Foundation 1 of 20 · Envision
What Is Strategic Thinking? Working On vs. In Your Business
A Packed Schedule Feels Like Progress. It Only Proves You Are Moving.
"We are booked solid every week, so why does it feel like we are stuck?" If every hour goes to serving customers and putting out small problems, nobody is steering. Strategic thinking is the habit of stepping outside the daily work to decide where the business is actually headed. Here is what it looks like and a weekly hour that makes it stick.
Last Updated: 11/02/2026 · Written by Dr. Paul Borosky, DBA, MBA
The Short Answer
What Is Strategic Thinking?
Textbook Definition
Strategic thinking is the deliberate practice of stepping back from day-to-day operations to examine the business as a whole, judge where it is heading, and choose a long-term direction that guides near-term decisions.
In Plain English
It is the time you spend looking at your business from the outside instead of running it from the inside. Strategic thinking asks two questions the daily rush never asks: where is this going, and why?
Why It Matters
Why Do Busy Owners Stop Getting Ahead?
Every new job, product, or customer request makes sense on the day it arrives. Each one is a small, kind yes. The trouble is that nobody ever lines them all up and looks at them together. A year later the owner is working harder, spending more, and keeping about the same amount. Busy is not direction, even when it feels like it.
Owners who practice strategic thinking carve out regular time for working on the business rather than only in it. That idea has its own guide on how to work on the business, not in it. The first question it should answer is simple: what should this business look like five years from now?
Signs you have this problem:
- Your calendar is full every week, but profit has barely moved in a year.
- You add new products or services when asked and almost never retire old ones.
- You have not taken a full day off in months and call it a good sign.
- Nobody on the team could tell you where the business will be in five years.
- Your answer to "what is the goal?" is some version of "more."
- You only look at the numbers when something goes wrong.
What It Looks Like
What It Looks Like When Busy Replaces Direction
From the Fabled Forest · Chapter 1
Colt, a horse who runs a tour company and also serves as mayor, had fourteen tours and every one of them was full. He was about to add a fifteenth. When Doctor Owl asked how the year had gone, Colt called it his best ever. Greta, the goose who keeps his books, quietly opened the ledger. Last year, nine tours had kept six hundred coins. This year, fourteen tours had kept the same six hundred, and Colt had worked eleven weeks straight.
Doctor Owl gave him an odd assignment: take a full year of booking boards to the empty town hall, lay them in a row on the floor, and just look. Walking the line that night, Colt saw what he had never seen from the trail. Every month added a tour, usually because someone asked. Not one tour had ever been dropped. The business was not climbing. It was spreading.
The next morning Colt set aside one protected hour every Monday to look at the business from the outside, with a short list of questions to answer. He could fill in where he stood and where he had been a year ago. The line asking where he wanted to be in five years stayed blank. That honest blank, Doctor Owl told him, is where real planning begins.
Colt's story is Chapter 1 of Strategy for Small Businesses, Book 6 of Dr. Paul's Fabled Forest Business School Series.
The Fix
How to Practice Strategic Thinking in 4 Steps
No retreat and no consultant required to start. Just one hour a week and a clear view of the whole year.
Block one hour a week and guard it.
Same day, same time, every week. Treat it like a meeting with your best customer. Colt chose Monday at nine, after the sunrise tour, and handed the creek walk to Greta.
Spread a full year out in front of you.
Pull twelve months of sales, jobs, or bookings and look at them side by side. Patterns that are invisible week to week, like an offer list that only grows, show up fast when the whole year is on one table.
Answer four plain questions.
Where does the business stand today? Where did it stand a year ago? Where should it be five years out? What did this week do to move toward that? Write the answers down, even when they are rough.
Describe the five-year picture in four parts.
Location, people, offer, and income. Give each part a real answer, not the word "more." Then turn that picture into a direction you can steer by, starting with a vision statement.
Dr. Paul's Insight
The most common mistake Dr. Paul sees is answering the five-year question with "more." More customers, more revenue, more services. That is a description of a heavier workload, not a picture of a business. Owners who skip the picture often slide into strategic drift without noticing, because every week still feels productive.
Sample: Colt's First Monday Hour
Here are the four questions from the Monday Hour with the answers Colt wrote at the kitchen table. Use the same four lines for your own business this week.
| Where are we today? | Fourteen tours, all full. 600 coins kept. No days off. Greta worn out. |
| Where were we a year ago? | Nine full tours. The same 600 coins kept. Sundays free. |
| What should the business look like five years out? | Blank for now. Location, people, offer, income still to answer. |
| What did this week do for that? | Can't say yet, because the five-year line is empty. |
Illustration from the book. Fill in your own numbers. A blank third line is normal the first week. Do not fill it with "more."
Watch
Watch: Organize-Plan-Grow, the Big Picture Behind Strategic Thinking
Two short videos from Dr. Paul on his Organize-Plan-Grow approach, the framework he uses to help owners step back, set a direction, and grow on purpose.
Dr. Paul's Organize-Plan-Grow Strategy for Startup & Small Business Growth
Dr. Paul Borosky, DBA, MBA. (5:18)
Organize-Plan-Grow your Small Business
Dr. Paul Borosky, DBA, MBA. (7:16)
From the Book
Read a Passage From Chapter 1
Chapter 1 · Strategic Thinking
Every Tour Full, Going Nowhere: A Horse’s Year on the Floor
Five of the boards had a new line on them. A new tour, chalked in at the bottom in Greta’s square hand, with a date beside it and, in three cases, the name of the creature who had asked. Skating, for the otters. Dry Wash Ride, for the ranch families. Dusk Lantern Walk, for the librarian’s sister.
Not one board had a line taken off.
Not one tour, all year, had ended. Every month the business had got a little wider, and none of it had been decided. It had all been asked for.
Read what Colt finally sees from the window end of the council room in Strategy for Small Businesses, Book 6 of Dr. Paul's Fabled Forest Business School Series.
Get the Book on Amazon →FAQ
Strategic Thinking Questions Owners Ask
What is the difference between working in and working on the business?
How much time should a small business owner spend on strategic thinking?
What if I cannot answer where my business will be in five years?
Is a full schedule a sign my business is healthy?
Keep Going
Related Foundations
Strategic thinking is the first of twenty strategy foundations. These pages build on it. New to a term on this page? Every one is in the strategy glossary.
What Is Strategic Drift?
How a business slowly falls out of step with what customers need.
What Is a Gap Analysis?
Measure the distance between today and your five-year picture.
How to Set Long-Term Business Objectives
Turn the picture into a few results you can count.
What Is Strategic Focus?
Choose a few things to do well and say no to the rest.
Written by Dr. Paul Borosky, DBA, MBA, business consultant and author of Dr. Paul's Fabled Forest Business School Series. Want help stepping back and setting a direction for your business? See growth plan and consulting options.
This page is for general educational purposes only. It is not legal, financial, or other professional advice. Dollar figures are illustrations. The Fabled Forest and its characters are fictional. For decisions about your own business, consult a qualified professional.