Recap: Entrepreneurial Fears - A Practical Guide for Overcoming 3 Types of Fears that Slow You Down

Rachel Recap_Maiko Sakai

Thank you to those who attended the Sept 2017 event, Entrepreneurial Fears: Practical Tips for Overcoming 3 Types of Fears that Slow You Down.

You were the most integral in making the entire experience unforgettable. Also, special thanks to those who bravely shared their business challenges, which was immensely helpful for me from an event planning perspective.

Going forward, I will continue to incorporate a 15 - 20 seconds intro for all attendees, for all upcoming events so that we can get to know each other better, and faster! I'd like to personally thank Daniel Green for the suggestion.

Here's a quick recap of the event, for those who could not make it. If you have any questions about the topic, feel free to reach out to both myself (@MaikoSakaiBiz) and Rachel (@HemmaHaridin).

Understanding Fears Based on 3 Stages of Entrepreneurial Journey

We broke down fears that are commonly associated with entrepreneurs in 3 different stages of entrepreneurship:

1. Starting Out
2. Growth Period
3. Pivoting

Starting Out:

2 Starting out.png

Fear of the unknown gives rise to unsettling feelings such as being rejected by prospects or peers, being judged by family members or friends, and feelings of embarrassment by possibly becoming a failure to others. When we talk about fears associated with entrepreneurs, this stage is the most talked about. Understandably, not knowing how the journey is going to go is the biggest fear of all.  

“If you are not embarrassed by the first version of your product, you’ve launched it too late.”
-Reid Hoffman


Growth Period:

3 Growth Period.png

Once things start rolling, and you feel you are on the path to great success as an entrepreneur, fear of success starts to bubble up. 

More success means more responsibilities.

This scares many entrepreneurs who feel that their moves are watched, studied and copied by many. Fear of success comes from pressure to stay relevant, managing high expectations, and the shift from “nothing to lose” to “more at stake.” Also, it could be uncharted territory for some who may have grown up without a successful role model, and as a result, fear of being an outcast among their network of struggling, hardworking peers.

“Too many people hide behind being busy, but producing nothing to avoid
facing their fear of success.”
-Robin Sharma



4 Pivoting.png

Once common characteristic about entrepreneurship of all sizes is that it pushes you to evolve. Most entrepreneurs experience the need to pivot by expanding to other areas/industries, selling their current business, starting a completely new business…or all of the above every 2 to 5 years. 

The fear of letting go and moving onto the next stage of entrepreneurship manifests itself in holding onto what used to work for you, convincing yourself that the timing isn’t right, being concerned about criticism from peers and customers about pivoting and being afraid of losing everything you built, especially your business identity. 

“Sometimes what you’re most afraid of doing is the very thing that will set you free.”
-Robert Tew


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Fear Will Never Go Away

As you can see, fears never disappear, they just show up in different forms at different steps of your entrepreneurial journey. If you are starting out, you might be thinking, "If I can only get to the next stage, I'll feel more confident, and be fearless."

Unfortunately, that is far from the reality. 

This is the reason many successful entrepreneurs constantly explore solutions to help them get over their fears quickly so that no time is wasted.

As Rachel explains:

“Fears trigger ‘lack based’ thinking – a place of lack - which will suck you into a vicious mental cycle. Example: don't have time, don't have money, don't have manpower, etc. Instead, flip the script and think how you can gain more time, more money and more manpower.”

We used an example of a business owner needing an assistant to help with smaller daily tasks, but who was concerned about not having enough money to pay. Rachel continued:

“Hiring someone to help you run a business will free up your time. With extra time you have on hand, you will work on what moves the needle to generate more revenues.  An increased revenue can not only pay the new hire, but also you can hire more people to form a team to repeat this process. So, you have to reverse your thinking that you cannot afford to hire someone to help your business.”

Continuous inflow of business starts from a place of abundance. Fears, obviously, will get in a way of your effort to stay in an abundant mindset.

Now, you understand what your fears can do to you. Let's master the tips on how to handle these fears.

How to Combat Fears in a Practical Way                                                                                                   

Tip #1: Dig Deep with Easy Questions

Questions like "What's the worst thing that can happen?", "So what?" and "OK, but why?” help put your fearful feelings in perspective. When you are being reactive to fears inside of you, it is important to ask these questions to yourself and start breaking down the main source of these fears, so you can find a way out of them. 

Rachel shared her personal story of when she became a franchise owner of four stores at age 23. Her business partner not only left her behind with the business, but also stole money. She was left with absolutely no money in her bank account. It was absolutely devastating. She had a small daughter at the time, and she needed a solution very fast.

She used this technique of asking simple questions of herself, came up with a few options she could pursue immediately, and the rest was history. Four years later, she felt it was time to move onto the next entrepreneurial endeavor, sold all four stores one by one, and now she runs Radiate Your Greatness.


Tip #2: Reverse Engineer from 3 Years into the Future

Envision, in detail, your 3rd year from now in business. Include how you feel, where you will be working, with whom, what you see, even what you smell. This is a crucial mechanism to use when you sense the fear of diving into something new. This process programs your brain to get used to the idea of where you will be three years from now. 

The key here is to hand-write as many details as possible. You can use a format, such as “a day in life,” to describe what kind of a day you would like to have in three years. Why hand-write? The act of writing by hand reinforces the stickiness of ideas in your brain.

Mind you, this is far from day-dreaming. On the contrary, you are telling yourself (whatever your three-year vision is) that it is real, attainable, and possible. 

Once your vision is drafted, reverse-engineer from that point backward to determine what you need to accomplish in bite sizes. Start from annual to quarterly, monthly, then weekly, respectively. You will notice that it is not as daunting a task as you initially thought. Once you break it down, your big, audacious goal is pretty attainable. Not to mention this planning exercise will be your roadmap to follow so that you don’t feel you are in the dark along the way.

If you would like to know more about this methodology, Rachel suggests a book by Cameron Harold, “Double Double: How to Double Your Revenue and Profit in 3 Years,” and you can check it out here:


Tip #3: Don’t Roll Your Eyes, Close Your Eyes

Meditation - Guided meditation that is designed to boost and regain confidence – can be extremely helpful tackling various fears.

Meditation is no longer a fad. There are good reasons why Silicon Valley is obsessed with meditation. Neuroscience now offers copious amounts of data regarding meditation and health benefits. (Related article from Business Insider: “Silicon Valley is obsessed with meditation, and there’s new evidence it changes the brain for the better.”

At the event, Rachel lead us through a five-minute meditation session for the attendees. It was an electrifying experience for the crowd. She is also offering a downloadable session, if you are new to meditation and not sure what to expect. You can send her a message by visiting her site, or via Twitter @RachelHaridin.  


So, What Did We Learn?

You are not alone. We all have fears.

Removing fear altogether is not the goal here. Fear serves an evolutionary purpose to keep you safe, and prevents you from doing life-threatening things like jumping off the cliff, or diving into a bonfire. What matters is recognizing when your fears keep you from pursuing your business goals, and having the tools to manage them effectively, instead of letting them take over your life. 

Also, having a community where we, as entrepreneurs, can get support from other members and have a safe space for candid conversations about our businesses, has an immense impact on our business growth. This is my true purpose for the Growth-Driven Entrepreneurs Worldwide meetup group.    

I hope to see you, especially those who couldn’t attend this event, at the next one!

For any suggestions for the future events or any feedback on the past events, email me at: