As you look around your small business, what do you see?

Is it the business you always imagined — operating like a well-oiled machine? 

Are you happy? 

Is the team doing meaningful work?

Are there wonderful systems to sustain and grow the business?

When tough times come, do you not fret because you’ve built margin and a strong culture to effectively endure?

Or, is it the opposite?

You’re constantly striving, regularly burning out your team, and floundering as people leave and you race to replace them. 

Does it seem as if things are crumbling around you or, at best, stagnant. 
Does it feel like you’re on the edge of a cliff where one slip up leads to what feels like an inevitable and tragic ending? 

Are you putting in a great deal of energy but failing to make any upward progress?

If you’re a business owner in the first group, congratulations. You’ve made The Jump

Those in the second, lets talk about how you can do the same.

Adult Development Stages

According to the Constructive Developmental Framework there are five potential levels of development we humans traverse in our life’s journey.
For the first few years, what we perceive is what we think is real (level 1). When a young child sees a jet in the sky, they literally think it’s two inches long. Around the middle school years, we fully shift to level two which is a win or lose black and white mentality (that’s why those years of parenting are so hard). While as much as 10% of the population, by some estimates, never moves beyond this stage, the rest roll into level three during their later teens and twenties. It’s an outside relational influenced stage that now understands conceptual frameworks and ideas (as opposed to literal understandings). Peer pressure, alternative authority figures, and outside idols play a large influence on our thinking and beliefs. 

These first three stages are outside-in perspectives that as much as we think are internally driven are mostly done outside of us.

This way of operating does not prepare and equip us to face the harsh challenges of life. We question everything as the way in which we see the world crumbles before us. Often, this is recognized at a mid-life transition (often in our forties), or crisis if it goes poorly. At this roadblock we have a choice as to whether we’ll take ownership of our perspective and how we see and make sense of the world (or not). As we lean in, doing the hard work we’ve likely been avoiding, we’ll begin to self-author who we are, what we believe, and how we’ll act in the world. We will craft our own paradigm. And for an extended period of time, it’ll bear great fruit equipping us to accomplish our goals, manage relationships, and get what we want.

But somewhere along the way, the world around us continues to change as we do not, and our way of doing things slowly becomes irrelevant. The effectiveness of our approach diminishes and we humans often blame the next generation and the changes to the system that have made our life more difficult than it once was. 

We’ll now face another fork in the road of either living cynically and bitterly or embracing this change outside us to change inside us. It’s at this level five where we are willing to let go of our paradigm and hold it with an open hand as we look through the world from other paradigm options. We learn from those who are so drastically different than us and see things we would not have seen on our own. And, this process is not just something we accept as it comes our way, but it’s an internal habit and mentality that causes us to proactively work it out. Often, it’s not until our sixties that humans make it into this stage, and only 10% of the population ever reaches this final stage.

The most effective leaders are those in level four and five. Most young-and-stuck small business owners are somewhere along the level three spectrum held back by the influences around them and the character depth they lack inside. Level three leaders must self-author their identity to make the jump.
Stuck level four leaders are using an approach that’s lost relevance in the current season and they’ve not yet accepted and embraced how they must change themselves to change their business.

The wonderful truth is that we can accelerate the developmental journey if we’re willing to lean into the things, events, and relationships which we’re not, otherwise, naturally inclined to do. 

It starts by facing our fears.

Facing Your Fears Is The Starting Point To Leveling Up As A Leader

What are you afraid of?

No, really. What are you REALLY afraid of?

What if your worst fear is holding you back?

Seriously. What if you’re being held back because you’re scared — scared that the alternative, of Jumping without assurances, could lead to a worse outcome?

Part of my struggle and floundering in the early years of business ownership came from a fear of failure. Growing up, there were numerous times, especially moments with my father, when I failed.

It is not unusual for an aspiring young man to face failure, but it was terrible and humiliating to experience the weight of the disappointment of others that followed. Lacking the perspective and maturity to navigate it, I instead never wanted to put myself in a situation where I would fail again. 

Ironically, fleeing our fears doesn’t make them go away. In fact, they often manifest to greater degrees and with more severe consequences.

My fear of failure led to making poor business decisions with my team and clients. Instead of pursuing a compelling and articulated vision, I was always looking over my shoulder to get away from this monster that was relentlessly pursuing me.

Fear of success was another one in hot pursuit. I was fearful that by becoming successful, the influence, affluence, and power that came with it would corrupt me. What if I became the very thing I feared becoming? What if by fighting the monsters, I became one of them?

“You Either Die A Hero, Or You Live Long Enough To See Yourself Become The Villain.” – Harvey Dent, The Dark Knight Rises

This fear, that my brokenness would lead to breaking others was not simply a mental concept, but something that was happening around me with the people I was leading and serving. I was corrupted, and it was leading me to hurt other people. Fearful of what could happen I was blind to what was actually happening. 

Facing our fears and looking in the mirror is not easy and often terrifying. But it’s the essential action required to not only move our business forward, but our life too. 

After we’ve leaned in and faced our fears head on (likely with help) there are three more stages for continuing the process of leveling up as a leader. 

  1. Take Responsibility: We must own our fears, how they’ve caused us to treat and behave towards others. And, through this ownership, we must decide and act on reconciling those past relationships and how we’ll operate towards current and future ones. We are not a victim but, going forward, an agent of change. 
  2. Lead Courageously: Facing our fears will help us to understand and navigate them, but it won’t eliminate them entirely. We’ll often still face scary and challenging situations. But our courage empowers us to think, act, and respond in the midst of our fear when we don’t feel like doing so. Often, we’ll need the support of others to embrace this courage. 
  3. Manifest Internal Change Outwardly: Authentic internal change will eventually lead to us thinking, speaking, and acting differently in the external situations we create or enter. True change will mean an external execution requiring the ownership of responsibility and courage to do so when the tensions around us make it difficult or intimidating to do so. 

Eventually, you’ll be forced to face your fears or you’ll be so tired of being “sick and tired” that you’ll be willing to do anything to change the context of your small business life. Courage and real change must soon follow if you’re to make the Jump

Once you take this step, there is a beautiful and meaningful small business on the other side.

Your Next Three Steps To Take Before Making The Jump

Leveling yourself up is the first of four steps to make The Jump towards creating the business you’ve always dreamed of operating. 

What follows are three more steps that further reinforce the first while also building upon it. 

  1. Build a Strong Business Foundation: Many small business owners start a company without clearly defining their intentions for doing so or clearly articulating the purpose, mission, values, and vision of the business. Failing to define these elements can cripple your efforts. These deeply-anchored intentions are crucial for creating a business that can sustain the most severe storms. 
  2. Bring Your Loyal Team Along: We cannot build a small business on our own, but not everyone is the right fit for the vision we’re pursuing. This step focuses on getting the right team to bring the vision to life, and leading them effectively.
  3. Sustain Bullet-Proof Systems: The final step before making The Jump has us operating with a mindset of maintaining a living business blueprint and building self-healing systems that allow for excellent execution and solid scalability.

Transforming your business from chaos to order starts with you as the business owner. If this is the business worth giving yourself to fully, it’ll require taking the essential hard steps to bring it to life. 

Dive Deeper Into The Jump And Explore A Five-Phase Process For Untangling Your Chaotic Business 

The preceding message is a survey of the high level concepts explored in my second book for stuck small business owners. 

The Jump: From Chaos to Clarity for Your Striving Small Business will walk you through my small business story, share insights, and guide you through a transformational process to help you move your perpetually small business forward. 

Click here to learn more about the book and how you can access the following free goodies.

Free Chapters (introduction plus the first two chapters)
The Jump Workbook Downloadable
Recommended Resources & Bonus Content
Top Ten Tools For Managing Your Small Business
Instructions On How To Access Your Free Digital Copy of Path of the Freelancer with the purchase of The Jump

Alternatively, click here to view on Amazon. Purchase the paperback edition and get the Kindle one for free. 

Share Your Thoughts Below

What do you think? Do you feel stuck in your small business? What above connects with you? Share your comments and insights below.

Jason Scott Montoya grows small business owners, teams, and incomes around Atlanta, Georgia. He also shares on his blog, stories and systems to live better and work smarter. A follower of the WAY, the Truth, & the Life, Jason lives with his wife and five children.