Thinking, Writing, and Building with Bets
How to make better decisions in writing and entrepreneurship
When was the last time you made a bet?
Unless you gamble on sports or play online poker, you may think it’s been awhile.
In reality, we all make bets, all the time.
Whenever we make a decision, we’re placing a bet on an uncertain future.
From big decisions (starting a new company) to small ones (what to eat for dinner), you’re betting that your choice is the optimal one.
And according to Annie Duke’s book, Thinking in Bets, we make much better decisions when we act like there’s money on the line.
Making Bets in Writing and Entrepreneurship
As a professional poker player, Annie’s success hinges on her decision-making skills. The more objective she is, the better she’ll do in the long run.
Decision-making is obviously important for entrepreneurs, too. We make decisions all the time, from pricing to hiring to prioritizing projects.
But decision-making is just as crucial when writing.
In fact, William Zissner has an entire chapter in On Writing Well dedicated to a Writer’s Decisions:
“This has been a book about decisions—the countless successive decisions that go into every act of writing. Some of the decisions are big (“What should I write about?”) and some are as small as the smallest word. But all of them are important.”
By improving our decision-making skills, we improve our writing. And by improving our writing, we can make better decisions.
Here are three skills I’ve learned from Thinking In Bets and how they apply to writing and entrepreneurship:
1. Focus on what you can control
After I missed a major business goal in March, my friend Andy Ellwood passed on this sage advice:
In summary: Focus on what you can control.
In poker — like life — luck plays a big role. Annie Duke can’t control when another player get a lucky break. All she can do is play the hands that give her the best odds of winning.
After I missed my March goal, I made a list of things In and Out of my control:
In my control:
Sales outreach
Improving my pitch
Updating my business model
Finding better leads
Out of my control:
Whether or not I make a sale
Everything else
The same is true with writing. We must focus on the things in our control:
Out of my control: Whether anyone reads or likes my writing
In my control: Writing every day no matter what
Out of my control: Social media algorithms
In my control: Starting a newsletter to own your audience
Focus on what you can control, and in the long run, you’ll find success.
2. Evaluate your decision-making, not outcomes.
Professional poker players know that good outcomes don’t always mean good decision-making.
The opposite is also true: Good decisions don’t always yield good outcomes.
It’s critical to separate the decision from the outcome. By evaluating your decision-making, you can achieve better outcomes more often.
Thanks to Annie’s book, I recently started tracking my decision-making. Every night I do an After Action Review (AAR) where I record:
Good decisions
Poor decisions
New decisions/Undecided
I previously focused on outcomes: What went well and what didn’t go well.
Now I’m able to identify poor decisions before they produce poor outcomes.
Start evaluating your decisions on a daily, weekly, and monthly basis. You’ll quickly see that there’s more in your control than you realized.
3. Place bets to improve your writing (and thinking)
Imagine if you had money on the line for every Tweet, newsletter, podcast, or book you published. If the content performs well, you make $100. But if it performs poorly, you lose $100.
Wouldn’t you work a lot harder to make sure your writing was up to standard?
By thinking is bets, we stop thinking our shit smells like roses. We look at our work more objectively. We consider other points of view. We better gauge our confidence level. We do our due diligence.
This level of objectivity is how good writing becomes great writing. It’s also what turns good thinking and average startup ideas into brilliant thinking and world-class businesses.
Force yourself to ask hard questions about your beliefs:
Why might my belief not be true?
What other evidence might there be for or against my belief?
How can I better gauge the accuracy of my belief?
What information could I have missed that disprove my belief?
Why might someone else be right instead of me?
You don’t literally have to bet on your writing to employ objective thinking.
Simply ask yourself, “Wanna bet?” every time you’re ready to hit “Publish.” This will remind you to double-check your work as if there was money on the line.
Our ability to make better decisions is directly correlated with our long-term trajectory.
No, you can’t control everything in life, but by focusing on the things you CAN control, you’ll make incremental steps towards success.
Thinking in bets will help accelerate your decision-making process. This mindset just as valuable in writing and entrepreneurship as it is in poker.
Wanna bet?
Clever, unique way of analyzing our own plans and success! Love it!