We were lucky to catch up with Dawn Jackson recently and have shared our conversation below.
Dawn, thanks for joining us, excited to have you contributing your stories and insights. Naming anything – including a business – is so hard. Right? What’s the story behind how you came up with the name of your brand?
So how do you capture in a name a faith-based life, leadership and spiritual formation coaching business that endeavors to take people outside to encounter God and discover who they are and what they want to live for? That was the question I was facing when I was praying through naming my business. It was a question that consumed me for months. Initially, I thought I would just name it Dawn Jackson Coaching and then present the heart behind the company in other ways. But that sounded boring and felt like I was missing an opportunity.
One day I was reading Os Guiness’ book The Call and he was explaining how we are wayfarers. (see page 228) He explained that some Christians talk about their faith as if they have arrived, They minimize the uncertainties and tragedies and live as if there is nothing more to learn and no risks or dangers on the horizons. Then he explained how there are are other Christians who are so conscious of the journey that it has become a journey without end and that ambiguity is everything with no thought of a destination. Guiness went on to explain that between these two extremes is a balance where believers recognize they are on a journey towrd a destination with all the costs and risks involved and that they have not yet arrived. However, they know where they are headed and, better than that they follow the one who is the Way. So we who are followers of Christ are Wayfarers following the One who calls us. This jumped out at me and I began to think about how to use the name Wayfarer. in the name of my business
While thinking through all of this I also regularly reflected on a liturgy I had come across a few years earlier called The Liturgy of Brendan the Navigator. This liturgy tells an amazing story about the adventure of a Celtic saint who decided to step out of his comfort zone and follow the call of God on a seafaring voyage. There is a phrase in this liturgy that has echoed in my mind every since I first read it.
“Have I the faith to leave old ways and break fresh ground with God?”
I began to think how this captured so clearly what Os Guiness was talking about when he wrote about being a wayfarer. A wayfarer leaves the safety of the old and predictable ways to follow the call of God. A wayfarer comes alive to that call. While Brandan is a seafaring story and my outdoor canvas is more mountain trails I felt that it still captured the heart and passion for life transformation that takes place as we journey forward following the One who is the Way. After processing all of this, This Wayfaring Life LLC was born.

Dawn, before we move on to more of these sorts of questions, can you take some time to bring our readers up to speed on you and what you do?
I was born and raised in SoCal, I am passionate about Jesus, the outdoors and seeing people come fully alive to the call of God on their life. I believe that life is a gift from God and how we live it is our gift back to him. I want to live it well. I would imagine others do too!
For 33 years I served as a pastor at my home church. Youth ministry, small groups, leadership development, executive leadership–I was entrusted with some incredible opportunities. The last couple of years I have had the privilege of serving on team with Propel Women where we developed and launched Propel Women’s Cohorts where we provide coaching for woman in ministry whether that be at church or in the marketplace. Ecclesia: Truth be told, I am and always have been a coach at heart. I love Propel Ecclesia and continue to coach with them on the side. I am also a certified professional life coach, a certified RevWild outdoor leader, a certified wilderness first responder and a part-time pastor at my local church.
As a little girl I played life “full out”–adventure has always been one of my core values. This love for adventure has led to all types of outdoor experiences: trail-running, backpacking, canyoneering, whitewater rafting, ultra-marathoning. I find the image of a trail to be a powerful metaphor for what it looks like to follow Jesus.
This Wayfaring Life brings together my faith, my love for coaching and my outdoor experience and combines it with a deep desire to see others come fully alive to the call of God on their life.
I offer various opportunities for coaching (individual, group, online) and am currently implementing outdoor experiences into my coaching portfolio. I am partnering with Canyon Adventures and taking a group of eight people canyoneering in our local mountains. This will be combined with leadership and risk management coaching. Later in the summer I will be coaching women on spiritual resilience and backpacking skills. We will close out our time together with a three day trip into the backcountry. Next year I hope to add in a few more backpacking trip and white water rafting.
The majority of my coaching addresses these areas;
– Clarifying life vision, purpose and mission and having the courage to make the changes necessary to live in alignment.
– Core needs and values clarification and how to get these met in a healthy manner.
– Life transitions.
– Healthy rhythms and contemplative prayer.
I am a speaker at conferences and collaborate with other coaching businesses to provide wholistic workshops addressing spiritual, emotional and physicl wellness.
I love that clients come away from these experiences feeling renewed, restored and refreshed. And perhaps a bit challenged to continue stepping out of their comfort zone. :)
Of course the core of all of this is this is a Jesus-centered business and that is what makes me the happiest. It is a joy and an honor walk with clients on thier journey of following the One who is the Way!

We often hear about learning lessons – but just as important is unlearning lessons. Have you ever had to unlearn a lesson?
Early on I hired a business coach and trusted his insight. It was my first venture into running my own business and he had some great ideas. However, I started to not trust my own insight and voice. Over time I realized what we were designing was not really an expression of me. It checked all the boxes for what one should do but it did not feel authentic to who I was. I eventually stopped working with him, changed the name of my business and rebranded it. The lesson I learned in all of this was to be very clear about what I really wanted and not allow another person’s enthusiasm for what they see to override what I want to build.
Can you tell us about a time you’ve had to pivot?
The biggest pivot I have made was resigning from a position at my church where I had served on staff for 33 years to launch my business. It is so easy to get comfortable in life. I had a comfortable salary and great health insurance and four weeks paid vacation. Those are difficulty things to give up to start a business when you are in your 50’s and single. It felt like swinging on a trapeze and having to let go of the trapeze bar and not seeing another bar coming towards you. A friend encouraged me that if I fell God would be the net under me to catch me. So I let go! And I didn’t fall. :)
Contact Info:
- Website: https://www.thiswayfaringlife.net/
- Instagram: https://www.instagram.com/rundawnjackson/
- Facebook: https://www.facebook.com/dawn.jackson.359

