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A Coaching Story: What's the Cost?

Today we have a guest post from Collective Gain coach Matt Mills. This post is the first in a series of coaching stories we're bringing straight to you so everyone can benefit from one client's learnings.

Jessica came to coaching for the same reason many clients I work with seek out coaching- she was at a major crossroads in her career.

Like many ambitious professionals who are yearning to grow in their career, Jessica followed a path laid out for her rather than leading one of her own design. Since college, she took opportunities presented to her to grow a career as an executive assistant to CEOs and heads of advertising agencies, major corporations and tech startups. She worked hard, was respected and in-demand for her skill set, and was well compensated. It was demanding work, but Jessica found success in the early years of her career because of her grit, resilience and work ethic.

As Jessica came into her 30s, her priorities and values changed. She began to focus on growing other areas of her life, particularly starting a family. As her career no longer felt like her first priority, she realized that the vision she had for her future was different than it was in her 20s. When this happened, she started feeling different about her current career path, and a sense of unhappiness started to build.

She kept up a brave face at work, but inside Jessica was struggling. She was ready for a shift, and to lead a career path on her terms, not on someone else’s.

When Jessica began coaching, she felt stuck, lost and frustrated and was on the verge of quitting her job. She started to feel desperate, not knowing where to turn or how to navigate the crossroads she was at. Not only was it affecting her work performance, but it also took a toll on her family life and her health.

Something had to change.

When we started our coaching work together, it wasn’t as simple as adjusting her work schedule, changing her communication style, taking a more proactive role at her company, or identifying her next job and creating a strategy to get it. If you really want to get unstuck and create a life and career where you can truly flourish, you have to go deeper, which Jessica was ready and eager to do.

To help guide Jessica in her discovery process, I asked her a lot of powerful questions to uncover what truly mattered in her life, and identify her strengths, skills, values and passions were that were being ignored in her current career.

It wasn’t easy for Jessica to be completely honest with herself, and it rarely is because it’s all too common for us to bury our purpose, passions and power deep down in service for what we “should” or “have to” do with our life and career, instead of what we truly desire.

As we uncovered more, Jessica spoke about her passion for design and creativity, and the side projects, like designing a conference room in her office, that she took on at work and in her free time that made her light up. However, the more she spoke about the joy she found in design, the more she felt guilty and a little ashamed even talking about it, because she was embarrassed about not expressing that side of herself more. It was like a secret she didn’t want anyone else to know.

Jessica was an admitted perfectionist, as most high achievers are, and she always wanted to do the best job possible, no matter what task was at hand. But constantly feeling the pressure to stay accountable to high standards can take a huge mental and emotional toll. Perfectionism can create issues when we are conforming to an image and standards we think others hold of us, rather than honoring the vision we want for ourselves.

Even though she was great at her job, and was regularly validated for her work, Jessica was miserable. Deep down, she felt called towards something greater, and opportunities were open to her to use her creativity, her design skills, and her true gifts and inner genius, even at her current job. However, she had a hard time seeing them. She was feeling a pull to follow a life that was led by her heart, but she kept it buried deep down out of fear, self-doubt and negativity.

At this moment I could tell the weight of neglecting this pull was so heavy, and I asked Jessica one question to know how worthwhile it was for her to stick with the status quo.

“What’s the cost?”

She sat in silence for a moment, she looked back with tears in her eyes and quietly said,


At that moment, it all changed for Jessica.

She realized the burden she carried not only wasn’t worth it anymore, but it also wasn’t sustainable. The toll it took on her personal well-being, her family, her health and her spirit and heart was too great, and things needed to change.

Acknowledging how great the cost was for following someone else’s path was all she needed to give herself permission to design and lead her own career path, and step into a bigger vision for her life.

After that moment, Jessica started to become a different person in our sessions. From our coaching work together, she discovered how she could integrate her creativity, leadership skills, and passion for design into her current job, as well as explore new possibilities to pursue. Jessica was more energetic, motivated, and inspired to take action towards meaningful change in her life and career.

In the months that followed, Jessica experienced many more big shifts in her life. She ultimately left her job as an executive assistant at a startup for a job opportunity to pursue her dream of becoming an interior designer. She bought a house with her husband, and she even signed up for acting classes, which was something she longed to do since she was a kid.

Since working together, Jessica’s outlook on her life and career has become significantly brighter. Instead of paying the cost of feeling burdened and trapped by her circumstances, she chose to invest in a future that was aligned with her dreams for her and her family.

All too often if we’re not careful we can become consumed by the limiting beliefs, interpretations, assumptions, and our inner critic telling us that we’re not good enough, that we don’t have what it takes, or that we can’t step into our true power unless we have more time, money or experience. This is all noise that drowns out the messages that our hearts are telling us. This comes at a heavy cost, and left ignored can affect all areas of your life beyond your career.

Everyone comes to a crossroads at different points in their career. The path you choose to walk down is ultimately your decision, and at these crossroads, you have to ask yourself what the cost is to continue following the path (although well-traveled) that is leading you to a destination you’re not looking to reach. Like Jessica did pursue the path you were meant to follow, and it will lead you to a more fulfilling and successful destination in your career.


If Jessica's story resonates with you, don't wait to make the shift in your own life. Get matched with a coach or book a discovery call with Matt directly.

About Matt: Matt has years of experience working with individuals at various stages of their careers, bringing practical expertise in guiding professionals to a thriving career path that is meaningful and more authentic to their best selves. Prior to becoming a professional coach, Matt worked in the entertainment industry as a film development executive, and in higher education as a career counselor guiding young filmmakers in their creative career paths. When not busy with his professional pursuits, Matt enjoys the Southern California lifestyle with days at the beach, staying active and training for his next marathon, and exploring the diverse culture of Los Angeles with his wife, Alyson.



I started Collective Gain out of a desire make work better, where being on a magic team was the norm vs. a rare chance occurrence. Through coaching, I discovered deep self-awareness, new perspectives and ways of working that I am passionate about bringing to you.

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