How to Shake the Fear of Being Your Own Boss

As it comes close to the end of the year you evaluate what you’ve achieved. You assess your job, career prospects and the people you are working for and quickly come to the conclusion: THIS SUCKS!

When you started this job it had so much promise!

The company was going places, your manager was a rock star and your colleagues were supportive and encouraging. You emotionally bought in and thought you found your dream company but now all you can think about is how much you hate your job.

Does this sound like you?

As an entrepreneur and angel investor, I’ve heard this story hundreds of times. Passionate,
hard-working folks are limited by management from doing their part to improve the world. When they ask my advice it’s universally the same, “Be your own boss!

Take your ideas, put your money where your mouth is and start your own company!”

It’s at this point the backtracking begins and the excuses come out:

  • “I don’t have the financial resources to do that…I’m not wealthy”
  • “I don’t care that much about money that I would sacrifice my family time”
  • “It is too hard, too risky, too….”
  • I get it, entrepreneurship is hard. 99 in 100 businesses fail in the first 10 years.

    Choosing to start your own business pretty much guarantees that you’ll work harder than you did as an employee, get paid less initially, have more stress, more uncertainty and less family time. It’s scary stuff. If you’re not frightened, you’re stupid!


    So why do it when it’s so scary?

    The main reason is to earn something very few people have – freedom. Freedom to have no one to blame, freedom to plot your course, freedom to change the world.

    Fear goes with freedom. Fear is the body’s way of saying to you, “This is uncertain, tread carefully because you’re doing something meaningful.” Overcoming fear is the body’s way of building confidence. Every time you overcome a fear or challenge, you’ll receive a rush of euphoria.

    Exceeding your previous limitations creates a self-reinforcing hit of endorphins that encourages you to push further. That’s the theory, here’s the practice.


    How to Shake the Fear of Being Your Own Boss

    Shake the Fear of Being Your Own Boss

    First off, being your own boss is a process of baby steps. Don’t make massive leaps that’ll
    paralyze you with fear and that you’re not equipped to handle. Astronauts didn’t wake up one
    morning, hop in a rocket and say, “Let’s go to space.”

    They built up to it! Being your own boss, or running your own business is no different.

    Here are the top five things I share with all first-time bosses:


    1. Identify Your Risk Profile

    Risk should never be taken on its own. It must be partnered with reward. One of the largest
    mistakes early entrepreneurs make is taking big risks with questionable rewards. Take a small risk and tie it to a small reward.

    For example, if you’re an employee at a manufacturing company and think there’s a way to do something better, speak to your manager and ask if you can develop a solution for them in your free time.

    IF they like it, there’s the potential they’ll buy it from you. The key thing here is small risks tied to a reward that builds your capabilities.


    2. Plan a Journey of Baby Steps

    Don’t quit your job…yet!

    The first 2 years of any business is really hard. When you add the financial pressure of having no income coming in, it’s no wonder 9 in 10 businesses fail. My solution is to start your business while you’re working.

    Yes, you’ll work harder and won’t have time to watch professional sports but you’re on a more important mission. Testing your ideas without the financial pressure of making your rent payment is key to overcoming fear.

    So, write a simple 5-10 stage and gate plan then stick to it.

    For example:

    Stage 1: Garage project.

    I’ll build a professional services business doing landscaping and exterior design. In this stage, I’ll find 10-20 customers and do the work myself on evenings and weekends. Gate: Once I have 6 months of my monthly household burn rate in the bank I’ll reduce my current job’s hours to part time.

    Stage 2: 50% of my time.

    I’ll hire my first salesperson and generate a business sales rate equal to both of our salaries. I’ll do all the work; the sales person will do all the sales. Gate: Once I have 3 consecutive months of 10 new customers a month, I’ll quit my job and go full time on the business.

    Follow your plan, or change it then follow the new one!


    3. Fear Means: Time to Act

    One of the first things an entrepreneur learns is how to use fear for something productive.

    Fear doesn’t mean stop. It means go faster, dig deeper and do something different. I keep a
    journal near my bed and even after all these years I wake up at 2:00 AM in a sweat wondering how I’m going to solve an issue in one of my businesses.

    I write down my fear, then acknowledge if it’s rational and I understand what’s driving it, or if it’s irrational and I need to dig in why I am scared. Then I go back to sleep. In the morning, I look at the notes and commit to act.

    This means set in motion an action that is different from what I am doing now, but only a pivot, not a whole scale change. Then I listen to my gut to see if the butterflies have gone down. If they haven’t, I keep working.


    Fear is your subconscious signaling you to get to work!


    4. Get a Mentor

    There are no extra points for learning things the hard way.

    Frankly, if I had to learn everything myself I would’ve given up long ago. Early in my career I was blessed to have mentors and well wishers who made themselves available for me to bounce ideas off of.

    This allowed me to create a group of advisers that had passed through the hurdles I was about to face. They were individuals who had built a product, found a first customer, and who had hired and lead small teams successfully.

    I leveraged their failures to ensure I wasn’t making mistakes that someone could’ve prevented.

    The key thing in forming this kind of mastermind around you is that you pick individuals who
    have recently been through the experience you are about to embark on, not someone with
    the most impressive resume.

    It’s also critical that you have an open and frank relationship, there is no topic off limits, and challenging difficult conversations should be the norm. The goal here is not a social club, it is the driving of your entrepreneurial dream.


    5. Have a Clear and Compelling Understanding of “WHY”

    There will be times where you’ll get discouraged and want to throw in the towel. When everything goes wrong, you can’t sleep, and the pressure is out of this world you will be tempted to just go back and get a job.

    Why break your back?

    A compelling and clear “WHY” statement will hold you to your dream of entrepreneurship. This WHY cannot be based on income or material gain alone, it has to be based on a meaningful transformation of yourself or your community.

    For example, many entrepreneurs are out to transform the world with their products and ideas.

    This is phenomenal. The thought of the world being a fundamentally better place through your influence can give you great comfort in the dark nights when it feels like nothing’s going right.

    Another alternative is to have an internal vision. This is my main reason for building companies. I feel like this is what I was put on this earth to do. When I am creating a business or supporting a business I know I am living out my life’s purpose and helping many people in the process.

    Any other activities feel like a waste of time. Your compelling WHY is the foundation of your success. Make sure it’s rock solid.



    Being your own boss isn’t easy and even after nearly 20 years, I still find it scary and difficult. The difference is today I can manage the challenges and turn them into amazing outcomes.

    I won’t go as far as to say I like the feeling of uncertainty and stress, but I love the euphoria that get when I know I have overcome a challenge and am living out my life’s purpose.

    In the end, the prize is the freedom that being my own boss gives me and the price is the frustration of having to figure it out with everything on the line.

    It’s not for everyone but if you use some of these tips, being your own boss is one of the most amazing ways to live your professional life!

    Are you self-employed? How did you shake the fear of being your own boss? Leave a comment below.

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