How to Plan Your Last 90 Days Before October Hits

It's the middle of August, and if you own a service business, there's a good chance you haven't looked at the goals you wrote down in January since sometime around April. That's not a character flaw. That's what happens when the year takes over. But here's the math that should get your attention: the last quarter starts October 1, which is roughly six weeks away. Which means whatever you do with the final 90 days of this year is being decided right now, while you're deep in the work and not thinking about it at all.

The good news is that six weeks is plenty of time to fix this. It's just not plenty of time to keep putting it off.

October is your execution window, not your planning window

A lot of owners tell themselves they'll sort out the fourth quarter once things slow down. In most service businesses, things do not slow down in October. October is when the wheels start coming off in a whole new way. Heating season starts. Holiday schedules start. Every customer wants their thing handled before Thanksgiving.

October is when you execute. If you walk into it without a plan, the plan gets made for you by whoever calls first. And then somewhere around the second week of December you look up and think, well, I'll get to that next year.

This is a visibility problem, not a discipline problem

Before going further, I want to be sure to nail down that this drift isn't a discipline issue. You're one of the hardest working people you know. You don't need somebody telling you to try harder. It isn't a goal setting problem either. You set good goals in January.

What you have is a visibility problem. You cannot see your business clearly from inside your business, and that's not a personal failing. That's just how proximity works. Your desk, your truck, your phone, your inbox, your shop, that entire environment has one job and it does it beautifully. It hands you the next urgent thing, every single day. What it will never do is hand you perspective. It isn't built for that.

So the only time you think about direction is in the fifteen minutes between one fire and the next, which isn't thinking...that's triage.

Here's what the drift actually costs: a whole year of genuinely excellent work that wasn't aimed at anything in particular. You worked as hard as anybody in your town, probably harder. You just can't tell anyone what it built.

You can't read the route while you're standing on it

Climbers don't plan a route while they're on it. They read it from a distance, where they can see where the ridge goes, where the ice is, and where that promising looking line dead ends into something unclimbable. They also ask people who have been up there before. Once you're on the mountain trail, you can see the next few feet and that's it.

Both views are true. Only one of them helps you choose where to go.

Right now you're standing on the mountain, inside the trail, and all you can see are the trees. The trees are every single thing pulling at your attention today. So before the last 90 days start, go get the other view.

Three ways to get distance, and all three count

The first move is physical. You have to actually leave your normal environment. There are three versions of this, and there's no snobbery about which one you pick.

Your own industry conference

This is the obvious one. A room full of people in your trade, talking about your trade. You benchmark. You find out what other shops charge, how they handle parts, what software they run, how they hire and onboard. You meet vendors built for your industry. You see your own trade from a higher altitude than you can see it from your own shop, and you get to mentor somebody a little behind you in the journey.

If the budget allows, bring your team. When an owner goes alone and comes home with a notebook full of ideas, what the team hears is that more work is coming. They didn't see it. They didn't feel the room. They're just receiving a list. When the team goes, they come home with ownership instead of assignments. Somebody hears a session about front office workflow and brings back an idea that's theirs, and they'll make it work because they found it. Somebody sits at dinner with technicians from four other states and learns they aren't crazy for wanting a certain tool. You can't buy that any other way.

A conference in an adjacent industry

This is the one almost nobody does, and it might be the most valuable.

Look at the shape of a business instead of the service it sells. Power washing, window cleaning, and Christmas light installation have nothing to do with appliance repair on the surface. But they all run trucks. They all run routes. They all have technicians, scheduling, seasons that carry the year, and customers who need work done at their house by somebody they trust. Same machine, different job.

In your own industry, everybody has the same blind spots you do. You all inherited the same assumptions about how pricing works, how scheduling works, what a technician is supposed to do all day. If everyone in the room learned the trade the same way, everyone in the room is stuck in the same places. In an adjacent trade, somebody already solved a problem you have using a model you've never seen, because they came at it from a completely different direction.

And there's the honest part nobody says out loud. At your own conference, the person with the best system in the room might be your competitor. They'll be friendly...and a little bit vague. In an adjacent industry, that same person will draw the whole thing on a napkin for you, because neither of you will ever take a dollar from the other.

Two questions find yours:

• Who serves the same customer I do but does a different job for them?
• Who has the same operational shape as me, the trucks and routes and scheduling and seasonality, in a different trade?

If you're a plumber, look at what pest control does with recurring service agreements. If you do lawn care, look at how a pool service company handles route density and seasonality. If you do bookkeeping, sit in a room full of insurance agents and watch how they handle retention. You're going for the model, not the content.

The retreat you build yourself

This one costs almost nothing, and it's the one most owners will actually do.

You do not need a conference badge to get the view. You need to not be at your desk. An hour away and one hotel night will do it. One year we did ours in Asheville. Another year we did it in Washington, North Carolina, where we wandered into a coworking space somebody else owned and walked out with an idea that changed how we built our smallest offices. We swapped cubicles for real walls with locking doors, which meant our members could list their business on Google and get verified. Inexpensive to build, and it mattered to every member who wanted it. That idea was never going to show up if we stayed at our own desks.

Five rules keep it from turning into an expensive weekend of nothing.

1. Leave the house, because your kitchen table has laundry on it and a dog that needs out and a kid who needs a ride.
2. Put a start time and a stop time on it, or it turns into scrolling.
3. Bring exactly three things: what you wrote down in January, your numbers, and a blank page, meaning an open mind.
4. Phone face down.
5. And don't leave the room until the decisions are written down, not the ideas. There's an enormous difference between those two, and the difference is usually about four months long.

Look back before you look forward

People often sit down to plan and immediately start writing new goals, because new goals feel like momentum. It's also the exact reason the same goal keeps showing up on the list three years running.

Pull out your January list and ask three questions, answering them like you're talking to a friend instead of defending yourself in court. What did I say I was going to do? What actually happened? And why?

That third one carries all the value. Not to beat yourself up, but to find the pattern. If four things didn't happen and all four depended on hiring somebody, you don't have four problems. You have one problem, and it has a name.

Then sort the list into three piles:

• Done (which you should stop and celebrate out loud, because otherwise you'll skip right past everything you accomplished).
• Still worth finishing.
• Not this year.

That third pile is where people get squirmy. Moving something there isn't quitting. It's you in August, with your eyes open, deciding that the website redesign isn't what's going to change this year, so it goes on next year's list and you stop carrying it around. Every item you release gives you back capacity. Not time on the calendar, capacity in your head. That's usually what you're actually short on.

One more thing while you're looking backward. Write down what you accomplished this year that was never on the list at all. There's almost always something big there, and it tells you where your real energy went. Sometimes it tells you your business decided something about its direction that you haven't consciously agreed to yet.

Pick the needle mover

Now you look forward. Most people leave a planning session with twelve things. Twelve things in 90 days, in the fourth quarter, while doing all your normal work, is not a plan. That's a wish with a big spreadsheet.

Pick one. Maybe two. Here's the test: if this one thing happened and nothing else on the list did, would this have been a winning year? If yes, that's a needle mover. If no, it's a task. Tasks are fine. Tasks aren't what these six weeks are for.

Then write it as a date and a number instead of a direction. Grow revenue isn't a goal; that's a hope. Add eight recurring maintenance agreements by December 15 is a goal, and you can work backward from it starting tomorrow. Get better at hiring isn't a goal. Have one qualified technician through a first interview by October 31 is.

Leave something for January

Some of what you do in the last 90 days isn't for this year at all. It's for the version of you who shows up on January 2. That's next year's pricing decided in November instead of panicked in February. That's clean books before tax season instead of during it. That's starting a hiring pipeline now so that when somebody leaves in March you aren't starting from zero.

Climbers stash supplies on the way up so they have what they need on the way back down. Do the same thing as a gift to the version of your future self in January.

The view is the work

Leaving feels irresponsible. When everything runs through you, taking two days to go sit somewhere and think feels like the least responsible thing you could do.

But nobody pays you for the hour you spend across the valley reading the route. There's no invoice for it, and it's still the most valuable hour of your quarter, because it decides whether the next five hundred hours are pointed at anything.

There's a leadership piece here that doesn't get said enough. Your team can feel whether you have a plan. Drift at the top always turns into anxiety underneath. When the owner is reacting, everybody's reacting. So when you come back and say here are the two things we're going after, and here's what we're officially not worrying about anymore, that isn't a management technique. That's a gift to people who've been carrying weight without knowing it.

And personally, I'd add this: we were built for rhythm. Work and rest, effort and stepping back. That pattern shows up in Scripture from the very first pages, and it was never framed as a reward you earn once the work is finished. It's part of how the work is supposed to go. There was a day of rest in creation, and before creation I imagine our Creator had a plan. Every time I honor that rhythm instead of powering through it, I come back with more than I left with. Not just energy. Clarity. Things tangled for months come apart in about forty minutes once I'm somewhere else. There's real joy in trusting that your business can breathe without you for two days, and in remembering you were never asked to hold the whole thing up by yourself.

What to do next

If this landed, the smallest useful step is downloading the free Get the View planner at outcomeacademy.com/episode35 and putting one date on your calendar before October 1. That's it. One date, one location.

And if you're not sure what your last 90 days should even be about, start there instead. Take the free Find Your Camp quiz at outcomeacademy.com/findmycamp. The needle mover for a business at Camp 1 is not the needle mover for a business at Camp 3, and chasing the wrong one is how a good quarter gets wasted. Once you know your altitude, the Eight Thousander Expedition™ is where owners climb the next stretch with people instead of alone.

Resources mentioned

• Get the View planner (outcomeacademy.com/episode35) — the free two-page companion to this article. Page one gets your trip chosen and booked, page two walks the planning session itself.
• Find Your Camp quiz (outcomeacademy.com/findmycamp) — seven questions, about two minutes, and it names the three specific hazards working against your business at your current stage.