“What happens if we can’t raise the money?”

I didn’t even want to ask the question. Because I was the leader I was afraid to show any doubt to the people around me. Despite my own fears, I felt I had no choice but to be optimistic. The company needed to raise this money and if it didn’t, it wouldn’t exist.

Fast forward to two years later. I can still remember how horrible I felt. I was uncertain of our future and I felt this incredible uneasiness in my stomach, as if the food I ate was constantly making me sick. My nights were sleepless and my energy slowly began to diminish. Each morning I woke up more tired than the last.

This is what entrepreneurs go through. Even though we choose to start companies because immense challenge is what makes us happy, we spend most of the time worrying.

What happens if no one buys our product? What happens if competitors copy us? What happens if mega-sized corporations enter our space? What happens if we don’t accept the terms on the table? What happens if we can’t deliver on our promise? What happens if we lose people’s money? What happens if we aren’t perfect? What happens if we fail?

The further you push your company to the brink of existence the more stressful these questions become. The more people you have on board the train, the more spectacular the head-on collision will be. The more promises you make and the higher you raise the expectations, the harder the fall will be.

These concerns never stop. Even for the most experienced entrepreneurs, these questions arise without clear answers, and they present unpredictable challenges that will ultimately define your journey.

So, if we know all of this, even before we start a company, why do we still worry?

Where It Comes From
Worry sits between fear and anxiety.

Being afraid is often an intense, short-term reaction to the perception of a threat. Your response to fear can be violent (fight or flight), dramatic (throwing up), or even paralyzing. And for an entrepreneur, the most terrifying outcome of all is failure. Putting people out of work, not delivering on your promise, and losing people’s money are hard enough to deal with. But worst of all is the unknown impact that failure will have on your most important currency: your reputation.

Anxiety, on the other hand, is a response to cope with future, potentially negative events. Often accompanied with nervous behavior, it can leave you restless, tired, and tense. The questions you wrestle with may not kill the company tomorrow, but their weight can add incredible strain.

I like to think of worry as the tension between fear (impacts today) and anxiety (impacts tomorrow). When you are constantly wrestling with a wide variety of unknown questions worry becomes the continuous state that you live in. It’s a feeling that doesn’t go away when you shut your laptop at night, and it doesn’t subside when you are on vacation. It’s a feeling that @bhorowitz so eloquently refers to as The Struggle.

What Not To Do
Ignore it.

Anxiety and fear are natural responses. They are an important part of developing the gut instinct that drives the key decisions that you make. But, at the same time, the intensity of these emotions can be dangerous. As you try to forget your worry, you focus on anything that is positive. Perhaps it’s a single metric that’s actually working, an aspect of the business that is safe, or the part of your role that you are most passionate about.

This is the wrong way to handle the situation. But it’s a pattern that is really hard to break, especially when it begins in the most innocent of ways. For example:

• You are slow to respond to negative emails and fast to respond to positive ones.
• You obsessively check metrics when they are increasing and ignore them when they are sliding.
• You only send updates with super positive news.
• When your significant other asks what’s wrong, you lie and say nothing.
• You don’t tell anyone your fears because you are afraid to look weak.

By not tackling these emotions from the beginning, they escalate in size. The long term results can be fatigue, tension, disturbed sleep, headaches, and even panic attacks. This burden will drain you both physically and emotionally, leaving you less able to make the best decisions for the company.

What makes this especially hard to confront is that most entrepreneurs are optimists. They see the world half full, so living in a reality where the very glass they hold may be crushed by the forces around them, is exhausting. The days of the work involving just a few people in a room without a worry in the world, are long gone, replaced with a whole army of people counting on your success.

Ways To Manage It
In small steps.

Everyone has their own process for dealing with the burden they carry, but here are some things that have worked for me.

• Imagine The Worst Case: working backwards from the end, what is the worst thing that could happen? You get fired, shut your company down, or have to start over. I’ve done two of the three and even though they were painful in the short term, in the long term they were important milestones in my journey. At the time I was afraid that the failure of my company would prevent me from building again. It turns out that if you are honest, reflective, and caring, people will follow you again. If you can deal with this reality, most of the worry subsides.
• It’s Just Money: there was a time period when you lived at your parents’ house happily eating peanut butter and jelly sandwiches. And although you may have a more expensive lifestyle now, it doesn’t mean you can’t be happy again with a simple life. Just because money is the metric by which most of the world judges its happiness, doesn’t mean it’s true. Having purpose, people who love you, and being healthy are all that really matter.
• Breathe: into the emotion that you feel. When you worry, feel anger, or get anxious your breath shortens and your body tightens. Instead of trying to deny these feelings, sit without distraction and take deep breaths. Starting from your head, through your shoulders, into your heart, and ending in your stomach. As you breathe, really try to understand the intensity of the emotion and why it’s there. This will take a bit of practice but soon you will be able to pass the tension from your body and move on to tackling the important subjects at hand.
• Prioritize Hard: don’t move your fears down your to-do list. Instead, move the hardest tasks to the top of the list and tackle them first. Reply to the emails you’re dreading, pick up the phone to deal with conflict, and be honest with your team about the realities the company faces today. The more practice you have at doing the hard things first, the easier it gets.
• Remember It’s A Choice: that you make every day to run a company. No one is forcing you to be there, which means you should enjoy the journey. There is no magic finish line or point where life becomes predictable. Don’t push off weekend adventures, family time, or vacations because there is never a better time than right now.

Startups aren’t predictable and if they were you probably wouldn’t be interested. And although their constantly evolving challenges are what drive your quest for perfection, don’t underestimate the personal burden they take. The pressure to succeed is something you can’t ignore because building companies will challenge your body, mind, and soul.

*Image Credit: Tom Coates via Creative Commons