Money worries

A day inside the mind of an entrepreneur turning off autopilot: Worries pass in an hour. Regrets stay for life. And choices make sense in retrospect.

Looking into the abyss of financial doom, for a day or two per week, is an unspoken part of the highs and lows of entrepreneurship. The fear is normal and you can control it. There are meditation techniques, [1] though to reason through automatic thoughts is more effective.

The social majority has forgotten about the humble beginnings of business. They regularly mistake risk-taking wealth-creators for "dot-con" artists [2], or the 1% powerful [3]. Starting a business, from nothing, is far from an enviable lifestyle. We're tricked into thinking that success comes overnight, while our business and entertainment celebrities spend a large part of their lives staring fear and hunger in the face. Starting a business is bloody hard work, and the day you worry about money is called “Tuesday”.

He who isn’t worried about money when exploring the unbeaten path is not exploring his own limits. If you could spend a morning in the mind of someone bootstrapping a business from the ground up, it would ring true to the tune of the following Tuesday in his every week:

He’s worried about money. It’s early in a week in Spring, and nature has put on a show. A gorgeous day beams with expectantly open arms outside. The horizon with its rolling hills offers an inspirational picturesque view. Green trees and grand houses glow majestically under the sun. And amidst all this, he’s not smiling. He’s struck with a dark sense of creeping worthlessness, while he stares the face of a vague but familiar fear that he cannot identify. Just yesterday, the entire world was destined to kneel before his vision. And today, it’s Tuesday.

Tears impulsively well up in his eyes, looking at those gentle hills, as he remembers riding on the shoulders of his father just half a life ago. “Behold!” would say dad, an awestruck boom of unbound fascination peeking from his voice: “Just look at those glorious hills!” he’d exclaim, “won’t you just want to stand on top of one, watching over the oceans like a king?” Where did so much positive energy come from? And "why has optimism forsaken me", the grown-up son asks himself, feeling even smaller.

The hills are a daunting reminder now of the years gone by. They glow without shame like the youthful faces of innocent and hopeful children running under the sun, as he takes a deep breath and adjusts the subtle ache and pain in his lower back and shoulders. Time has no mercy on mortals, and the road to the kingly vista over the hills is paved with hard-working men.

His hard work has been shared with only a few, if not performed in total solitary for the last year or two. There are barely any witnesses to celebrate or commiserate with. And despite sweating through the pains, no treasure has thus far been gained. He calms his thoughts: it’s not like he’s starving. He still affords the bare minimum, dipping from savings or into the kindness of friends, family and fools [4]. So the very fear for survival is as theoretical as the grandiosity of the celebrations and miseries without witnesses. Alas, even theoretical fear can cripple you to the point that you can stop doing real work.

Projections and expectations cripple work. Smart people are trained to project numbers into the future. Projection is useful when it comes to material predictions; though for spiritual undertakings, it’s quite useless. Mondays are spent dreaming about the idealistic and exciting Plan A, and Tuesdays are wasted stressing out about their detachment from reality. The rest of the week is invested in working on the pragmatic Plan B of the present. Perhaps every week should start on Wednesday? But he knows better. This fear is an essential part of the pilgrimage.

An hour of walk on the street outside the window of business rush hour can brush you off against the homeless man, ignored by everyone for countless hours, sitting by the road, still raising his cup and hoping for the next dollar that will salvage the day.

Fifteen minutes of observing strangers inside a cafe on a midday can turn into a conversation with many an 80 year-old man, whose heart is overwhelmed with the exciting prospect of a listening ear for its two thousand untold stories.

And each of these small experiences remind one of his own vulnerability and mortality. When you’re an entrepreneur, the steps of uncertainty could be leading to homelessness, with the certainly of old age getting just a little bit closer. Taking the plane of life off of autopilot and flying it manually makes you hyper-conscious of the cost of every decision. These are hundreds of decisions that others make automatically every week. But unlike them, your skin is actually in the game:

He who wants a kingly panorama above the hill will suffer the sweat and aches of a long hike along a rocky road. We all drive right by the beautiful hill on a sunny day, every single day in our roofed cars, and find ourselves straight in the office. We get four hundred chances in a year to climb that hill spontaneously and never will, because we live on autopilot. He who takes the plane off of autopilot gets the rush of flying dangerously, with the responsibility that comes with a crash. He may twist an ankle for that panoramic view. His pockets may whisper sadly in destitute before his heart chants joyously in the realm of realized imagination. These are the adventures and misadventures of living life off of the autopilot mode. Tuesday makes the rest of the week happen. It's Tuesday that makes a king out of the ordinary; and it's the survival of many Tuesdays that turns the entrepreneur into an out-of-reach urban legend.

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Our human emotions are articulated most vividly when we stop living and thinking by default and automatically. The very sense of human empathy, essential in marketing a product or service to customers, is at heightened sensitivity when your survival depends on your actions.

The realistic worst case scenario to an entrepreneur is not to become homeless; it's to give in and go back to the sentence of a cubicle life defined by others. He is worried about money because he has finally experienced living with the responsibility of his own actions; and now having that responsibility replaced by the protections of a certain and automatic way of life is no longer appealing.

He is now awake, and his worry about money is his fight against being put back to sleep.

The gaze into the horizon suddenly becomes a determined stare at the road unrolling ahead before him. He becomes cognizant of the perfect hour staring at beautiful hills, each dancing in freedom, rolling gently, under an all-embracing sun. The worries about the uncertainties of the days ahead slowly vanish and give way to a simple truth: that their tyranny pales in comparison to the tyranny of days spent in a cubicle, regretting the certainty of living a scripted life.

A slowly brewed and strong cup of coffee starts to call his name, as he decides suddenly to leave off worrying about money till tomorrow. The smile returns, as he ponders about his great work sitting in the briefcase and awaiting his return.

And someday, he thinks to himself, he’ll show those hills to his kids with an awestruck voice of boundless fascination. "Watch those hills!", he'll exclaim, "They do look glorious."


  1. Facing the fear every week is the price of living like no-one else. So remember what's at stake, and don't look for external empathy and understanding. When the fear comes, stand right here and right now. Hold the reality-checking of the future and the achievements of the past at a distance; and concentrate on the very conscious reality of this present moment. Notice your every breath; and give the monster an hour to pass.

  2. "Douche-bags" in the popular culture, originally from the late 90s, who manipulated Venture Capitalists into blindly signing checks for millions during the rush of the Internet world transformation.

  3. Orwellian wealthy "pigs" in the popular culture, who sit on their wealth-preservationist throne, lobbying the tax and legal system in their own favor and clipping interest coupons on their vast portfolio

  4. In Northern California during the Gold Rush, foreign immigrants arrived on savings and survived in farms and ranches while digging for gold. Silicon Valley has inherited this legacy. Immigrant and upstart founders typically start out of proverbial garages and eat proverbial ramen noodles. Some participate in hackathons to afford food and sleep in their cars as shelter. Not everyone goes to such extremes; but depending on the potential for a change in one's socio-economic class, the prices we pay are different.

Amin A.

Written by

Amin Ariana

A software entrepreneur from San Francisco

Special thanks Tanya P.