Asking Yourself the Hard Questions on Your Entrepreneurial Journey

The entrepreneurial journey is different for everyone. There’s no one size fits all path to success. And it always should begin by asking yourself some hard questions.

On a recent volume of The Psychology of Entrepreneurship, I sat down with Fred Schebesta, co-founder of, one of the most popular comparison sites on the web. Fred describes himself as a “bootstrap entrepreneur”. He always knew he would forge his own path in this world, and do whatever it took to be successful. However, he didn’t realise that in order to do that, he had to do some hardcore self-discovery.

How committed are you to self-discovery?

Fred was swimming along on his entrepreneurial path, climbing to the top of the food chain. However, “I didn’t feel worthy of anything,” he said. Something wasn’t right. Anytime something went even slightly wrong in his business or his life, he would beat the hell out of himself in his head.

When we talk to ourselves in such a negative way, it’s impossible to feel hopeful or grateful for much of anything. This constant berating can take quite a toll on your psyche, as it did for Fred.

Eventually, the stress of an ongoing divorce led him to seek the help of an emotional coach. The first question his coach asked him was “How committed are you to discovering yourself?”. Sure, discovering myself, that’s easy, right? No, actually it’s not. It’s hard, emotional, painful work. But it must be done if you want to see any sort of tangible personal growth.

How do you talk to yourself?

Once Fred was able to see how terribly he was talking to himself, he was able to see the amount of damage he’d done on his own self-esteem.

His coach used a brilliant example of encouraging your children to walk. How do you talk to them when they fall down after those first few steps? Do you yell “What are you doing? What the hell was that? Get up off your ass!”? Of course not! You gently say something like “Wow! Good job! That was so amazing. Are you ready to try again?”

See where I’m going with this? Why would you torture yourself for making little missteps and falling down on your entrepreneurial journey? Or in anything in life? Every time you talk down to yourself for failing, you’re only discouraging yourself from trying again. It’s self-sabotage! And so incredibly counterproductive.

Change Your Tone

Once Fred’s coach was able to get him to see the error of his ways, it was a game-changer. Fred put his new lessons to action the next time something didn’t quite go his way in his business.

“Well you know, it didn’t work out this time, but you put yourself out there and tried something new. You should be really proud of yourself. You’re doing awesome,”

he said to himself, or something to that effect.

“This energy came over me,” Fred gushed. “It was amazing!” This simple change, this small act of self-awareness, changed everything for Fred. He was able to see the bigger picture and knew what to do going forward.

This is all easily-applicable stuff that you can implement as an entrepreneur. It seems so simple, just change the way you’re talking to yourself. It must be too good to be true, right? It’s not, I promise! I have seen the same results in my own journey and in my own life. How you talk to yourself is monumentally important. And it can be the very thing holding you back from the kind of success you’re looking for.

To learn more about Fred’s journey, click here.

Author: Ronsley Vaz

Ronsley is the founder & chief day dreamer at AMPLIFY. He is an author, speaker & serial entrepreneur.

He has a Masters’ degree in Software Engineering and an MBA in Psychology and Leadership. He is known as the creator of We Are Podcast – the first Podcasting Conference in the Southern Hemisphere, and the host of The Bond Appetit Podcast and Should I Start a Podcast. He has an audience of over 3 million in 133 countries.

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