Courage is essential for every investor. Putting your money, time, and energy into a project without a guaranteed payoff is frightening. That fear keeps many people from even starting in the field. Courage emerges from the routine practice of overcoming fear to do the things you know will bring you closer to your goals.

What Are You So Afraid Of?

Fear is uncomfortable. It manifests in all areas of our life – socially, professionally, and intimately – and there is little we can do to control it when it comes up. In real estate investing, overcoming fear is critical to moving from the simple task of finding a deal and underwriting it to closing.

Consider some of the fears involved in sourcing, underwriting, and closing a deal:

  • Sourcing – fear of looking like an impostor, fear of not finding any good deals, fear of your employer finding out that you’re hustling on the side, fear of spending too much time on sourcing and not enough time with family
  • Underwriting – fear of not having enough or the right information, fear of not seeing the most important items on your property tour, fear of overcommitting on the operating pro forma, fear of missing the offer date
  • Closing – fear of negotiating a subpar deal, fear of missing important steps in the transition, fear of overpromising to investors, fear of not getting a loan on time, fear of losing your deposits, fear of spending too much money on due diligence

Above all else, the greatest fear may be one that you don’t even consider – the fear of success.

Success is a double-edged sword. It comes with a lot of benefits, but it also delivers new responsibility. Our instant gratification world trains us to expect results immediately. An immediate reward comes with instant responsibility, which is paralyzing.

Your life is comfortable right now. Even though you’d love to have the benefits of success, it’s natural to feel afraid of the change that comes with it.

The good news is that success takes time and hard work. You are not the person you were five years ago, and you will not be the same person five years from today. New responsibilities will become part of your life when they are supposed to.

Fear’s Physiological Foundation

Fear has a very important evolutionary function. It activates a variety of physiological responses to active threats where our life is in imminent danger, like a potential physical attack. Similarly, more passive, longer term threats trigger stress responses that motivate different actions, like working for money to support a family.

Reflex and instinct are the two fear responses triggered by the reptilian brain. Reflex is the instant, uncontrollable action that protects you from harm, like blinking or breathing. Instinct is a more controllable action that triggers a practiced or learned response to potential threats, like swerving from a car entering your lane.

We learn to fear most things in our upbringing and socialization.

Child development is a terrific case study in learning and overcoming fear. Many of the human functions that we take for granted required years of practice and failure to become proficient. Walking, talking, reading, writing, learning, and many more seem like natural aspects of life. Still, these characteristics evolve as you grow up.

Babies fall a lot when they learn to walk. The natural parental inclination is to rush over and make a big deal about the fall to protect their child. Most falls are not painful, as the child is low to the ground and well padded. However, parents that overreact risk teaching their children to be afraid of taking developmental risks.

Think back to the fears you’ve built up over time. More than likely, you learned them from failing and giving up. The punishment from giving up was not nearly as bad as the expected pain of failure.


Fear links depression and anxiety. Anxiety results from a fear of the future, whereas depression emerges from a fear of the past. Control is a common characteristic of each.

You have no control over the past. What’s done is done.

The story you tell about your past has a big influence in the type of person you become. One can interpret a personal history in a variety of ways – positively and negatively. Too much weight given to negative interpretations results in a depressed present state.

Your present state has a lot to do with your future.

A positive outlook will motivate you to take productive steps toward reaching for your dreams. Whereas a negative outlook will keep you stuck in the fears of the past. Therefore, anxiety results from having no idea if your actions will create the results you want.

This fear is crippling for many. Overcoming fear of the future is a matter of moving the axis of control from outside to within you.

Overcoming Fear

People create comfortable grooves in their daily routine that help avoid scary situations. We have pre-built, well-reasoned excuses to enforce those channels. However, the only way to overcome fear is by reverse engineering the source.

Courage comes from comparing your values to your fears and determining that values should dominate. This is difficult, and early forms of courage are strictly and exercise in willpower.

That said, the elemental first step in overcoming fear is identifying your values and deciding that they are more important than anything else in your world. Beyond that, the only way to eliminate the fear is to make it boring.

Define Your Fears

Think about some fears in your life – spiders, heights, swimming, darkness, etc. In most cases, you know that these fears are not well-founded. In the right setting, there is no danger. Still, you avoid them because the discomfort of confrontation is greater than the benefit from eliminating the fear.

Your fears hold you back from achieving your dreams. They’re yours to keep until you decide that you don’t want them anymore.

Most fears live within your subconscious mind, and you unconsciously create routines and habits that help you avoid those fears. Therefore, it’s difficult for most people to see for themselves these things that hold them back.

Take some time (after you read this) to make a list of all the fears in your life.

Ask family, friends, colleagues, and mentors for their opinion on the things that are holding you back. More than likely, you can tie these to a fear created without you knowing when you were much younger.

After you identified the fear, tie these fears to the worst-case scenario from acting against them and the benefit from overcoming fear. You’ll probably realize that the worst-case isn’t that bad, and the upside is much greater.

Eliminate Novelty

Can you remember the first day of your first real job?

If you’re like most people, the first day of your first real job was daunting. People that you thought were your buddies started giving you a lot of work to do. You thought they expected that you knew exactly what you were doing. You expected that the deadline was yesterday, and you thought that you couldn’t ask for help.

Boredom and stress come quickly and easily to most people in their first day on the job.

This is a recipe for tremendous anxiety and stress. However, you need the job to pay your bills, so you endure.

Things start to change over time. You systematically start to confront and eliminate each mini fear that crushes your soul throughout the day. It’s more important to be happy at work than fearful so you stand up to that fear.

Nothing is easy in the beginning. In fact, your experience is supposed to be terrible when you start out. That’s how you know you’re doing it right.

You’ll find that courage becomes easier the more you expose yourself to the scary situation. Conversations become easier the more you pick up the phone to call someone you don’t know. Analytics becomes more natural with each new Excel sheet you open.

Exposure creates new neural pathways that expose your fears as nothing more than self-manifestation. This, in turn, works to improve your emotional literacy.

You can’t become great at something if you never step onto the field.

Train Your Response

Your response to external stimulus defines you.

We all know people that had terrible things happen to them, but they continue in life with a cheery attitude and use those experiences to fuel a great life. Similarly, we know many more people that use their experience as an excuse to explain why they don’t have all the things they want in life.

Twelve-step programs, like Alcoholics Anonymous, work by guiding people through a system of identifying and confronting their learned responses to external stimulus. They use positive affirmations, mentoring, and accountability to redirect anxious energy to productive means.

Unlearning a behavior takes time and practice. Attention is the most powerful tool in overcoming fear.

The National Science Foundation published an article in 2005 that suggested that the average human has 60,000 thoughts per day. Further, most of these thoughts are repetitive, which means you’re thinking about the same stuff all the time and don’t really know it.

Attention to your mind is essential to controlling your fears. Unfortunately, our increasingly secular world rapidly moved away from internal focus through meditation and prayer. Today, the external, material-focused world of social media, reality TV, and sensationalist news dominates most of our attention. These latch on to and perpetuate your learned fears.

Gain control of your thoughts by practicing mindfulness. A consistent meditation routine will teach your conscious mind to catch your instinctual reactions, which allows you to reposition your thinking on the spot.