5 Ways I Scared the Shit Out of Myself

A few months ago I read Amy Poehler’s “Yes, Please!” I expected it to be a light, funny read but was surprised by how much it moved and motivated me personally and professionally. I am telling you, I took a lot of notes while reading this book. One section that truly spoke to me was about doing things that are really, truly scary.


After reading the book, I was inspired to make a list of things I have done that scared the shit out of me and why I am glad I did them. The list was fairly long with over 25 items ranging from the first time I went out to dinner alone, to cutting my really long hair into a short bob, to riding in a helicopter (it was scary but I am a total thrill seeker).

In the interest of being authentic, vulnerable and brave, I have decided to share five of those items with you. I am going to get really raw with you. This post was much harder for me to write than I anticipated. I sat on it for days and days. Normally words flow freely and I have to cut myself off. This time, for whatever reason, the level of vulnerability seemed deeper than normal. I felt naked and exposed. I am not sure why this was different than any other time since I’m normally an open book. So, thank you for being gentle with my heart as you read this piece and for understanding that sometimes things just feel extra difficult. I truly believe that is when we need to push through the most.


Here goes … my top 5 scariest moments and why I am unbelievably glad I did them.

Taking a vacation alone.

Ok, I will admit this was not supposed to be a solo vacation. I had originally planned to visit Atlanta with my best friend from middle school. At the time, fresh out of college, funds were tight but I was really excited about this visit. About a week before I was scheduled to fly out of Chicago, my friend let me know she wasn’t going to join me. I was heartbroken. I couldn’t get my money back so I decided to go anyway, alone. Have you ever gone on a solo vacation? I mean, as a 43-year-old woman I think it would be awesome but as a 23-year-old it was terrifying. But off I went, alone. On my first day there, I remember finding a sweet little restaurant that was, aptly named the “Vickery Cafe.” I sat down, ordered lunch and pulled out a book. It was then that it hit me, “I am pretty fun. I can totally hang out by myself.” It isn’t that I don’t need or want other people, it is simply that I don’t require other people to be fulfilled.

Singing Publicly.

A few years ago a good friend of mine was hosting an open mic night at a local bar with a live band. Since I have a background in musical theater and had done some singing as a child, she asked me to sing on this stage. When I agreed to do it I thought I would be singing to a fairly empty room in front of mostly strangers. As it turned out the lineup grew to be full of people I knew! Holy shit! I had to sing on stage for the first time in 25 years in front of a bunch of people I knew?! To say this was terrifying is an understatement but I had prepared and I was going for it. I even took my daughters with me for rehearsal. Looking out at their tiny little faces, seeing how proud they were of me, that was my payoff moment. I might not have been the best singer on stage that night but I was the proudest mother. I did something super brave and showed my girls that nothing can stop them from achieving their dreams and even if it feels scary, it’s worth it!

Coming Out.

Ok. Well, this one is pretty obvious. Coming out is hard. Really hard. And the truth is, it never stops. I have to come out almost every day in some capacity or another. My coming out happened over time and with each conversation, my heart became a little more whole. As each person I told welcomed me and showed their love and support, I began to feel like a real girl (you know Pinocchio or Velveteen Rabbit style). All of a sudden, an entire person emerged that I felt really comfortable with. It was me, for the first time. Hello Heather Vickery, nice to meet you.

Getting Divorced.

This one is hard. Based on the aforementioned coming out, divorce was a likely outcome — but let me remind you that people don’t get married to get divorced and just because something is right that does not mean it is easy. There are all sorts of difficult things that come with getting divorced. For me, the hardest part was the fear of hurting my children and my then spouse. But once I got to the other side, that new girl I mentioned got wings. I was finally able to throw myself out there all the way and make any kind of magic I wanted.

Starting a Brand New Business.

Speaking of magic! I have been a business owner and entrepreneur for nearly 20 years. I was super comfortable in my role and had a fantastic, well-respected business on my hands. But then I was faced with this new version of myself, this authentic and empowered woman who simply knew there was something else out there. Once I stopped shaking and started listening to the universe, I realized I had some amazing gifts that could really help others elevate their lives and business. Fast forward several years and this shit is working!! My business is thriving. I have a full roster of amazing clients who honor me by allowing me into their lives. Each day is still a rollercoaster and I am along for the ride but damn it feels good!

So there you have it … The cliff notes version of the scariest shit I have ever done and why I am so grateful for having done them. Now it’s your turn! I would love for you to drop me a line and share some moments in your life where your bravery shined when you were terrified. As always, you can reach me via email, Facebook, Instagram, and Twitter. I love hearing from you.

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Choose Bravely!

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About the Author

Heather Vickery
Heather Vickery
Heather Vickery is an award-winning business owner and global leader with over 20 years as an entrepreneur. She leverages her entrepreneurial skills and expertise to coach individuals towards greater personal and professional fulfillment by helping them leverage their fear into intentional bravery. Heather says “When we choose bravely, on purpose, we choose bigger, have bigger successes and it’s contagious” A celebrated public speaker, Heather inspires audiences and empowers attendees with the tools they need to live bold and successful lives through creating balance, time management, mindfulness, as well as countless systems, strategies, and boundaries. She’s the author of Gratitude Journal: Shift Your Focus and Grow Grateful: A Gratitude Journal for Kids and Families. Heather is also the host and executive producer of The Brave Files Podcast.