The Freedom Most People Chase (And Why It Doesn’t Work)

There’s a particular vision of freedom that dominates online spaces:

Quit your job
Travel the world
Work from a beach
Answer to no one
Wake up without an alarm
Never attend another meeting

And look, I’m not saying those things are bad. In fact, most of us want many of them.

But here’s what’s missing from that narrative:

Those aren’t escapes from a life you hate. They’re options you can choose when systems are working.

Maybe you want to travel extensively with your family. Crystal clear water. Rainforests. Waterfalls. Experiencing the world with your kids while they’re young, not waiting until retirement.

Maybe you want the flexibility to work from different places – a beach one week, the mountains another. To use portable monitors and modern technology to work from anywhere.

Maybe you want to explore opportunities that excite you – new technologies, different teams, better alignment with your values – without the fear of losing security.

What most people don’t want is to be forced into a single rigid version of what “freedom” looks like.

They don’t want to have to choose between:

Having roots AND traveling extensively
Having a stable career AND building something of their own
Providing stability for their kids AND showing them the world
Working from a well-equipped space AND working from anywhere
Building generational wealth AND experiencing life now

What they want is systems that make multiple options possible over time.

Systems that let you excel in your current role while also building parallel capacity.

Systems that let you own land where your family has roots while also traveling for extended periods.

Systems that generate income whether you’re at your desk or exploring a new country.

Systems that create choices instead of constraints.

That’s a different kind of freedom. And it requires a different strategy.

What Real Freedom Actually Looks Like

One of my mentors, Jess Ekstrom (founder of Mic Drop Workshop), once shared something that stayed with me:

If you want to know whether you really want something, imagine you couldn’t tell anyone about it. If it stops feeling shiny when no one is watching, you’ve learned something important.

Real freedom isn’t necessarily impressive from the outside.

It doesn’t have to look like:

Instagram-worthy travel photos
LinkedIn posts about quitting your job
Perfectly curated morning routines
Viral threads about passive income

Real freedom can look like:

Saying no without anxiety. Declining opportunities that would pay well but cost too much in time, energy, or alignment.

Making decisions without needing approval. Not because you’re rebellious, but because you’ve built the infrastructure that gives you autonomy.

Choosing presence over performance. Being able to actually be with your kids instead of thinking about the work you should be doing.

Having margin when things go wrong. Because they will. And when they do, you want options, not panic.

Building something that works when you’re not working. Systems that generate results whether you’re actively managing them or sleeping.

For me, real freedom looks like:

Online international school for my kids without financial stress
Taking family trips when it makes sense for us, because I have flexible PTO that allows it
Building our homestead at the pace that fits our life
Working full-time in a job I value while also building parallel income
Never having to choose between showing up for my kids and showing up for my work

That’s not dramatic. It’s not viral-worthy. But it’s what actually creates the life I want.

The Problem: We’re Optimizing for the Wrong Metrics

Here’s what happens to most high-achieving professionals:

You get good at your job. You get promoted. You earn more money. You buy a bigger house in a better school district. You optimize your 401k. You hit your metrics.

From the outside, you’re winning.

But internally? You feel trapped.

Trapped by the mortgage you can’t afford to walk away from. Trapped by the lifestyle inflation that happened so gradually you didn’t notice. Trapped by the golden handcuffs of good benefits and stock options that require 60+ hour weeks. Trapped by the fear that if you step off this path, you’ll lose everything.

You’re not building freedom. You’re building a prettier cage.

And here’s the painful part: your kids are watching you live this way. They’re learning that this is what success looks like. Work hard. Earn well. Stay tired. Repeat.

Unless you show them something different.

How Freedom Is Actually Built

When a child learns to walk, it always starts with action.

They stand up. They try. They wobble. They fall.

And every time they try, they get evidence.

If I lean this way, I fall. If I shift my weight like this, I stay up a little longer.

They watch other people. They adjust. They try again.

Then something changes.

They take one step. Then two. Then four.

Confidence shows up after the evidence.

Eventually, they’re walking. Then they try running.

What’s interesting is that falling never becomes a judgment of who they are. We don’t look at babies learning to walk and decide they’re “bad at walking.” We don’t make it mean anything about their character.

We have compassion and understanding that they’re learning. We even feel pride that they keep trying, because we know consistency pays off.

Give that grace to yourself.

Because here’s what I know about building real options:

It doesn’t start with confidence. It doesn’t start with a perfect plan. It doesn’t start with feeling ready.

It starts with action.

The Framework: How to Build Freedom Through Action

This is The Connector Method™ – the framework I used to go from teacher salary to enterprise tech sales, from renting to owning 10 acres mortgage-free, from exhausted to intentional.

1. Action Reveals Truth

You can’t think your way to clarity. You have to move.

Most people spend months researching the “right” way to build passive income. The “right” platform. The “right” niche. The “right” strategy.

But all that research doesn’t tell you what will actually work for YOU with YOUR constraints and YOUR energy and YOUR goals.

Action tells you.

When I started building digital systems alongside my corporate job, I didn’t know if affiliate marketing would work for me. I didn’t know if I could maintain a blog. I didn’t know if my audience would care about AI automation.

I took action to find out.

Some things worked immediately. Some things flopped. Some things worked, but drained me. Some things generated income, but didn’t align with where I wanted to go long-term.

The action gave me information I couldn’t get any other way.

2. Evidence Guides Pivots

Here’s where most people go wrong: they treat evidence as judgment.

If something doesn’t work immediately, they conclude they’re “bad at it” or “not cut out for this.”

But evidence isn’t judgment. Evidence is data.

When my first few blog posts got zero traffic, that wasn’t a referendum on my writing ability. It was information about SEO, topic selection, and distribution strategy.

When my initial course idea got lukewarm responses, that wasn’t proof I had nothing valuable to offer. It was information about positioning and solving the right problem.

When I launched my Substack and immediately felt resistance, that wasn’t failure. It was evidence that this platform didn’t fit my actual goals and systems.

Evidence tells you what to adjust, and that’s not quitting. It’s pivoting.

The baby learning to walk doesn’t quit after falling. They adjust their weight distribution, their foot placement, their arm position. They use evidence to get better.

3. Confidence Accelerates Results

Here’s the beautiful thing about this framework:

Confidence comes from doing, not from preparing to do.

Every time you take action and gather evidence, you build a library of proof. Proof that you can start things. Proof that you can pivot when needed. Proof that you can solve problems as they arise.

That proof becomes confidence.

And confidence lets you move faster.

When I first started exploring parallel income systems, every decision felt huge. Should I start with affiliate marketing or digital products? Should I focus on my blog or my podcast? Should I post on LinkedIn or build my email list?

But now? I have evidence. I know what works for me. I know my strengths. I know my constraints.

So I can make decisions quickly and confidently not because I’m sure they’ll work, but because I trust my ability to adjust if they don’t.

4. Results Create Transformation

The goal isn’t just to achieve specific outcomes.

The goal is to become someone who knows how to create those outcomes again.

When you build freedom through this process, you’re not just getting to a destination. You’re:

Developing the skill of building freedom itself.

That’s what changes everything.

Because here’s the truth: life will always throw curveballs. The economy shifts. Your industry changes. Your family needs evolve. Your own priorities transform.

If your freedom depends on everything staying exactly as it is, that’s not freedom. That’s fragility.

But if your freedom comes from your ability to take action, gather evidence, build confidence, and create results? No one can take that from you.

What This Means in Practice

So how do you actually build this kind of freedom?

Start With Honest Assessment

Before you can build options, you need to know what options you actually want.

Not what looks good on social media. Not what your parents want for you. Not what you think you “should” want.

What do YOU want?

For me, it was:

Keep my corporate job (I like it)
Build income that doesn’t require my active time
Own land where my kids can grow up with space
Have capacity to be present with my family
Create systems that compound over time
Use AI to multiply my effort, not my hours

Your list might look completely different. And that’s the point.

Build in Small, Visible Increments

You don’t build freedom overnight.

You build it in small actions that create evidence:

Saving your first $1,000 that isn’t earmarked for bills
Creating your first piece of content that ranks in search
Making your first $100 from something other than your job
Setting up your first automated system
Saying no to a project that pays well, but costs too much

Each one of these is a small win. Each one creates evidence. Each one builds confidence.

And eventually, you look back and realize you’ve built something substantial.

I didn’t buy 10 acres in one transaction. I built the capacity to save and earn. I learned about land. I made offers. I negotiated. I closed.

Each step was small. The compound effect was transformational.

Use Systems, Not Willpower

Freedom doesn’t come from working harder or being more disciplined.

It comes from building systems that work whether you’re motivated or not.

For me, that looks like:

AI workflows that turn my writing into multiple formats
Affiliate systems that generate income from recommendations I’d make anyway
Content systems where one blog post becomes 10+ pieces of distributed content
Financial systems where savings and investments happen automatically

The less I have to “try hard” to maintain momentum, the more sustainable my freedom becomes.

Protect Your Capacity

This is the part most people miss:

Building freedom isn’t just about adding income streams. It’s about protecting your capacity to think, choose, and act.

Every commitment you make is a promise to maintain it.

Every platform you join requires attention.

Every system you build needs occasional maintenance.

So be ruthless about what you add to your life.

I shut down my Substack after one week because it would have consumed capacity without creating it.

I don’t take speaking engagements that require me to be away from my kids overnight unless the fee justifies the cost.

I don’t build income streams that require constant active management.

Freedom requires saying no to good opportunities so you can say yes to great ones.

The Long Game

Here’s what I know after years of building this way:

Real freedom isn’t a destination. It’s a practice.
Makeda Boehm

It’s the practice of taking action before you feel ready.

It’s the practice of using evidence instead of only emotion to guide decisions.

It’s the practice of building confidence through participation, not preparation.

It’s the practice of creating results that compound over time.

And it’s the practice of giving yourself the same grace you’d give a baby learning to walk.

You’re going to wobble. You’re going to fall. You’re going to try things that don’t work.

That’s not failure. That’s learning.

And every time you get back up and try again, you’re building the kind of freedom that can’t be taken away from you.

Where This Actually Leads

I’m not promising you’ll quit your job or travel the world or become a millionaire.

I’m saying you can build a life where:

Sunday nights feel glorious instead of dreadful
Monday mornings are sacred instead of suffocating
You have margin when things go wrong
Your kids see you choosing presence over performance
You’re building something that outlasts your employment
You have actual options, not just the appearance of success

That’s the kind of freedom I care about.

That’s what I’m building for my family.

And if you’re trying to do the same – to build real options while working full-time, raising kids, and staying sane – you’re in the right place.

Because freedom isn’t found. It’s built.

One action. One piece of evidence. One confident decision at a time.

Ready to start building?

The first step isn’t to create a perfect plan. It’s to take one small action that gives you evidence.

I’ve put together a guide that walks through 3 Ways Families Build Income Online – real systems you can start testing this week, even with a full-time job and kids at home.

Each approach is designed to create capacity, not consume it. To give you evidence, not just theory.

Get the free guide here and take your first action.

Because freedom isn’t found. It’s built.

One action. One piece of evidence. One confident decision at a time.

And if you fall? Get back up. Adjust. Try again.

Just like you did when you learned to walk.

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