Following the Desire [Pt. 1]

This series is my 2023 story: the wins, challenges, lessons, and the exact steps of a drastic career transition. By documenting it, I aim to give you an inside look at my process with hope that it helps you. Know that if you're making change, you're not alone. If anything resonates, drop a comment below. I'd love to hear from you.

What started out as a small project to reflect on my past year somehow ballooned into a 10,000 word clusterf**k of insights.

I spent a month editing, tweaking, and breaking up said clusterf**k into multiple parts that could actually be consumed by someone other than myself.

I'll bet that you'll see yourself in many of the topics in this reflection:

• Maybe you're in the midst of an unplanned, difficult career change
• Maybe you're considering a major transition but you're frozen in place
• Maybe you're confused AF and don't know what's up from what's down

While I originally wrote this series for the version of me that will look back years from now wondering WTF I was thinking in 2023, I also kept you in mind.

Whether you're employed, self-employed, an entrepreneur, or someone who experiences any type of change in your life, if you have the attention span to get through this series, I guarantee there will be something for you to learn.

If you're reading this, I admire you. Godspeed.

The Calling for Change

At the beginning of 2023 I knew I wanted to switch careers. I set an intention that by the end of the year I’d be doing something different.?

I didn’t know what it was going to be and I didn’t know how I was going to get there.

In January, after many years of operating my career consulting business, “The Remote Job Coach ,” writing “Remote for Life ,” and passing other milestones in the remote work and coaching industry – I noticed myself craving change.

For a while, I tried to ignore this yearning. My ego chimed in daily:

• “But, you’ve spent so much time building this business, you can’t stop!”
• “But, you’re just now seeing the benefits of an engaged audience!”
• “But, there’s still so much left to try and so much more to accomplish!”

So many “buts.”

Every time I thought about changing my entire personal brand and “undoing” all the leg-work I’d put in over the years, the overwhelm put me in a spiral.

Enter the sunk-cost fallacy.

Fortunately, I’ve learned more and more, especially in recent years, that ignoring my intuition ONLY ends in disaster. The overwhelm of making this change couldn’t possibly outweigh the lasting impacts of disregarding my authentic desire.

Thus, change was initiated.

Discovering My Why

I sat with myself for a while.?

I evaluated what was pushing me toward change, and I noticed a paradox.?

On one hand, I had this insatiable urge to flip my entire life upside down, to burn the boats, and say “f**k it.”

On the other hand, I encountered deep resistance that was paralyzing me from doing anything, fueled by fear of making a tragic mistake.

I knew to get unstuck I needed to discover my underlying motivations, surrender to the unknown, and establish a lens for evaluating future opportunities.

I mean, if I was going to walk away from what I had worked so hard to build, it damn well better be worth it.

The Reasons for Change

I thought I was a business owner… but I really owned a job.?

When I started my self-employed coaching business many years ago, I didn't realize I was building a trap.

See, I didn’t want to work for other people, but, like many others who fall into self-employment to “get out of a job,” I really just created one for myself.

For years I built a brand around ME, constantly needing to be involved in what I was creating and fulfilling for my clients.

If you’re familiar with the cashflow quadrant by Robert Kiyosaki, I went from:

E (employee) ?? S (self-employed)

And, it's not to say it's totally bad.

It's a reasonable way to make this change, and there's a lot I learned from the process. However, there's an issue with creating your own job:

It's a job you can't clock out of!

When I desired space and time off from my business, unlike someone who takes PTO from a traditional workplace, I couldn't afford to do it.

While some things delivered passive income (book sales, courses, and content ad revenue), most of my earnings were tied to coaching, consulting, or an exchange of time for money without any leverage.

I made a strong intention that I would hop over from the self-employed side of the quadrant to the B (business), and begin building myself a system and an asset that I could eventually exit (sell) or step away from without losing any income.

I wanted to serve a different market.?

Catering to job seekers over the years has been difficult.

Many job seekers are out of employment, most are price sensitive, a lot of them need education on why coaching is valuable, and the kicker – as soon as I helped them find a job – they didn’t need me anymore.?

Don't get me wrong, the highs are high:

When a client lands a job that changes everything possible in their life, it's one of the most fulfilling sensations I've ever experienced.

But, for years I've relied on hustling to get new clients at all times to cover my turnover and lack of recurring revenue. It put me in a position of always chasing rather than being able to strategically take myself out of the day-to-day work.?

Not to mention, when I was injured in 2021 with a fully torn ACL and had a massive knee surgery – my business crumbled while I laid in bed – unable to work, walk, or even move without sharp pain coursing through my body.

That was a huge wake up call.?

My business model always felt fragile and I wanted to build something solid.

I was tired of working alone!

I wanted to work with someone else. As a Solopreneur coach, it has been exhausting to be the only one pushing my vision forward.?

Over the years I’ve hired many part-time freelancers (25+ actually) – a few of whom worked with me for more than a year and a half in my business – but none of them were in high level, strategic roles.

Meaning, it's always depended on me to drive innovation and growth.

And while we had SOPs and systems in place for many of our processes, we were all working in our own silos on the tasks I assigned.

Because I hired others for tasks rather than responsibilities, and I didn’t build a solid team culture, there was never a path for my business to be sustainable long term without my involvement.?

I knew I wanted to work with a business partner, especially a more experienced entrepreneur. I wanted to not only collaborate with them, but I wanted someone who saw my value as a leader, and someone who could push me to develop.?

I desired to be part of a team where roles were clearly defined, where I had a strategic counterpart, and I didn’t have to be only one focused on building.

I believed in a myth.

The biggest myth of entrepreneurship?

People think understanding the technical work is the same as understanding a business that does the technical work.

When I left my job to be a coach, I assumed my ability to do the technical work of coaching meant that I was a true entrepreneur.

I was wrong, and my inner "technician" was in control.

See, the entrepreneurial archetype has 3 distinct business personalities:

1. Entrepreneur: The visionary who drives the business forward.
2. Manager: The planner who creates business stability.
3. Technician: The doer who executes the tasks.

It's recommended to split time evenly between the 3, yet the reality for most Solopreneurs is that they spend a majority of their time in technician mode.

The problem with that?

If you're mostly in technician, or "do" mode, creating a self-sustaining business is a laughable impossibility.

• I burnt out from being a technician in my last business.
• I saw my business model for how flawed it was.?
• I noticed how little leverage I had to grow.?

Instead of doing all the daily activities, I wanted to learn how to truly delegate, oversee, and "steer the ship" to relieve myself from the burden of all outputs being dependent on my inputs.

Soliciting Mentorship

With my motivations known and intentions in place, my first intuitive step was to create a mentorship proposal.?

I’ve spent years developing my network, keeping up with mentors and mentees, building relationships strategically, and it’s always my first stop for everything.

The proposal was a straightforward, 5 page document that outlined my purpose, objective, skills, and a call to action.

I offered 5 hours a week toward revenue generating initiatives to 4 different CEOs that I knew, admired, and wanted to learn from.?

The exchange was for their time and guidance. My thought? This would give me a playground to try different opportunities, ultimately leading to the clarity I needed.

I’d also be exposed to the team environments that I'd been craving.

Why the Proposal Was Effective

• Proactivity and Initiative: I didn't wait for an opportunity, I was creating it. By sending this out, I showed my ambition and desire. They noticed.
• Value Focus and Brevity: I was straightforward and my scope was defined. I desired growth and experience. I offered 5 hours a week and valuable skills.
• Intentionally Targeted: I chose CEOs I admired, knew personally, and companies I could make an impact for. I tailored my messaging each time.
• Created Leverage: I flipped the script and positioned myself as a desired mentee. The mentors were “applying” to the opportunity with me.

This is one strategy I'd recommend to anyone going through a career change. It can open doors in a way you wouldn't have imagined.

That’s exactly what this approach did for me. Spoiler alert:

• All four of the CEOs responded favorably.
• Two of them hired me as a paid consultant.
• One of them is now my business partner.

As a result, this simple plan changed my life and career trajectory forever.

But before we get into the details of how it played out, let's take a detour.

As I waited for these mentorships to develop, I didn't just sit on my ass. I was unsure if anything would come from these efforts, and wanted to create a larger surface area for luck.

So, I simultaneously took action on other paths I could create on my own.

My goal? GET MORE DATA POINTS!

In the next edition, I'll talk about how to use passions to get data points for your career change, 4 different career "experiments" that "failed" and what I learned from them, and the ONE sign I had to pay attention to understand which decision to ultimately make. Stay tuned.

NEXT: Read "Chasing the Data [Pt. 2]"