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In a recent episode of The Deep Dive podcast, I had the pleasure of sitting down with host Jay Hummel to share my entrepreneurial journey—from scaling and selling kasina to redefining success and helping others design careers that fit their lives, not the other way around.
For too long, many of us have approached career decisions as if they were life decisions. We choose a profession, commit to a path, and then attempt to shape our lives around it. But what if we flipped the script? What if, instead of bending our lives to fit our careers, we intentionally designed careers that aligned with our values, aspirations, and well-being? That’s the philosophy behind my work at Coaching Metta—helping professionals and entrepreneurs make intentional choices that lead to success on their own terms.
Lessons from Founding kasina
During our conversation, Jay and I explored the lessons I learned while building kasina, a data analytics firm serving asset and wealth management institutions. From the outset, I knew that success wasn’t just about having a great product—it was about understanding the market, making strategic decisions, and knowing when to pivot. One of the most valuable lessons I took from kasina was the power of reverse-engineering success. Too often, founders build businesses without a clear exit strategy. I took a different approach—I envisioned what a successful acquisition would look like and worked backward to position the company accordingly. That level of strategic foresight not only led to a successful sale but also set the foundation for my future ventures.
Coaching Entrepreneurs: Strategy and Mindset Matter
After selling kasina, I applied those same principles to coaching entrepreneurs. Building a business isn’t just about working hard—it’s about working smart. Many founders get caught in the daily grind, losing sight of the bigger picture. My role as a coach is to help entrepreneurs step back, gain clarity, and make decisions that align with both their business and life goals. One of the biggest mistakes I see is entrepreneurs defining success by external markers—funding rounds, media recognition, industry accolades—without asking themselves whether those achievements truly lead to fulfillment. My advice? Define success on your own terms. Understand what you want from both your business and your life, and make decisions that serve that vision.
Helping Executives Lead With Intention
Beyond working with entrepreneurs, I also coach executives navigating high-stakes leadership roles. The reality is, climbing the corporate ladder doesn’t always lead to satisfaction. Many professionals reach a point where they ask themselves, Is this all there is? I help executives shift their mindset from reacting to career opportunities to intentionally designing their next chapter. That means aligning career choices with personal priorities, setting boundaries, and making decisions with clarity rather than fear. Whether it’s a career pivot, stepping into a leadership role, or planning an exit strategy, my approach ensures that professional success doesn’t come at the cost of personal fulfillment.
Final Thoughts: Success is More Than a Job Title
My conversation with Jay was an opportunity to reflect on the lessons I’ve learned over the years—both from my own journey and from the leaders I’ve coached. If there’s one key takeaway, it’s this: Your career should serve your life, not the other way around.
If you’re feeling stuck or uncertain about your next move, take this as a nudge to pause and reflect. Are you building a career that aligns with your values? Are you defining success in a way that genuinely serves you? If not, it may be time to make a change.
A big thank you to The Deep Dive for having me on!
#MidlifeRemix #SuccessSecrets #Entrepreneurship #Leadership #CareerPivots #Happiness #LifeLessons #PersonalGrowth #stevenmiyao #JayHummel #DeepDive
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