An Open Letter To Aspiring Entrepreneurs: Face Your Fears in Business by Madison Errichiello

What were you like as a child? Some days I really envy my childhood self -- rambunctious, self-assured and bold for the things I wanted in life. The only thing I was afraid of was the imaginary monsters under my bed or the ghosts in my closet. Somehow, as I’ve grown older those things have reversed and I find myself confident in knowing that there are no monsters under my bed or ghosts in my closet, but my once loud and creative self is tucked away behind fears.

One year ago, I officially decided to take the plunge and become a business major. I was going into my junior year, I had already switched my major twice, and I honestly felt ridiculous telling people I had changed my mind once again. The thing is, I had never even considered business as a career option before -- but everything in life had pointed me this way and I knew in my heart that it was right. So, I filled out the paperwork with shaking hands and a racing heart and made it official. Since then, I have never looked back.

I know what it is like to fear the future, to be unsure of yourself, and to pursue something that seems crazy and maybe even unexpected. However, if there is one thing that I have learned in the last year of being immersed in the business community, it is that whenever you are faced with fear, don’t let it discourage you. Instead, lean into that feeling of fear and do it anyway -- do whatever is daunting or seems impossible. Of course, this is easier said than done, but I have put together a list of 10 things that have helped me grow in my pursuit of fear-facing and business endeavors, and I hope that it can resonate with you.

1. Travel

Travel has given me more courage and determination than I ever knew possible. In the past year, I have had the opportunity to live abroad in Paris, France, and the Middle East. There is something about getting out of your home culture and completely immersing yourself in another that gives you a sense of boldness and adventure. You are completely responsible for yourself and your interactions, you learn to let go of the little things and refocus on what really matters. Suddenly your eyes are opened to all the things you realize you have yet to learn in this life. Learning a new way of living is exhilarating and frustrating all at the same time. And when it's over, you hold this secret inside of your heart where words fall short of justice when attempting to explain all the things you’ve seen, people you’ve met, things you’ve done, and places you’ve been.

2. Grace

Just a rule to live by -- life requires grace for ourselves and grace for those around us. The truth is, everyone is a little scared of something and everyone just shows it in different ways. Allow yourself to be ok with feeling afraid! Lean-in and press on. If we back down every time we are intimidated, we would never get anywhere in life! Find motivation in fear instead of letting it hold you back from starting that business you have been dreaming of or creating something new.

3. Say Yes

When I was a freshman in college, I came up with a new rule for myself that I would say yes to everything even if that wasn’t necessarily my first, gut answer. Of course, there must be guidelines around this as there is a point where saying yes can mean burnout and people pleasing, and that is not the kind of yes that we are talking about. What I mean is, saying yes to the opportunity to grow. There were so many times my freshman year that I hadn’t felt like saying yes but did anyway and ended up feeling glad that I did! Sometimes we allow fear to say no for us, but sometimes we just need to say yes.

4. Count Down From 5

When you feel fear holding you back, count down from 5 and just do it. You force yourself into action after you reach 1. I found this inspiration from a Donald Miller podcast I had been listening to and it has forever changed my perspective on the element of motivation. You can apply this to any situation -- getting out of bed in the morning, finding the motivation to do your dishes, or facing a fear and moving forward.

5. Be Encouraging

Often I find that when I encourage others to pursue their dreams, I myself am encouraged to do the same. Recently I was talking with a friend who was telling me about the dreams she had but how it just wasn’t the right time to pursue them. The truth is the time is almost never right. Sometimes we just have to pursue our dreams without having the time stamp of approval and see things happen. So I encouraged my friend not to wait for time to roll around, but to just go for it. During this pep talk, originally meant for my friend, I realized I was preaching to the choir. Later that day, I took out my to-do list and got to work pursuing my dreams with the time and resources I currently had.

6. Just Ask

One year ago I was a nanny for three little kiddos and 6 months later I am the Communications Manager at a local Minneapolis business -- all because I had the courage to ask. First, I found a business I loved and cold emailed the owner asking for an informational interview. I asked for an internship, and then I asked for a paid position. Don’t be afraid to ask. People are more apt to say yes than you think they are! People are waiting for you to ask!

7. Strive For No

A friend of mine once told me about a podcast she had been listening to in which the speaker trains entrepreneurs to become bolder in their entrepreneurial life. One of his methods is to encourage the entrepreneur-in-training to put themselves in “risky” situations where they are likely to be told “no.” One of the more risky situations he uses to train entrepreneurs is to sit in another person’s assigned seat on a plane. If approached about the seating adjustment, ask if it is okay to switch seats with them and go on from there.

So, a couple months ago I was traveling to Paris and I decided to try this little tactic and challenge my entrepreneurial self. I boarded the plane and found a seat that wasn’t mine and sat down. For a little while I thought (hoped) I wouldn’t be confronted with the fact that I was sitting in someone else’s seat. However, as they closed the doors to the plane, a lady jumped on and I knew it was over. She came up to me and rightfully seemed confused, so I put my brave face on and tried to bargain with her, asking if she would mind if we switched seats. She spoke back to me in French. With my French skills being at an embarrassingly insufficient place, I just stood up, walked back to my middle row seat, and climbed over a few strangers’ legs. After the embarrassment had passed I realized the point is not to get a yes, really the point is to receive a no. Never pursuing something because I am afraid is a lot scarier than being told “no”.  Ask for things even with the possibility that you will be told no.

8. The Comfort Zone

Do things that scare you, challenge yourself and push yourself out of your comfort zone. If you are uncomfortable or maybe a little intimidated by things you are pursuing, that is a good sign you are on-track for success.  I have set a goal for myself to do something that scares me every day. It could be as small as asking to get coffee with someone you’ve admired for awhile or going somewhere new by yourself.  Sometimes, I am overwhelmed by a number of things that I get intimidated by, but I do them anyway! Nothing great ever comes out of comfort zones.

9. Don’t Settle

When I was in 7th grade, Converse shoes were the coolest trend. So one day I was shopping with my dad and I found this off-brand pair of Converse and begged my dad to buy them for me. He told me not to settle for the knock-off brand and wait until we could get the real Converse. To this day I still remember that conversation during times where I am tempted to settle in life. Fear can force us into making rash decisions. Don’t make compromising decisions simply because it's the first opportunity that comes your way.

10. Find Accountability

Create a community of people for yourself who will fight for your dreams just as much as they fight for their own. Surround yourself with people who are dreamers, and doers, and true friends. When you have a community of people around you who are creating space for you to pursue your dreams alongside their own, you will go farther than you could by yourself.

With these 10 tips, tricks, and coping mechanisms (kind of kidding), I hope you are feeling inspired and encouraged in your entrepreneurial journey. Fear is one of the biggest hurdles for entrepreneurs to jump over and it is an ongoing work out. Just remember, lean-in when you feel intimidated, find your healthy tension point and push forward. You are going to do incredible things, conquer great feats, and change the world!Don’t let fear stop you from doing those things.

Don’t let fear stop you from doing those things.


Xo, Mads


Madison Errichiello

Madison Errichiello is an Indy-grown, Mpls-dwelling, 21-year-old entrepreneur with a love for world travel and a mind for all things inspiring. She is currently the Communications Manager at Minny and Paul, a full-time Business student at North Central University, and an aspiring artist. Find her on Facebook, Twitter, Instagram, LinkedIn