Thinking Time - The Distinct Advantage 90% of Entrepreneurs Ignore

One of the most important things entrepreneurs can do is spend more time thinking.

Even as I write those words, part of me wants to roll my eyes like my teenage self when my father told me anything of importance. “Ugh. Thanks, Dad. I know that already.”

But do I value thinking? How much time do I make for it?

Judging by the number of authors, leaders, and luminaries who have called out a lack of thinking across two millennia, the lack is more common than its opposite. More on that in a moment.

Human beings are impressive in part because of our ability to categorize and automate various decisions—that is, to think less about them. Much of our lives follows predetermined patterns, from how we make breakfast to the route we drive to the office, and that autopilot isn’t all bad when you consider how time- and resource-intensive rethinking every decision every time would be.

Sticking to patterns can have benefits.

By always ordering the same thing at my favorite restaurant, I waste no time re-reading the menu and give my full attention to the person I’m eating with while also ensuring that I will enjoy what I eat. A triple win.

Most of life consists of situations where the consequences of not thinking and making worse decisions are negligible. I don’t risk or suffer much when I make a snap decision to order the daily special, and the meatloaf ends up being bland and dry.

The trouble is, we’re always forming habits, and those habits work against us in the ten or twenty percent of situations where not thinking can truly hurt us.

Business and entrepreneurship is one of those high-stakes domains. Forensic accountant and investor Anthony Scilipoti once said in an interview, “Business is judgment. People run companies; they don’t run themselves.”

Bad judgment pops up all over the place like a rash of mushrooms. An email written and sent in anger can derail a longstanding and fruitful partnership. A pricing mistake that with some foresight could have been avoided can destroy the quarter’s profit. An ill-considered marketing campaign can create a publicity nightmare that eventually kills the company.

No entrepreneur needs to be reminded of the consequences of bad judgment or value of good judgment. We overthink decisions and second-guess ourselves precisely because we know the stakes.

So why don’t more of us put thinking time in our calendars?

Why don’t we schedule good judgment?

Our pace of life and the very fabric of society, at least in the West, fights this type of intentionality. Duties, distractions, and details encroach on every side, like acid eating the edges of a paper.

But before you and I try to blame Modern Life or Culture or some other vague capital-letter Enemy, we ought to do some reading and then take some responsibility.

You see, a lack of it isn’t a modern problem.

A Roman Emperor and philosopher you may have heard of, Marcus Aurelius, wrote down this reminder for himself in Meditations sometime between 161–180 AD:

“You must reclaim your mind from distractions.”

Um, excuse me, Marcus, do you realize how good you had it in a pre-industrial-digital-Internet-mobile-social-AI age?

Daniel Defoe was a merchant before he was a writer, and in The Complete English Tradesman, published in 1726, Defoe doesn’t mince words: “The want of thinking is the ruin of many a tradesman.”

In the 1920s Thomas Edison went so far as to post this reminder on signs around his laboratories: “There is no expedient to which a man will not go to avoid the real labour of thinking.”

Edison’s friend, Harvey S. Firestone, who founded Firestone Rubber and Tire Company, wrote this on the first page of his 1926 business memoir, Men and Rubber:

“For the most difficult thing in business is first getting yourself to thinking and then getting others to thinking. I say this is difficult because, in the natural course of business, an infinite number of details come up every day, and it is very easy indeed to keep so busy with these details that no time is left over for hard, quiet thought—for thinking through from the beginning to the end.”

Aurelius had too many distractions, and Firestone had too many details. Has the thinking problem improved over the last century?

In Michael Eisner’s 2010 book Working Together (2010), Warren Buffett says, in effect, “No, it hasn’t”: “I insist on a lot of time being spent, almost every day, to just sit and think. That is very uncommon in American business.”

Admittedly, this brief survey of “evidence” from (mostly) dead white men presents a lopsided view of the not enough thinking problem, but still, I hope that these three points hit home:

1. It’s important to recognize high-stakes situations for what they are.
2. It’s harder to do that and to make good decisions if you don’t improve your judgment through dedicated thinking sessions.
3. Entrepreneurs who force themselves to do more thinking have a distinct advantage over those who don’t.

I say “force” because, if achieving the focus, attention, and self-possession required for clear thinking was difficult two thousand years ago, then you and I have our work cut out for us.

Here’s how entrepreneurs can fix their thinking problem:

1. Shoehorn thinking time into otherwise packed calendars.
2. Do more thinking on the go.

My favorite example of scheduled thinking time is Sara Blakely’s “fake commute."‍

“I’ve identified where my best thinking happens, and it’s in the car,” she said. “I live really close to Spanx, so I’ve created what my friends call my ‘fake commute.’ I get up an hour early before I’m supposed to go to Spanx and I drive around aimlessly in Atlanta with my commute so that I can have my thoughts come to me” (bold mine).

Do any reading at all, and you’ll discover that the most successful entrepreneurs of any generation made a habit of deliberate thinking.

They planned for it and protected it though it isn’t easy or convenient and can feel indulgent, counterproductive, and wasteful.

Thinking is important. If it’s important, you’ll plan for it and put it in your calendar. What gets scheduled gets done.

As for more thinking on the go, when I started looking for the space, I found it.

Recently, as I waited in the checkout line at the grocery store, I reached for my phone in my back pocket. I froze mid-grab as a thought occurred to me. I could spend the five-minute bubble of time thinking instead of checking my inbox or social notifications.

At first my mind pinballed among questions. What’s on my mind? What has been bothering me? What do I need to think about?

I soon arrived at a real concern fizzing with anxiety: bookkeeping. I loathe it, and yet I’d formed a new LLC with a partner and wanted to do right by him, which meant keeping accurate, up-to-date books.

The solution arrived in seconds. Hire someone. Duh. But hire how and where?

Again, the answer came quickly. Hire in the Philippines. That had worked well for my full-time assistant and podcast editor.

The full plan unfurled in my mind like a hot air balloon, and before I had even gotten home, I had used the voice memo app on my phone to draft the job description.

Good for me, but let’s not skate past the point of the story. My progress didn’t require a cold plunge, offsite planning retreat, or solitude-rich walk in the woods. It came from five minutes’ worth of deliberate thinking in a busy, loud, crowded place.

Though certain environments make thinking harder, the act matters more than its setting.

Thinking is available to everyone. We can think anytime, anywhere, for free, without help, permission, or special equipment.

Thinking shouldn’t be an advantage, yet it is. The relatively few folks who make a habit of it have a predictable way to have (or receive) more great ideas, to improve their judgment and make better decisions, and to get extraordinary results, whether in a material sense with better-than-the-market returns or in a harder to quantify sense like not entering what would have been a miserable partnership.

I’ll end with practical ways I squeeze in more deliberate thinking:

• Questions. Keeping and updating a Journaling Questions document in Notion where I can always go to find thought-provoking questions. Better questions lead to better insights.
• Journaling. I journal most days, if only for a few minutes. I start by practicing gratitude, and then I often ask myself, “What’s on my mind?” Julia Cameron’s Morning Pages exercise from The Artist’s Way is worth a look.
• Weekly Planning. I use Hyatt Co.’s Full Focus Planner and plan out my weeks on Sunday afternoons. The planner has built-in reflection questions.
• Monthly Retrospectives. I’ll be spending an hour or so at the beginning of each month reflecting on the last month. I use the same template each time.
• Quarterly Planning. I reflect on the last quarter at the beginning of each new one.
• Annual Planning. I take myself through a Year in Review and a Year in Preview exercise each December.
• Miscellaneous Habits for Making Space.
  • Making a point to not turn the radio, music, or a podcast on in the car and driving in silence.
  • Not reaching for my phone in the interludes between activities and simply thinking instead. See the grocery store example above.
  • Runs. As much as I love listening to podcasts, I’ll also take out my AirPods and think.
  • Walks. When I’m wrestling with head trash, a creative conundrum, or an opportunity or gnarly business situation that requires judgment, I’ll walk around my neighborhood.
  • Prayer and meditation. Obviously.
  • Solitude. In Digital Minimalism Cal Newport draws on a helpful definition of solitude from Lead Yourself First by Russell Hittinger and Kethledge Erwin: “a subjective state in which your mind is free from input from other minds.” So, I purposefully cut out otherwise good inputs so I can think on my own.

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