Does Start Dating Belong in a Business Plan?
The end of the year is always synonymous with one thing for entrepreneurs: The Business Plan.
For me, preparing the 2025 strategy was a meticulous process of iteration, projection, and pruning. But there was one line item that refused to settle: "Actively re-engage in dating."
I added it. I deleted it. I added it back, convinced myself it was fluff, and deleted it again. This went on four times as I crafted my final document. Yet, as I sat with the finalized plan over Thanksgiving weekend, a profound clarity hit me. I couldn't articulate the why, but I knew it had to stay. It was a non-negotiable component of my future success.
Why? Because the hardest truths in business—the breakthroughs that lead to real growth—often come from the messy, uncomfortable work we do on ourselves. My dating journey became a microcosm of my business transformation.
The Mastermind Breakthrough: Facing the 1999 Error
For the past year, I've been part of a fantastic Mastermind group. These groups are designed to push you past your comfort zone—and they deliver.
In March, we had a multi-day, in-person retreat, an essential part of my Mastermind experience. I leaned into every challenge: the terrifying ropes course, a full-on professional photoshoot with hair and makeup. But the moment that changed everything was when we were asked to admit a long-held secret—a shame, something we had never admitted to anyone.
BINGO.
I won't share the details, but suffice it to say I confessed to something from way back in 1999. Admitting that truth, saying it out loud to a room of my peers, was like releasing a 25-year-old anchor. That night, I slept deeper than I had in years.
The next day, exhausted but present, we did breathwork and a sound bath. The imagery and emotions that surfaced were undeniable. I finally admitted to myself the destructive pattern I had been running: I had been intentionally selecting worse and worse partners until I could do nothing but throw my hands up and quit altogether.
If I’m truly honest, I hadn't genuinely dated in four or five years—and definitely not since moving to Greenville, SC. The prospect of re-entering the market after a hiatus that long felt staggering. The group’s challenge was direct: Set up a profile. Go for it.
Startup Round 1: Debugging the Attraction Model
For someone who regularly solves complex tech problems, I found the dating apps frustrating. But the technology was a secondary issue. The primary problem was my attraction model. I was attracting men seeking "open" relationships, men still living with ex-wives, and other full-stop no-gos.
I realized I was bringing my old, boundary-less self to the new marketplace.
After a month, I hit the Pause button. This wasn't the multi-year, full-stop shutdown of the past. This was a deliberate, healthy, "let me work on this" pause. At a subsequent Mastermind retreat in May, I shared the news. The pause felt good, productive, and intentional. I also learned the Thanksgiving connection was when the Modern Entrepreneur program had been fleshed out in detail by Melissa Henault and Sam Harper over that same weekend my business plan landed on its last addition.
The Hard Inner Work: Setting the Vision and the Boundaries
For the last five months, I’ve been doing the hard inner work that is essential for any successful venture.
Many of you see me as successful, organized, and brave. The secret? I was also a master of compartmentalization—the business success was separate from the deeply guarded personal life. I was the helper, the savior, the shoulder to cry on, often at the expense of maintaining my own crucial boundaries.
Just like a business needs a clear vision and strong operational boundaries to succeed, so did my personal life.
Business Vision: What does success look like in 2025?
Personal Vision: What does a healthy, fulfilling partnership look like in my future?
Late October: Relaunching the Product (with New Boundaries)
I decided to dip my toe back in. That first step, after years of standing still, was the hardest part. Of course, tech again plagued me (it took two weeks to get a profile the system would accept!), but when it finally published, the response was overwhelming: the degree of likes, matches, and messages.
This time, the boundary work paid off.
Instead of letting the overwhelm win and chatting/meeting everyone, I've been able to slowly and thoughtfully filter my way through conversations. I've had coffee with a few men, and I'm happy to report there have been second dates. The holiday season has actually helped reduce the pressure to rush, allowing me to simply enjoy the process.
The line item I added to my 2025 business plan is no longer just "Start Dating." It is an affirmation of the growth, self-worth, and boundary setting I’ve spent the last year building. I’m simply enjoying this season, leaning into the growth, and as the great Sam Harper said: "Letting the Universe Cook."
Key Takeaway for Business and Life:
The thing you are resisting or avoiding in your personal life is often the anchor holding back your professional one. Your ability to set firm boundaries, articulate a clear vision, and face your deepest fears is a transferrable skill. My 2025 plan wasn’t just about revenue—it's about becoming the whole, integrated person who can achieve it.
If a line item in your plan feels vital but terrifying, chances are, that's the one that needs to stay.