5 Things I’ve Learned About Life’s Obstacles

Historically, I’ve struggled a lot with life’s obstacles. In 2022, I got a flat tire while visiting a city and had a complete meltdown. In 2023, I made a goal to deep dive into life’s obstacles. Learning how to dance with them instead of breaking down. 

Try something new Tuesday has been a fantastic battleground for practicing interacting with obstacles. Some Tuesdays, my day feels too full to intentionally live my life. On other Tuesdays, things don’t go as planned. It rains when I was looking forward to an outdoor adventure, I wake up with a headache, there’s a client emergency. And some Tuesdays, don’t even feel like a Tuesday; looking at you Tuesdays after holiday weekends. 

My deep dive into life’s obstacles this year has been eye-opening, humbling, and encouraging. Here are the top five things I’ve learned about life’s obstacles so far.

1. Not All of Life’s Obstacles Are “Bad”

Here’s the funny thing about obstacles. When you’re facing them, they feel horrific. They feel like the roadblock between you and your heart’s desires. It’s not until you’ve gained some distance that you can look back on your life and see that the obstacle you perceived as “bad” at the time was actually a fantastic turn of events. 

Buddhist monk Thich Nhat Hanh, dropped the mic on this concept in the book How to See. He shares “It is not possible to judge any event as simply fortunate or unfortunate, good or bad…You must travel throughout all of time and space to know the true impact of any event…Every event is both fortunate and unfortunate.”

There’s Opportunity in Life’s Obstacles

When we first were looking for a house in the Asheville area, we had our hearts set on West Asheville. It reminded us of Denver’s Uptown neighborhood that we were moving from – quirky, walkable, and surrounded by activities. We put in four bids, one a month, on homes in West Asheville, and each one we disappointingly lost. 

By the fourth home, we were discouraged. So we switched strategies and opened our search up to include the neighboring town of Black Mountain, North Carolina. That same week our now home appeared on the market. A year later, we’ve fallen in love with Black Mountain and are incredibly grateful that the homes in West Asheville didn’t work out.

2. Sometimes You Are Your Own Obstacle

This has probably been the most life-giving lesson I’ve learned on my Obstacle Mission. For months, I kept a daily record of the obstacles I faced to better understand them and remind myself to get curious when facing obstacles instead of shutting down. 

Some Obstacles Are Just Your Feelings 

From the obstacle logs I kept, at least 25% of the obstacles I faced were in my own head. They were perceived obstacles, not something that existed or that I was physically facing. Often these self-induced obstacles were feelings-based: 

• I felt overwhelmed by my to-do list. 
• I didn’t feel like working on a specific task. 
• I was stressed about taking a new hike and that stress manifested into an obstacle of the mind. 

Identifying these self-created obstacles has helped me dig deeper into the triggers causing the feelings. They’ve also helped me save my energy for life’s larger obstacles.

3. Everybody Experiences Life’s Obstacles 

Thanks to social media, it’s never been easier to peek into other people’s lives and think they’re perfect. That they don’t struggle or have never struggled. Everyone, and I do mean everyone, faces obstacles. We all shoulder disappointment from unrealized expectations. We’ve all started out in one direction only to be detoured to a place we never planned to go.  

Ryan Holiday’s book The Obstacle is the Way does a phenomenal job telling the story of historical icons who each faced massive obstacles. Like Thomas Edison’s lab burning down or when Steve Jobs was fired by the company he founded.   

They’re Not Personal, But They Are Personal

In a way, obstacles aren’t personal. It’s not a sign that God hates you or that you’re doing life wrong. But in the same breath, they are personal. The obstacles you face are on your unique life’s journey to teach you something or take you down a needed path.

4. Life’s Obstacles Don’t Mean You’re Doing it Wrong

Somewhere in my life, I started believing that if you’re on the right path and you’re doing the right things, everything will go your way. Insert laugh track. 

We live in a broken world, surrounded by imperfect people and things we can’t control. Obstacles are guaranteed to happen no matter what path you’re walking on. 

The Story We Tell Ourselves Matters 

Author and counselor, Mary O’Malley, shares eight stories that we tell ourselves about life in her book What’s in the Way IS the Way. These stories that have been taught to us or inspired by fear include: 

• I must control life. 
• I must do it right. 
• I am not doing it right enough. 

I think one of the reasons I’ve struggled with obstacles is they’re a reminder that I can’t control life. Some of my goals will fail. Some of my dreams will never be realized. Obstacles force me to accept a life that isn’t perfect or maybe wasn’t what I hoped for. They put me in a humbling position to trust that it’s all for my good.

Obstacles force me to accept a life that isn’t perfect or maybe wasn’t what I hoped for. They put me in a humbling position to trust that it’s all for my good.

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5. Life’s Obstacles Are a Full Body Experience

When you run into an obstacle what’s the first thing you notice? Does your mind start to go into a worst-case scenario script? Do you feel clenching in parts of your body? Do you start to feel sad, discouraged, and/or teary-eyed? Welcome to life’s obstacle course. 

In addition to learning to dance with obstacles, I’ve also been diving into the full-body connection to better understand how the mind, heart, soul, and body are all connected and work together.

What is Your Body Trying to Tell You?

When I encounter an obstacle, real or imagined, I check in with myself:

• How do I feel? 
• What’s my primary emotion? 
• Where do I feel that emotion in my body? 
• What script(s) is my mind playing? 

Once I understand how I’m showing up, I can get curious about the obstacle (more to come on that later!). And then decide how I want to show up. Blowing past my initial emotions or thoughts hasn’t been helpful. Those defaults have been years in the making and deserve to be acknowledged and then released. 

Welcome to Life’s Obstacle course

Life’s obstacles are a wild ride we all face. What has your life taught you about obstacles? Comment below and follow me on Instagram for more habit-changing inspiration.