750 Sessions, Oh My

I had a wild realization yesterday when meeting with my assistant, Alyssa. We were updating our client tracking spreadsheet when something caught our eye. After accounting for May's meetings, I have conducted 750 coaching sessions since leaving my prior career in 2019. This doesn't include consultations, touchpoints, one-off meetings, or providing insights to non-clients—750 formal coaching sessions with clients. I initially thought that was an error, but nope (!), it's the real deal.

While every family's situation differs, some consistent and common themes repeatedly pop up. This was never more evident than one day when I had back-to-back coaching meetings. The first was with a first-year elementary teacher trying to carve her path into adulthood. The second was with an NFL player who recently signed an eight-figure contract while navigating multiple endorsement opportunities. I think you and I would agree these two individuals live in entirely different worlds. Here's the thing, though. I had nearly the exact same conversation with both of them. That's the wonder of the human experience and our psychological wiring. While life presents differently for each of us, we often experience similar situations, challenges, and obstacles. It's a beautiful and ironic reminder that money is NEVER about money.

So today, I thought it would be appropriate to share with you 10 insights from my first 750 coaching sessions:

  1. Debt does not discriminate based on income. It's not the lack of income that leads us into debt, but rather our decisions. Debt is a trap that's crushing people from every age, race, income, education, profession, and geography.

  2. A family's ability to make progress in any area of life is only limited by their belief in the outcome and their discipline to see it through. Countless people have achieved feats that make my accomplishments look like child's play. Never underestimate the power of someone crazy enough to believe it's possible.

  3. Combining finances in marriage always yields better results. Better financial results. Better relational results. Better alignment of meaning and purpose. Better execution of the plan. I'll die on this hill. Yes, we can do ok with separate finances, but it's like driving a five-speed car and only believing there are three gears. That third gear feels fast if we don't know the fourth and fifth gears exist.

  4. If you pursue money, you might find it. It will be cool and exciting. But if you pursue meaning, you will absolutely find it.....and you'll likely find some money along the way. People who pursue meaning live ridiculously amazing lives. Not easy lives; amazing lives.

  5. A well-executed budget is the gateway to any and every goal you want to accomplish. Once you unlock that, anything is possible.

  6. Work that matters matters. You wear it in your eyes, and it leaks into every aspect of your life, whether you want it to or not.

  7. People are usually doing better than they think, but they have nothing to compare it to other than social media.

  8. Nothing changes lives like joyful and sacrificial generosity. Nothing! And I'm not talking about the recipient....the giver!

  9. You SHOULD spend money on wants, but only those that add value to YOUR life.

  10. Simplify, simplify, simplify. The simpler you make your finances, the more time and energy you can invest in living a meaningful life.

Sorry for the long post today, but it just felt right. Have an amazing day!

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