I’ve coached VC-backed founders, 7-figure creators, and bootstrapped entrepreneurs across industries (AI, CPG, tech, media, etc.).
Each of them struggled with at least one major issue that was leading them toward failure.
I could lecture you about all the things you need to do to build a successful business, but that would be long and boring.
Instead, here are 9 ways to guarantee your business fails…
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1. Let Fear Stop You
The most common limiting beliefs that hold entrepreneurs back from putting themselves and their ideas out into the world are what I call the Four Horsemen of Fear.
Fear of Failure whispers things like:
- What if I’m not good enough to make it work?
- What if I can’t figure it out?
- This probably won’t work.
It tricks you into giving up before you even begin.
Fear of Ridicule whispers things like:
- What if my audience or customers hate it and leave?
- What will my friends and family think?
- People will probably make fun of me.
It tricks you into staying small and never taking a chance.
Fear of Uncertainty whispers things like:
- I have too many ideas to choose from.
- What if I make the wrong choice?
- I need more info to feel “ready.”
It paralyzes you in a constant state of over-analysis.
Fear of Success whispers things like:
- What if I become corrupted by power and influence?
- What if I don’t deserve success?
- What if I lose my ambition?
It tricks you into abandoning your path right as you’re on the edge of victory.
So keep letting the Four Horsemen of Fear hold you back instead of facing them and developing the courage to move forward.
You’re guaranteed to fail.
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2. Believe Your Toxic Personal Narratives
Personal narratives are the stories you tell yourself about:
- Who you are
- What you deserve
- What you’re capable of
Personal narratives can come from:
- How we were raised (cultural pressures, critical parents)
- Past relationships (shitty exes or unsupportive friends)
- Career experiences (awful boss, toxic work environment, business failure)
Our personal narratives become the white noise in the background of our mind—a quiet but constant hum of insecurity and inadequacy.
If you believe you’re “broken” or “unworthy,” or if you believe the world is corrupt and against you, it affects every decision you make and skews your perception about what’s possible.
So keep rehearsing your toxic personal narratives instead of learning to deconstruct and rewrite them to be more empowering.
You’re guaranteed to fail.
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3. Chase False Goals
Every goal, idea, or opportunity has the potential to get you one step closer to—or one step further away from—the life and business you’re ultimately trying to build.
Most entrepreneurs obsess about the “best” goal-setting frameworks and other productivity hacks.
But they never take the time to differentiate false goals from optimal goals.
False goals give you a sense of progress but don’t actually move you closer to your ultimate desired outcome—so optimizing them is pointless. False goals include things like organizing your inbox, “branding” brainstorming sessions, and researching tech stacks.
Optimal goals, on the other hand, actively move you closer to where you’re trying to go. Optimal goals might include things like launching your product, talking to customers to improve your product, and negotiating partnerships to expand your business.
So keep focusing on optimizing false goals instead of clarifying optimal goals.
You’re guaranteed to fail.
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4. Fail to Ruthlessly Prioritize
Most entrepreneurs think they’re too busy, when they actually just suck at prioritizing.
They try to be on every social platform at the same time, theorycraft how to build a complete content ecosystem and robust value ladder from day one, and constantly tinker on multiple projects at the same time.
Instead of clarifying what actually matters and ruthlessly saying no to everything that isn’t that thing.
Or they try to do everything themselves until they inevitably become the bottleneck in their business.
I coached a tech founder who was spreading themselves too thin trying to be involved in every minute aspect of their business, which had led to stalled revenue growth and constant stress. With a simple prioritizing exercise, they were able to free up 15 hours every week from their schedule—business grew, their stress reduced, and they were able to spend that extra 15 hours a week on higher leverage work (and sometimes relaxing and playing the guitar). The only reason they were “too busy” was because they weren’t effectively prioritizing.
So keep trying to do everything instead of focusing on the few things that matter.
You’re guaranteed to fail.
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5. Over-Index on Measuring Outcomes
Outcomes are important to succeed in business and easy to measure.
But you don’t actually control outcomes.
- You don’t control if you hit a certain MRR.
- You don’t control if people buy or subscribe.
- You don’t control if you hit a certain conversion rate.
And when you focus on things outside your control, two things can happen:
You feel frustrated and helpless when you don’t achieve the outcome that was never in your control in the first place.
You chase the outcome to the point you compromise your integrity, sacrifice your reputation, or create new problems along the way (like the Cobra Effect).
So keep focusing on outcomes outside your control instead of identifying the processes you do control.
You’re guaranteed to fail.
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6. Focus on Your Weaknesses
Humans are wired to find problems.
So it’s easy to make excuses instead of changes.
It’s also why so many people are great at listing out all their weaknesses, but suck at identifying their superpowers.
Because identifying your weaknesses is natural, while identifying your strengths is a skill most people never take the time to practice.
And until you know what you’re great at, you’ll never know how to leverage it to succeed.
So keep focusing on your weaknesses instead of learning how to take an inventory of your strengths and superpowers.
You’re guaranteed to fail.
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7. Try to Brute Force Everything
Who’s stronger: the person you can lift 1,000 lbs with their bare hands or the person who can lift 100 lbs with their bare hands?
Answer: It doesn’t matter
Because if the “weaker” person applies leverage with a fulcrum and lever, they can move whatever they want—way more than any single human is capable of moving on their own.
Leverage is powerful—outsourcing, delegating, and creating systems that divorce your time from income.
Yet the least successful entrepreneurs try to brute force their way through business, trapping themselves in a 1:1 ratio of effort exerted to whatever piddly outcomes they can eke out.
So keep brute forcing everything and avoiding developing powerful systems that allow you to tap into incredible leverage.
You’re guaranteed to fail.
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8. Stay in Reactive Mode
If you’re constantly:
- Jumping from one decision to the next
- Putting out one fire after another
- Running from project to project
You’re living in a constant state of reactivity.
When you’re in reactive mode, it means you’re stressed, and stress cripples your decision-making abilities.
You’re never ahead of the problem or thinking long-term. You’re constantly trailing behind the problem, trying to catch up and survive day to day.
Being in reactive mode also prevents you from uncovering blindspots in your business that can lead to failure.
So keep staying in reactive mode instead of developing systems to switch into a proactive mindset.
You’re guaranteed to fail.
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9. Stay Unaligned in Everything You Do
Doing unaligned work is a surefire way to live in mediocrity, then get to your deathbed and look back at your life with regret.
Yet so many entrepreneurs choose to build businesses that are unaligned with their values, the impact they want to have, and the life they want to live.
When your work doesn’t resonate with you on a deep level, one of three things happens:
- You give up.
- You half-ass it because you’re not committed to making the sacrifices it’ll take.
- Or you “succeed,” but victory feels hollow because you spent your life chasing the wrong things.
Because when you choose money over meaning, you end up miserable.
So keep doing unaligned work and living in mediocrity instead of building a values-aligned life and business.
You’re guaranteed to fail.
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Final Thoughts
If you’re dead-set on guaranteeing your business fails, these strategies are phenomenal. Every founder, entrepreneur, and creator I’ve worked with struggled with at least one of these. Thankfully, they were able to course correct before they continued down the path that was ultimately leading them to failure.
It reminds me of one of my favorite Charlie Munger quotes:
“It is remarkable how much long-term advantage people like us have gotten by trying to be consistently not stupid, instead of trying to be very intelligent.”
— Charlie Munger
Oftentimes, achieving success simply comes down to avoiding failure.
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P.S.
If you’re tired of feeling like what you’re putting all your time, energy, and attention into isn’t getting you closer to the life and business you ultimately want to build—here are a few options that can help:
- Book a laser coaching call with this link. In this one-off coaching session, we’ll go deep on a single obstacle, goal, or idea you need to work through. You’ll walk away with the clarity and strategy you need to move forward.
- Check out my on-demand coaching course here. You’ll get all the foundational skills that help my private coaching clients succeed in life and business by clarifying what matters, overcoming obstacles in your way, and developing a specific plan to succeed on your terms.
And if you want to learn more about success, check out How to Make Success Inevitable (7 Skills Anyone Can Learn) next.
