Your Work Doesn’t Have to Be Your Calling (It Just Needs to Be Aligned)

The Dream That Started This Reflection

A few weeks ago, I had a vivid dream.

I was trading crypto on a lightning-fast chart, clicking in and out of positions with uncanny precision. Every trade landed perfectly. It felt effortless, almost magical — as if I had found the hidden rhythm of the market.

Then suddenly, everything was liquidated.
My balance dropped to near zero.

I refreshed the screen in confusion…
and saw over a million dollars waiting there.

When I woke up, I did what any curious, slightly-too-hopeful dreamer might do:
I tried to make the dream real.

For a week I built a trading bot — testing indicators, tuning parameters, calculating slippage and fees. It looked amazing in backtests. But the moment I accounted for real-world chaos — spreads, timing, volatility — the fantasy dissolved.

Later, when I asked ChatGPT for a Jungian interpretation, the message was clear:

The dream wasn’t really about money.
It was about control.

My desire for effortless success.
My desire to bypass the messy parts of life.
My desire for things to “just work” so I could stay free.

And it hit me:
That wasn’t just about trading.
It was the story of my life.

The Chapter I Lost (and Loved)

For over a decade, my family and I lived a version of freedom I had once only dreamed about.

We were nomadic for 11 years — sometimes rooted for a season, sometimes moving every few months — but always free enough to follow curiosity. Bali became our longest home base, but we explored 45 countries and lived lightly.

This was possible because the software business I built eventually ran itself — a freedom earned over years of effort.

Life felt spacious.
Simple.
Expansive.
Aligned with what mattered most to me: presence, creativity, family, and freedom.

And then, that chapter ended.

Partly because my business needed more tending than I gave it.
Partly because our family was ready for more stability so our kids could pursue their own big dreams.
Partly because life nudged us into a new season.

It wasn’t a failure.
But it was a loss.

And there was some grieving that accompanied that loss.
The grief of a life that worked beautifully… until it no longer fit the season we were in.

Finding Meaning, Losing It, and Letting Go

There was also a chapter where I created something that felt truly meaningful — the Family Adventure Summit.

I founded the event, gathered an amazing team, and together we built a global gathering for traveling families that brought hundreds of people together each year across multiple countries.
It was a space for families living outside the norm — long-term travelers, alternative educators, creatives, and entrepreneurs — to connect, learn, and support each other in living adventurous, purposeful lives.
It was values-driven — acceptance, courage, kindness, adventure, sustainability — and included dozens of speakers, performers, and a huge kids program that many families still talk about. We also donated all profits to local charities.

It was beautiful work.
And also time-consuming — especially finding affordable venues around the world that matched our vision. That process shaped a lot of our travels and quietly contributed to my kids’ burnout with being so public and always on the move.

I loved the event, but as my main business declined and my family needed more stability, I felt the alignment shifting. When COVID hit, I had to let it go, and that brought its own layer of grief — not just the loss of the event itself, but the identity I had wrapped around being a “family travel” person, and some guilt about disappointing the community it served.

After we settled in the U.S., I also sold the software business that had supported our travels for so many years — another chapter I eventually had to release once I realized I no longer had the alignment or energy to give it what it needed.

A Chapter of Real Success (and Real Misalignment)

As that chapter ended, I bought another small software company — one far removed from what I personally cared about, but full of potential.

I applied my strengths: simplifying systems, improving processes, building a solid team, and clarifying the product. Within three years, it grew tremendously and I sold it for ten times what I’d paid.

It felt like a genuine win.
Proof that my approach to buying and improving businesses actually works.

But it also reminded me of something important:

Just because I can grow something doesn’t mean I should keep it.

The business served a niche that didn’t resonate with who I was — software for rabbit breeders — and I never enjoyed talking about it. So even though it was doing well, I sold it — and I’m still glad I did.

Since then, I’ve quietly started helping others buy, grow, and sell businesses too.
Not as a big consulting practice, but selectively — when the fit feels right.

Trying Another Shortcut

Right as I was nearing the end of that business chapter, I turned to crypto trading.

Maybe this would be the next efficient, low-effort way to support my life — without needing to manage a team.
Maybe this was the path back to spaciousness?

I invested in coaching and training for 18 months.

And what I learned was:

• trading can make money
• but not without emotional mastery
• not without risk
• not without constant engagement
• and not without accepting full responsibility

In other words:

It’s work.
Serious work.

But it did teach me something meaningful.
Trading pushed me to confront uncertainty, accept what I couldn’t control, and stay grounded when things moved fast.
It was inner work, for sure — something Trading in the Zone helped me see more clearly.

But over time, I also saw why it wouldn’t be my path.
It demanded constant attention — urgent decisions at unpredictable times — and it began to feel like it controlled my schedule more than I controlled it. I struggled to make consistent profits. And the work felt hollow to me, like I wasn’t contributing anything real to anyone. I missed the steadiness and impact of building SaaS businesses.

And again, the familiar tension appeared:
wanting an easier, more spacious way to live
and realizing that every path needs presence and participation — even the ones that look effortless from afar.

The dream made sense now.
It was pointing me toward a deeper kind of freedom than the one I was chasing.

Where I Am Now

These days, my work feels different — grounded, intentional, and strangely peaceful.

I’m running HelpSite, a simple SaaS business I bought that aligns with my love of clarity, organization, and systems. I enjoy improving it, supporting my team, and creating something useful.

I’m also staying active in acquisition entrepreneurship — buying, improving, and eventually selling businesses — not as a “shortcut,” but as a craft I genuinely enjoy.

Not because every industry excites me.
But because I love:

• clarifying messy systems
• building healthier teams
• simplifying complexity
• helping entrepreneurs feel supported
• creating stability for my family

I’m realizing something:

My work doesn’t need to be my calling.
It just needs to support the conditions for a life that feels aligned and alive.

For years, I wanted to minimize work entirely so I could “get back” to my real life — music, travel, retreats, creativity.

Those things still matter deeply to me.
And I still make time for them.

But I’m seeing work differently now:

Work can be a practice.
A dojo.
A place to show up with awareness and heart —
without pretending it’s my identity.

It doesn’t need to be something I escape,
or something I disappear into.
It’s simply a place where I can engage consciously
and contribute in a way that feels aligned.

Letting Purpose Emerge Instead of Forcing It

I still don’t know what my deeper calling is.

I love AI and technology.
I love music and group singing.
I love dreamwork, consciousness, and non-ordinary states.
And I love exploring the edges of what’s possible in all of these areas.
I could imagine building something at the intersection of tech and spirituality, leading retreats, or creating experiences that facilitate awakening.

But for the first time,
I don’t feel pressured to figure it out.

I’m learning that purpose doesn’t come when I chase it.
It comes when I’m grounded enough to notice what’s already calling.

My role right now is simple:

• Strengthen the foundations of my life and work — the systems, the team, the stability for our family.
• Build consciously, without rushing or forcing.
• Create from alignment rather than pressure or fear.
• Make time for curiosity and genuine creativity.
• Trust the timing — and let clarity emerge when it’s ready.

Freedom might not look like eleven years of nonstop travel anymore.
Maybe it looks like a grounded home with seasonal adventures.
Maybe it looks like a feeling of spaciousness inside myself — a sense of ease instead of urgency.

Either way, I’m rebuilding from awareness — choosing my next steps with clarity, honesty, and a little more spaciousness than before.

Lesson

Real freedom doesn’t come from finding the perfect path — it comes from showing up with presence and alignment wherever you are.

Invitation

Where in your life are you waiting for certainty, instead of showing up to what’s already here?

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Pair This Post With…

🎵 In the End — Olivia Fern
A song about what really matters: living well, loving well, and learning to let go.

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