4 Ways Successful Entrepreneurs Gaslight Themselves (And How to Stop)

Editor's Note: This post was originally published in July 2023 and updated in December 2025 with insights specific to entrepreneurs who gaslight themselves into staying in businesses they've outgrown.

If you're a successful entrepreneur who feels stuck, chances are you've become an expert at gaslighting yourself.

You tell yourself you "should be grateful" when something feels off. You dismiss your dissatisfaction as "just needing a holiday." You convince yourself that if you just hired better, systemised more, or pushed harder, everything would feel right again.

This is self-gaslighting — and it's one of the main reasons entrepreneurs stay stuck without ever getting clarity on what they actually want.

We all have an inner voice that guides us, warns us, and celebrates our achievements. But somewhere along the way, that voice stopped supporting you and started undermining you. It downplays your reality, dismisses your needs, and convinces you that what you're feeling isn't valid.

The problem isn't that you don't know what you want. It's that you've been gaslighting yourself for so long, you can't hear your own truth anymore.

Let's explore four common ways successful entrepreneurs gaslight themselves — and how to stop.

What Is Self-Gaslighting?

Gaslighting, traditionally, is when someone manipulates you into questioning your own reality. They make you doubt your perceptions, memories, or feelings.

Self-gaslighting is when you do this to yourself.

You override your own instincts. You dismiss your feelings. You convince yourself that what you're experiencing "isn't that bad" or "other business owners have it worse."

For entrepreneurs, self-gaslighting becomes second nature. You've built this business through grit, determination, and pushing through discomfort. So when your gut is trying to tell you something, you gaslight yourself into ignoring it.

The result? You stay stuck — not knowing if you should stay, redesign, or leave. Because you can't get clarity when you're constantly dismissing your own reality.

Way #1: "I Should Be Grateful" (When You Actually Feel Something Else)

What It Sounds Like:

• "I built this from nothing — I should be grateful."

• "Other people would kill for this kind of success."

• "I'm just being ungrateful/spoiled/entitled."

• "Look at the revenue — I have no right to complain."

• "I should be happy with what I've achieved."

What's Really Happening:

Something feels off. Maybe you dread Monday mornings. Maybe you fantasise about doing something completely different. Maybe you feel trapped. But admitting that feels dangerous — like you're ungrateful or you've failed somehow.

So instead, you gaslight yourself into believing you should be happy.

The truth: Success doesn't automatically equal fulfilment. You can have a profitable business and still feel disconnected from it. You can be grateful for what you've built AND want something different.

Why Entrepreneurs Do This:

You've tied your identity and self-worth to this business. Admitting you're not fully happy feels like admitting failure.

But here's the reality: Feeling disconnected from your business doesn't mean you failed. It might mean you've changed. Or the business has changed. Or both.

And you can't figure out what to do next if you won't even admit how you actually feel.

How to Stop:

Ask yourself: "If I removed 'should' from the sentence, what would be true?"

Instead of "I should be grateful," try: "I built something successful. And something still feels off."

Both can be true at the same time.

Way #2: "I Just Need to Fix My Mindset/Systems/Team" (When You Won't Consider That Deeper Change Might Be Needed)

What It Sounds Like:

• "I just need better boundaries."

• "If I systematised this better, I'd enjoy it again."

• "Maybe I should hire a VA/COO/marketing person."

• "I probably just need a holiday."

• "It's a mindset issue — I need to work on my gratitude practice."

What's Really Happening:

You're gaslighting yourself into believing the problem is always fixable with optimisation — because considering that you might need deeper change is too scary.

The truth: Sometimes better systems ARE the answer. Sometimes you DO just need better boundaries. But sometimes, the issue is more fundamental. Maybe you've outgrown your role. Maybe the business needs to evolve. Maybe you need to redesign entirely.

You can't know which it is if you won't even consider the deeper possibilities.

Why Entrepreneurs Do This:

Because if it's just a systems problem, there's a clear solution. But if it's something deeper — like fundamental misalignment with who you are now — then you have to face bigger questions. And that's uncomfortable.

How to Stop:

Ask yourself: "If I had perfect systems, perfect boundaries, and unlimited help... would this feel completely right?"

If the answer is "I'm not sure" or "probably not," then it's not just a systems problem.

Try this instead: "Maybe better systems would help. And maybe I also need to look at the bigger picture."

Way #3: "I Can't Change Anything — Too Many People Depend on Me"

What It Sounds Like:

• "My team needs me."

• "My clients would be lost without me."

• "I can't just change everything — what about everyone else?"

• "It's selfish to want something different."

• "I owe it to everyone who believed in me to keep going exactly as I am."

What's Really Happening:

You're using other people's needs to gaslight yourself out of even considering what YOU want. You've convinced yourself that your desires don't matter as much as everyone else's.

The truth: You exploring what you want doesn't mean abandoning your responsibilities. Whether you end up staying and redesigning your role, or transitioning strategically — either way, you can do it responsibly.

But you can't make good decisions for anyone (including your team and clients) if you won't even admit what you need.

Why Entrepreneurs Do This:

Because admitting you want something different feels selfish. You've built something that employs people, serves clients, and generates revenue. Even considering change feels like betrayal.

But here's what nobody tells you: staying in a role that's draining you while never exploring alternatives doesn't serve anyone. Not your team, not your clients, and certainly not you.

How to Stop:

Ask yourself: "Can I care about my team AND explore what I need? Are those really mutually exclusive?"

The answer is no. You can be responsible AND honest about what you want.

Try this instead: "I care about my team. And I'm allowed to explore whether this is still the right role for me."

Way #4: "I Built This — I Can't Question It Now"

What It Sounds Like:

• "I've invested 10 years into this — I can't question it now."

• "What would people think?"

• "All that work would be for nothing."

• "Real entrepreneurs don't doubt themselves like this."

• "I just need to push through."

What's Really Happening:

You're using the sunk cost fallacy to gaslight yourself out of even considering whether this is still the right path. You've convinced yourself that because you've invested years, you're not allowed to question whether it still fits.

The truth: Those years you invested aren't wasted, regardless of what you decide next. You learned. You grew. You built something. And now you're at a crossroads.

Maybe the answer is staying and redesigning your role. Maybe it's transitioning out. Maybe it's something in between.

But you can't figure out the right answer if you won't even let yourself ask the question.

Why Entrepreneurs Do This:

Because questioning whether you want to continue feels like admitting the last 10 years were a mistake. It's not. You built something real. And now you're entering a new phase where you get to decide what's next.

That's not failure. That's growth.

How to Stop:

Ask yourself: "If I could design my ideal relationship with this business (or my ideal next chapter) without judgment, what would it look like?"

Let yourself answer honestly. Not what you should want. What you actually want.

Try this instead: "I built something successful. And I'm allowed to explore what I want next — even if the answer isn't what I expected."

The Cost of Self-Gaslighting

When you constantly gaslight yourself, here's what happens:

• You stay stuck in confusion for years — unable to make a decision because you won't even admit how you really feel

• You lose trust in your own instincts and desires

• You can't move forward (whether that's redesigning or transitioning) because you're still pretending everything is fine

• You disconnect from who you actually are beneath the "business owner" identity

• You waste years of your life dismissing your own reality

Self-gaslighting doesn't make you more grateful or more committed. It makes you stuck.

How to Stop Gaslighting Yourself

1. Notice When You're Doing It

Start paying attention to the phrases you use:

• "I should be grateful"

• "I just need better systems"

• "Other people depend on me"

• "I've invested too much to question it now"

These are red flags that you're gaslighting yourself instead of getting honest.

2. Challenge the Thought

When you catch yourself self-gaslighting, ask:

• Is this objectively true, or am I dismissing my own reality?

• What would I tell a friend who felt this way?

• What am I afraid will happen if I admit how I really feel?

3. Give Yourself Permission to Be Honest

You don't need to have the answer figured out. You just need to start being honest about the question.

Practice saying: "I built something successful. And I don't know if this is still the right fit for me. Both of those things can be true."

4. Get Support

Breaking the self-gaslighting habit is hard to do alone, especially when you've been doing it for years.

Working with a coach can help you:

• Recognise when you're dismissing your own reality

• Get honest about what you actually want (not what you think you should want)

• Explore your options without judgement — whether that's redesigning your role or transitioning out

• Make a decision you feel confident in (instead of staying stuck in confusion)

Stop Gaslighting Yourself Into Staying Stuck

If you recognise yourself in these patterns, know this: you're not ungrateful, weak, or broken. You've just been trained to dismiss your own reality for so long that you can't see it clearly anymore.

But it doesn't have to be this way.

The Redesign helps entrepreneurs stop gaslighting themselves and start trusting their own experience. Through 6 months of coaching, you'll:

• Recognise when you're dismissing your own needs to stay "grateful"

• Get honest about what you actually want (stay and redesign, or transition out)

• Explore your options without the noise of "should"

• Build confidence in your decision — whatever it ends up being

Not sure where to start? Book a free 50-minute clarity call. We'll get honest about what's really going on and whether coaching is right for you. No pressure, no sales pitch — just truth.

You deserve to trust yourself. And you deserve support in figuring out what comes next.

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