Business would be a lot easier if we didn’t keep getting in our own way. But the reality is that the biggest obstacles to our business success are usually ourselves. We fear taking chances or being rejected, we procrastinate about doing what we know is needed, and we doubt our ability to succeed. Welcome to the wonderful world of entrepreneurship!

Overcoming saboteurs

In Parts 1 and 2 of this series, I described how to get clear about your mission and define your business model. Clarifying your mission and model can definitely help with overcoming fear, procrastination, and self-doubt.

But when you’re an entrepreneur on a mission, these saboteurs can be even more powerful than with a garden-variety business. Embarking on a venture that’s based on deeply-held beliefs can trigger fears of losing your identity, breaking your dream, blowing your chance to make a real difference, and much more. It’s common for mission-based entrepreneurs to encounter stronger than usual opposition to their business ventures, too. Well-meaning friends and family members tell you, “You can’t make money at making the world better,” or “You’ll never earn a living doing what you love.”

Don’t believe for a minute that you are the only entrepreneur who sometimes feels afraid, puts off important tasks, or doubts yourself. All business owners feel this way at times. But the successful ones find ways to keep going regardless of these barriers, and so can you.

Overcoming fear, procrastination, and self-doubt is a process rather than an event. It’s a rare entrepreneur who wakes up one morning and is no longer hesitant or afraid. What does happen, though, is if you continue to work at reducing doubt and fear, they gradually diminish. And as they become less powerful, you discover that you can move forward even when you find yourself nervous or unsure.

Below are some strategies I use when working with my clients on overcoming these obstacles.


Fear stems from the most primitive part of our mind, known as the “reptilian brain.” It shows up when we think we are in danger or feel threatened. When we truly are in danger, fear is a good thing. It kicks us into a fight-or-flight state, so that we can defend ourselves or run away.

The problem, though, is that sometimes our fear is triggered by events or concerns that are not actually dangerous. They simply remind us of events in our past that were harmful or unpleasant, usually those that occurred when we were too young to protect ourselves from them.

For example, when I was young, my family moved a lot, so I was always the new kid on the block. Kids being how they are, this meant I was frequently excluded from activities because I was an outsider. I often felt hurt and lonely, and didn’t have many friends. As an adult, I’ve learned how to make friends with new people and be more resilient, so going to new places is no longer “dangerous.” But because of my childhood experiences, it can still trigger fear for me.

To manage fears like these, a helpful strategy is to make friends with your fear. Recognize that your fear is trying to protect you from harm, and find out what it wants and needs in order to loosen its grip on you.

Here are some coaching questions to ask yourself to help diminish fear:

  • What are you afraid of? Get as specific as you can. Do you fear rejection? Ridicule? Embarrassment? Disapproval? Failure? Success? The unknown?
  • What does this fear remind you of? Is there an experience in your past that brought up a similar fear for you?
  • Fear is sometimes described as False Evidence Appearing Real. What false evidence may be presenting itself to you? What is the truth about the situation?
  • What might reassure your fear that there is no real danger here? Consider the opposite of whatever fear you are experiencing: qualities like confidence, self-assurance, comfort, believing in the possibility of success, believing that success is okay, knowledge. What might help you build those qualities in yourself?


Procrastination is a symptom, rather than a cause. When you find yourself putting off things you know you should do, it’s usually because you fear something that might happen if you completed them, because you find the activities themselves difficult or distasteful, or because you are making poor choices about how to use your time.

Curing procrastination with better time management is the first approach to try, as it’s the easiest fix to accomplish. If there is a task you are always deferring, try working on it first thing in the morning, before you check your voice mail or email. Or set aside a specific block of time to work on it, and treat that appointment as seriously as you would an appointment with a client. Or notice what other activities you are working on instead, and if they are less important, defer them, dump them, or delegate them.

Allow yourself 2-3 weeks of experimentation with how to manage your time better. If you haven’t solved your current procrastination issue by then, it’s time to consider other approaches.

Turn up the volume on noticing what happens when you think about working on tasks you’re delaying. Do you detect emotions like fear, resistance, or distaste? If so, these are likely causes for your procrastination, and no amount of better time management is going to make them go away. You’ll need to tackle them head on to get yourself unstuck.

Here are some coaching questions to ask yourself to reduce procrastination:

  • What is the source of your procrastination? Are you not paying enough attention to how you use your time, or is there something deeper going on?
  • When you think about performing tasks you’re avoiding, or when you notice you have been ignoring them, what emotions come up? What do you feel in your body? Is there something you fear? Something you’re resisting? Something about the task that makes you uncomfortable? Get as specific as possible.
  • Take a break from considering the task, and instead, think about your goals and dreams. What made you want to put that task on your to-do list to begin with? What will it do for you to accomplish that task? Where are you trying to go that the deferred task will help you get to? Visualize the end result as clearly as you can.
  • Imagine yourself accomplishing the delayed task easily and cheerfully. What would that feel like? Picture how the task leads to accomplishing your dream or goal. If you allowed yourself to complete the task and achieve the end you want, what would your life be like?


We all doubt our abilities from time to time, and feeling a bit nervous or unsure now and then is normal, and no big deal. But when self-doubt becomes incapacitating, holding us back from creating the business we want, it needs some careful attention.

Self-doubt often takes the form of negative messages that we imagine hearing, for example, “You’re not good enough,” “You don’t know what you’re doing,” or “Who do you think you are?” These messages are often echoes of a parent, teacher, or other authority figure from our childhood. Or they can be cultural messages we’ve absorbed, whether or not we consciously believe them. Some people refer to this voice as the “inner critic” or “the committee.”

Until you begin to pay attention, these messages can be unconscious. For example, one of my coaching clients was stalled about writing her book. Despite having a clear vision for the book, managing her time well, and knowing that she needed the book to accomplish her mission, she wasn’t making progress.

Once she began noticing her inner dialogue, she discovered the message she had absorbed from her upbringing was, “You have to be amazing.” Because she didn’t think her book could possibly be “amazing,” she was avoiding writing completely.

The keys to resolving immobilizing self-doubt are awareness of these negative messages and developing alternative beliefs.

Here are some coaching questions to ask yourself to manage self-doubt:

  • What is the message you hear that makes you doubt yourself? What are the exact words?
  • Where in your life have you heard this message before? What might be its source?
  • What is the truth of the matter? Is this message correct or can you dispute it?
  • What alternative belief would you like to adopt or consider each time you hear this message?

I hope you’ve found the ideas in this series valuable. Being an entrepreneur on a mission can be challenging, but also extremely fulfilling. Keep your mission in mind, continue to refine your business model, and don’t get stopped by your inner saboteurs. You can do this.

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