Stepping Outside

A virtual retreat for connecting with the clarity, confidence and the courage to be you

Imagine the excitement of a new year ...

The past year felt so right, so on target, so very - y.o.u.

The sense of inner ease and flow of being true is like no other.

Listening to your inner nudges and prods didn't steer you wrong.

Curve balls and hurdles were so much less a big deal.

Your clarity deepened.

Decisions were easier to make.

Plans were filled with meaning rather than planning to make plans.

yeah, right

How about fairy tales and unicorns too?

Facing the new year, well ..., sort of sucks. Hard not to question what's going to make this year different from any other.

What is it they say - insanity is doing the same thing over and over expecting different results?

Logically what you lay out makes sense. Follow the plan and all should be well.

Except it isn't.

You have a solid track record of being no further ahead, and more so feeling the unjoy of wading off in weeds. Hopes and resolutions always seem to get buried in dust of everyday life. What you really want just isn't coming true.

Will anything really make this new year any different?

Yellowed calendar pages showing last two weeks of the month

caught up in do-do

Like clockwork, December is flooded with messages for making the best year ever.

The next greatest planner will keep you organized this time. Learn the secret to ultimate productivity in less time. Make your dreams come true in the blink of an eye.

A gazillion variations to Sunday blast you on how to make everything come true ... yesterday.

Only problem is, they're all are focused on what you can do.

Let's flip this upside down

Start with you instead of do.

Doing more, even doing less, isn't the answer. Efficiency and effectiveness feel good, but only get you so far.

There's one common thread, however, woven through everything you do:


Scoping out plans, making decisions, and following your dreams can go in very different directions based on where you place your attention.

Focus on what to do

Bounded by what you know or what you can dream of right now

Value placed on action, busyness, movement

Need a defined end result out there to work towards

Manage time and activities for quickest results

Inherently linear thinking impacted by the influences of outer chaos

Focus on being you

Allow room for what you don't know to change everything

Comfortable with inspiration, creation and change, like metamorphosis, isn't always perceptible

Use curiosity and trust in yourself to hear signs and messages for navigating the unknown

Remain open to what's appearing and emerging patterns

Awareness and presence create a sense of flow and resilience through what gets thrown at you

What does that actually mean?

What you can expect starting from you over what to do.

  • Plans change

    Putting you first doesn't mean tossing plans out the window. Planning becomes a hybrid processing of setting out, paying attention, and making adjustments along the way. You don't have to wait for a clear, definitive end point before starting.

  • Stuck isn't so sticky

    Feeling stuck comes from a lack of alignment and clarity about what to do. Wherever you are is where you can start from because you always have you as a reference point. Every small step gives you something to use for the next one.

  • On the move

    Don't get fooled by the "Being Myth." Being isn't all about stillness and navel gazing. Being your true self is allowing who you really are to shine all the time and allowing your natural GPS system to provide direction as to where to go and what to do. 

  • going in spirals

    Two points form a line. There's nothing saying the line in between must be straight. Or fast. The richness of Life is found in the scribbles. Going back over old ground and heading off on tangents is you experiencing you all over again as you evolve.

Stepping outside what's expected

December 28/2020- January 06/2021

Welcome to the retreat

Imagine yourself at a (virtual) cozy cabin retreat from the comfort of your home.

Mornings start when you do. 

No alarms. No schedule to follow. A hearty breakfast of your choosing always steaming hot.

Find yourself by the crackling fire or out for walks in the woods.

You'll have lots of time for inner reflection along with getting to know others staying here too.

Our focus will be on guided obserflection to get to the heart & soul of what you want for you in the year ahead.

No more making resolutions or plans without bringing you to life.

During our end of year getaway, we'll take a deep dive into:

  • clarifying where you are right now
  • acknowledging the inner nudges
  • giving voice to what you truly desire
  • looking at what appears to be in the way
  • taking steps towards what's next

The techniques can be used over and over at any point to:

  • identify patterns and signals you can rely on going forward
  • feel aligned and a sense of peace about what's ahead
  • create a foundation to build on and fall back on
  • call out the stories trying to hold you back
  • see day-to-day happenings with new eyes

Theme 2020: saying yes

Including a theme influences your guided self-directed journey in two ways:

#1 - what you specifically want to explore more deeply.

#2 - the subtle backdrop and larger container holding all of our work. 

Don't worry about being clear about you want. That is why you're here.

Shhhhhh ...

Don't tell anyone. The cabin has magical qualities. Or perhaps magnetic might be a better word.

Seemingly simple questions lead to deeper explorations that keep you coming back.

Don't be surprised finding yourself connected to this haven in the woods. You'll be thinking and seeing differently while you're not even here. This is good.

Awareness integrated into everyday life is what the cabin is all about. Being here all the time isn't critical. Spending some you time is. Even if you have to sneak an hour each day.

Guest book

Author & artist on a mission to celebrate the absurdities of life

When I signed up for Stepping Outside, Lorraine Watson's virtual retreat, I never expected to experience a life-changing epiphany - but that's what I got. I'm not going to share the details or family history behind it, but suffice to say that Stepping Outside enabled me to move much closer to my life-long dream of becoming a working artist. Thank you Lorraine for creating such a fun, immersive, and thought provoking program.

Lisa Sinicki
Founder of Active Acceptance Project

What I got was a deeper understanding of how I want to engage with my connector community, and a needed and consistent reminder to be true to myself whether others cotton to me or not, and to accept I can't control the outcomes.

Anny Rusk
Author who believes good writer's read!

It's a strange truth that the most important questions in life are the hardest to frame and, consequently, a major challenge to answer. Stepping Outside offers a magical space to encounter your big questions. It's large enough to wander, wonder, and play, yet small enough to find safety and support. Lorraine Watson's warm style of leadership leaves you free to dig as deeply as you need with the knowledge that, if you get stuck, she's ever ready with the right query, prompt, or insight to get you going again.

Carrie Ann

Lodgings & Amenities

What to expect during your time at the virtual cabin.

Oversized couch and chairs around fireplace in log cabin family room

As your host

Think of me as your guide - part sherpa, part nudger - to find the answers waiting within.

What I’ve created for you is:

  • a small, intimate community
  • an online private group space
  • two live group conversations (online) 
  • livestreams and written support material
  • my very active participation every day in the online group space

More importantly, I'm here to:

  • create a space for you to sink into
  • ask the questions you need to explore right now
  • nudge when you need poking and be there when you need resting 
  • serve up a feast of food for thought
  • celebrate what goes unnoticed

as a guest

Stepping Outside is designed to be an obserflective, experiential journey.

You'll get the most out of your getaway if you:

  • give yourself an hour each day, and more if you like
  • participate, share and engage as fully as you can
  • ask questions, ask A LOT of them
  • bring an extra change of clothes for when things get messy
  • pack an abundant supply of curiosity
  • create a safe space for yourself and others to explore deeply
  • be open to seeing past experiences differently
  • celebrate even the tiniest shifts
Central rustic fireplace in log cabin


Two options for changing your year ahead.

package #1

Year-end immersion

Dec 28/2020 - Jan 06/2021

Ring in the new year with a most enlightening experience of clarity, confidence and courage to be you.

Your all-inclusive retreat includes:

  • 10 days of guided inner exploration & coaching
  • 2 group video calls
  • challenges & activities
  • BONUS: 1 - 1:1 call

$350 CDN

You won't receive other unrelated emails. Promise. Get the details on emails, preference settings and privacy

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package #2


In addition to the year-end immersion, check back in and bring yourself back into focus throughout the year for support with staying on track and working, dealing with struggles and working with what's appearing.

Your all-inclusive sneakaways include:

  • year-end immersion
  • Weekend in March, June, and September (6 days total) for focused inner exploration & coaching
  • 1 group video call each visit (3 total)
  • challenges & activities
  • BONUS: 1 - 1:1 call

Contact me for details.

* This package is available for all previous Stepping Outside Year End Immersion guests.

the fine print

Things you might wish you knew ahead of time.

Perfect timing

Jumping into Stepping Outside and exploring the year ahead will be a shifting experience if:

  • You have a decision to make, something needs to change, but not sure what, you need the courage for what's next, you're holding back, your plans feel fake or empty
  • You find year end a time of introspection and reflection
  • You like a mix of being part of an intimate group and time by yourself
  • You want a different experience
  • You want next year to feel more like your true self
  • You enjoy hanging out in your flannel pajamas or sweat pants
  • You know when you give something your attention and effort, even when it gets messy, you get results.

When Next year might be better

This retreat might not be the right timing for you if:

  • You have complete clarity without questions
  • Your plans for next year are rock solid
  • You have no time for yourself between deadlines, company, travel, family, etc. 
  • You're not quite ready to dive deep or get squirmy
  • You want to work on your own
  • You prefer to be given answers rather than discovering them

book your reservation

The Loft, Casita, Northern Lights and any room of your imagination are yours for the choosing when the cabin opens December 28, 2020 for your Stepping Outside online retreat.

Leave your contact information to put your name on the waiting list. The front desk will contact further information as the time draws closer.

[Only 10 rooms rooms are available to ensure you'll get the most out of your getaway experience.]

You won't receive other unrelated emails. Promise. Get the details on emails, preference settings and privacy

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unsure if the cabin is for you?

In a former life, I took an assignment at a field location.

I moved from the Big City to a small town at the end of the highway.

The 18 months living there are fondly remembered.

But being at the end of the road took getting used to.

When something came to town, you went or you missed it.

There was no "maybe next week."


Stepping Outside is kind of like living at the end of the road too.

It only happens once a year.

You're in or you've missed it for another year.


Honestly, I hate that it feels like some bad scarcity tactic.

That's not my intention at all.

This is a super special experience specific to this time of year.

Offering an evergreen version or having multiple entry times throughout the year would water it down.

That's not what I want for you.

So for now, Stepping Outside is truly an annual retreat.


If you're in that middle space between saying "hell, yes!" and "meh, no thanks," please get hold of me.

Let's have a quick chat about your questions and hesitations.

I'll tell you straight out if I don't think the timing is right for you.

Pinky swear.

There may be a better way or better time for us to work together.

Or not at all.


What I don't want is for you to miss out on something that would make a difference for where you are right now.

Double pinky swear promise - there will be no convincing you to sign up.

So, please. ask.

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