

They live based on habits, expectations, and what they think they should do.
But at some point, usually after a big change or a quiet moment of reflection, these five questions start bubbling to the surface:





They might keep you up at night.
Or show up as that low-grade frustration that never quite leaves.
These questions shape the choices you make, the direction you head in, and the energy you bring to every part of your life — relationships, work, health, and spirituality.
If you’ve spent years doing everything right, and still feel like something is missing, this is your invitation to do something different.
You’ve read the books.
You’ve taken the courses.
You’ve probably been told to “just be grateful.”
And sure, there’s a lot to be thankful for.
But under the surface, there’s a quiet sense that your life isn’t quite aligned.
You find yourself going through the motions. Ticking the boxes. Doing what’s expected.
But deep down, you wonder:
Is this really it?
You might not be falling apart. You might not even be struggling.
But you’re definitely not thriving. You’re not creating. You’re not fully connected to that deep inner knowing — the part of you that knows you were meant for more.
Not more achievements or possessions. But more clarity, meaning, and alignment.
More of you — the real you — showing up in every area of life.
That ache you feel isn't a sense of being out of sync, but a sign that you're ready to design your life with intention.
When I was growing up, we didn’t talk about designing a life.
We talked about surviving it.
My father died when I was just two. My mother raised three kids on her own, and we lived in poverty. Early on, I absorbed this belief that life would always be hard — that you just do your best, keep your head down, and hope things don’t fall apart.
And for a long time, I lived that way. I became a therapist. I helped others heal. But inside, I was unraveling. I struggled with depression. I battled addiction. I stayed in relationships that broke my spirit.

Me at [AGE]. Since I was young, I experienced events that shaped my beliefs — thinking that life would always be difficult.
I even found myself homeless at one point — financially broke, spiritually numb, and completely lost.
It wasn’t that I lacked knowledge. I knew all the techniques. I’d read the books.
But knowledge isn’t enough when your foundation is built on beliefs you never chose.
Eventually, I realized something had to change — not just externally, but at the level of identity, values, purpose.
So I began to ask the questions I’d never truly asked before.
Not the ones the world throws at you — “What do you do for a living?” or “How successful are you?”
But the real ones.
1. Who am I, really?
2. What do I deeply value?
3. Why am I here? (not in a grandiose way, but in a grounded, tangible sense)
4. Where do I want to go next?
5. And how do I get there without burning out or losing myself?

Those five questions became my compass.
As I started answering them — honestly, without judgment — I felt something shift.
I began to rebuild from the inside out.
In the years that followed, I went from being broke, in recovery, and uncertain of my future…
To building multiple seven-figure assets, including waterfront homes I once never imagined I could own.
I went from surviving depression and addiction… to being invited to teach consciousness work alongside world leaders across the world.
I’ve spoken on wellness panels tied to the Olympics.
And I now appear in films next to people I once considered mentors like Michael Beckwith and Marisa Peer.
But most importantly?
I live in deep alignment with who I am, what I value, and why I’m here.
And that process — built on those five core questions — became the foundation of what I now teach in Life Design.
Because this isn’t about just feeling better or staying busy with another self-help checklist.
It’s about finally pausing long enough to ask the questions that most people avoid their whole life.
It’s about becoming the person you were meant to be, and building a life that reflects it.

“Life Design has been a gift for me. I have struggled with depression, anxiety and addiction for most of my adult life. It gave me the tools I needed to break free from the bondage of my ego and open the door to discovering the power of my true essence.”


“Life Design provided a structure to reevaluate all the areas of my life. I now see clearly what I came here to do and what talents I could use to be of further service in the world."


“I've paid back taxes, doubled my income and have become a Licensed Teacher in my Spiritual Center. I am doing and accomplishing things now that before seemed like just a dream.”


"Life Design is an amazing program for those who want to be intentional about living their best possible life! I would recommend it to anyone who would like to get into action on taking their life from mundane to meaningful and magnificent! I loved this program so much that I became a Life Design Coach!"

"I took Life a Design several years ago. It is a expansive, and impactful coaching process. Truly life changing ! So much so that I became a certified life design coach, I would highly recommend this"

"Not only was it insightful at every step, but incredibly useful in helping me to navigate an especially interesting and changing time in my life. Her kind and caring nature made it easier for me to uncover some of the beliefs I have had."

“I have taken Jackie Woodside ‘s Life Design program twice. The process is transformational. What I love is that it combines concrete activities to assess and change your life to reflect your desires and provides easy strategies to shift the negative underlying limiting beliefs and fears."

This program is not about therapy (did that), self-help books (done that), advice (my mother will give that for free) or mentoring (my sister has that market covered); it is about personal transitions in areas of your life you rarely take inventory of.

Jackie's paradigm of content and context is spot on and if you follow the guidelines you'll live a life of ease and accomplishment. Importantly, you'll accomplish your goals in all areas of your life, not just work. We can live in alignment with our values.
Video #1
An introduction to the Life Design course
Video #2
How to make the most of this program
Video #3
Providing context
Video #4
Coaching model and setting intention for your life
Video #5
"Where do we begin?"
Video #6
The Life Design Formula
Video #7
Your life's purpose
Video #8
Definition of success and failure
Video #9
Circle of satisfaction and strong foundation
Video #10
Strong foundation goals
Video #11
Evaluation section
Video #12
What are your core values ?
Video #13
Life's mission
Video #14
Your vision and it's importance
Video #15
Vision to goals
Video #16
Ego to essence you and your ego
Video #17
The 'LOC' model
Video #18
High Consciousness attribute gratitude
Video #19
Completion exercise
Video #20
A final recap and conclusion of the program



If you go through the course and aren’t completely happy with the value, contact us by email within the first 365 days (one whole year!) and we will refund you 100% - no questions asked!

"Jackie is an amazing teacher whose insights and concepts in the area of managing your daily life and living your life's purpose are inspiring yet practical & effective.She really knows what it takes to snap you out of your old habits and elevate your life to a new and exciting level energetically, spiritually and materially."

"Coach Jackie calls you forth to be more selective and true to the business plan of you. Using her structure and framework for understanding your self and your day and your intention for your own life produces clearer vision about what matters most. Clear decisions with energy behind them, yes!"

Jackie Woodside has an amazing insight on consciousness and offers great toolls in raising our own awareness to living a higher vibration. She models what she teaches and is a great mentor.
The difference between living life by design and life by default?
One leads to peace. The other leads to frustration.
If you’re reading this, something inside you knows it’s time to step out of the confusion, the half-lived goals, the quiet ache that says you were meant for more.
This is your invitation to get clear, get focused, and start building a life that finally feels like yours.
Click below to join the Life Design program now..

Copyright 2026 | Jackie Woodside | Privacy Policy | Contact: (508) 333-5520 or [email protected] | Address: 52 Western View Drive Marlborough, MA USA 01752