How to Conquer Your Fears as an Entrepreneur

Selfie shadow with RICOH GR II x ERIC KIM NECK STRAP, Osaka 2018
Selfie shadow with RICOH GR II x ERIC KIM NECK STRAP, Osaka 2018

Dear friend,

If you can focus on just one only thing to help you become more successful in your entrepreneurial pursuits, your street photography, or your life — what would it be? Conquering fear.


1. Be a hyper-realist

Cindy shadow osaka

In today’s world, fear is mostly irrational. We no longer have the risk of dying from wild animals, common diseases, or death by neighboring warring tribes. We should be grateful to have modern laws that prevent our neighbors from stealing our stuff, modern diplomacy which prevents (most of us) from going to war, modern medicine which prevents us from dying untimely deaths, and social structures which allow us to not starve to death (government welfare for food, water, basic shelter) even if we get ostracized by our families and local communities.

Fear kept us alive in the past. Now, most of the manifestations of the physiological feeling of “fear” is mostly useless and holds us back in today’s modern world.

osaka night looking up

Thus, if we are “hyper-realists” (to use Ray Dalio’s word in his book “Principles“), we should know:

To be hyper-realistic, we don’t really have any practical reason to let fear hold us back from our dreams, ambitions, and hopes in life.

To be a hyper-realist knows that regardless of whatever entrepreneurial or photographic pursuits we have in life, we will not die. We will not die from starvation from lack of food, we will not die of thirst, nor will we freeze to death. This is kind of a Stoic way of thinking.

2. Why does society want us to be generic?

torn face osaka

Also realize:

Your dreams, hopes, or ambitions in life are great and important.

Not only that, but it is difficult, scary, and challenging to pursue your dreams in life.

Why? There are so many haters, nay-sayers, and other people trying to hold us down. We have society trying to hold us down, because society doesn’t like people who deviate from the “norm”. There is a status quo bio that affects all of us (the bias that everyone should be the same, generic, and part of the herd). Thus if your co-workers, friends, family, or colleagues see you deviate from the “norm”, they will try to force you to conform to be “one of them”. There is an ancient Chinese saying:

“The nail that sticks out the most must be hammered (back in) the hardest.

osaka urban landscape

Thus, modern society doesn’t want you to stick out. Modern society wants you to fit in, conform, and follow the herd.

The reason why modern society wants us to fit in is simple: if we didn’t all conform to the rules of our modern capitalist economy, the whole social structure wouldn’t work. We need people to obey the law, we need people to put in their 40-hours at their jobs. We need people to buy stuff, consume, and purchase stuff to keep money moving around.

If we refuse to play by the rules of society, authority-figures (our bosses, parents, etc) try to use fear-tactics to hold us back. They tell us that we will bring shame/disgrace upon the “family”, that we will be socially-stigmatized and perceived as being “losers”/”failures”. We are scared into thinking that we will not be able to get a “normal” job, and thus become homeless and die on the streets.

Authority figures do this for two reasons. First, to hold onto their own power and authority over you. Secondly, if the authority-figure in your life is your parent, elder, partner, friend, etc — they actually love and care about you, but they too are also afraid. They are risk-averse, they want to see you take the “safe” route in life — because they don’t want to see you fail.

3. Dictate your own path in life

espresso osaka

But what if we disregarded petty fear, and we dictated our own path, our own direction, and our own goals/dreams in life? What if we disregarded traditional markers/totems of success like buying our own home, buying a nice car, and going on fancy vacations/going to nice restaurants. What if we chose freedom over material comforts? What if we chose pursuing meaningful work over high-salary jobs? What if we chose to work for ourselves with less security, instead of working for “the man” or a big corporation (that on paper seems more “secure”, but in reality, they can fire you at any time).

What if we pursued our own path in life? Would we feel happier and more fulfilled in spite of having less security and not having a steady paycheck?

If we were able to conquer our fears, and not let our fears hold us back from pursuing our own path in life — wouldn’t we be able to achieve more personal greatness/grandeur for ourselves, create more value for society, and just live a more epic life?

4. Be a deviant

“No great mind has ever existed without a touch of madness.” – Aristotle

If you want to achieve something great and epic in life, you must be a deviant. You must go “against the grain” from the rest of society. Rather than being a sheep and following the herd, you must become an eagle, soar high, and scorn the masses. You must fly high on your own wings, and dictate what direction you are going to fly.

Man in suit and trees. Lisbon, 2018

Every great innovator/artist/philosopher/poet in history has been deemed a bit crazy. Amelia Earhart wanted to fly solo across the Atlantic Ocean and was seen as crazy. Gandhi was seen as crazy for wanting to overthrow the British empire in India without violent means. The same goes with Martin Luther King Jr. who wanted to make civil rights change without violence. Elon Musk wanted to make a new car company in America, and also wanted to make it electric. Oh yeah, Elon also wanted us to go to Mars and made SpaceX. Of course he was seen as nuts. When Steve Jobs announced the original $400 iPod, he was seen as crazy.


The morale of the story is this: Whenever you attempt something that hasn’t been done before, of course everything is going to think you’re a little crazy, mad, foolish, and dumb. Because there hasn’t been a “precedent” set before. But of course once someone innovates something new, and is actually “successful”, then everyone is going to have the hind-sight bias and say, “Oh, of course he succeeded, because of X,Y,Z” and disregard the fact that everyone during their time thought that specific innovator was crazy/foolish.

The power of us as individuals to change the world is phenomenal. We should never put a limit to our own human potential — because we are capable of achieving so much more than we think we’re capable of.

5. The power of collaboration

The biggest benefit we have as humans is the power to collaborate to make our dreams come true.

For example, whenever I see great skyscrapers that pierce the heavens, I gasp in awe, and think to myself:

“How is it possible that humans were able to collaborate to build such a magnificent structure?”

Everything great that has been created in human history isn’t only from the genius of one individual. That one genius individual might have had the original idea, but the EFFORT of building something great is from the combined labor of many people.

osaka coffee

For example, I am so grateful to have Cindy Nguyen (HAPTIC INDUSTRIES CEO), Neil Ta (my manager), ANNETTE KIM (designer) on my team. They’ve been instrumental in several ways:

  1. They give me great insights/their perspective/expertise to strengthen my ideas/creative products.
  2. They help me with production/management/business/coordination/logistics which allows me to focus on my personal strength: producing ideas.
  3. They give me great constructive criticism/ideas which helps improve my creative ideas/products.

Not only that, but having a creative team gives you less fear. You know that you have your “squad”/team supporting you, empowering you, and they carry some of the creative burden/load. Thus you realize that you don’t have to worry or be as afraid– because you’re not shouldering the entire burden yourself (you’re not like ATLAS, holding the weight of the whole world on your shoulders).


Thus as a practical suggestion: Create your own creative team of close friends/family who believe in the same mission statement as you do. It doesn’t have to be a big team when you’re starting off– 3 other people seems to be a good number.

6. Push yourself to the point of failure

Selfie. Hanoi, 2016

In powerlifting, I practice the type of lifting in which I try to increase my “1-repetition maximum.” In practical terms when I am improving my deadlift, I try to increase my maximum lift by 2.5 pounds every week. And of course, there are weeks where I’m not strong enough to add that extra 2.5 pounds. But, I’m pushing myself hard enough to the point of failure. And if I do fail, I don’t let it get to me– I keep on pushing myself, until I can break through my plateau.

Selfie in kyoto. Eric Kim.

I also think as entrepreneurs, we need to be pushing our maximum until the point of failure. Because if we’re not pushing ourselves to the point of failure, we will never know what we’re capable of.

Going back to Elon Musk, consider how many failed attempts he had launching the SpaceX shuttles. Or consider how Jeff Bezos/Amazon has had many failed products (remember the Amazon Fire phone?). Bezos has kept pushing what Amazon is capable of (remember, they started off as an online bookstore, and has essentially became everything).

kyoto curve sand abstract

Even for myself, not all the workshops or products I create with HAPTIC INDUSTRIES is a success. Some of the new workshops I attempt don’t get any signups (or a very few signups) and I have to cancel them. Some of the HAPTIC products we release don’t have massive sales. But I think that is good — because we are pushing the boundaries, experimenting, and seeing if it will become a success. Because no entrepreneur (no matter how smart he/she is) can ever predict with 100% accuracy whether a product/service will be successful.

kyoto sunset

What we must do is to treat every new product or service we create as a small experiment — and not being afraid of trying something new.

7. “Stop-loss”: Cap your maximum loss

Cindy laughing at red shrine. Kyoto, 2017.

In stock trading, there is a concept of a “stop-loss”. The basic idea is that you set a pre-determined “failure” point. If your stock drops below that price, then it will automatically sell itself (to cap your losses).

In business and real life, we can also apply a “stop-loss” to our pursuits.

For example, let’s say you want to start your own photography business. You might tell yourself:

“I am going to invest $5,000 into my business. If I end up losing all that money, that is OK– because that is the maximum amount of money I’m willing to lose.”

CINDY NGUYEN w/ TOKYOGLASS by HAPTICLABS / Cindy on the streets of Kyoto.

This is a good strategy, because you know what your maximum loss is, and you determine what your maximum loss is going to be.

Or let’s say you want to create a new business/service, and you tell yourself:

“I am going to dedicate the next year of my life to this pursuit. If it doesn’t go anywhere, then I will stop it, and move onto something else.”

kyoto wood

So you can set a “stop-loss” in terms of your money or your time, or your effort. And you can dictate this maximum loss for yourself (just follow your gut).

8. Don’t go bankrupt

Another practical tip: avoid bankruptcy.

That means, don’t put all your eggs in one basket.

A practical suggestion I’ve read:

Don’t put more than 10% of your money in any entrepreneurial pursuit.

This will prevent you from going bankrupt.

For myself, I find the best thing for an entrepreneur to take more risks is to have a “financial buffer” (cold hard cash in your savings account, in case things go south financially). In practical terms this means that I try to be as economical and frugal as I can in my everyday lifestyle, in terms of not wasting extra money on new equipment I don’t need for my business, and living BELOW my income/means.

Too often I hear stories of people who have a grand idea for a business or entrepreneurial pursuit, and they put 100% of their life’s savings into it. While I do admire this boldness and brazenness, I think it is kind of a dumb idea. Because what if you lose all of your life’s savings? Then you have to go back to your (crappy job) and you might never be able to rebuild your savings to invest in something else.

A better solution:

Invest less of your personal savings into your business idea, and see if you can launch your idea with less money than you think you need.

Suits at night, street photograph with flash. Tokyo, 2017

Having less money can actually be a benefit: it forces you to be more resourceful. IKEA apparently is still quite frugal (their big bosses still fly economy), and even AMAZON is quite frugal with their expenses (no free lunches for their employees). Paul Graham gives the advice: “Do things that don’t scale” (which essentially means don’t hire other people to pursue your big idea, try it out for yourself before wasting money on staffing).

9. Ignore the feedback of others

Istanbul man in suit, with flash through glass. 35mm, Leica MP, Kodak Portra 400.

I generally think it is useful to get constructive feedback from people you admire/trust. But if you’re the type of person that you have a hard time overcoming “creative inertia” and just “doing it” — I suggest:

Ignore others.

Just do it.

Don’t ask others for their opinion/feedback on what you are doing.

Man in suit in San Diego hotel lobby. He owned the hotel.

Don’t ask other people what they think of your idea before you pursue it. Just keep your idea to yourself, and just do it, just build it, and then maybe later you can ask for feedback.

Suits and can

To be honest often when we ask for “feedback” from others, it is just a sign that we are uncertain or unsure of ourselves. Not only that, but Nassim Taleb has the theory that when we ask others for their feedback, we are just looking to find a scapegoat (in case we fail, we can blame that person for their “bad” feedback).

10. MEMENTO MORI entrepreneurship

With your entrepreneurial pursuits, ask yourself the question:

What is the smallest step forward I can make in my business, today?

Also ask yourself:

If I knew I was going to die tonight, what is the “minimum viable action” I can do in my business, which would make me happy/proud?


Of course in some businesses, we need to think long-term. You might need to build up your blog for a year before you get any traction. It takes months to get people to signup for your workshops. It takes several years before you can build the trust before you can sell products online.

But, think to yourself — what is the smallest possible thing you can do today to build up your personal empire?


Some practical ideas:

  • Write a blog post on your own site(blogging tips)
  • Upload a YouTube Video (how to start your own YouTube channel)
  • Email a potential client, and offer them your service, or product
  • Arrange a phone call with a prospective business client
  • Announce a new service/product
  • Do a guest blog post or article for a popular website/blog (to drive more traffic to you)
  • Start prototyping or brainstorming ideas for a product or photography-business.

The only way to change your own life, and your own reality is to DO SOMETHING, MAKE SOMETHING, or produce something. We must seek to everyday put a (tiny) dent in the universe. We cannot do this without practical ACTION. I know for myself, ACTION CURES FEAR. The more I act, the more I get my creative and confidence ball rolling, and the more I produce, and thus the more value I create, and the more money and influence I make, and the more people I help. And the more I help others, the happier I am, and the more purposeful I feel my life is.

We must always MEMENTO MORI: remember that we will (and must) die.


Have confidence in yourself.

Know that your chance of death from pursuing your entrepreneurial pursuit in life is close to 0. The only thing we have to realistically fear is others criticizing us. Many of us are afraid of being judged negatively by others, or having others laugh at us for failing and then saying: “Told you so!” from the sidelines.

But realize– the fact that you are taking a chance and taking a RISK, and having “skin in the game” makes you grand. You’re a soldier on the front lines, exposing yourself to attacks from the enemy.

In Greek times, your honor as a hero didn’t depend whether you won or not — rather, it was all about the courage, bravery, and boldness you displayed.

So in practical terms:

You might fail in your entrepreneurship, but that is OK. Remember you can always dust yourself off, and try again. Feel good about yourself, because you have the courage to stomach risk, and attempt something new!



Photography Entrepreneurship 101


How to Succeed as a Photography Entrepreneur

The Modern Photographer: Tips, Strategies, and Tactics to Thrive as a Visual Artist in the Digital Age


Marketing, Branding, Entrepreneurship Principles For Success

MODERN PHOTOGRAPHER is your new philosophical and practical primer to succeed as a modern photographer in today’s digital world.


How to Monetize Your Photography


Why Become a Photography Entrepreneur?

Take control of your own photographic destiny:

  1. Photography Startup Manual
  3. On Risk Taking and Entrepreneurship


Photography Entrepreneurship Articles

Google advance up arrow




Table of Contents

Learn how to make a living from your passion:

Photography Business 101

How to Make Money with Photography


Photography Marketing 101


How to Hustle.

Entrepreneurial Principles

How to be a Full-time Photographer

Photography Blogging

How to Teach Photography

Social Media

How to Save Money