How to Choose the Right Coach: My Coaching Journey as a Female Entrepreneur

My Coaching Journey Started Long Before I Ever Knew I Needed a Coach

If you have read my chapter in Letters to the Sisterhood, you already know that my coaching journey began long before I realized I was being coached. During one of my early career roles, I unintentionally turned a former boss into a mentor simply because I kept asking questions, absorbing everything I could, and wanting to understand how the business worked behind the scenes. Yes, he absolutely had an invested interest in shaping my growth because my success meant success for the business, but those early conversations planted a seed that made me realize how much I love learning from others and applying what they teach in ways that fit my own style. Looking back now, that was the earliest version of coaching in my life, even though I did not yet have the language to describe it.

How Starting My Business Led Me to Seek Out Coaching More Intentionally

When I launched my business in 2021, I did not have a clear sense of what type of coach I needed, but I knew I wanted guidance from someone who had already built what I was trying to build. By early 2022, I found myself deep into virtual assistant coaching spaces, listening to people who were several steps ahead and had created systems and strategies that I wanted to learn from. One particular coach ran a masterclass/challenge that shook me out of my comfort zone, and that one week became a turning point. It pushed me to expand my ideas for my business and taught me that stepping into growth requires stepping into discomfort, even when I felt unsure or unprepared.

From there, I began working with different coaches who each offered support that matched a specific season of my life and business. Some helped me focus on strategy and systems, while others helped me understand my own patterns and the mindset challenges I was avoiding. I even worked with a business plan coach who unintentionally helped me discover something essential about myself. I learned that my business has always been in constant movement, and trying to write a perfect, static business plan in one sitting was never going to work for me. It probably frustrated him, but it taught me that my ability to pivot quickly and adapt to new opportunities is not a weakness. It is one of the main reasons I have been able to grow.

How Coaching Communities Strengthened My Growth as an Entrepreneur

Some of the most impactful coaching experiences came from communities that offered group coaching as part of their membership. These spaces helped me expand my thinking, meet like-minded entrepreneurs, and get support from people who understood the reality of running a business while also juggling a personal life.

In The Conspiracy by Michael Bungay Stanier, I participated in monthly coaching ateliers where Michael coached individuals on their Big Worthy Goals, and I found that I learned just as much from watching others get coached as I did from the insights I applied to myself. Each session offered something new depending on where I happened to be in my life at that moment, and that ongoing exposure to different coaching styles helped me understand what works for me and what does not.

Mamas & Co. gave me weekly Monday morning coaching calls, and those calls became a valuable source of inspiration, even when the topic did not directly relate to what I was dealing with at the time. There was always one sentence, idea, or reminder that stayed with me long after the call ended.

These communities also connected me with accountability groups, new friendships, and peers who were growing alongside me. Groups like the ones in The Conspiracy, Mamas & Co., and Sheridan Rise Program offered a level of connection that made the entrepreneurial journey feel significantly less isolating.

Working One on One With a Coach Brought the Deepest Transformation

In the past year, my work with Anthony Gordon through the RISE program provided some of the most personalized and transformative coaching I have ever received. Anthony had a way of meeting me exactly where I was, understanding the fears and insecurities I was not fully acknowledging, and helping me uncover the mindset patterns that were quietly affecting how I showed up in my business. It was not that I did not know the strategies or the steps I needed to take. It was that I needed someone who could hold the space, reflect things back to me, and guide me through the internal work required to actually take those steps.

The peer groups in RISE also became an important source of support. People like Jason, Hezzy, and Nat became part of my entrepreneurial circle, and their support helped me stay grounded and focused during one of the busiest and most transformative years of my business.

How I Knew It Was Time to Find a New Coach

By the end of summer and the beginning of fall, I could feel that I was entering a new chapter of business growth. I could not yet articulate what type of coach I needed next, but I knew that I needed someone who could challenge me differently once the Rise program came to an end. As I attended the High Vibe Conference and MamaCon, I started paying attention to what I resonated with, what inspired me, and what made me feel ready for a bigger level of impact.

Little by little, clarity formed. I realized that I was ready for a coach who understood my lifestyle, my capacity, my business model, and the direction I want to grow in over the next year. After meeting several coaches and giving myself time to reflect on other who I had also met over the past year, I made the decision to work with Lianne Kim of Mamas & Co. This decision felt aligned, supportive, and grounded in timing that works for me and the goals I want to pursue in 2026. I am deeply grateful to be stepping into this next chapter and even more grateful to be joining Mamas & Co as a Mama Mentor in 2026.

How to Choose the Right Coach as a Female Entrepreneur: What I Learned

If you are searching for a coach or strategist and want to feel confident in your decision, here are the biggest lessons I learned throughout my coaching journey:

1. Make sure the vibe is right before committing

The energy between you and your coach matters. Someone who does not resonate with you today might be perfect for you a year from now, so trust your timing.

2. Understand what you actually need help with

Sometimes you need strategy, sometimes you need systems, and sometimes you need mindset support. The right coach depends on your current season, not your long-term vision alone.

3. Choose an investment level that reflects your goals

The more you want to grow, the more likely you will invest in coaches with experience, proven results, and decades of knowledge. Choose based on value and alignment.

4. Pick a time that works with your real life

The right coach in the wrong season will not help you transform. Timing is everything.

5. Be willing to do the work

Hiring a coach feels exciting, but the real transformation happens when you apply what you are learning and take action between the calls.

Where Coaching Has Brought Me Today and How It Connects to Your Next Step

Coaching helped me uncover parts of myself that were ready to grow, even when I felt overwhelmed or uncertain about my next steps. It helped me rebuild confidence after burnout, reconnect with my strengths, and run my business with a clearer sense of direction and purpose. Each coach I worked with supported me in a different way, and every season of support prepared me for the next stage of my life and business.

As I step into this next season with even more clarity and certainty, I cannot help but reflect on how essential it is to find a coaching experience that meets you where you are while still stretching you toward where you want to go. That balance of support and challenge is what moved me forward, and it is the foundation of how I support other women entrepreneurs today.

If you are reading this and wondering whether a coaching program could help you gain the same clarity, structure, direction, and confidence in your business, the Scale to Clarity Program may be the next step for you. It is intentionally designed for women who want their business to support their life instead of overwhelming it, and it blends strategic planning, operational systems, mindset support, accountability, and personalized guidance so you can move from chaos to clarity in a way that actually aligns with your lifestyle and goals.

Whether you are growing, rebuilding, restructuring, or preparing for your next level, this program can help you identify what you need, organize it in a way that feels manageable, and take aligned action on the goals that have felt too big or too heavy to tackle alone.

If you want to explore whether this program is the right fit for your business and your season of life, I invite you to learn more, ask questions, and see if the timing aligns with your vision for the year ahead. You deserve support that feels aligned, encouraging, and empowering, and if the Scale to Clarity Program is right for you, I would be honoured to support you through it.