This narrative recounts the transformative decision of an individual who transitioned from a lucrative role at a major tech company to embrace a career in coaching startup founders, a move that brought increased personal satisfaction and a better work-life balance.Embracing a New Path: Prioritizing Purpose Over Corporate Prestige
The Genesis of a Career Shift: From Product Manager to Entrepreneurial Coach
I am the driving force behind Refactor Labs, serving as its founder and CEO. My expertise lies in executive coaching and resolving cofounder disputes. My professional journey began with a two-year tenure as a product manager at Etsy, where I specialized in developing the seller-focused mobile application. Following a series of significant organizational layoffs, I transitioned to contract product management for an emerging B2B SaaS venture. During this period, I also participated in the TED Residency, an incubator for innovative ideas, culminating in a TED Talk on the future of recruitment.
Founding and Acquisition: A Winding Road to Meta
In November 2017, I co-founded Headlight, a technology recruitment platform, alongside a former colleague from Etsy. By 2019, we strategically redirected our focus to voice AI products for the gaming industry, subsequently rebranding our company as Midgame. In July 2020, our company was acquired by Facebook, now known as Meta.
I dedicated nearly three years to Meta as a product leader before making the deliberate choice to depart in June 2023 for a sabbatical. My coaching endeavor, initiated during my time at Meta, truly gained momentum and became a serious business in January 2024.
The Unexpected Turn: Meta's Acquisition and Professional Growth
Our initial ambition was not to be acquired by Meta. However, the prevailing circumstances of global lockdowns, particularly in New York City, made the acquisition feel like a necessary emergency landing for a company running on fumes. My experience at Meta significantly broadened my professional capabilities. I honed my skills in championing my team's initiatives during high-level product reviews with Vice Presidents and successfully launched social features to millions of users while simultaneously managing multiple product teams. The caliber of my colleagues was exceptional, and I relished the collaborative environment. Yet, over time, my professional life became a relentless cycle of back-to-back meetings, extensive document reviews, and an overwhelming influx of information. The organization was in a constant state of flux, witnessing numerous managerial changes, restructurings, and layoffs. While the compensation was substantial—my total cash earnings, encompassing salary and bonuses, amounted to approximately $250,000 annually at that juncture—I could not envision myself continuing in this role for another two decades.
The Financial Calculus of Departure: Forfeiting Millions for Fulfillment
My tenure at Meta surpassed that of any previous employer. During my employment, I was accumulating 230 restricted stock units (RSUs) from Meta each quarter. Had I remained for an additional three years at the same vesting rate, I would have accrued an extra 2,760 RSUs. Valued at a recent Meta share price of approximately $609, these unvested RSUs would have been worth roughly $1.68 million before taxes. In preparation for my departure, I strategically liquidated a portion of my investment portfolio, setting aside approximately $150,000 as capital for launching my coaching enterprise.
Discovering True Vocation: Aligning Passion with Profession
In the latter half of one's thirties, a clearer understanding of one's innate talents and their market value often emerges. At Meta, my contributions included fostering a resilient community of hundreds, orchestrating workshops, and mentoring burgeoning professionals. These activities, though deeply fulfilling to me, were categorized under “organizational impact” and constituted only a mere 10% of my performance evaluation. The work I found most enjoyable and excelled at was not the primary focus of my corporate remuneration. Influenced by my mother, a gymnastics coach, and my father, an educator and community leader, coaching came to me quite naturally. My previous startup benefited immensely from the guidance of an executive coach, making it more successful than my first venture. Witnessing two professional acquaintances successfully transition to full-time coaching fueled my belief that I could achieve similar success. Starting a new business still presented considerable risks, particularly as my wife and I were planning to start a family. I realized this was my window of opportunity, as launching a business with a newborn would be insurmountable. My contingency plan was to secure another product manager role and avail parental leave if my coaching business didn't gain traction within a year.
Balancing Work and Life: A Fulfilling Coaching Practice
I dedicate approximately 20 hours per week to my work, yet I maintain a comfortable living. In the past year, my coaching practice generated $369,000 in revenue. While this figure is substantial, it's important to account for business expenses such as credit card fees, marketing, software, coworking space, and health insurance. The majority of my clients operate on a monthly retainer basis, whereas those navigating cofounder disputes typically opt for three-month packages. My primary responsibilities revolve around virtual meetings. I deeply value and respect my clients, a significant advantage of running my own enterprise. Although I previously had an executive assistant, I've since mastered the use of artificial intelligence to optimize my time and efficiently manage client tasks. While some individuals are driven by the ambition to create experiences that impact millions, I find that concept abstract. My true gratification comes from witnessing my clients develop self-assurance, expand their businesses, and enhance their relationships with their cofounders. This translates into a tangible and profound impact for me.
Pursuing Personal Passions: Creative Endeavors and Family Life
Currently, I am immersed in writing a book titled "Deep Ambition," which explores how former overachievers can transcend superficial ambitions to construct a meaningful life on their own terms. Concurrently, I am rigorously training to achieve a personal best in the Murph challenge. My weekdays conclude at 5 p.m. with either a trip to the playground with my daughter or a stroller run. Dinner is at 6 p.m., followed by bath time, milk, and bedtime by 7:30 p.m. Prior to our daughter's birth, I made a solemn promise to my wife that I would not allow parenthood to impede her career, which is creatively driven, non-corporate, and profoundly important to her.
Reflecting on a Pivotal Decision: Gratitude and Future Aspirations
I am profoundly grateful for having departed Meta when I did. While the prospect of an additional few million dollars in my bank account is tempting, it's an outcome that would have necessitated years of relentless effort. My current work week is markedly less chaotic and stressful compared to my tenure as a Product Manager. My business is still in its nascent stages, only three years old, with considerable potential for expansion. A key objective is to surpass the comprehensive compensation I earned in Big Tech, with a target date of 2028. Additionally, I hope to be a father of two by then. The current job market is exceptionally competitive, marked by widespread layoffs across numerous companies. I believe that many seasoned tech professionals could discover greater fulfillment in coaching or consulting than they might anticipate. While it demands courage and substantial resources to initiate such a venture, the ultimate rewards in terms of personal and professional satisfaction can be immensely greater.
