Ready is Never Going to Happen

Ready Is Never Going To Happen

Words & Photos by Erin Sullivan, Erin Outdoors

This is for the dreamers who overthink everything, the planners, the people who want a guidebook and a how-to lesson for every single step.

I know a person like that: me.

Five years ago, I went to Portugal by myself. On paper, my plan was flawless. I had a place to live, I lined up a job, I studied Portuguese, I planned out weekend trips and a whole summer of travel. I had flights and accommodations booked. I had two types of ugly beige money belts.

I thought I needed to feel ready. I thought that without copious planning, I would be totally lost. I simply could not go if I wasn’t “prepared.”

It turns out I felt totally lost regardless. All of my planning and micromanagement didn’t matter once I got there. My planning protected me from having to do things that scared me. It stifled my growth—halted my exposure to new people and experiences. Navigating your travels in real life is completely different than what you imagine sitting in front of a computer screen.


Do you know that feeling in your heart—the one that gives you butterflies and says, “I really want to do that”?

Don’t drown it out with facts and figures. Don’t say that for it to come to life, it needs meticulous plans and a year of research. How maybe you will get to it eventually, once you have a safety net. Waiting for a safety net will dull your dreams entirely.

You may never get to a moment where you feel completely ready. There will be selective preparedness and calculated unknowns, but never all-the-way ready. You figure out your own balance as you go.


Prepare enough. But risk enough too. Risk will teach you far more than over-thinking anything ever will.

Have a plan. A flexible plan. Yes, do the research on visas, health insurance, safety, what to pack. But you can probably skip buying those zip-off quick-dry “travel” pants.

If you can hear that voice, the one that says, “let’s do it,” listen to it. Trust yourself that you know where you are going. You know a lot about your own journey, after all, you’ve been walking it your entire life. Take the first step, trust that you will be caught—trust that you will learn. Trust that you will fail, you will make plenty of mistakes, and you will learn how to stop being so hard on yourself.

Trust that every message you receive from yourself is there for a reason and needs to be heard.


We say to ourselves, yeah, I really want to go on that trip, write that book, move out of this city, and I can’t wait until I can do it, but I’m just not ready yet.

Ready is an excuse we tell ourselves so we can safely sit at our desks, eat another average donut and look at photos of the life we dream of. Ready is the safe word we use when we choose to go to another happy hour instead of saving money—because then we would have to start planning a trip. And that is scary, risky.

Ready is a myth. Waiting for ready means we don’t have to make ourselves vulnerable to the world. We don’t have to create, we don’t have to risk, we don’t have to do what scares us. We get to stay in our comfortable-enough world. The one that doesn’t challenge us, that doesn’t present newness.


Do not be satisfied with waiting for a “ready” that may never come. Don’t spend your time shopping for ugly beige money belts just because someone said you might want one.

If you can hear a desire you have, it’s loud enough. Listening to yourself, trusting yourself, and taking on the challenge that comes with jumping into a world of unknowns—this is what will nourish your growth. It will support you far more than waiting for ready ever could.


See more from Erin Sullivan on her blog and Instagram.

Leave a Reply

Your email address will not be published. Required fields are marked *