The Expedition of the Barefoot Executive by Carrie Wilkerson

Jacob Kuta
5 min readFeb 20, 2021

The Barefoot Executive written by Carrie Wilkerson contains valuable information and inspiration that can help all entrepreneurs succeed. She gives advice based on her experience of running a business at home along with adoption and a successful weight loss. Throughout this book, I have learned to have the right mindset and what is necessary to prepare for a successful business. This can be applied at the beginning of our businesses. Although it is best to read it throughout the duration of our business. During my journey throughout this book, I have collected the key points and incorporated them in different ways. They are all gathered here for convenience without the need of reading the book over again.

For the first section of the book, I gathered my points in image posts with quotes. Wilkerson warned us that the “book might not be popular with [our] spouse, [our] parents, [our] friends, and most especially [our] boss”. Simply state we “cannot make them understand”. We must be brave enough to put faith in ourselves. However, we must not go through it on our own. The people that we surround ourselves with must be “of high caliber”. These people must not discourage and if possible allow us to bounce ideas off of each other. This might mean ending some relationships while starting new more meaningful ones. In order to overcome these obstacles, we must not live “life in fear of losing”.

Throughout my video, I explained the three major mistakes people make that prevent them from receiving financial freedom. The first one is chasing after other people’s dreams that are not ours. Often parents set a precedent for their children but we can not allow this to hold us back. The next one is chasing after too many things. It is better to put our effort toward one thing and succeed than seek after many things and fail. The third mistake is making money our priority and reason for going into business. There will never be enough money. In order to receive the peace and happiness that we are seeking after we must place our priorities elsewhere. For example, wanting to achieve more financial freedom to spend more time with family is a worthy cause that will be upheld throughout the challenges that will be faced.

In my infographic, it explores the methods of success. The first method is the mindset of success. In order to find success, we must believe that we can make it. Along with this, we must surround ourselves with people that will reassure our winning mentality. It can not simply be a hobby. Masterminding builds upon this method. It is all about finding the right people that have different niches that can build us up. The next method is finding a mentor that also goes along with creating the best atmosphere. Finding someone that has already been down this road can be extremely beneficial. They have seen their share of challenges and can help provide the best advice to overcome ours. Reading this book is fulfilling that method. Carrie Wilkerson is already successful and has provided advice that we must take advantage of. The final method that my infographic goes over is taking action. Nothing will happen if we do not do anything. Once again we can not be afraid of failing. These methods can bring us the same success as Carrie has achieved.

In the next section, I did a podcast with my insights over the business models that she presented. The service-based model is the easiest to obtain. Although, it must be assessed first because it can result in failure. It is not something to stop you from obtaining your goals. It should help you narrow your focus on something that is likely to succeed. Expertise-based business models can not be for everyone. It is more for entrepreneurs who have already been in the regular workforce for some while. Goods-based models can be highly competitive. Your product must be unique to succeed. They mention E-commerce which is growing exponentially. Many people buy their products online or at least browse. Referral-based has been more popular recently. Youtubers and other influencers use this model. They endorse products for money. If done correctly this benefits both parties greatly. (Podcast:

Carrie Wilkerson is not without fault in her advice. In another article, I wrote my grievances about the book. There is not much to critique but what is there is important to look at. At times it appears that she contradicts herself. She talked about taking risks and not worrying about failure. Although she also states that she recommends having a steady source of income before doing this. She does have children dependent on her so it makes sense but still seems to be on a different mindset. This contradiction occurs in a few other philosophies. (Full article: