I made plenty of big decisions in my business years—some smart, some that make me wince when I drive past the old office park.

The older I get, the more I trust a short list of questions over any single flash of insight. Successful people, in my experience, don’t rely on genius or gut alone.

They run the moment through a small set of filters that cut through noise, ego, and panic.

Here are ten questions I’ve watched serious operators—and learned elders—ask themselves before they pull a lever that matters.

1. What problem am I actually trying to solve?

Most bad decisions start with a misnamed problem.

We treat symptoms like causes: “We need more staff” (when we really need better training), “We need a new relationship” (when we really need to fix how we show up in the one we have), “We need a rebrand” (when the product needs repair).

Successful people interrogate the premise. They write the problem in one sentence without adjectives. If the sentence includes “and also,” it’s two problems. Solve the first one first.

Field check: If I can’t describe the problem on a postcard, I’m not ready to choose a solution.

2. What will be true in a year if I do nothing?

Action has a spotlight; inaction has a track record. Before deciding, the best people I’ve known take a hard look at the default future.

Sometimes doing nothing is a disaster; sometimes it’s the wisest move possible. This question exposes urgency theatre. It also reveals quiet decay. In my forties, I almost greenlit a costly expansion because “opportunity doesn’t wait.”

A mentor asked me this question. The honest answer was: a year from now, we’d still be profitable and less stressed. I saved us money and two migraines.

Field check: If “do nothing” looks like rot, move. If it looks like compost, wait.

3. What are the options I haven’t named because they’re inconvenient?

We all have a mental short list—A or B—but big choices usually hide C, D, and E.

The inconvenient options are the ones that require humility (admit a mistake), mess with our identity (change roles), or disrupt comfort (start over).

Successful people force a third option onto the table: “What would a 20% version look like?” or “If we had to spend half, what would we do?” It’s amazing how often the best path is the one our ego edited out.

Field check: If my choices all make me look good, I haven’t found the real set yet.

4. What does my future self thank me for?

It’s a corny prompt and it works. I imagine a calmer version of me six months out—better sleep, less drama—writing a short note backward. What did I choose? Where did I say “no”?

Successful people build from the timeline, not just the to-do list. They’re willing to trade a little discomfort today for compound interest later. In marriage this sounds like: “Will Friday Frank thank Thursday Frank for scheduling the hard conversation?” The answer is almost always yes.

Field check: If the future-me letter is vague, the decision needs more shape.

5. What is the reversible version of this decision?

Jeff Bezos popularized the “one-way door” vs. “two-way door.” The best operators apply it in real life. If a choice is reversible, they bias toward action and learning.

If it’s irreversible, they slow down, add redundancy, and gather more signal. We treat too many decisions like one-way doors because it flatters our anxiety. Most are two-way: pilots, trials, pilots of the pilots. Successful people separate the two and act accordingly.

Field check: If it’s actually reversible, pick a date to review and stop catastrophizing.

6. What’s the cost in attention, not just money?

Every yes rents space in your head. People who’ve built things worth keeping measure attention the way accountants measure cash.

A “cheap” decision that spawns weekly check-ins, endless context switching, or message traffic at 10:43 p.m. is expensive in the currency that matters: focus.

When I ran teams, I learned the hard way that the wrong hire is twice as costly in attention as in salary. Successful people ask, “What will this require me to think about every week?” Then they price it honestly.

Field check: If I can’t see where the attention will come from, I’m buying with debt.

7. What are the second-order effects (and who will pay them)?

First-order thinking asks, “What happens now?”

Second-order asks, “And then what?” A discount boosts sales—does it also train customers to wait for the next one?

A move saves rent—does it drain culture? A personal pivot brings excitement—does it quietly increase travel and erode the time you promised your kids?

Strong decision-makers run a quick simulation: two moves out, three. They identify who bears the cost—staff, spouse, future self—and bring that person into the room early.

Field check: If someone else will bear the weight, they deserve a say before I choose.

8. What does the data say—what does my body say—and where do they disagree?

This isn’t “trust your gut” vs. “trust spreadsheets.” It’s both. Successful people hold numbers and nerves together like two hands of the same person.

If the data is green and my stomach is red, I ask why: Is there a risk not captured? Is there a pattern my experience recognizes that the model ignores?

If my gut is excited but the data is shaky, is my excitement novelty or signal? In my seventies, I listen to my body as an early-warning system—then I verify with facts.

Field check: Disagreement between data and body is not a stop sign; it’s a research plan.

9. Who benefits if I choose wrong—and am I unconsciously protecting them?

Ego loves decisions that rescue our past selves from embarrassment. I’ve watched leaders double down to avoid admitting that an old strategy aged poorly. I’ve done it.

The question that saved me was, “If this fails, whose story gets defended?” If the honest answer is “mine,” I know bias is in the room. Successful people are willing to disappoint their past in service of their future. They let old versions of themselves retire with dignity.

Field check: If I’m arguing with reality to preserve my image, the decision is already bad.

10. What would this look like if it were easy (not effortless—easy)?

This is an underrated question. It doesn’t mean “avoid hard things.” It means: remove unnecessary friction.

The best operators ask, “If this worked simply, what would the path be?” That framing often reveals a cleaner order of operations, a smaller pilot, or a partnership that dissolves half the obstacles.

I’ve seen “easy” expose the real blockage: pride in complexity. Strong people don’t worship grind; they respect it—and then they go looking for leverage.

Field check: If my plan reads like a maze, I’m in love with effort, not outcomes.

Two stories, because stories carry lessons farther than slogans.

Story one: the office move that almost ate our culture.
In my fifties, our lease renewal coincided with a tempting offer across town—nicer space, lower rent, better parking. The spreadsheet smiled. My body didn’t. I ran the questions above. #6 (attention cost) and #7 (second-order effects) screamed. The new location added 30 minutes to most commutes and split our lunch spots into car-only options. We would “save” money and spend trust. We paused, surveyed the team, and negotiated a shorter lease where we were with a staged redesign to fix the worst of it. We still moved two years later—on our terms, with hybrid hours and a relocation stipend. The spreadsheet was less pretty; the people stayed.

Story two: a late-career writing risk.
After I retired from management, I got the itch to write full-time. The safe version was a blog no one read. The brave version was a public column with my name on it. The reversible question (#5) helped: I could commit to twelve essays, then evaluate. The attention cost (#6) was clear: two mornings a week, protected like medical appointments. The “future self” letter (#4) was a grin. I sent the first piece and felt like I’d jumped into cold water. Two years later, I still thank that earlier man for giving me a test that had a real clock and a real cadence.

A few practical moves to make these questions usable instead of inspirational:

• Write the answers, don’t just think them. A half-page per question, even scratch notes. Writing burns off fog.

• Time-box the decision cycle. “We decide by Friday at 4.” Questions expand to fill the calendar; a clock forces clarity.

• Invite one disinterested brain. Someone smart with no stake. Ask them to attack your favorite option. You’re buying their skepticism, not their approval.

• Use pre-mortems and post-mortems. “Imagine this failed—why?” before you choose; “What did we learn?” after. Success has amnesia; document while the blood is still warm.

• Name the trigger for reversal. If it’s reversible, define the metrics that force a pull-back. Courage includes the courage to turn around.

And a short note on emotions: successful people don’t amputate feeling; they domesticate it.

A big choice will stir fear and hope. Fear often sounds like prudence; hope often sounds like recklessness.

These questions give both emotions a job to do. Fear identifies risks you can design around. Hope points to the future you’re actually trying to buy.

Parting thoughts

Big decisions don’t reward bravado; they reward disciplined curiosity.

Before you leap, ask: What problem am I solving? What happens if I wait? What options did ego hide? What will Future Me thank me for? Is this reversible? What will it cost in attention? Who pays the second-order bill? What do data and body say? Whose image am I protecting? And how could this be easier without being flimsy?

Run your choice through those filters.

You’ll make fewer heroic rescues and more boringly excellent moves—the kind that compound into a life you actually want to live.

In my seventies, I’ll take boring excellence every time.

It gets you home with your dignity, your people, and your Tuesday intact.