Transition Coaching for life’s big changes.

Transform uncertainty into clarity, growth, and purpose.

From Confusion to Clarity 

Life’s transitions can feel overwhelming and disorienting. It’s no exaggeration to say that in a big transition, a part of you is dying. Even when it’s a change you’ve chosen - it can be painful and scary.

Whether you’re an entrepreneur (starting, growing, or closing a business), contemplating a career shift, or trying to finding yourself after a relationship ends, the uncertainty can cloud your judgment and stall your progress.

Sometimes you just don’t know what you want - you only know it’s not “this.”

As a coach, I help guide people through these transitions toward a more centered, aligned, and confident you. My deep coaching approach helps you shed self-imposed limitations and old identities to find and align with your true calling.

Confidently navigate life’s pivotal moments, transforming confusion into clarity.

  • Think of me as an integrative business coach. Or even a business mindset coach. I coach you while you run your business.

    My favorite thing about coaching business owners is that they’ve answered the call. They’ve done the hard work of stepping into business and, in doing so, they’ve created a container for growth - personally, financially, even spiritually.

    Business constantly forces us to grow. It brings up our stuff in countless ways. And when our stuff comes up - there’s an opening to see it and transform it… to let it go.

    Business, from that lens, is a container and catalyst for transformational personal growth. If you have the courage to grow with it.

    I’ve worked with business owners in almost any industry you can imagine, guiding them through all transitions that business necesitates -

    • Identity shifts - from worker to owner

      • This is a big one that most small business owners to know - or don’t know how - to make. Most of us start a business because we’re great at doing the work that the business produces.

        In the beginning, that’s a great strength, but without an identity shift, it will hold us back from growth and scale. You need to find new ways of being and doing to really grow. All of this brings internal growing pains.

    • Growth Phase transitions

      • The growth of your business will always be limited by your internal capacity to navigate the changes.

        Business growth requires owners to shift internal beliefs, mindsets and ways of being. “What got you here won’t get you there.”

      • Putting yourself out there in the marketplace can be scary. “What will people say?” “They’ll reject me.” “I’m bothering them.” Fear of rejection and being criticized can cripple us if we don’t grow through it.

    • Maturation Phase transitions

      • As a business grows or changes, the roles and responsibilities of an owner change with it.
        I’ve had many business owner clients struggle internally with the transition to the business depending on them less. We root much of our identity in “being essential to the business.” The shift to a higher-level leadership role can be a painful (if liberating) transition. But it requires a shift in identity and a letting go of who and how we’ve been so far.

    • Transitions out of business

      • Whether selling the business, shutting it down, or just trying to figure out “What now?”

        When our identity is rooted in who we are as a business owner, this transition feels can be especially disorienting. You worked for years to get here - blood, sweat and tears…

        So… what’s next for you?

      • *My own transition out of my first business was one of the most painful (though, in the long run, rewarding) periods of my life. It led me closer to me and started me on the path that I’m on today. As with any big transition, it was a painful letting go of who I’d been which created an opening for more of who I am.

    • Transitions into Leadership and Management

      • Managing people can be one of the most difficult but rewarding parts of business ownership. And leadership comes with a heavy burden.
        Learning to ask for what we need, hold people accountable, communicate clearly, delegate well, hold boundaries, have hard conversations, steer the ship, inspire and excite, and more…

        These are the demands on a manager and leader. And all of them can require big shifts in our approaches and our beliefs.

    • Shifting with the market

      • If only business happened in a vacuum - where our plans always came seamlessly to life…
        But it doesn’t. There are market realities - buyer preferences, hiring constraints, and more.
        When our plans don’t go to plan, it can be painful and frustrating. It can send us into a tailspin of self-doubt and worry.

        I can help you keep your focus pointed in the right direction, find the gifts in every obstacle, and your truth through all the frustrations.

    • Creating an Aligned Business

      • Many business owners start their business from a place of frustration - “I can’t work for that person anymore.”

        Or our motivation that isn’t really aligned to who we are and what we want.
        Building the business that you want takes courage and a deep alignment to your Self. I can help you find your why and create the business that aligns to that.

  • You’re feeling a call to start a business. Maybe you’ve been feeling it for a long time.

    But something is keeping you from doing it. Maybe it’s…

    • Self-doubt…

    • Fear of the unknown…

    • Fear of letting go of the life or job you have now…

    • Fear of letting people down…

    • Fear of failing…

    • Imposter syndrome…

    • Not knowing where to start…

    Or maybe it’s a combination of those things or others.

    It feels important but you just can’t seem to pull the trigger.

    Many people get stuck here in various ways. There’s nothing wrong with you. The fear doesn’t mean you’re not up to the task - in fact, it likely means it’s the right next growth edge for you.

    There’s just something you need to let go of.

    I can help you

    • Find your way to clarity and a strong start.

    • Shed the fears and limiting beliefs that are keeping you stuck.

    • And launch your business with clarity, purpose and confidence.

  • Sometimes we choose job or career changes and sometimes they choose us.

    Whether you have a nagging sense that you’re in the wrong career - you’ve climbed the wrong ladder - or you just feel a pull toward something new, you’re in the midst of a career transition.

    …If you have the courage to answer the call.

    That nagging sense, that layoff, that pull to something new… that’s your purpose calling.

    …But often it’s hard to hear it through the limitations we imagine and the fears we have about making the change.

    We often form our identities around our work. It’s not just what we do - it’s who we are.

    A career transition can be a powerful (if painful) time of introspection and renewed alignment. It can be a time to re-evaluate our hopes and aspirations. It can bring us closer to who we are so that we can bring more of fullest selves into the world - and lead a purposeful life.

    My friend, the world needs more of you.

    I can help you sort out the longings from the fears. I can help you reinvent yourself and your contribution to the world.

  • Life is funny. Sometimes we’re thriving and on-purpose. Other times we feel lost, stuck, or discontent.

    Many coaches (including me) can talk all day about the ways to make change in our lives. I can even give you a four step formula:

    1. Let go of what’s holding you back,

    2. Set a compelling vision for the future,

    3. Take aligned action,

    4. And stay focused on what you want.

    And that formula works.

    But in its simplicity, it misses one crucial element - and most coaches miss it too…

    …It’s hidden in the context in which that formula exists. It’s hidden in the seasonality our lives naturally exude. It’s hidden in plain site…

    It’s the emerging readiness to change.

    It’s like the earth in which we plant those seeds of change. The earth needs to be tilled and nurished to allow the seeds of change to take root.

    Your stuckness? Your discontedness? Your restlessness? Your lack of motivation or drive?

    Those are all signs that there’s a readiness emerging in you.

    The trick is to see them as the calling that they are. To recognize that they represent a shift in the soil - a shift in you.

    Exploring those signs to find the calling they’re calling you toward - that’s tilling the soil. That’s preparing to make the change.

    When you’re ready, we can do the work, but you have to create space first to hear the longings from deep within you.

    I can hold space for you to explore those emerging shifts and find the calling that’s calling you.

  • Someone recently told me “I just got out of a 15 year relationship and it’s like I don’t remember who I am anymore.”

    Relationships are like a bedrock in our lives. They teach us about ourselves and we form identities around them. The help to shape our values, beliefs, and goals.

    When new relationships begin or old relationships end, it can feel like a loss of identity.

    And that’s because it is one.

    Beginnings and endings of relationship represent moments of dramatic change in our lives. And an invitation to transformation.

    We’ve all known people who jump quickly from one relationship to another. And with each change, find the same old patterns - the wrong types of partners, the same types of fights. New, but not different.

    These people haven’t transitioned through the loss of the old relationship, they’ve just changed partners.

    Change is like moving the furniture around - a new couch in a different location. Transition means using the change as a catalyst to learn more about yourself - what you really want, who you really are, what patterns you need to let go of.

    As with all big transitions, we have to answer the call if we want to transform.

    Relationship changes can be a pathway back to a more aligned you. You just have to have the courage to go within and discover what life wants you to learn.

Who I help

Find clarity through the turmoil of change

Proven methods that unravel the perplexity of change.

I can help you…

Navigate life and business transitions

Personalized coaching sessions tailored to your unique journey.

Unlock your fullest potential

Strategies that transform change into personal and professional growth.

And at a deeper level,

Our work together is about way more than navigating a transition.

It’s about becoming more of who you are

…and bringing that into a world, a business, a relationship that needs more of you.

As your coach, I’ll help you:

✔️ See your situation in a bigger (more empowering) context.

✔️ Find clarity, confidence and alignement by learning to hear your inner wisdom.

✔️ Become the person you’re meant to be.

What my clients are saying

  • “I want to give you a lot of gratitude. We had what I saw as an impossible task of helping me find my life’s focus and within just two coaching sessions I really believe we’ve accomplished it.”

  • "I've been shocked at my internal and outward change since the breakthrough session. I've felt much more at peace and felt like a better dad and employee. This has already been a big game changer for me."

  • “The more we talk, the more it leads me to the path of where I actually want to be. I’m becoming more honest and true to myself about how I want to live and what I’m working toward.”

  • "I always leave our calls feeling energized and with a greater sense of clarity. Dan asks great questions and challenges me to look at things through a different lens that has helped me in addressing issues with both my business and my employees."

  • “You have been an inspiration and a God-send. I would have closed up shop 2 years ago had you not come along. I truly appreciate the ways that you look at things and how you get me to think about things differently. (and get me to ask the right questions)”

  • “I had this big vision but I had no idea where to start. That’s why these meetings are so helpful to give me perspective, guidance and direction.”

  • "I just wanted to thank you for all your help, I feel alive again and excited for what our future holds."

  • "I absolutely love the coaching. Dan always breaks it down, guides me through my thought process, and leads me to greater understanding."

  • "I love my coach, Dan! He is awesome! Understanding where I am coming from, Guiding me, Listening and asking thought-provoking questions."

Having a coach means having someone to walk with you

toward the life that’s calling you.

…and helping you find the courage to answer that call.

I’ll be…

A guide on your path

Guidance through your transition to help you understand and navigate the process of transition. We’ll find your answers to the challenges you’re facing and navigate the change together.

At every moment we have the choice to participate in the unfolding of our lives unconsciously or consciously (as an active, co-creative participant.) I choose the latter. From this perspective, life is a process of creation and evolution and the your experience is literally a heroic journey.

Always-in-your-corner support

The transitional path can be hard work. You’ll have to let go of who you’ve been and of the beliefs that no longer serve you. You’ll have to look honestly at yourself and your situation. You’ll have to listen closely to your inner longing. You’ll learn a lot about your Self. It’s hard work but rewarding.

This journey will grow you spiritually, mentally and emotionally. And I’ll be with you for every step of it.

A you-focused spiritual partner

Transitions can be lonely, scary, and disorienting. I believe that our higher selves are deliberately attracting people, circumstances and events to us as opportunities to grow into our best selves.

Whether change feels positive or negative, I’ll help you see and trust that all of it is for your own highest good.

A mirror to find your deeper sense of self

The ego is powerful. It’s our sense of self And it serves us well, until it doesn’t. Sometimes it gets in our way - especially in times of big transition. We get stuck in patterns and beliefs that aren’t really ours and that keep us from the opportunities for growth and transformation that life is offering us.

I’ll help you find, hear, and answer your deeper longings.

Meet your Guide.

Dan Oliver

Life transition coach Dan Oliver - based in Bend, Oregon but serving clients globally (Online coach)

I admire people who are willing to risk the unknown in the hopes of something better. People who embrace the transitions of life.

Transition has been a cornerstone of my life.

Like many of us, I’ve always had (and nourished) an underlying desire for more…

…To know myself more deeply. To accept myself more completely. To flourish more fully.

As anyone who lives on a growth path knows - growth necessitates transition.

When I found my way from a career as an arborist to a career as a business coach (talk about a big transition!), I’d finally found a path that allows me to bring my gifts of empathy, intuition, and levity into the world in a more impactful way - helping my clients transform their lives and businesses.

And as my journey as a business coach has unfolded, I’ve continually found my interest purely in business strategy waining (though I love those things too…). I’ve found myself more and more interested in the heroic journeys of transformation that my clients were walking.

The changes - personal, professional, spiritual - that their businesses and lives were calling them into. Those journeys have been my favorite to support.

And to my surprise, these transitions often create the most impactful changes in the circumstances around us - our businesses do better, our relationships improve, and our careers flourish, when they’re aligned to who we are are at our core.

Go figure… maybe there’s something to being more of who we’re meant to be in the world.

What are you waiting for? What’s it costing you to stay stuck?

Coach Dan Oliver

  • "The cave you fear to enter, holds the treasure that you seek." - Joseph Campbell

Let’s build your new life together.

The journey begins with a single step:

Step 1

Schedule a free Discovery Call

We’ll meet to explore your situation and answer any questions. If it’s a mutual fit, we’ll go to work. Our coaching will take a customized approach to addressing your unique needs - where you are, and where you want to go.

Step 2

We’ll let go of what’s holding you back and build a vision for the future

There’s a version of your you out there in the future that lights you up and inspires you. The you that you’re meant to be. We’ll work together that you - even in the midst of big change - and bring you into a new beginning.

Step 3

Start taking aligned action as soon as the path becomes clear

When your whole heart is behind something, you’re virtually unstoppable. We’ll sift through the noise to discover your aligned answers. We’ll stay focused on building the life or business of your dreams.

What are you waiting for?