From daTeeechur's Desk: Know When to Hold Em...

Hello, friends! It’s been a long time. I’m going try to get on here more often. Anyway, I’ve been going live lately for a 10-day challenge on Facebook and LinkedIn, but today I have a blog for you. It’s story time, so break out the popcorn. Here we go!

When I was in my early 20s, I had a friend who was my boss at a record store (RIP to Kemp Mill Music). Even after the store closed, we stayed tight and spent a lot of time hanging out, usually playing free games of Texas Hold’em poker at local restaurants. We played often, sometimes multiple nights each week, and I even found myself playing free poker games online when I got home. There were also paid games too, but I never really got into that — I just loved playing for fun. It was the perfect mix of strategy and luck.

After a couple of years of this, I decided it was time to test myself. So, on a group outing to Atlantic City, I hit the tables. But things didn’t quite go according to plan — I lost all my money within about three minutes of sitting down at the table. Shortly after that experience, I saw myself playing less and less.

Fast forward to tonight: at a retreat with my business mastermind group, our amazing coaches set up a fun activity for us, Casino Night with free chips. For a while, I was killing it. As soon as I got back into the game, a ton of memories came flooding back. Pretty quickly, I had an unexpected realization — the way I play poker is almost exactly how I run my business.

First off, I don’t bluff. Not really. It’s just not my style. When I have a solid hand, I bet confidently, placing bigger bets and pushing forward strategically. It’s exactly the same way I operate in business. When I see a good opportunity, something that I genuinely believe in, I don’t hesitate — I go after it decisively, stepping on the gas to maximize the outcomes. When I was playing more regularly, I would raise my bets strategically, but lately I’ve been known to take full advantage of the opportunities when they presented themselves (both in business and in tonight’s poker event).

On the flip side, if I get cards that don’t look promising, I’m quick to fold, especially if I’m not the big or small blind (no skin in the game). This mirrors my approach to business initiatives that don’t pan out. If I try something and it’s clearly not working, I don’t waste energy or resources — I tend to pivot quickly, cut my losses, and move on to something better. It’s all about efficiency and effectiveness.

Another quirky thing about my poker play is that I have certain favorite poker hands that might seem weak or random to others, like a 2–7 or 3–9. I play these hands anyway because, surprisingly, they’ve often brought me luck. In business, this possibly relates to projects or strategies that might look low-value or unconventional at first glance. Sometimes these seemingly odd or overlooked choices end up having a bigger impact than expected simply because they’re different or unusual enough to stand out from what everyone else is offering.

Towards the end of the poker game, especially as things started winding down, I noticed I became more aggressive in my betting. To be clear, this isn’t about challenging or intimidating anyone; it’s about clarity and understanding everyone’s level of commitment as they evaluate their hand. I start to bet bigger because I want to clearly see where everyone stands — are you in, or are you out? This is a lesson that I can take to my business style, particularly when we’re approaching critical moments or major decisions. I think respectfully encouraging everyone involved to clarify their commitment would ensure we’re all aligned and moving forward together.

Reflecting on all this, it’s honestly pretty wild to see how closely my poker strategies align with my business strategies. Both poker and business require decisiveness, adaptability, calculated risks, and sometimes embracing unconventional methods. But above all, it comes down to knowing yourself and your style, and then confidently leveraging that awareness to achieve your goals.

As I thought about these parallels, it reminded me of something my mentor and business coach, Dr. Erica Jordan-Thomas, is doing soon. She’s hosting a completely free 5-day event, the 7-FigurED™ Business School, designed specifically for educators who are thinking about stepping into education consulting — or who have already started but want to elevate their game. Dr. Erica’s been incredibly successful at turning her education expertise into a thriving business, and she’s offering to share her insights with other educators ready to take that leap. It’s happening May 12th to 16th, and you can find more information and register right here if you’re interested: 7-FigurED™ Business School. If you do it, please share your takeaways with [email protected].

Have you ever noticed similar parallels to poker in your own life? I’d genuinely love to hear your stories!

References
OpenAI. (2024). ChatGPT (Mar 13 version) [Large language model]. https://chat.openai.com/