When Is the Obstacle the Way? And When Is It a Sign to Stop?
Have you ever read The Obstacle Is The Way by Ryan Holiday? Greg and I just finished recording a podcast episode where we talked about this book and some lessons we took from it.
Essentially the whole premise is that obstacles are meant to be pushed through.
There are three main parts to this idea:
How you choose to look at the obstacle.
Taking action instead of sitting around thinking about it.
Staying with it long enough to get through it.
I love this concept and I loved this book. It makes a whole lot of sense to me.
BUT I’ve recently come to terms with an obstacle (or at least that’s how I had perceived it) that may not actually be the right “way” for me.
I do not like facilitating anything.
I do not like attention.
I do not like a microphone.
I do not like recording videos and putting myself out there.
I just don’t.
And believe me, I’ve tried.
People are constantly telling me that I’m good at it. That I’m a natural. That it will get easier the more I do it and eventually it will become second nature.
And for a long while, I believed them.
“Push through the discomfort, Whitney. Keep going. The Obstacle Is The Way.”
I didn’t quit. I gave it time and trusted that the people around me were right. If I just keep going, it will all be worth it. Maybe this is just discomfort. Maybe this is the obstacle I’m supposed to push through.
Well… it’s been over a year now and it hasn’t gotten any easier.
It still drains my energy. Every. Single. Time.
Before facilitating or presenting something, I feel a knot in my stomach. Which of course many people feel, and I know is normal. During it, I’m counting the minutes until it’s over. And after it’s done, I feel like someone literally pulled the batteries out of my body. It’s brutal and it’s exhausting.
A coach and close friend of mine, Natalie Dumond, would say (and did say) there are narratives in my head that keep pulling me down and keeping me small. Being small and unseen is where I feel safe. And she’s totally right.
So while I absolutely need to continue to explore my confidence and ignore my itty-bitty-shitty committee (it’s an ongoing battle), I’ve also been asking myself a different question.
Maybe this obstacle isn’t something I’m supposed to conquer.
Maybe this obstacle was the way of showing me that I’m just not meant to do that particular work in our business.
Maybe it was pointing me toward something else.
Once I started paying attention to my energy, I noticed that there are parts of running our business that I really like and KNOW that I’m really good at.
Things like brainstorming and being creative.
I like writing and marketing.
I like creating our newsletter and building our website.
I like thinking through every word and every small detail of our retreat and the experience for people attending.
Basically, I like the parts where I can sit quietly with a coffee, build something cool, and not hold a microphone.
I like what I like.
Which brings me back to the question that’s been bouncing around in my brain lately.
How is a person supposed to know the length of time they should push through an obstacle? How long should I continue to facilitate and present and go through literal physical and emotional distress before enough is enough?
Because I do believe that sometimes resistance means:
Keep going.
Keep pushing.
Figure it out.
But I also think sometimes resistance is actually information.
Sometimes it’s the universe tapping you on the shoulder and saying,
“Hey… you might be walking down the wrong road here.”
And the tricky part is that those two things can feel very similar.
So maybe the real question isn’t just whether the obstacle is the way.
Maybe the question is:
Are you supposed to push through it?
Do you actually have the energy to keep pushing?
Or is it trying to teach you something?
Sometimes the obstacle IS the path forward.
And sometimes it’s the sign that it’s time to take a different one.
