Friday, October 09, 2026
A new market, a new product line, a second location: most lose money the same way, by skipping the three numbers that would have told them how big the opportunity really was.
Nearly four in five small business owners now say long-term planning is difficult, and almost a third call it very or extremely difficult, according to 2026 research from the Small Business Expo Research Desk. Only 8.4% say it isn't hard at all. If your last planning session felt like pulling numbers out of thin air, you are the rule, not the exception — and the fix isn't a better template.
Every planning framework on the market starts the same way: fill in a revenue target, fill in a market size, fill in three strategic priorities. It's a spreadsheet wearing a strategy costume.
The trouble is sequence. A template asks an owner for a year-three revenue number before that owner has pictured what year three actually looks like — what a normal Tuesday feels like, who's still on the payroll, what the business does without them in the room. Ask for the number first and you get a guess dressed up as a plan. No wonder 78.7% of owners find it difficult: they're being asked to do arithmetic on a picture that doesn't exist yet.
This is why so many strategic plans gather dust by March. It was never the owner's picture of the future. It was a spreadsheet someone else's template told them to fill in.
Cameron Herold, the entrepreneur behind 1-800-GOT-JUNK's scale-up and the author of Vivid Vision, built a career on a simple reversal: write the destination in vivid, present-tense detail before you build the plan to get there. Not a mission statement. Not a set of bullet points. A page or two describing the business as if it already exists three years from now — what it looks like, sounds like, earns, and feels like to work in.
Inside the Simple-Growth System™ — built on over 30 years in business and 200+ owners coached one-on-one across 30+ industries — Kevin uses a simplified version of this exercise with owners building their first real growth plan:
1. The Tuesday Test. Describe, in present tense, a normal Tuesday in your business three years from now — who's in the building, what you're doing (and not doing), what the customer experience looks like.
2. The One Number That Matters. Not five KPIs. One number — revenue, margin, hours worked, whatever actually represents "we made it" — written down with the date it's true by.
3. The Who's-Still-Here Question. Name the roles (not necessarily the people) still standing in three years, and the ones that won't exist anymore because the business has outgrown them.
Only once that picture exists does a plan get built to serve it — not the other way round.
"He really got our vision from the beginning and has been a huge help in putting together a clearer plan and strategy for the next five years. Working with Kevin D'Ambros-Smith has given us the space to pause and reflect — on where we are now, where we want to be and how we get there."
— Gabby Kirk, Papier Hq
Most owners know, in some form, that they should have a long-term picture. Few actually sit down and write one. Not because they're lazy — because writing a vivid, specific picture of success feels exposed in a way a spreadsheet doesn't. A spreadsheet can be wrong and it's just math. A vivid vision can be wrong and it's personal.
The real obstacle isn't knowledge, it's accountability. Nobody is checking whether the picture got written, let alone whether this quarter's decisions are still pointed at it. That's the gap a second set of eyes closes — someone whose job is to ask "does this still match the Tuesday you described" before a distracting opportunity, a bad quarter, or a new hire quietly drags the business somewhere else.
If you've never put your three-year picture on paper, that's the first session worth having. Have it, and you become the owner who can describe your next three years in detail and make this quarter's decisions match.
Source: Small Business Expo Research Desk, 2026 survey of US small business owners, "Long-Term Planning Is Getting Harder For SMBs"