I think there’s an 83% chance you actually read this.
Success is the intersection of preparation, opportunity, and luck.
Recently, my four-year-old has been learning two different games. My dad has been teaching him chess, and I’ve been playing a lot of Marvel Battleworld with him. In that game, you play Marvel characters with different powers, roll a die, and win or lose battles based on probability. Most of the game comes down to having a certain percentage chance of rolling the right numbers.
And weirdly, the kid is insanely good with some dice (and getting better with the math). It’s like a hot craps table, just without the financial upside.
As we play these games, and as someone who read Rich Dad, Poor Dad as a parenting book, this feels like the ultimate breakdown of that book. My dad is totally the “poor dad.” Not that we were poor, but he delivered mail for the Post Office and worked overtime around the holidays to earn more money for Hanukkah presents.
Chess is the ultimate poor dad game. It’s perfect in theory, no luck other than who you play. Same pieces, same rules, same options. It’s entirely skill-based. And it’s nothing like life.
In life, you don’t have the same pieces, rules, or resources. Almost nothing is black and white, it’s all shades of gray, with luck mixed in.
For example:
Francis Ford Coppola threatened to walk off The Godfather if they didn’t hire an unknown actor who looked Sicilian, enter Al Pacino.
Penicillin was discovered because Alexander Fleming forgot to cover a petri dish.
Jay-Z avoided a massive sting operation because he happened to be in London working on an album.
School teaches us to memorize the correct answer. Life teaches us that there are many right answers and we need to find the most right one.
So how do we make better decisions? Glad you asked.
How to Make Better Decisions
- Know Yourself
- Think About Regret in Advance
- Use the 10-10-10 Breakdown
- Work Backwards
- Pre-Mortem
You don’t need to use these in order. You might use one, some, or all of them, but start with knowing yourself and see what else fits.
Know Yourself
This helps you understand what you need to make good decisions. I’m a quick doer, which is both good and bad. To me, things either work or I learn from them. But when choosing a business partner, I want slow doers. If Greg or my wife ever immediately agree with me, I know it’s a good decision. Otherwise, they stop me from lighting money on fire with half-baked ideas.
The better you understand how you think, why you act, and what appeals to you, the easier it is to put yourself in positions where good decisions happen.
Think About Regret in Advance
Regret is a powerful emotion, but it’s a lagging indicator. You only feel it after the decision. “I did X, and now I regret it, so I won’t do X again” (hello butterfly lower-back tattoo, Ted).
I think about this from a deathbed perspective. I’m not officially middle-aged yet, but I’m close. Focusing on mortality helps because most things don’t matter long-term. It strips the emotion out of small decisions.
I never regret working out. I never regret time with my kid. I never regret a fun networking event. A lot of decisions boil down to: does this move me closer to overall life happiness or not? And many decisions just don’t deserve the mental energy we give them.
Use the 10-10-10 Breakdown
How will I feel about this in 10 minutes?
10 weeks?
10 years?
It’s similar to the deathbed idea just less morbid. More Doctor Strange time loop than Lost purgatory. I don’t use this one often, but it’s useful. Most decisions won’t matter in 10 years, even if they feel terrible in 10 minutes (like eating an entire box of Domino’s brownie cookies is worth it).
Work Backwards
This one I use all the time.
No, not literally turning my chair around, but mentally. Start with your big, hairy audacious goal. Maybe it’s the elusive seven-figure firm (which I hate as a standalone goal, nothing wrong with money, but profit and life matter more).
Imagine you’ve already achieved it. What does your firm look like? Your marketing? Your day-to-day life? What are you doing in the final days before hitting that goal?
Now work backward. Five years. Four. Three. One. Six months. Three months. Next week. Tomorrow. Now.
Working backward often reveals the habits required to reach the goal whether you like them or not.
Pre-Mortem
This is one I don’t do enough, but should.
Instead of a post-mortem (“this is why it failed”), do a pre-mortem. Assume it already went wrong. Identify why. Then put steps in place now to prevent those failures.
I don’t do this enough, but it’s powerful.
So How Does This Help My Firm?
Making better decisions gets you where you want to go faster. For a more specific conversation about you and your firm, we’d need to do a free consult, but here’s the broader point:
Almost no one knows as much as they think they do.
The Great Wall of China can’t be seen from space.
A penny dropped from the Empire State Building won’t kill someone.
My wife doesn’t like red velvet cake.
As lawyers, it’s worse. At best, you think you have a 90% chance to win a motion. At best, past cases suggest a certain outcome. At best, your webinar metrics tell you what might happen again—but you never really know.
So be honest about probabilities. Choose decisions with the highest chance of success or the highest upside based on your risk tolerance.
And use that honesty as a marketing advantage. While it would be terrifying for a pilot to announce there’s an 83% chance you arrive on time, wouldn’t it be better if airlines were transparent in advance? Same with movies, “13% chance you’ll like it” sounds more believable than “it’s amazing, trust me.”
So tell clients the truth.
Tell them 95% of your clients don’t go back to jail.
You get policy limits in 72% of cases.
100% of estate plans are used after death, and 99% avoid probate.
Market your numbers. Explain real probabilities. Acknowledge that life is a series of bets with luck involved, but that you can stack the deck in your favor.
Until then, have a wonderful weekend.