – The Embarrassment of Asking for Help,

    Asha acknowledges that many women of color entrepreneurs feel embarrassed or ashamed to ask for help. She emphasizes that asking for help is necessary for growth and success in entrepreneurship.

  • 00:02:30 – Mistakes of Doing It Alone,

    Asha shares her own mistake of assuming she had to do everything on her own to be successful. She explains how this mindset isolated her and kept her stuck and frustrated.

  • 00:04:06 – The Harmful “Shoulds,”

    Asha discusses the harmful thoughts of “should” that can prevent entrepreneurs from seeking help. She shares examples of how her own “should” mindset led to mistakes and wasted time.

  • 00:08:58 – Overcoming Pride and Reaching Out,

    Asha shares her experience of overcoming pride and embarrassment to seek coaching for her business. She highlights the transformational impact of working with a coach and learning from others’ experiences.

  • 00:14:28 – The Power of Connections,

    Building connections can help your business grow faster as others recommend your services and become a marketing tool for you.

  • 00:15:18 – Going Far Together,

    Building a business that lasts requires the support of a community. Going fast alone may be possible, but going far is achieved by working together.

  • 00:16:17 – Feeling Alone,

    Many entrepreneurs feel alone on their journey, especially when deviating from expectations set by parents or culture. However, joining a community of like-minded individuals can provide support and understanding.

  • 00:18:03 – Seeking Support,

    It can be uncomfortable to ask for help, but starting with one person can make a difference. Asha Wilkerson offers one-on-one coaching to provide support, accountability, and help to reach your goals.

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.

  • 1:1 Coaching spots with me will open again in September. Be the first to know by joining the waitlist!

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. Welcome back to another episode of Transcend the podcast. I am so grateful that you are here, just like I am every week. And this week, we’re going to talk about not feeling embarrassed to reach out and ask for help. Now, I talked to hundreds of women of color entrepreneurs.


That’s what I do. I coach women of color entrepreneurs. And so many of us have felt like we are alone or by ourselves or have been siloed on our entrepreneurial journey. And there’s this embarrassment or this shame that shrouds us, overcomes us, covers us, and often prevents us from asking for help. I totally understand and resonate with that, but I’m here to tell you today that asking for help is not embarrassing.


And not only is it not embarrassing, but it is also necessary for you to grow and be successful on your path in entrepreneurship. Early on in my journey and to be 100% transparent, even sometimes now, I still feel a little bit embarrassed when I’m asking for help. But the reason why I can tell you not to be embarrassed and why I’m telling myself not to be embarrassed is because the times that I have gotten out of my own way, moved past my ego, and have reached out for assistance, I have been transformed by the support that I have received. Part of my mistake in the beginning of my entrepreneurship journey was that I assumed that everybody was doing it on their own. And because I assumed that they were doing it and being successful on their own, the they, whoever they is or they are, I felt like I also had to do it on my own in order to be successful.


Or that if I reached out and asked for help when I didn’t know something or didn’t know how to do something, that that meant that I wasn’t successful in that line of thinking. All it did was isolate me, kept me stuck, kept me frustrated, spinning out in my own wheels, going like losing my mind. Not actually, but feeling like I wasn’t sure what to do and how to do it. And I ended up internalizing a lot of that stuff and feeling bad when the solution would have been Asha, pick up the telephone, get on the internet, go to a group, reach out for somebody who knows how to do the thing that you are struggling with right now. I kept telling myself, I’m smart enough.


I should be able to figure this out. Have you said that a lot of my clients say that, especially when it comes to taxes, for whatever reason, and I’m not entirely sure what that is. Maybe people are much more comfortable with numbers than I am, but I know a number of people who say, oh, I do my own taxes. I can just figure out my business taxes. It shouldn’t be that complicated.


Let me just tell you, people go to school and get whole degrees in accounting. While you may be able to input the right numbers, understanding the process of accounting and what deductions apply and how to carry forward losses that can really help your business should be left for an expert. Yes, my dear, you are smart, but unless that is your niche, please reach out to someone who knows what they’re doing to help you. I also said to myself often, I should be able to do this without somebody else’s help. I should the shoulds I was in one of the coaching groups I used to be in.


They would say, don’t should all over yourself. I use shoulds a lot. Let me reframe that. I used to use shoulds a lot in my business because I felt like, again, I should be able to figure this out. I’m smart enough.


I don’t know anybody else who is asking for help in this kind of a realm. I should just figure it out. That is language. Those are thoughts that will hurt you and not help you. So let me tell you about a couple of times.


There’s more than a handful of times when I got myself into a position that really didn’t benefit me. All because I thought I should have been smart enough, or I thought I should have just been able to figure it out. Now, I’ve given this example before, especially here on this podcast, but let me remind you, and it has to do with taxes. Now, when I first started out in my own law practice, of course I had learned about law and law school, but I didn’t know that much about running a business, and I certainly didn’t know anything about using accounting software. I knew enough to know that I needed to get QuickBooks.


I didn’t know anything about how to set up QuickBooks, what the charts of accounts meant, what the different categories meant. But I thought, I’m smart. I should be able to figure this out. And not in a way of, I’m so smart I could do it. But I felt like I didn’t have the money to hire the right person.


So my default was I should be smart enough to figure this out. So I go into QuickBooks and I change everything around. QuickBooks has like a default. Any accounting software has default categories. What I learned in the end was that those default categories match up to the tax return categories.


So when you use your numbers from the bookkeeping software and put them into the tax return, the categories should match because I didn’t have any kind of background in bookkeeping or accounting. I didn’t know that. So I changed so many of the categories to fit how I wanted to classify the business that I was running. So I would create different categories, like contingency, flat, fee, things that were helpful for me to know what kind of business and clients I had coming in, but things that had nothing to do with the bookkeeping process. So at the end of the year, I find a tax repairer, and I give her my books.


I’m like, I’ve already done this.


You can just fill out the forms. As I’m saying this to you, I’m realizing how arrogant this sounds, and I’m kind of embarrassed. But anyway, I brought the books to her, and I said, okay, here, I’ve done this stuff. Now if you could just fill out the tax returns, that’d be great. So she looks over the bookkeeping, and she’s like, what is this?


How did you do this? And I tried to explain it to her. She’s like, that’s not how it’s done. And guess what? She had to go back through from January 1 to December 31 and reorganize all of the transactions that I had in my business.


So not only had I spent hours doing my own bookkeeping, but I spent hours doing it incorrectly. And then when I took it to the expert, she had to go back in and spend hours correcting it because I didn’t do it correctly. Now, if I wouldn’t have had that thought, oh, I’m smart enough to figure it out, or I just should be able to do it, I could have worked with somebody along the way, found somebody. I could have afforded, at the very least, thought about getting educated in the area so that I can figure out how to do it properly. So that’s the first time that I can think of right now when the shoulds right, I should be smart enough, I should be able to figure it out.


Really, actually was detrimental to my business, made me lose money and time. The second example I can think of is also in the law practice. And this has actually happened to me a couple of times as a business coach too, but it was refusing to reach out for coaching. I shouldn’t say refusing. I wish that I would have known that I could have hired a coach.


When I first started my business, I had no idea that coaching even existed. Now, I did surround myself with other attorneys who are a couple of years ahead of me in terms of having their own practice, but I didn’t think to reach out for a coach who could coach me specifically and help me build the business that I wanted. So I went through a lot of trial and error. I made a lot of decisions that I ended up remaking later or undoing later. And thankfully, nothing is final right?


You can always redo a decision. But I spent so much time figuring it out. Whereas if I had had a coach to tell me these are the three options that work in this kind of a business for the lifestyle that you want, pick one and we’ll build it out for you. That would have saved me hours, that would have saved me lots of emotion, lots of tears and frustration and I could have built a practice that was thriving and successful much more quickly than I did, having to figure it out on my own. And I’ll give you one more example in terms of the coaching space.


I switched to business coaching away from practicing law a couple of years ago now and I was stuck because I felt like, again, I’m an attorney, I used to run my own law practice. I should be able to figure out how to run this coaching practice. And in the beginning when I started, I got some traction and then it slowed down because the way you market a law firm is totally different from the way you market a coaching practice. But my pride was so front and center and the pride was there to protect my ego because I was embarrassed that I was not as successful as I wanted to be. And however you define success, right?


I was embarrassed that I wasn’t getting clients coming through my door right away. I was embarrassed that I wasn’t very confident when I first started as a business coach, even though I actually had years of experience coaching, I just coached under the law practice. I was embarrassed that I was whatever age that I was in my thirty s and felt like a beginner again, I was not comfortable with where I was. And in order to protect my ego and my pride, I didn’t reach out for business coaching until about a year in. And now that I have, it has been absolutely transformational, particularly because I can see the areas where I need to grow and I’m able to see the skills that I’ve developed already and to put those together.


So I’m not starting from zero now, I’m starting from wisdom. But that coupled with a coach who has been there, done that, I found people that I admire who are living a lifestyle that I want to achieve and I am following the advice that they’re giving me to help me build my own business. I wish I would have done that two years ago and I wish, I wish I would have done that eleven or twelve years ago when I first opened up my own law practice. So, all in all, refusing to ask for help immediately. And maybe you’re at a point where you’re not saying, I don’t know how to do this yet, but maybe you’re just starting out.


And that is a great time to surround yourself with experts who can pour into you and help you build your business. Don’t make the same mistakes that I made. Because what it did for me is it slowed down my progress. It made me frustrated. It really gave me, unfortunately, the space to internalize my struggles and make it about me.


Instead of realizing that the business struggle was a business struggle. Maybe you can relate to that. Maybe you’re in a similar position where you feel like, gosh, I should be able to figure this out. Or you feel like because you started in one career, you should just get it in this second career or this third career that you’re on? Or because you’re talented, because you’ve been smart all of your life, that it’s really uncomfortable for you to say, I don’t know how to market I don’t know how to create this contract.


I don’t know how to position myself so that I can be the expert. But you, my dear, are not alone. By letting your pride and your ego stand in the way from getting yourself the help that you desire, you just end up becoming more frustrated. Now, I told you my QuickBooks example, but how many times have you sat on Google or on YouTube trying to figure out a concept, and then later you talk to an expert and they explain to you in 30 minutes what you’ve been working on for 30 days? Frustrating.


Totally frustrating. Maybe your ego is preventing you from reaching out to find out how much you should charge for your services. In my own experience as well, because I felt like I should know. It was hard for me to reach out to see what the industry standard for pricing was or hard for me to ask other people what they would pay or how much they valued the service. Because oftentimes so what happened after I left the law firm years ago was that I didn’t know what the other rates were in the industry.


And I ended up undervaluing myself and being afraid to charge higher prices because I didn’t surround myself with community or with experts who were a couple of steps ahead of me. So I ended up losing money and or doing work at a rate that was below the value that I had. Refusing to get out of the way of your pride and your ego can also keep you stuck trying to solve for the same issue month over month or year over year. Is there something in your business that you just can’t figure out or that you just can’t get right? For me, over the past couple of years, it has been selling the one on one coaching offer, and it wasn’t because the offer isn’t good and it isn’t valuable.


I’ve helped a number of people, but it was my discomfort with selling it. And once I got into a program and called in the resources to help me work on my sales, things have really turned around. It wasn’t the product and that’s what I went to go fix. But it was how I was thinking about the product and communicating about the product. So what is that one issue or what are those two or three issues that you keep dealing with over and over again that you have not yet sought out help to address, refusing to ask for help and to call in the experts around you keeps your circle small.


There is power in connections. When you hire the expert to do your website, not only are they doing your website much faster than you could do it, but they also will keep you in mind when they have somebody else in their community looking for your services. Also, when you’re in community with other people, your name starts to move around the community. People know what you do and then they can recommend others to come and talk to you and to use your services. They become a mouthpiece for you, a marketing tool for you.


And you didn’t even have to do anything except for just show up and be in community and have conversation. So when you create relationships, when you expand your circle, even if it’s not always about an exchange of services, your community grows and so does your client base. There is an African proverb which I think is funny because it seems like when people don’t know where something is from, they call it an African proverb. And Africa is huge, right? Way bigger than the United States.


But anyway, this African proverb that I’m sure that you have heard before says, if you want to go fast, go alone. But if you want to go far, go together. And it is so, so true that if you are trying to build a business and build it fast, do it by yourself. But if you’re trying to build a business that’s going to go far and is going to last for a while, you need the community and the support to help you do it. So, like I said, I talk to a number of business owners all the time.


We often feel like we’re the only ones who are doing this. Like we’re by ourselves. It’s our own journey to walk. And to some extent it’s true, it’s your own journey. But let me tell you this.


A few weeks back, I led a Women of Color entrepreneurship circle. And everybody in that circle throughout our introductions mentioned at some point in our lives feeling alone, whether it was because we were deviating from the path that our parents wanted us to join. Particularly if you come from an immigrant family, then your parents probably want you to be a doctor, a lawyer, an accountant, right? One of those jobs that screen stability. And if you were striking out on your own, particularly in an area that your parents don’t even understand, could be an area of a career, then sometimes it’s hard for them to support you.


But the reason why is because they want what is best for you and what is safe to them. And best for you is something corporate, something that has a lot of respect. So if you have deviated from what your parents want you to do or from what’s culturally acceptable in your community, that often feels very much like you’re alone. On my own journey, I have a couple of friends who are entrepreneurs. But in the beginning, I didn’t have a lot of friends who were running their own law practices.


A lot of my friends were working at big law firms, making big time money, and our experiences were completely different. The work of the law was the same, but running the business and working in a business, two completely different experiences. And I often felt like I was on this road alone, by myself. But the truth is, we’re not actually alone, because everybody in that circle could resonate with what everybody else was saying. If it wasn’t the exact same experience, it was a similar experience.


And I don’t want you to feel like you are alone on your journey anymore, because the truth is, you are not. If you’re still feeling like, okay, Asha, I get it. I hear you. But it’s still too uncomfortable for me to tell the world that I need help with this business. Start by telling one person.


Start by telling me, I will be there for you to help you grow your business, to help you work on your mindset and for you to set goals so that you can get to where you were trying to go. I have been there before. It’s part of my journey. And now I am willing and able to hold space for you so you don’t have to feel alone like I felt. Not only will I hold space, but I will also make sure that I give you business strategies so that you can see your goals come to life.


I will lovingly call you out on your BS and tell you when you’re tripping, because that’s important too. I will hold you accountable. I will make sure you understand the numbers that you need to hit to live this dream life. I will also make sure that whatever strategies we implement and put into your business are in alignment with who you are and how you are as a person, so that this business that you’re building gives back to you in the same way that you are giving to your business. I have spots now open for my one on one coaching container.


The waitlist spots are open now. So if you are looking for that one person to give you some support, or to start with one person to give you some support so you can say, hey, Asha, I need some help. I’m not sure what to do about this. I’m feeling vulnerable, but I’ve got these big dreams and I’m just not sure what to do head to the Show Notes of this podcast and click the link to register for the one on one coaching container. Waitlist.


I promise you that when we work together, you will not be the same as when you started. You will strengthen your mindset, you’ll have your goals written out, and you will be well on your way to building the business of your dream so you can live the life that you deserve. I’ll see you next time. 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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