Suit and trees. Lisbon, 2018

On Risk Taking and Entrepreneurship

What is entrepreneurship? To me, it is taking risks for the sake of the collective of humanity, and discovering knowledge, wisdom, and utility for our fellow human beings.

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A shift

Suit and trees. Lisbon, 2018
Suit and trees. Lisbon, 2018

I’ve been thinking a lot about the purpose of my life, and which direction I desire to take my life onwards, especially as my 30th birthday advances.

Doing a brief survey on my life so far, I’m quite proud of all the knowledge I’ve contributed to the field of street photography. Street photography was my first love and passion, something I’ve dedicated about 12 years of my life to (from when I was 18 to around 30 years old).

I still plan on shooting street photography and sharing my passion for it until I die. However a new adventurous field I hope to pursue on is thinking more about Entrepreneurship: empowering others to find freedom, flexibility, and more happiness in their life.

What do you do once you’ve achieved your dreams in life?

Cindy with red scarf, blue tiled walls. Lisbon, 2018
Cindy with red scarf, blue tiled walls. Lisbon, 2018

As of 2018, I’ve achieved a lot of my life goals. My goals included to travel the world, become “famous”, having solo exhibitions, published books, and teaching all around the globe. I’ve also been able to successfully monetize my passion for photography, and I genuinely believe that everyone deserves this privilege.

Yet the tricky thing is this: even after I’ve achieved all of my life goals, have freedom and flexibility in my life, a solid income, and external trappings of success, I still don’t feel 100% satisfied. And of course, no matter how much money I make, I still worry about finances, the future, my personal image, my purpose and direction in life.


Golden handcuffs. Berlin, 2012
Golden handcuffs. Berlin, 2012

I know when I’m dead, I can’t take nothing with me. I cannot take my money, fame, or external markers of success. I believe when I’m dead, all I will leave behind include my (future) children, my knowledge and information, and the lessons I’ve shared with others. And I know realistically, as long as I continue to work hard, I will never go broke. Sure I won’t be rich, but I certainly won’t starve to death.

Which brings me to the realization:

Logically, it makes the most sense for me to devote my time, energy, and focus on helping empower other people, and helping drive the human race forward.

This also makes sense for me because I gain the most personal satisfaction and happiness when I am helping empower others. I feel the most alive when I’m teaching, sharing life experiences with others, and also making art and sharing that art with others.

Thus, I think that true happiness and fulfillment in life is connected with empowering and sharing the joy of life with our fellow human beings.

What is my purpose in life?

My mom having fun by the water in Lisbon, 2018
My mom having fun by the water in Lisbon, 2018

I already have everything I need and desire. I got my health, Cindy, flexibility and freedom in my everyday life, a platform (this blog), ideas, and a passion for life and living. I prefer to live minimally and simply; no need for a car, fancy furniture, fancy food (I prefer my evening egg snacks), and I prefer using my small RICOH GR II with ERIC KIM NECK STRAP.

Finger pointing to monument. Lisbon, 2018
Finger pointing to monument. Lisbon, 2018

At this point, having additional money is always useful — being able to use the money as a tool to travel more with my two moms, help empower my sister (who is on HAPTIC payroll), and feeling less anxious about money in order for me to keep giving and helping others.

Shadow on man's face. Lisbon, 2018
Shadow on man’s face. Lisbon, 2018

But still: now that I know that my basic needs are met, I must devote the rest of my life by taking risks for the sake for others in society, and for future generations.

Entrepreneurship revisited

Man and shadow on face. Lisbon, 2018
Man and shadow on face. Lisbon, 2018

Sorry for the random autobiographical musing. Back to the topic at hand.

Based on my philosophical studies, “true happiness” is deeply connected with freedom. Freedom over your time, attention, energy, and schedule. A lot of people think that happiness has something to do with money and income, but I beg to differ. Most people conflate money with freedom. You can have a lot of money, but no freedom. Conversely, you can have a lot of freedom but not much money.

Therefore, the biggest benefit of becoming self-employed and becoming an entrepreneur is to gain more freedom and flexibility in life.

Entrepreneurship is a state of mind

Map of Lisbon, Portugal.
Map of Lisbon, Portugal.

First of all, ask yourself the question:

“Do I really want to become an entrepreneur, and self-employed?”

It’s not for everybody.

Some people prefer security, and the predictability of a 9-5 job. And to be honest, I think a lot of people will be happier just having a steady 9 to 5 job, and pursuing their passion and hobby on the side. Having to monetize your passion in life is tricky: even though you’re the smartest and hardest working person on the earth, without a bit of luck, you won’t be able to make a living from your passion.

Building an appetite for risk

Pink wall selfie. Lisbon, 2018
Pink wall selfie. Lisbon, 2018

Now the good thing:

I believe anyone can be taught to become an entrepreneur, and to build their confidence, and appetite for risk.

I do believe that biologically, some of us are more prone to anxiety to others. For example, I’m pretty lucky, I’ve never been an anxious child growing up. I’ve always loved “extreme sports” as a child, and was an adrenaline junkie. Perhaps my interest in street photography comes from the thrill, and the challenge and fear of it.

Pigeon diving. Belen, 2018
Pigeon diving. Belen, 2018

Also for me, I value freedom almost over everything else, like the cynic/stoic philosopher Diogenes.

So even if you’re more of an anxious and worried person and more introverted, but still desire to be self-employed, no worries; you can.

Mental strengthening

Woman begging outside of Lisbon church

To be honest, I think that entrepreneurship is about 80% mental: you need to build your confidence in yourself, to wisely not doubt yourself, and to have extreme conviction in what you believe in and do.

Rust abstract. Lisbon, 2018
Rust abstract. Lisbon, 2018

Also being self-employed: it is a fact that you will never feel 100% “stable” or “secure”, but that’s the thing. A true entrepreneur doesn’t desire stability or security. Rather, the entrepreneur desires to innovate, make new things, go on adventures, and take risks.

Start your side hustle

Graffiti wall and walking woman. Lisbon, 2018
Graffiti wall and walking woman. Lisbon, 2018

Regardless of your situation in life, you can start your side business, or your side hustle right now.

I started this blog while I had my full time job. I just devoted all of my free time to building up my following, to writing, doing research, and the good thing about having a full time job was that I wasn’t too worried about money.

Cindy with hand over face. Lisbon, 2018
Cindy with hand over face. Lisbon, 2018

Thus, if you have a full time job, and want to attempt to make a full time living from your passion, this is my advice:

Do the minimum amount of work at your 9-5 job not to get fired, and pursue your passion on the side.

To me, this makes sense, because you will have less anxiety in your everyday life. I do believe that having a steady income is very beneficial to building up your side business. Because, in my experience, it took me at least 2 years of building up my side business before I was able to gain “critical mass” of followers, before I could successfully monetize my passion.

Family portrait of Cindy and my two moms. Lisbon Airbnb, 2018
Family portrait of Cindy and my two moms. Lisbon Airbnb, 2018

How do I know when to jump ship from my job?

Man cutout and Lisbon tiles.
Man cutout and Lisbon tiles.

I was lucky, I built this blog for about two years while having a full time job. My company ended up making me redundant, and that gave me the opportunity to pursue my passion for photography and blogging full time.

To be honest, I don’t know if I would have had the guts to quit my job, and pursue my passion for a living. I still remember trying to save up money from my 9-5 job, and I wasn’t very successful.

Cindy shadow. Lisbon, 2018
Cindy shadow. Lisbon, 2018

My initial strategy was this:

Save up 6 months to a year of income, then quit my job.

I was only able to save about 1 month of expenses while I was still fully employed. But I was lucky because when I was made redundant (laid off), I got some stock options and a severance bonus, which equaled around 3 months of living expenses.

My mom and food. Lisbon, 2018
My mom and food. Lisbon, 2018

But now that I think about it, not having that much financial security was a good thing, because it made me hustle and work harder. Hunger is the ultimate driver.

I think having 3 months of monthly expenses was a bit tight, but it ended up working for me. I was able to also extend that money by cutting all unnecessary expenses: I stopped eating out (only cooked at home), stopped going out, and became much more economical and frugal with my money (a good thing in general).

Yellow dots, abstract Lisbon street photo.
Yellow dots, abstract Lisbon street photo.

Therefore if you’re starting off as an entrepreneur, even when you have your full time job, figure out what superfluous expenses you can cut. Can you cut your cable bill? Can you stop going out to restaurants, clubs, and bars? Can you get rid of your car? Can you get rid of your smartphone data plan? Can you move into a smaller apartment, or share a room? Can you stop shopping for new clothes, and go to thrift stores instead? Can you reduce the price of your grocery bills? Make it fun, like a game — see how little you can get by with.


Cindy GoPro on eye

Some ideas that you can incorporate to start your journey as an entrepreneur:

  1. See how much you can reduce your expenses by, and how little you can get by with. The easiest way to become rich or increase your profits is to reduce your expenses. It is a “via negativa” approach to wealth; easier to cut superfluous expenses, rather than add income.
  2. Vividly imagine the worst case scenario: If you pursue your passion as a career, or start your own business, what is the worst case scenario? If you go bankrupt, can you move in with your parents, or reduce your lifestyle? What is your ultimate fear? Just be honest with yourself, and write it on a piece of paper. For myself, my ultimate fear is going bankrupt and dying — but whenever I put it to writing, I realize how silly it is. By vividly imaging my worst case scenario, I realize it’s actually not so scary at all, which encourages me to take more risks in my life and entrepreneurial endeavors.
  3. Turn your excuses into a positive thing: A lot of us want to pursue our passions for a living, or we want to start our own business. Yet, we have excuses like not enough time, or not enough money. How can you use your excuses as a positive thing? Perhaps not having enough time will allow us to be more focused. Perhaps not having enough money will allow us to innovate in novel ways. Or perhaps not having enough money will encourage us to work harder. Turn any negative you have in your life, and turn it into a positive.
Evolve and innovate modern photographer
You must evolve and innovate as a modern photographer. Spread from MODERN PHOTOGRAPHER

As entrepreneurs, we are risk takers for the sake of humanity. You have a noble task. Don’t let your own personal fears and concerns hold you back. Rather, let the fear push you and drive you forward.


For more strategies, motivation, and insights to empower yourself as a photography entrepreneur, pick up a copy of MODERN PHOTOGRAPHER: Your Personal Blueprint For Success.

Photography Entrepreneurship 101

Learn how to make a living from your passion:

How to Monetize Your Photography


Why Become a Photography Entrepeneur?

ERIC KIM x HENRI NECK STRAP  by HAPTIC INDUSTRIES // Portrait by Benjamin Thompson

Take control of your own photographic destiny:

  1. Photography Startup Manual


Photography Entrepreneurship Articles

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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


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