Why Entrepreneurs Sabotage Their Own Success (and How to Stop it)
If you lead a healthcare organization or run a private business, chances are your biggest threat is not the economy, insurance reimbursements, or hiring challenges. The biggest threat is more personal. It is the subtle but persistent way leaders quietly undermine their own progress just as growth begins to feel real.
On a recent episode of All Things LOCS, we explored why so many driven entrepreneurs experience breakthrough moments and then slip backward into old patterns. As Dan said during the episode, "You hit a point of success, and then you do something on purpose to hurt yourself and sabotage."
This pattern shows up as impulsive decisions, unnecessary drama, switching strategies too quickly, avoiding key conversations, or taking on tasks that belong with someone else. The result is growth followed by contraction, clarity followed by confusion, and a business that never quite reaches the next level.
This guide breaks down what self sabotage looks like in leadership, how it erodes organizational culture and operations, and what practical actions help leaders expand into the next version of themselves instead of shrinking back into comfort.
Remember, you started your own business not to self sabotage it. You started it to serve others, while simultaneously wanting to create a sustainable success.
What Is the Upper Limit Problem?
The Upper Limit Problem, a term coined by Guy Hendricks, is the tendency to subconsciously create a setback when life exceeds your internal “thermostat” for success, love, abundance, or happiness.
“People unconsciously sabotage themselves when they experience more success, more love, abundance, or happiness than they believe that maybe they’re allowed to have.”
The key word is unconsciously.
Most entrepreneurs are not sitting at their desk thinking:
“How can I purposely screw myself over?”
But from the outside, the behavior can look obvious. Your business coach sees it. Your spouse sees it. Your team definitely sees it.
As Dan said:
“From the outside… someone is sitting there saying, ‘What the hell are you doing? How isn’t this so obvious?’”
The Upper Limit Problem creates a hidden ceiling. When you get close to breaking through it, your nervous system tries to pull you back to what feels familiar, even if familiar is chaotic.
Common Self Sabotaging Behaviors in Business
Self sabotage is not always dramatic. Sometimes it is subtle and sometimes it is loud. Sometimes it is disguised as “being strategic.” One thing it isn't? A sound business strategy to be used by all successful business owner. However, if you are one of the leaders who self sabotages, the first step is being self aware of the pattern.
Below are the most common ways this pattern shows up for business owners, healthcare leaders, and founders.
Impulsive decisions that break your normal logic
One of the clearest tells is when a normally analytical leader suddenly starts making emotion-based decisions.
“If someone is pretty analytical… and then you start noticing that they’re getting more impulsive, that’s a dead ringer for us.”
This often looks like:
Changing pricing without thinking it through
Firing off reactive messages
Saying yes to the wrong opportunity
Buying a new tool because it feels exciting
Making a major hiring decision on a whim
Overcommitting to busy work that feels productive
This is the entrepreneur classic.
“Overcommitting and overbooking themselves with busy work that is not productive.”
It is not laziness. It is avoidance disguised as effort.
Busy work gives you a hit of control. It also keeps you from facing the real growth tasks like delegating, holding people accountable, having difficult conversations, and making decisions that change the business permanently.
Switching strategies constantly (even when it is working)
This one is brutal because it damages momentum and destroys trust.
“You have something that you found out that it works, and then you decide, ‘Let’s do something different. Let’s take a sharp 90-degree turn here.’”
Even worse, it often comes with poor communication:
“Not communicate that to the team at all and expect to maybe have a good outcome.”
In healthcare organizations, this can wreak havoc across scheduling, patient experience, billing, and staff morale. In any business, it creates whiplash.
Creating problems that do not exist
Sometimes self sabotage looks like emotional chaos.
“Everything’s so good… and then they gotta come in just one day screaming, creating drama, creating unnecessary conflict.”
This is what happens when a leader is addicted to chaos. Calm feels unsafe. Calm feels unfamiliar. So the leader creates a storm to feel normal again.
Avoiding systems and critical decisions
Avoidance is a self sabotage strategy because it delays the very actions that would stabilize growth.
Avoiding delegating
Avoiding raising prices
Avoiding firing or role changes
Avoiding accountability
Avoiding tough conversations
And in healthcare, this has a compounding cost: it affects patient experience, employee retention, and revenue cycle performance.
Sabotaging revenue spikes by overwhelming fulfillment
One of the most overlooked patterns is what happens after a win; and it's one of the biggest indicators that that not only are you self sabotaging, but you are afraid of success.
You said it clearly:
“When you do make a sale, you have to fulfill on that transaction… then you can overwhelm your team.”
It is common to chase growth without building the operational structure to hold it. That creates stress, drops quality, and can trigger even more sabotage.
The Motivating Factors Behind Self Sabotage
Imposter feelings and self doubt
It is one thing to recognize self sabotaging behaviors in yourself. It is another thing entirely to understand why those behaviors show up in the first place. Research suggests that more than 80 percent of entrepreneurs and small business owners experience imposter feelings throughout their careers, which means the majority of high achievers wrestle with internal questions about worthiness even as results improve.
As one study noted:
"The imposter phenomenon correlates with self sabotaging behaviors, especially when success feels threatening."
These persistent negative thoughts distort perception and make growth feel unearned or fragile. As a result, leaders often retreat or hesitate when progress becomes visible, not because they lack ability but because they fear exposure, judgment, or disappointing others. In this state, expansion feels risky while shrinking back into familiar patterns feels safer.
A practical tip:
To combat imposter syndrome, small business owners can intentionally collect proof of success. Keeping a written record of wins, testimonials, positive feedback, and moments of progress creates an evidence based foundation that counters negative self talk.
Returning to this record during moments of doubt reinforces self awareness and strengthens self confidence, especially when success begins to accelerate faster than internal belief.
Identity lag when success comes quickly
Rapid growth can create a gap between what you are achieving and who you believe yourself to be. This gap is often subtle and shows up internally before anyone else notices it.
"Someone has the identity of six months ago but they are experiencing the success of what we planned for three years from now."
This identity lag feels disorienting because external validation rises while internal self perception stays anchored in the past. When growth moves faster than identity, the mind often reacts by slowing momentum or creating friction that brings results back down to a level that feels emotionally familiar. Leaders do not sabotage because they want to fail. They sabotage because their current environment outpaces their internal story, and the nervous system prefers what it knows.
Fear of outgrowing the people you care about
Leadership growth is not only about performance metrics. It also involves relationships and the stories leaders carry about belonging, loyalty, and responsibility. Some entrepreneurs quietly worry that success will distance them from family, friends, or peers.
"Maybe I am doing better than my parents or the circle I grew up with. I do not want to make them feel bad."
This deep rooted fear rarely enters open conversation, yet it influences decision making. Leaders may soften goals, limit opportunities, or avoid bold moves because unconsciously they equate success with separation. Rather than risk discomfort or potential conflict, they reduce their own potential and stay small. The cost is not just financial. It is emotional, and it shapes who they allow themselves to become.
How Hidden Behaviors Damage Your Team and Culture
One of the strongest motivators for personal change is recognizing how our behavior affects others. Self sabotaging behavior rarely stays contained. Even when rooted in personal doubt or fear, it creates a ripple effect throughout the business.
"He came in screaming over the smallest thing. Now everybody is on edge."
This type of inconsistency leads to:
Defensive communication
Low accountability
Quiet resentment
Loss of trust
As shared in the episode:
"I want you to understand what this is doing not just to your business, but to the people in your business and your clients."
Teams watch leadership closely. When the leader takes one step forward and then two steps backward, high performers begin to feel uncertain about the future. The most capable employees naturally gravitate toward environments that reward growth and provide stability.
If your leadership patterns repeatedly create confusion or instability, great employees will quit and the culture will drift toward mediocrity. Momentum slows not because the team lacks skill, but because the leader unintentionally blocks progress.
Measuring the Cost: How Much Is Self Sabotage Really Costing You
If the consequences of self sabotage feel vague, make them visible. Mapping behaviors allows leaders to connect internal patterns with external results. Start by identifying a triggering action and follow the ripple effects through your operations and your key performance indicators.
"You can overlap the flowchart with your KPIs and see how these behaviors impact the team."
When this level of clarity is applied, leaders often discover the true cost of hesitation, inconsistency, or emotional reactivity. These costs frequently include:
Turnover expenses
Reduced revenue per provider
Increased cancellations
Lost opportunities
Lower retention
Once leaders clearly see how self sabotaging behavior reduces business success, accountability shifts from optional to necessary. The decision to change becomes easier because the consequences are no longer theoretical. They are measurable and impactful.
How To Break the Pattern and Lead at a Higher Level
1. Notice your sabotage pattern
The first step is to recognize your go-to response when stressed or stretched. Common patterns include:
Becoming autocratic and controlling
Avoiding tasks and decisions
Acquiescing and saying yes to everything
Attacking and picking fights
"That is your biology informing you of where your state is."
Once you can name it, you can interrupt it.
2. Pause and ask: "What would my genius self do?"
When you feel triggered, do not respond immediately.
"Give yourself a moment before you respond to anything. It is easy when we are in that emotional state to just react, and that is not good to do."
Instead, ask:
"What would the most elite version of me do in this situation?"
This simple question pulls you out of survival mode and into leadership mode.
3. Delegate before you feel ready
Waiting until you are underwater guarantees sabotage.
"Waiting until you are overwhelmed guarantees sabotage. In so many words, it just means get help."
Look at your task list and ask:
What am I doing that I am terrible at?
What am I good at but hate?
What is someone on my team excited to take on?
Give them a chance to surprise you. Delegation is not weakness. It is alignment.
4. Design your Zone of Genius
We talked about a simple matrix:
Zone of incompetence: you are not good at it and do not like it
Zone of competence: you are capable, but it drains you
Zone of excellence: you are very good and it makes money
Zone of genius: you do it effortlessly and it drives the business forward
"When you keep someone in their zone of genius, self sabotaging behavior goes down. It is hard to sabotage when you are doing something you enjoy and are good at."
Your job as a founder or leader is to spend as much time as possible in your zone of genius, then build systems and people around everything else.
5. Celebrate wins and normalize success
If you only ever move the goalpost, you train your brain to believe you never measure up.
"You hit a milestone and then say, 'It could have been better.' Then you ask, 'Why does my confidence suck?'"
Celebration is not fluff. It is identity work.
"Normalizing success raises your internal thermostat. Winning becomes normal."
For your team, recognition is often the difference between staying and quietly looking for another job. For you, it is the antidote to the belief that you are always behind.
Celebration is not indulgence. It is reinforcement. It sends a powerful signal to your nervous system that success is not temporary. It is a habit you can sustain, and one that is necessary to improve mental and physical health, while also helping break free from self destructive behaviors.
Questions To Reveal Where You Are Holding Yourself Back
These prompts encourage self awareness and help uncover patterns that limit potential:
When things go well, what do I do next?
Where do I repeat two steps forward and one step back?
What uncomfortable decision am I avoiding?
What is the cost of maintaining this pattern?
How would my future self respond to this situation?
Reflection creates clarity. Action creates change. Sustainable success requires both.
Final Thought: Growth Requires Identity, Not Just Strategy
Self sabotage does not happen because leaders are weak. It happens because growth demands an identity that matches the size of your goals.
As Antonio said:
"Your time is precious. If you can integrate these things into your life, the compound effect is through the roof."
Spot the pattern and break it once. Then build systems and support that keep you expanding instead of shrinking. Your team, your business, and your future self are waiting for the version of you who believes growth is not a threat, but a responsibility.
🎧 Want to elevate your practice?
If this topic hit a nerve, the full episode goes even deeper into how business owners unknowingly limit their own success, how to break those patterns, and how to step into the next version of your leadership.
👉 Listen here and Subscribe so you never miss an episode
Your next breakthrough is not another tactic. It is learning to stay grounded when things start working.
➡️ Ready to eliminate operational chaos, improve financial performance, and build a practice that grows without burning you out?
Book a discovery call with Best Practice Strategies and take the first step today.
Frequently Asked Questions About Self Sabotage in Business
What does self sabotage look like in business?
Self sabotage in business often shows up as impulsive decisions, switching strategies too often, micromanaging, avoiding hard conversations, or abandoning what is working when success finally arrives. These patterns quietly limit growth because they create instability for the team, disrupt operations, and prevent leaders from building repeatable systems that support long term momentum.
Why do entrepreneurs sabotage their own success?
Entrepreneurs self sabotage for several reasons, including imposter feelings, identity lag, fear of success, and trying to stay in familiar patterns even when those patterns restrict growth. When external results move faster than internal beliefs, leaders often pull back to a level that feels emotionally safe, even if it limits profit and progress.
How do I know if I am holding my business back?
You may be holding your business back if you feel resistance right after wins, avoid decisions you know you need to make, switch strategies frequently, or notice recurring patterns that stall momentum. If team members are confused, frustrated, or adapting to constant change, those reactions may also signal self sabotaging leadership behaviors.
How can I stop self sabotaging my business growth?
The most effective first steps are identifying your self limiting behaviors, pausing before reacting, delegating work before you feel ready, and spending more time in your zone of genius. Pairing mindset shifts with strong operational systems helps you break old habits and lead with clarity when success starts to scale.
How does self sabotage impact organizational culture?
Self sabotage erodes trust because it introduces unpredictability into leadership decisions. When priorities constantly change or team members are blindsided by new initiatives, employees become hesitant to take ownership. Over time, the culture shifts from proactive to defensive, which increases turnover and lowers morale.
What is identity lag and how does it limit entrepreneurs?
Identity lag happens when your business grows faster than your internal identity. You may have the revenue, systems, or team that match the next level of success, but your self image still reflects the past version of you. That disconnect feels uncomfortable and can cause leaders to shrink their goals or revert to old behaviors until they feel worthy of growth.
Should I get coaching or consulting to overcome self sabotage?
Coaching or consulting is valuable when you recognize recurring patterns but cannot consistently break them alone. Expert support can help you see blind spots, build systems that reduce chaos, and create accountability so your leadership behaviors align with the level of growth you want.
About the Author
Daniel Neissany, DPT is a healthcare entrepreneur, consultant, and co host of the All Things LOCS podcast, where he helps leaders improve their Leadership, Operations, Culture, and Strategy so they can grow without burning out their teams.
Dan has led and advised outpatient clinics through multi million dollar growth, built systems that reduced chaos in busy practices, and helped healthcare owners use real data to make better decisions.
