Stepping into Risky Business
My journey has been anything but predictable—full of challenges, faith, and lessons learned the hard way. My Yellow Shoes is a reflection of that path, shaped by experiences like an early childhood moment when a simple choice made me the target of ridicule. That moment, and many others, taught me about resilience, the weight of choices, and the importance of tuning into God's plan rather than the world's expectations. This book-blog isn’t about easy steps or clichés; it’s a raw, honest exploration of faith, business, community, and the struggles we all face. I’ll share my scars, my failures, and my wins—not as a prescription, but as an invitation to walk alongside me. You don’t have to agree with me; this is my journey. But if you choose to join, I hope it sparks something meaningful for you too.
Table Of Contents
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Protect me as the pupil of your eye; hide me in the shadow of your wings from the wicked who treat me violently, my deadly enemies who surround me. They are uncaring; their mouths speak arrogantly. Psalms 17:8-10 CSB
One's life journey can, more often than not, be characterized as the dark night of the soul. As Jesus' followers, we can easily mask the pain associated with our path in our roles, professions, relationships, etc. The path of His Way is hard, it's deceitful and filled with heart-rending obstacles. That's certainly been my journey, and I know many others. My journey of entrepreneurship, or as I like to call it 'Risky Business', has not been anything I could have ever foretold. It's like writing a business plan; it becomes a living document. It never happens in the way we design it.
Why 'My Yellow Shoes' you may ask?
Yellow shoes, more specifically, Dijon mustard yellow, are among my favorite color of shoes. The very first time, I dipped my toe in the rather limited pond of yellow shoes, I didn't measure the impact of the risk I would be taking. That’s not a common process for a 9 year old girl. For example, no one confided that the innocent process of choosing a color would come with a high price tag. Those shoes made me the target of schoolyard jokes and ridicule for months. At least, until I could effectively wear those shoes into oblivion. Which I attempted to do quickly.
That defining moment, along with other formative events, quickly opened my eyes to the reality of life choices. No one needs to tell you or me that life is comprised of choices; those we make, and those made for us. If our delicate human nature is not well prepared, the impact of those choices can sideline us. We can allow the opinions and judgments of others to radically damage us. So much so that we potentially 'opt-out' from completing our life journey in the manner for which we were created. We quit. We don't finish out in the manner for which we were created.
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Psalms 139 is a pretty good starting place to learn about our initial formation. It's the beautiful poem of how God considers each of us, as He's weaving His creative genius into our physical and spiritual beginnings. As a life-long Jesus follower, I have come to realize Jesus came to set me free from the opinions and judgments of others. I don't need to follow the endless list of man-made conventions which only serve to deviate me from His navigational compass in my life. He came to set me free from silly rules, from rigid thinking, from cultural biases, from judgment, from harsh criticism, etc. I can choose to tune into His frequency in my life and tune-out the world. I can ignore the false narratives designed to control me, and 'keep me in line.' In reality, He has come to break the chains, often constructed by the organized church - the religious. Those chains, that don't serve to protect us, but rather constrain us. I guess you might say, I am now a "ruggedized" version of who I was years ago.
This book-blog, organized in a somewhat random fashion, some will tell you often like my mind, represents my musings on faith, business, marriage, community, love, responsibility, and of course the biggie - sin. It's my thinking, undergirded by His, as to His call on our respective lives to be His salt and light to the world. Using the amazing spiritual and physical gifts He has granted us, for the purpose of equipping us.
I'm not going to prescribe the ‘5 easy steps' to accomplish something. I'm not going to give you the prevailing Christian cultural soundbites. I'm not going to create a new language to speak to the original mission for which He created us. I'm going to speak from my experience, my understanding, and more importantly my scars. All gained through my failures and my successes, and if I’m to be honest, those are still occurring. Yes, I do sin. Like the Apostle Paul, I do the things I don’t want to do, and I don’t do the things I should.
I'm also going to ask others to contribute to my musings, from their own set of life experiences. There is much more 'gold' to be found, when in the presence of many miners, than just with one. My experiences are limited. Coupled with the wisdom and advice of others, I hope to pour into those who are following this narrative. I invite you to join. I hope it is a fruitful choice for those who do join. Just don't expect to agree with me. You don’t have to, it's not your journey. It's mine.
You can't be great without the greatness of others. Nick Sirianni, Head Coach, and Philadelphia Eagles.
Hey there,
As many of you are building, scaling, thinking next thing, I want to draw your mind to the idea of 'key man' insurance. While entrepreneurs need to think about this from a pragmatic perspective...God did not give us the date or time He is taking us, I am asking you to think about this from a more 'whole-istic' perspective.
Your investors want this info, or they should, before they put any money in your gig. If they don't think that way, they are foolish. No guarantees in life.
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Several of you have invested significant time and resources into some amazing technology solutions. Millions of lines of code. Platforms architected to solve monumental problems on a global scale. Simply cool stuff, in just about every industry/domain that exists.
When I speak about 'key man', I'm asking the question... who is going to pick up the ball, and carry the mission to completion, if you get taken out of the game? Who in the org has the same passion to see this 'thing' finish well? Who has the vision, who has the drive, who has the willingness to finish the race?
That person may not have the tech skills, but they have the understanding. They can see it through. This could be a spouse, a co-founder, a relatively new individual to the God team Abba has been assembling with you... I don't know He does. Make plans for sure, but know you can exit at any time. Moses only got to see the promised land, he was taken out of the game due to disobedience.
That's what I want to know as a kingdom investor, and as an advisor/coach for some of you. I'm investing in God's vision executed through you. But not only through you, through those others who have come along side.
Some of you are not good at trusting others, for a variety of reasons... some reasons good, others not. That's a skill deficiency on your part that you need to endeavor to upgrade. Quickly.
Have you allowed the Lord to expand your vision in how you need to hold your biz stuff open handed?
I'm pretty sure not one of you is going to save the world. That's His job. We're just His sidekicks. Hebrews 9:27
Why did I fail? I did it by the book. I listened to my advisors. I corrected the course based on what others recommended…”
“The business was a good idea, the timing was probably just off…”
“I knew I was in God’s will. He would provide and make it successful. How could I go wrong with Him on my side? I can’t figure out what happened…”
Does any of this sound familiar? Has this, or a variation of this, narrative been your own?
If this has been your own experience, how do you begin to dissect and understand what happened?
The Standard Reasons for Failure?
Most business experts can easily recite the top five to seven reasons for business failure. However, the reality is… the reasons for failure in any particular business cannot be summarily reduced to a quick list.
The manner in which we think about our failures is flawed because we are flawed. Failure is multi-faceted, and complex, just like the humans who craft the scenarios in which failure thrives.
I believe that when we think about failure – our own failure – we can’t remove ourselves from the final equation. We tend to think more readily of ourselves as the masters of our success, yet we are equally the masters of our failure.
God Created Us to Think “Whole-istically”
God created humans to think like Him about his creation. He created us in His image – the Imago Dei – and to think about and operate within His creation “whole-istically:” When sin corrupted his plan, his image in us did not change. What did change was our perception of, and response to, His imprinted image. Let me explain…
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I Am More Than Just “Business Me”
Whole-istic thinking does not come easily to us. We tend to compartmentalize the many tangible, as well as intangible, elements of God’s creation – from the spiritual to the physical to the social. We rarely consider our work from the perspective of the integrated whole, even though his creation is the embodiment of intricately designed inter-dependencies.
When I walk out the door to head to the office each morning, I don’t just bring the business side of me. Accompanying “business me” are the spiritual, emotional, and physical boxes that make up the total package of “me.”
Tucked within those boxes are all the problems, concerns, and anxieties I thought I left safely locked up on the other side of the door. Some of us are better at hiding certain boxes than others. However, for most of us, some of those unwanted boxes will eventually make it into our business domain. No matter the mechanisms we construct to prevent this.
This ability to create and operate within “islands” of life is how we attempt to exist within our structures, systems and institutions. Not to say this is entirely wrong, however, I believe it is incomplete and gives us an incomplete perspective.
Flawed Failure Postmortems
When we undergo the process of evaluating business failure, our postmortems tend to look at the cross sections rather than the integrated whole of the business. If a doctor attempts to diagnose a brain problem from a tissue sample or cross-section, rather than an entire brain scan, the bigger problem will most likely remain undiagnosed. Is it any wonder all prevailing business wisdom comes from looking in the rear-view mirror? Every situation is always contextual. This is why Good to Great, eventually morphed into How the Mighty Fall. No two companies carry the same context or the same humans. Each has DNA unique to that organization.
When highly paid consultants walk into a dysfunctional or failing organization, most will only look at discrete organizational cross-sections. They will study the financials, marketing strategies, sales quotas, customer demographics, management experience, etc. Many don’t have the time or understanding to look into the ”command and control” center of the organization. The unspoken burdens, the cultural sticking points, the deeply rooted behavior patterns that originated in childhood, and the fixed, often unbending mindset of the founder or CEO. All of these narratives coalesce to give rise to the eventual toppling of the organization.
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Evaluating and Doing Business in a More Wholistic Way
How then do we seek to understand, learn, and apply the lessons learned from our unique experiences? How do we reframe our narrative so we are less likely to fail catastrophically in the first place?
Here are some suggestions:
​Consider your “Why”
As founders/CEO’s we have been given a vision for our work. The problem is we immediately build our plans, and execute to ultimate vision, instead of starting with what we have initially been given (think lowest-hanging fruit). We don’t allow the Master Designer to craft towards the vision at his pace and in His time, changing course, and bringing resources as He has planned. Abraham was given a vision for his inheritance, but that is not where he began. He was given Isaac as the starting point. God crafted the rest of that story in a manner that Abraham would have never conceived. We are given the vision – not to understand and create the exact 5-year plan for how we will get there – but to fuel us in our reason “why” we do what we do. Our “vision” is the reason we get out of bed every morning.
Consider your operational style
Our origins and behavior patterns established at a young age will be key in the formation of the operational styles we employ as adults. I worked with a young woman who grew up in difficult circumstances and faced many life obstacles. It was the behavioral style she developed as a child to overcome obstacles that heavily influenced her operational style as a young CEO. The reactive nature she developed in her youth has not always served her well as a founder. She was often over-reactive and tended to respond to the “tyranny of the urgent.” It has been difficult for her to approach her organization from a strategic and intentional mindset. Her plans were lacking and her focus was weak. This may be great for PR, but it did not bring her to a strong, sustainable organization. She needed to learn to wisely prioritize her limited resources, recognize her deficits, and bring in the talent necessary to complement her skills.
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Consider your ability/inability to be transparent
Much like first-date behavior, we always want to put our best foot forward. This is especially true with potential funding partners, donors, key employees, and partners. We want people to see us, our plans, our business, and our vision from a visualized picture of perfection. We don’t want to let people into the messy truths of our lives, and for good reason. When we let people get a glimpse of the real “ick” we have going on, there is every potential for harsh criticism, judgment, and possibly disengagement.
If you are reading this pre-failure, ask yourself, “If this is how I’m presenting myself and my business, will I glorify God in my misrepresentation?” If you are going through this exercise post-failure, the question becomes “Was I living this lie to my closest constituencies?” A very wise piece of advice I once heard was to always lead with your key weaknesses. Let people know that you know you have the potential to fail. And give them the reasons why failure could be a real possibility. You are not fooling anyone, except yourself, when you attempt to paint a perfect picture of a company that is already well on the road to success. A few good books I would put on the top of my list in helping you to realize and conquer this self-deception are Daring Greatly by Brené Brown, and Leadership and Self-Deception by The Arbinger Institute.
Recognize the danger of isolation
We can’t do this alone. Don’t even attempt it. God created us to operate with others in all facets of life. To all the women entrepreneurs out there, I am shouting this at you, as for some reason women often feel they have to do it alone and are very reluctant to ask for help.
No person possesses every talent and skill required to build a successful organization. Behind every charismatic and successful entrepreneur is an entire organization of well-equipped, smart-thinking, empowered individuals. If you don’t have the ability at your current stage to bring in all the right talent, you need to beg, borrow, and steal to get the right people to pour into you with the “right stuff” until you can bring in the complete team. If you are afraid to ask for help, then you have no business doing what you're doing.
Think of the world the way our Lord does
This is where I believe a good many of God’s people woefully miss the mark. We are to be in the world, but not of it. Use whatever worldly resources are at your disposal to promote and grow your organization. Jesus created all things good. There is a lot of good stuff out there, use it for His glory in building your company. Think craftily about how you will tackle the problems of competition, corruption, gaining favor, and scaling your business. Read the parable of the shrewd manager in Luke 16. Think of how your enemies and opponents would act in any given situation, then use that knowledge and understanding, undergirded by His Spirit in you to outsmart them at their own game. Be shrewd as serpents, we are fighting on a battleground, and there is much at stake. Be shrewd, but be gentle, do no wrong. You may only get one opportunity to do what you are doing. Understand the world you are operating in. You will be less likely to be deceived by what you understand.
Rethink your business model
We look to the world for the foundational principles of our business. Let’s go back to the basics of who God created us to be, and how we should be operating within his creation model. From our funding models to our operational models to our employee engagement models, and more. How this plays out will be different, based on your context. But his Word contains the wealth of wisdom by which we should be patterning our practices. For example, should an investment term sheet be looking at something different rather than only returning wealth to a few investors? Should it be a more comprehensive document? Investment is not financial only, investment is spiritual, mental, emotional, relational, and physical. What could a God-honoring, people-lifting, life-reconciling, Jesus-centered investment term sheet really look like if we put our best brains in a room to craft it? Dare to think differently about what he has given you, and how he wants you to steward it.
Use what he has given you wisely and use it to its fullness. What you have today may not be here tomorrow. Failing at business should not be an expectation or a foregone conclusion. Operate and think like you’re going to win. Our attitudes and the mindset we adopt in our lives directly correlate to our behaviors and actions. People who think like winners tend to act like winners.
You are in this to win, not for yourself, but for the Master Designer.