Inside the Making of Our 5-Day Challenge for Future Cash Flow Investors
We’re turning our story into a step-by-step path to financial freedom.
That damn fly wouldn’t give up.
It’s been trying to escape for the last 20 minutes by aggressively flying into the window pane of our sliding door.
All of its effort. Over and over.
It’s almost as if the fly believes that if it just tries a little harder, a little longer, it’ll finally escape.
And the chances of this fly dying in its pursuit of the outside are pretty high, especially if my husband sees him and breaks out his electric fly swatter.
It kinda reminds me of how we used to live our life.
Working full time or longer, saving every penny to buy a bigger house or for the elusive retirement.
Working harder.
Aggressively struggling.
The beautiful outside (or retirement) so close, yet so far.
And that’s if we even made it there with our health and our family present.
As I’m watching this fly, I can’t help but wonder if he sees it.
Sees the open door, seven feet to the left.
If he would just see the door and spend 3 seconds flying left instead, he’d be free.
I really feel like this is what happened to our family when we figured out how to invest for cash flow, live off our dividends & become work optional in our 30s.
I feel like we found the open door.
We flew through it.
And now, we’re free.
If you read last week’s entry into The Freedom Diaries, you might remember that I realized that the experience of early retirement is EXACTLY as amazing as I expected it to be…
…but something still felt off.
From this self discovery birthed the realization that I am put on this planet to grow.
It is my soul’s whisper to seek my edge.
In picking up where I left off last week, I want to bring you in on what my husband and I plan on building to find our edge together and push ourselves to our capacity.

The Door
We realized that it was only 3 years ago that we were the fly, unable to see freedom just feet to its left.
But we saw it and we still continue to look for our next door.
This experience has deeply changed our lives and we realized it was almost as if we have some guided responsibility to help other people find the door before they die.
Find the door instead of spending the rest of their lives working harder and harder, flying against the window pane of their lives, freedom just on the other side of the impenetrable glass.
What if we could teach others to do what we did?
They didn’t need to travel the way we did or live out of a suitcase, but chase their own version of freedom.
What if we taught people HOW to decide on a future, chase after it and pay for it with cash flow from their investments?
What if we could pivot the direction of someone’s life just with an idea?
Create that life division for someone else, dividing everything into before and a dreamed up version of after?
This is what we will be building for you.
A guide to finding your door to freedom.
Five Constraints
Having grown my 10 year health consulting business to six figures annually, I understood how to make money.
However, this time is different in one big way: we don’t need to make money because our cash flowing portfolio covers our expenses.
The traditional pressure of covering the mortgage, ensuring the car has gas in it and that food is in the fridge no longer burdens our decision making in what we want to create.
We can go in any direction we want.
And because we want to honour our newfound freedom in building this new business, we wrote down a list of constraints that it would have to fit into:
It has to be location independent. We want to travel 6-7 months per year for at least the next 2 years, so we can’t be tied down to a physical location.
It has to be time zone independent. We will be in Bali, Spain and Philippines over the next two years with our home city in Vancouver. With swings of up to +15 hours in time zone changes, it needs to be something we could operate on whatever time zone we travel to.
It has to be stable internet independent. We’ve travelled enough already to know that internet and power can go out multiple times per day or slow down to a trickle. I’ve missed a day of meetings in the Dominican when the internet went down and when we were in Panama, we struggled with slow, 5-7 MBPS speed for a month.
It has to fit within our bandwidth. As parents, our priority is our kids and each other. We want slow, unplanned days and plenty of time to do nothing. We don’t want to work 5 days a week or 3 hours a day or be on calls all day. Living is our priority.
It has to feel fun. If I’m going to spend my time doing it, I really want to enjoy it.
With those constraints in place, we began to brainstorm all of the ways we could help other people and grow a profitable business.
And the list? It was long.



Working Backwards
First, we needed to figure out what result we wanted to help people with that was enticing, unique and fully within our wheelhouse of experience.
The door to freedom is that result.
We want to help our community so easily visualize what’s on the other side of that window and then show them where the door is.
That’s the cool thing - freedom for YOU might look wildly different than it does for us.
We are currently thriving while living out of a suitcase, without a home base and retired in our mid 30s.
You might love your work and want to be able to fund more life experiences.
Or maybe you do want to quit work now.
It’s freedom on YOUR terms.
But what could we easily create that would help bring that to reality across a broad scope of personalities, ages, experience levels and starting points?
Extra income for you, every month that you don’t have to trade your time for.
Income to cover your expenses so you can become financially independent.
We are going to teach you how to become a Cash Flow Investor.
Just Regular People
Now, you’re right if you might be thinking that we aren’t financial planners or advisors.
We didn’t go to school for it. We aren’t certified in anything.
It’s interesting - in an investment focussed Facebook group we belong to, a member posted that they asked if they could see their financial planner’s portfolio.
Apparently, the financial planner replied that it was inappropriate to share it.
As you probably pick up on, Flynn and I have a deep value in transparency.
How many of the people we turn to for advice, financial or otherwise, have actually achieved the result we want?
How many accountants or financial planners or money gurus online have actually, transparently, shown how they have done it from the ground up?
Not many.
Flynn and I aren’t wildly rich either.
We’ve never made more than $120,000-$130,000/year take home (and that was at our peak!).
We are just two regular people who are willing to figure it out and share it with you, wins, losses, and everything in between.
So the result we are going to help you create?
Your FIRST $100/month in cash flow from your investment portfolio.
Why $100/month?
Because you first need to get to $100/month before you can get to $1,000/month, and then $5,000/month.
You need the skills and confidence with the basics, step by step from the ground up on how to invest and feel good doing it all BEFORE you worry about bigger numbers.
And we decided to make it fun - it’ll be set up as a 5 day challenge.
There will be 3-5 short videos for you to watch per day as you go from a “some day investor” to a cash flow investor.
We’ll even walk you through putting your first $100 into the market.
It’s a full breakdown of the strategy that now has us generating $8,066.11 on average each and every month without having to work a single hour.
Pretty cool, huh?
Small, Daily Steps
One thing we agreed on is that we wouldn’t sacrifice our peace, contentment and happiness to build this.
So, we are building it slowly, right in theme with our slow living lifestyle.
We spent the first hour organizing everything that would go into building this challenge on a Trello Board.
This gives us clear, small steps to work towards every time we sit down to work.
Once it was organized, we decided on the flow of the lessons and what order the content should be taught in.
From there, we are building out our five days of content.
So far, we have titled our 5 day challenge The Cash Flow Investor: A Complete Step-by-step Plan for Financial Independence.
Here is the layout for each of the five days:
Day 1 - Build Your Vision: Map Out Your Freedom Plan
Day 2 - Your Freedom Number: The Path to Financial Freedom
Day 3 - Our Cash Flow Investor Strategy Explained
Day 4 - How We Pick the Best Funds for Cash Flow
Day 5 - Ready, Set, Invest: Launch Your Cash Flowing Portfolio
Once we had each of the lessons on each day organized and titled, we went to work drafting the outlines for each video training.
One day at a time.
We are just over 4 weeks into building this challenge and we have finally wrapped up our last lesson outline.
Have you ever created something and had that feeling of ‘WOW this is so freakin’ good’?
Yeah. That’s what this feels like.
Final Thoughts
Five years of experience and educating ourselves, compressed into 5 days.
It’s designed to be consumable, simple and everything we have learned so far.
As long as our lifestyle allows it, we plan to do a really juicy pre-sale with some sweet bonuses in mid May.
It’d be really cool to have it available for you by June.
Regardless of if this is something you’d join us for or not, I hope it has at least been fun to walk the road with us as we create this.
I hope to continue documenting this occasionally with diary entries here on The Freedom Diaries because who knows what this will turn into?!
All I know is it’ll be really cool to look back on as part of our story.
And even better? To bring you in on our story and to have you pick up the pen and begin to write your own.
This could be your year.
Your pivot point.
This could be the start of something wildly unexpected for you in which you finally get clear on what your future will look like…
…and then build it starting NOW.
There is just one thing I want for you, regardless of the path you take to get there - don’t be the fly that dies on the windowsill, spending the last of its life struggling against a life always out of reach.
I wish for you that you find your door.
I wish for you that whatever is on the other side of that glass is so damn exciting that it jumps you out of bed every single morning.
And most importantly, I wish that when you do find that door, you fly as fast and as high as you can dream.
The door is open for you.
You just need to fly through.
Tanessa
Read the next instalment in this series:
P.S. - Want to be the fly that finds the door? 😂🪰
If you want to learn how to earn $100 per month in cash flow (and how to scale up from there!), click here to learn more.
I am interested! We worked together for health coaching a few years ago, and it was so valuable! I’m enjoying reading and learning again from you in this new phase!
Wow this awesome please fill me in when you launch the challenge.