Do successful entrepreneurs still experience self-doubt? 

Aug 23, 2022 | entrepreneur, imposter syndrome | 0 comments

Do you think that there’s a point you’ll get to with your business where you no longer experience imposter syndrome, self-doubt, or fear of failure? Where you’ll no longer find yourself procrastinating? 

Often my clients tell me that they feel like something is wrong with them because they haven’t arrived at that place yet. They’re outwardly successful, but still full of self-doubt and struggling to motivate themselves to keep going.

I’ve spoken with quite a few entrepreneurs, in a variety of fields and points in their career, who are from countries around the world. Based on those conversations, I am pretty sure that there is no such thing as “entrepreneur nirvana” where you suddenly arrive and are free of all the stress and self-doubt. 

However, I recently decided to do some digging and make sure I wasn’t biased. After all, my clients usually come to me to talk about places they’re struggling. (Also, sidenote – as a coach and former therapist, people in all parts of my life, even strangers, tend to open up to me about their problems).

I decided to do some very unofficial “research” which consisted in doing an Instagram poll and asking about people’s experience in a Facebook group for entrepreneurs.

Successful Entrepreneurs share their struggles with self-doubt

In my Instagram poll, several people said that truly successful entrepreneurs do reach a point where they’re free from procrastination, self-doubt, imposter syndrome, and fear of failure. 

I can definitely see why people would say that.

But I suspect it’s more a case of people *wishing* that this state existed (it sounds pretty nice, right?). 

The Facebook group results however were unanimous. Taking your business to a new level will always lead to more internal challenges and even more demands to work on your mindset.

Here are a few statements I want to share with you –

“My imposter syndrome shot up after I had a $124K month! I had to sort through a lot to be able to move forward again and believe it wasn’t just a fluke.”

“I start to feel this “buzz” and sometimes the fight or flight mode is activated…after $5K months it started to show up and takes continuous mindset work.” 

“No, actually, the more you make, the bigger it becomes.” (response when asking a guru in their industry if imposter syndrome ever goes away)

“There’s always more as you work on the next level. I wouldn’t say it’s a new batch of concerns, it’s usually just the same ones adjusted for the new goal.” 

The takeaway was this – New level, new (or same old) devil. 

I was so appreciative of those business owners who shared their own struggles with mindset. Not only because it helped me feel more confident in my own hypothesis. But even more because for every person that responded in the group I’m sure there were many others reading their comments and breathing a sigh of relief to know that they were normal for feeling the same way. 

So if you’re experiencing self-doubt as you up-level your business, I want you to know that your experience is completely normal, regardless of how “successful” or not you may feel. Try reframing your self-doubt as the inevitable growing pains of a successful entrepreneur. And growing pains happen when we’re growing and making progress which is actually a pretty great thing! 

If you want to learn how to cope with self-doubt and imposter syndrome so that it doesn’t hold you back or drain you as an entrepreneur, set up your free 45-minute game plan call with me. In this call, we can discuss how my 1:1 coaching can help you to feel more confident and better able to handle the ups and downs of entrepreneur life. 


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I'm a therapist-turned-coach who loves working with clients around the world! I work with the globally mobile community to support them through transitions as well as entrepreneurs who need support navigating the rollercoaster of entrepreneur life.

I'm also the co-founder of the Location Independent Therapists (LIT) Community, a mom, a self-compassion advocate, and an aspiring author.