Expand, Push and Challenge Yourself | Jessica Draper


Have you ever found yourself in a situation where your back is up against a wall? The path moving forward seems less than desirable, but you know you have to slip off the ledge you’ve been clinging to and actually make a choice? This was the position I found myself in a few years ago. We all have to make hard choices. And often, the most terrifying choice is taking that first step off the cliff and away from what is comfortable. 


For most of my adult life, I’d been coupled—in one long-term relationship. Ultimately though, I realized the partnership was slowly (and painfully) coming to a grueling end. For the first time since I was a teenager, I was solo. Other than making sure I had a job that paid for a few bills and a roof over my head, I found myself with no strings attached.


This untethered feeling made me question my current path, and I needed a new perspective. Through a friend (of a friend), I found out about a program that helps people work remotely while traveling to twelve different cities all over the world in twelve months. I was extremely insecure, filled with self-doubt and not even sure how to make something like this materialize. I had a group of supportive family and friends cheering me on to do something that would cultivate self-growth, get me out of this funk and hopefully put me on a path to discovering those parts of me that I had long forgotten or if nothing else find a sense of happiness.

So what did I do? I hung there for a while, gripping nervously to the preverbal cliff. I regretfully took a deep breath, closed my eyes and… I let go. Scared shitless, I enrolled in the program and began making plans for the next year. I had never traveled halfway across the world. I had never worked remotely for more than a week. I had never left my home state by myself, let alone the country. Here I was, packing my entire life down to a checked bag and two carry-ons. So that was it. I was flying solo, focused on self-growth and terrified.


 “Choose courage or comfort—you cannot have both.” – Brené Brown


I chose courage—the courage to step away and re-examine my life. The time I spent living and working abroad did indeed give me a new perspective. I found three key insights very helpful. (This is by no means the perfect how-to list, but perhaps they could help you discover your own.)


Write that shit down, then do something about it. Before I kicked myself in the butt and started to create change for my life I was surprised by a handful of (we’re talking tiny hands here) journal entries. They were little windows into my past: self-doubt, after-math of arguments to clear my head, aspirations, dreams, and funny stories with friends. It took me back and really opened my eyes to, “Wow, am I still talking about  ___Fill the blank___ after all this time?” – The sad but true answer was yes. Yes, I was. All talk, and no action. You know the expression: If you’re going to talk the talk, then you better learn how to walk the walk?  Well for years I was talking but looking at my feet, they were as useful as they are in that nightmare where you’re flailing around but your feet aren’t taking you anywhere, ie. trying to run from Freddy Kruger. You know the one.  Writing this stuff down was comforting. But, here’s the thing about being comfortable . . .


Feeling a little too comfy? If you’re comfortable right now, you’re probably stuck in not being awesome. Action is uncomfortable. I can’t tell you how many times I talked myself out of a project, conversation, or trip because it was easier to do nothing. Unfortunately, even though inaction might feel more cozy and comfortable (there’s that word again), the truth is, it turns into complacency which can lead to self-doubt and depression. If you’re doing the same stuff you were doing a year ago, give yourself a little nudge off that cliff of being comfortable. Throw yourself into something new and exciting, preferably in the direction of that project or idea you haven’t had the *cajones to actually try. (*Cajones: Spanish for coconuts, I’m pretty sure. Don’t look this up.)


Stop waiting for perfection. While speaking with a close friend about how I was going to move forward, she shared this advice (I hope I do it justice): “Just fu**ing let it go. Stop trying to be perfect. Stop trying to obtain a perfect balance. Just start doing shit. This is life. Not an Instagram contest. Not a marketing project. It’s messy. It’s a jumble of fu**ing moments and emotions. When you stop trying to control it, then you can enjoy it. It’s the only way to find progress, happiness, and growth.” I am so grateful for friends like this!




In the first months abroad, I was terrified to travel solo. I’d only vacationed with friends or family. I’d never gone solo. Full solo. Han Solo! But I kept leaning into that uncomfortable feeling. Eventually, I gained more confidence and worked through my hang-ups by believing in my own momentum and by being gentle with myself when I made mistakes or came across a fear-inducing obstacle. I learned how to ride the wave of chaos when solid ground was hard to find.


When my twelve months with the program was finished, I wasn’t ready to come back home. I felt there was still one more hurdle I hadn’t faced. Again I procrastinated, waited until the last moment, but finally, I took that last deep breath and jumped! This time it was a little easier. I planned a multi-city adventure-focused solo trip through Chile, Bolivia, and Peru. A year ago I wouldn’t have had the coconuts to pull something like this off; I would have been scared stiff!


I took the first leap to gain independence and the second leap to have a life-changing experience. Now that I’m home, I have a few more experiences in my figurative backpack and I am not willing to stop there. I’m ready for more adventure. I want to build a bigger life for myself, and this time I won’t be waiting on the edge, fearful of what’s to come. This time I’ll give a final nod to that comfy place, get a running start, and take the leap into being uncomfortable!


Two things I am currently working on: thinking outside the box (thinking big) and putting those big ideas into action. One of the hardest things for people to do is come up with obtainable dreams. Sometimes it’s hard to imagine what’s possible? Where do I want to be? How am I going to get there? Don’t let being scared stop you from making the next step. With that nervous energy comes an excited energy. Use that excitement to propel yourself forward! And remember to be kind to yourself.


<Read Shannon Dee’s “Simplicity” take on Expand, Push and Challenge Yourself.

Read Lyn Christian’s “Courage” version of Expand, Push and Challenge Yourself. >