How Entrepreneurs Sabotage Themselves (And What to Do About It)

Most entrepreneurs don’t fail because they lack talent, intelligence, or opportunity. They fail because of one thing—self-sabotage. Whether it’s procrastination, overthinking, or constantly shifting focus, the truth is: most of the barriers to success are self-imposed.

In a recent episode of Transform Your Future, host Edward Isin sat down with JM Ryerson, author of Champion’s Daily Playbook, to unpack the hidden ways entrepreneurs sabotage themselves and—more importantly—how to break free.

Edward, a business strategist, content creator, and expert in reinvention, brought his own personal insights into the conversation, sharing real-world examples of how limiting beliefs and bad habits nearly derailed his own entrepreneurial journey.

“If you keep hitting the same wall, over and over again, it’s probably not the business, the market, or the competition. It’s something in your mindset, in your approach, that needs to change.” — Edward Isin

JM Ryerson echoed this, adding, "The biggest challenge most people face isn’t their business plan, their competitors, or even their skills. It’s the stories they tell themselves about why they can’t succeed."

In this article, we’ll break down the common patterns of self-sabotage and give you practical tools to shift from frustration to momentum.

Struggling to Hit Your Goals? This 90-Day Playbook Will Get You There Ep 56 Featuring JM Ryerson

The Audio Version at Transform Your Future With Eddie on Apple Podcasts

Youtube Video Version below

The Root of Self-Sabotage: Self-Limiting Beliefs

Most entrepreneurs don’t realize that their thoughts dictate their results.

If you believe:

• “I’m not a great salesperson.”

• “I’m not ready to take the next step.”

• “Other people have more resources than I do.”

Then you will make decisions that validate those beliefs, even when opportunities are staring you in the face.

Edward put it bluntly:
"I’ve seen so many entrepreneurs who are doing everything right—except they don’t believe they deserve success. And that belief alone is enough to hold them back.”

JM Ryerson agreed, explaining, "Most people don’t realize that success is an inside job. If you don’t work on what’s happening in your mind, all the strategies in the world won’t make a difference."

Self-sabotage isn’t always obvious. It shows up in subtle ways—perfectionism, fear of failure, overplanning without execution, avoiding tough conversations, or staying 'busy' without actually moving forward.

How to Stop Getting in Your Own Way

JM Ryerson’s Champion’s Daily Playbook introduces a simple, repeatable 90-day system to help entrepreneurs break through limiting beliefs and rewire their habits for success.

Here’s how to start:

1. Get Out of Your Own Head

Edward explained that one of the biggest shifts in his career happened when he stopped overthinking every decision.

“Perfectionism is just fear in disguise. If you’re waiting for the perfect time, the perfect opportunity, or the perfect circumstances, you’re going to be waiting forever.” — Edward Isin

JM Ryerson backed this up, saying, "If you can just get out of your head and start taking action, everything changes. Clarity comes from movement, not from sitting around thinking about what to do next."

Instead, focus on progress over perfection. Set deadlines, take action, and course-correct as you go.

2. Set a Daily Intention

Success doesn’t happen by accident. It happens when you approach each day with purpose.

Before starting your work, ask yourself:

• “What’s the single most important thing I need to accomplish today?”

• “How do I want to show up in my business?”

• “What energy do I want to bring to my team, my clients, my work?”

By practicing this daily for 90 days, you start leading your business instead of reacting to it.

Edward summed it up this way:
“You can’t win the year if you don’t win the month. You can’t win the month if you don’t win the week. And you can’t win the week if you don’t win today.”

JM Ryerson added, "Every great achievement starts with a single, intentional day. If you keep stacking those days, success is inevitable."

3. Replace Negative Thoughts with Gratitude

Negative thoughts are six times more powerful than positive ones.

That means every time you focus on what’s not working, your brain strengthens that pattern.

JM and Edward both agree: the fastest way to shift your mindset is to practice gratitude daily.

"If you want to change your life, start with gratitude. It rewires your brain to focus on abundance instead of lack," JM explained.

By taking two minutes every morning to write down three things you’re grateful for, you train your mind to focus on opportunities instead of obstacles.

4. Track Your Effort, Not Just Your Results

Many entrepreneurs get discouraged when they don’t see immediate results.

The problem? They only measure success by outcomes.

Instead, JM and Edward suggest measuring two things daily:

1. Your attitude – Did you bring the right energy today?

2. Your activity – Did you take meaningful steps toward your goals?

By tracking your habits instead of just waiting for results, you create momentum and eliminate self-doubt.

"Most people quit before success has a chance to show up. If you focus on the work and not just the outcome, you’ll be ahead of 90 percent of people." — Edward Isin

JM Ryerson added, "If you just commit to showing up and putting in the work every single day, eventually success will have no choice but to show up."

Breaking Free from Self-Sabotage

If you recognize any of these self-sabotaging habits in yourself, the good news is you can change them—starting today.

JM Ryerson summed it up perfectly:
"The greatest breakthroughs happen the moment you stop making excuses and start making moves. The world isn’t waiting for you to be perfect. It’s waiting for you to take action."

If you struggle with staying motivated, check out my free course, 8 Ways to Supercharge Your Motivation Workshop + Bonuses.

This workshop will help you:

• Identify your biggest motivation killers

• Learn how to reignite your drive

• Develop an unstoppable mindset

Get instant access here:
Supercharge Your Motivation

Final Thoughts: Take Back Control

Most entrepreneurs don’t struggle because of a lack of strategy—they struggle because of a lack of mindset discipline.

If you’ve been stuck, spinning your wheels, or procrastinating on what you know you should do, it’s time to break the pattern.

"Success isn’t a secret. It’s a decision you make every single day." — JM Ryerson

Want to Go Deeper?

Get JM Ryerson’s book, Champion’s Daily Playbook: Buy on Amazon
Learn more about JM Ryerson: Visit LetsGoWin.com

For more insights on entrepreneurship and personal growth, subscribe to Transform Your Future Podcast and follow Edward Isin on YouTube at@EddieIsin.