What up y’all! Welcome back. Newsletter 2 of the relaunch - buckle up.

Went exceptionally deeper than I was planning.

And slightly nervous to share.

But here we go anyways - taking action in the face of fear.

Today’s Agenda:

Taking Risks (ie: my sabbatical)

That’s it.

Let’s get into it.

Taking Risks

As mentioned in last week’s newsletter, I quit my software sales job last year, took sabbatical (mini retirement? career gap? living? what do you call this thing?), and bought a one-way ticket to Bali.

No plan. No itinerary. Just an open mind, curious heart, and adventurous spirit to lead the way.

This wasn’t a spur-of-the-moment decision. Nor did it feel reckless or spontaneous.

Rather, it felt like the only decision based on where my life was at that time.

The most significant relationship of my life ended.

I was doing therapy 2x per week.

Questioning everything.

Doing deep work.

Trying to listen to my intuition even though logic tried to justify.

Writing, talking, crying, feeling, and looking in the mirror to get brutally honest about who I am, what I want, and where I wanted to take the next chapter of my life.

Basically, I blew up my life (and, heartbreakingly, the lives of others - and the person I loved the most).

Now before going further, let’s take a step back to where it all began.

Working 10+ years in sales (7+ years in software sales), I loved my career -

After a DUI in 2018 put me $4k in debt and back to living at my parent’s (literally had to borrow money from my parents to pay attorney fees, story for a different day),

Software sales gave me the opportunity to reinvent myself and create a life I was excited to pursue.

I decided the DUI would be the best thing that had ever happened for me.

Hungry and driven, I poured everything into my career and growth:

Always one of first in office, last to leave (with 5-6 hour commute)
Devoured books on sales, business, financial literacy, personal development
SDR of the Year
First SDR in company history to get promoted to Account Executive
- (instead of Account Manager which was company standard)
And eventually moved out of my parent’s house, got my own apartment, and earned a move to the big city

Throughout my career, I made over 100,000+ cold calls, sold millions of dollars of software, developed valuable skills, and made lifelong friends.

It provided me financial freedom, autonomy, work/life balance, and a sense of purpose for that season of my life.

I would do it all over again if I had to.

But deep down, I had a feeling that my life was meant for more.

Something different.

That I wasn’t on this planet to sell technology forever.

After my relationship ended, it took me over three months to step foot in my house again. I couldn’t fathom the thought of being in the house alone. Without my best friend.

But I knew I had to go at some point. I could barely see on the drive over because of the tears in my eyes.

I trembled at the door, shaking uncontrollably. Could barely put the key in the lock.

When I opened the door, my knees buckled and I fell to the ground, laying there for an hour. Crying. Balling. Making sounds I didn’t know were possible.

I wanted to run. Escape. Go back to my parents where it felt safe.

But I forced myself to lay there. And keep laying there.

To embrace my new reality. The reality I created. No running, no hiding.

Sit in it, feel it.

Once I was able to pick myself up, I started packing the house - pictures, letters, cards, memories; one of the most sickening experiences I’ve ever gone through.

If you’ve been through this, you know what I’m talking about. If not, you’re not missing out. I promise.

Why I share this is because through the tears, heartbreak, and cleaning out my house, I found an old yellow goals journal I wrote about 10 years ago.

I opened it:

Buy a one way ticket across the world
Live out of a backpack for 6 months
Live out of a backpack for 12 months

My heart skipped three beats.

I stopped dead in my tracks. It was time. I knew it. An indescribable feeling of knowing. No logic needed.

It was time to take off.

Not to escape. But to explore.

To wander.

To do something radical I had dreamed about for years.

To do it now, while I can.

Before later became never.

Because if not now, when?

(*Note - this did not remove or hide the pain of the situation. Almost the opposite. Traveling remained a huge part of the healing journey. But this was something I needed to do before I stayed in a state of dreaming forever)

So I started brainstorming how to make this dream come true.

Worked hard at my job, saved as much money as possible, moved back into my parent’s house, sold all my belongings or gave them away (everything I own is in a 12×10 storage shed), and then bought a one-way ticket.

And went for it.

Me headed to Bali on a one-way ticket! Two backpacks (one full of journals & books) and a water bottle, ready to rock

🌱 For you: I believe we have the power to make profound changes in our life.

Some circumstances may require more work, negotiation, communication, sacrifice - but I believe we can make it happen.

If you really want to.

For me, it required making the hardest decisions of my life, breaking the heart of the person I loved most, leaving a life of comfort and stability, and taking a leap of faith to bet on myself and pursue the unknown.

If you’re wrestling with a tough decision, here’s something that helped me:

“What would Little (your name) say?”

Little Colin told me two words: “Be honest.”

And with that, I’ll leave you with a quote I got tattooed on my leg from Pulitzer Prize winning poet, Mary Oliver:

“Tell me, what is it you plan to do with your one wild and precious life?”

Stay tuned for next week’s episode where I’ll dive more into the sabbatical finances and decision-making process.

Until then, follow your heart.

One aligned action, moment, and day at a time.

Keep Plantin’ 🌱

Colin