Free with Me

Free with Me

Ever wonder how you ended up where you are in life, like somehow your life isn’t yours anymore? If you've been looking for a way back to yourself, you've come to the right place. Dr. Jessie Benson walked away from a career as an anesthesiologist and ICU doctor to reclaim her own life and follow her dreams to become a life coach, professional artist, yoga-meditation teacher, and full-time adventurer. She helps her listeners figure out what isn't working in their inner and outer worlds and build a life they are excited to live. She also offers a weekly relaxation practice.

Episodes

September 22, 2026 • 19 mins

There are many personality typing systems out there, and this week Dr. Jessie shares her favorite: The Enneagram. Learn about the 9 Types and see where you and your loved ones may land. When we understand ourselves and our loved ones better, life and love flow more freely.

Want to connect with Dr. Jessie for a free 30-minute coaching call? Here's her calendar link:

https://calendly.com/jessiebensoncoach/30-minute-clarity-session

...

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Mark as Played

Sometimes we can veer out of our best self and become an emotionally unsafe person for those around us, and often not even know it. Join Dr. Jessie as she shares how this can happen and what to do about it.

Want to connect with Dr. Jessie for a free 30-minute coaching call? Here's her calendar link:

https://calendly.com/jessiebensoncoach/30-minute-clarity-session

And if you'd like a dose of coaching wisdom in your inbox each wee...

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Mark as Played
September 8, 2026 • 13 mins

We often focus on being self-sufficient and can have a hard time allowing others to help us. Join Dr. Jessie as she shares about the gift of becoming a receiver.

Want to connect with Dr. Jessie for a free 30-minute coaching call? Here's her calendar link:

https://calendly.com/jessiebensoncoach/30-minute-clarity-session

And if you'd like a dose of coaching wisdom in your inbox each week, sign up for Dr. Jessie's newsletter, The I...

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Mark as Played
September 1, 2026 • 15 secs

Often we talk about what would we do if no one was watching and judging us. What about the life we spend doing things we don't really want to do because we think people are watching and might judge us if we don't? Join Dr. Jessie as she guides you through a way to be more true to you.

Want to connect with Dr. Jessie for a free 30-minute coaching call? Here's her calendar link:

https://calendly.com/jessiebensoncoach/30-minute-clari...

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Mark as Played
August 25, 2026 • 16 mins

As humans we tend to focus on what's missing. Join Dr. Jessie as she helps you discover the joy that's already there. 

Want to connect with Dr. Jessie for a free 30-minute coaching call? Here's her calendar link:

https://calendly.com/jessiebensoncoach/30-minute-clarity-session

And if you'd like a dose of coaching wisdom in your inbox each week, sign up for Dr. Jessie's newsletter, The Invitation.

http://eepurl.com/hdJ51z

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Mark as Played
August 18, 2026 • 14 secs

When what we want seems like it may never happen, we can be tempted to lower our standards. In this episode Dr. Jessie shares a personal story about the moment she decided not to settle and how it tuned out.

Want to connect with Dr. Jessie for a free 30-minute coaching call? Here's her calendar link:

https://calendly.com/jessiebensoncoach/30-minute-clarity-session

And if you'd like a dose of coaching wisdom in your inbox each we...

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Mark as Played
August 11, 2026 • 16 mins

How we feel in every moment of our life can be traced back to a simple question our nervous system asks. How we think can determine the answer it gets and the ultimate quality of our life. Join Dr. Jessie as she guides you through answering this question for your own life.

Want to connect with Dr. Jessie for a free 30-minute coaching call? Here's her calendar link:

https://calendly.com/jessiebensoncoach/30-minute-clarity-session

...

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Mark as Played
August 4, 2026 • 15 mins

Could you use more energy? Join Dr. Jessie as she helps you boost your energy so you can do more of what you love.

Book Dr. Jessie mentions in this episode: How To Stop Being Toxic by Julia Deloach

Want to connect with Dr. Jessie for a free 30-minute coaching call? Here's her calendar link:

https://calendly.com/jessiebensoncoach/30-minute-clarity-session

And if you'd like a dose of coaching wisdom in your inbox each week, sign u...

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Mark as Played
July 28, 2026 • 15 secs

How we are in our adult relationships can be traced back to how we were treated as children. Join Dr. Jessie as she helps you discover your Attachment Style and how to have healthier, deeper relationships.

Want to connect with Dr. Jessie for a free 30-minute coaching call? Here's her calendar link:

https://calendly.com/jessiebensoncoach/30-minute-clarity-session

And if you'd like a dose of coaching wisdom in your inbox each week,...

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Mark as Played
July 21, 2026 • 14 mins

We typically think our way of doing things is best. Sometimes we can impose our method on others and even though we think we're helping, we can actually undermine our connection with the other person. Join Dr. Jessie as she shares about giving space to others. 

Want to connect with Dr. Jessie for a free 30-minute coaching call? Here's her calendar link:

https://calendly.com/jessiebensoncoach/30-minute-clarity-session

And if...

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Mark as Played
July 14, 2026 • 12 secs

Cognitive distortions are a part of being human. The more we learn about them, the more we can avoid using them and the harm they cause. Join Dr. Jessie as she shares about black-and-white thinking and what has helped her on her own journey to avoid this cognitive distortion.

Want to connect with Dr. Jessie for a free 30-minute coaching call? Here's her calendar link:

https://calendly.com/jessiebensoncoach/30-minute-clarity-sessi...

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Mark as Played
July 7, 2026 • 9 secs

Life doesn't wait for us. And if we aren't careful, we can wake up one day and wonder where our life went and realize we didn't do the things we really wanted to. Join Dr. Jessie as she invites you to look at the areas of your life where you may waiting until we're ready so you don't wake up one day with regrets.

Want to connect with Dr. Jessie for a free 30-minute coaching call? Here's her calendar link:

https://calendly.com/jes...

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Mark as Played
June 30, 2026 • 14 mins

Most of us have a list of things we want to do "someday". Sometimes that day never comes. Join Dr. Jessie as she takes you through a journey to making that someday today.

Want to connect with Dr. Jessie for a free 30-minute coaching call? Here's her calendar link:

https://calendly.com/jessiebensoncoach/30-minute-clarity-session

And if you'd like a dose of coaching wisdom in your inbox each week, sign up for Dr. Jessie's newslett...

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Mark as Played
June 23, 2026 • 20 mins

In the outdoor adventure world, backpackers have a term called the Backpack Shakedown. Join Dr. Jessie as she applies this principle to life in general and guides you through the process of seeing what needs to be removed from your life backpack so you can be free.

Want to connect with Dr. Jessie for a free 30-minute coaching call? Here's her calendar link:

https://calendly.com/jessiebensoncoach/30-minute-clarity-session

And if ...

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Mark as Played
June 16, 2026 • 13 mins

When we're on our growth journey, an unexpected sign can show up, and it may have us wondering if something's wrong. Join Dr. Jessie as she shares what it is and what to do if it arrives in your life.

Want to connect with Dr. Jessie for a free 30-minute coaching call? Here's her calendar link:

https://calendly.com/jessiebensoncoach/30-minute-clarity-session

And if you'd like a dose of coaching wisdom in your inbox each week, sig...

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Mark as Played
June 9, 2026 • 12 mins

We aren't born knowing how to be a good romantic partner, and if we had bad role models, our chances of going astray are pretty good. Join Dr. Jessie as she shares 3 ways to be a good partner. 

Want to connect with Dr. Jessie for a free 30-minute coaching call? Here's her calendar link:

https://calendly.com/jessiebensoncoach/30-minute-clarity-session

And if you'd like a dose of coaching wisdom in your inbox each week, sign up ...

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Mark as Played
June 2, 2026 • 15 mins

Do you find it hard to say no? Does anyone in your life ask you to do things you don't want and you'd like an easy way to tell them no? Join Dr. Jessie as she teaches three easy ways to say no. 

Want to connect with Dr. Jessie for a free 30-minute coaching call? Here's the calendar link:

https://calendly.com/jessiebensoncoach/30-minute-clarity-session

And if you'd like a dose of coaching wisdom in your inbox each week, sign up...

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Mark as Played

Do you find yourself staying in situations only because you've already been in it so long? You might be getting trapped by what psychologists call Sunk Cost Fallacy. Join Dr. Jessie as she explains what this is and how to get free from it. 

And if you'd like to continue the conversation, or talk about another part of your life, connect with Dr. Jessie for a free 30-minute coaching call:

https://calendly.com/jessiebensoncoach/3...

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Mark as Played
May 19, 2026 • 18 mins

We all know it's important to be careful when choosing a romantic partner, but we typically don't put the same level of care into selecting our friends. Join Dr. Jessie as she guides you through The Friends Inventory to see if your friends are helping your life, or hurting it.

And if you'd like to continue the conversation, or talk about another part of your life, connect with Dr. Jessie for a free 30-minute coaching call:

https://...

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Mark as Played

We're often afraid of differences in our relationship, worried they will drive us apart. Instead of being a source of conflict, we can allow our differences to bring us closer.

If you'd like to connect and figure out ways to make your relationship and life better, book a free coaching call with Dr. Jessie. 

https://calendly.com/jessiebensoncoach/30-minute-clarity-session

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Mark as Played

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