When we hit roadblocks in our careers, there's often an insidious voice that whispers: "Figure it out yourself. Save the money. You can do this alone."

After more than a decade as a coach, I've come to recognize this voice as one of the most dangerous obstacles to genuine growth. Looking back at my own journey as a Coach, I can identify two pivotal moments when hiring a coach didn't just help me overcome challenges—it completely transformed my trajectory.

The Entrepreneurial Leap

During my first year as a Coach - after pulling the ripcord on my career at Microsoft - I experienced what many new solopreneurs face: early success and high levels of motivation followed by a devastating drought and discouragement. Despite pouring in endless hours, clients weren't signing up. Bills were continuing to come in, and my savings were slowly dwindling. I began questioning whether coaching was financially viable, and started contemplating alternative career paths where my skills might transfer, and perhaps even returning to my past as a leader in the Tech industry. 

That's when I met Andrew.

Hiring Andrew wasn't an easy decision. His coaching fee represented a significant chunk of my meager earnings as a Coach at the time. But I faced a clear choice: continue stumbling around in the darkness alone, or invest in guidance from someone who'd already walked the path.

Over six months, Andrew helped me understand something crucial: being a real entrepreneur is fundamentally different from being entrepreneurial within a company. He taught me the subtle art of sales—not as manipulation, but as a form of service. I learned to clarify my unique offering and to confidently extend that offer to people I genuinely believed I could help.

Instead of viewing each conversation as a pass/fail test, I began seeing them as valuable steps in my learning journey. By the end of our work together, I had doubled my business and developed a sales process that felt authentic—low stress and high impact. It wasn't sales at all, it was the art of being in conversation with people to see if / how I could best help them. 

Without Andrew's guidance, I likely would have abandoned independent coaching altogether or joined a company as an in-house executive coach. While either path might have worked, I'm profoundly grateful for the direction my career took instead.

Beyond Techniques to Transformation

Several years later, I found myself at another crossroads. My coaching practice was established and growing. Clients were referring their friends, spouses, and bosses to me. From the outside, everything looked on the up and up.

But something felt deeply off and I was ready to give up.

I remember one session with a client who had achieved remarkable results during our six months together. He ran an online business and during our time together he came up with the idea for and launched an entirely new line of business that would eventually become a seven-figure venture for him. Yet, instead of taking even a moment to celebrate these achievements during our final coaching sessions, he impatiently demanded, "What's the next goal?" It was like he was sprinting to catch a fictitious train that had left the station! He was hell-bent on continuing to effort his way forward, unwilling to pause and savor what he'd accomplished.

In that moment, I realized I had become skilled at helping people use willpower more effectively—but at what cost? My clients were achieving external success while missing the peace of mind and quality of life they also deeply desired. 

The truth is that I had been relying heavily on tools and techniques, providing the blueprints and prescriptions clients thought they wanted. But in my heart, I knew the real breakthroughs always came from insight, fresh thinking, and creative sparks—not from following a formula.

That's when Michael entered my life.

Through our work together, Michael helped me understand that there's a more powerful way to coach than offering prescriptions and how-tos. What truly moves the needle is cultivating a deep sense of trust in the wisdom, intuition, and intelligence that not only drives the world forward but also beats our hearts and powers our creative insights.

I began dropping many of the frameworks I'd learned - slowly at first, then all at once - and committed instead to being fully present with clients, responding spontaneously to what emerged in the moment. Our conversations became deeper and more impactful. While some clients were uncomfortable with this shift, many embraced it—and their results not only improved but came alongside greater well-being and peace of mind.

Had I not invested in working with Michael, I might have abandoned coaching altogether or continued on a path that felt increasingly inauthentic. Instead, I discovered a way of serving clients that aligned with my deepest values and produced more meaningful, holistic results.

Your Crossroads Moment

As I reflect on these two pivotal moments when I chose to invest in myself—times when I needed help seeing what I couldn't yet see and learning what I didn't even know I needed to learn—I wonder about you.

Where are you standing at a crossroads in your career or business right now? What challenges have you been trying to solve alone, perhaps for months or even years? What growth might be waiting for you just beyond the limits of your current perspective?

The most significant shifts in my professional journey - both during my over 13 years at Microsoft and now over a decade as a Coach - didn't come from reading more books or watching more videos. They came from investing in relationships with people who could guide me past my blind spots and illuminate possibilities I couldn't see on my own.

What might become possible if you stopped trying to figure everything out by yourself? What transformation might be waiting for you on the other side of asking for help?

After all, the investment you make in yourself today could be the decision that changes everything tomorrow.

If you need help, just let me know.