Jake Heilbrunn - How Asking Why Led to a Healing Journey to Central America

My Big Story

Jake Heilbrunn had the desire to pursue something to believe in, compelling him to travel to Central America to discover a greater awareness — and now to share his inspirational journey and help others find a deeper why.




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Jake Heilbrunn’s story started in college when he was overcome by a wave of anxiety and depression, and wasn’t sure how to move forward on his path. He then set on a journey to Central America to explore the world—in turn learning about himself. Christopher and Jake talk candidly about feeling lost and searching for more. Jake knew something wasn’t right for him and needed to figure it out. They discuss who Jake met on his travels and their impact on him, why his journey matters, and how he’s sharing his experiences with others.


Key Takeaways

[1:42] What motivated Jake to deviate from the expected course?
[8:11] Why travel was the answer for Jake.
[11:04] Why Jake felt compelled to pursue something he believed in.
[13:29] How Jake ended up in Central America.
[15:19] Jake shares his experiences traveling and the people he met along the way.
[22:44] How Jake’s travels gave him a greater sense of appreciation for the things he has.
[25:58] How questioning his path and his why brought Jake internal peace.
[32:20] How did Jake find the answers he was seeking and how did it guide his next steps?
[36:49] Jake shares a few specific travel experiences that have shaped his journey.
[43:27] How Jake has influenced others because of his awareness.
[47:40] Who does Jake look up to and who has inspired him?
[50:32] Jake continues to expand his why and looking toward the unknown.
[53:16] How to find Jake online and his book, Off the Beaten Trail: A Young Man’s Soul-Searching Journey Through Central America.
[54:44] Any thoughts or questions you’d like to share? Send us a message or post a comment on Facebook or tweet us @accidentalinfo using #LivingYourJourney.


Mentioned in This Episode

@accidentalinfo on Twitter
Accidental Information on Facebook
#LivingYourJourney for Tweets
Jake Heilbrunn Website
@Jake_Heilbrunn on Twitter
Jake Heilbrunn on Facebook
@jakeheilbrunn on Instagram
The Happiness of Pursuit by Chris Guillebeau
Into the Wind: My Six-Month Journey Wandering the World for Life’s Purpose by Jake Ducey
Pencils of Promise



“When you vocalize it, it let’s you see it at face value for what it really is.”

“The trip was about experiencing different ways of life. That’s what I wanted out of travel.”

“The trip was for me. It almost felt like a healing journey for me.”

“If you fuel your journey on the opinions of others, you are going to run out of gas.” — Dr. Steve Maraboli

“It was definitely about shaking things up, but it was about taking the leap of faith to pursue the thing that called out to me.”

“I’d always planned things and I needed to kind of get out of the confines of a system.”

“A big part of the trip was just being open to life more.”

“[Travel] breeds awareness and it sounds like you want to foster that desire to find more awareness in your life.”

“Take the time to question, what do you consciously want to create in your life?”

“I felt like the most powerful way to inspire someone is to never tell them what to do, but just to show what worked for you.”

“A lot of great things take work.”