Solopreneurs Should Ditch Annual Plans for 90-Day Cycles

One former tech executive says solo business owners should stop planning in years and start planning in quarters — because a single client's decision can make January's goals obsolete by March.

The author, who served on the executive team at a tech company before going solo, describes how corporate planning worked there: annual goals set every January, with monthly and quarterly comparisons against what had been planned. Running a solo business, the author writes, is "very different." The reason is the sheer number of variables. A single client's decision can drastically alter the course of the business, and so can a change in the market.

"I stopped planning in years and started planning in quarters," the author writes.

Goals can be annual. Roadmaps need flexibility

A large company can adjust mid-year when revenue swings. It might trim a department's budget or move people to a different project. The big goals for the year stay mostly intact, and the rest of the business keeps running.

Solopreneurs don't have that luxury — at least, not in the same way.

Goals still have their place, according to the author: it's good to work toward something. But plans should take the form of a roadmap. A solo operator might have a specific revenue goal, and the roadmap tells them, step by step, how to get there.

The roadmap is the part that's impossible to plan for a full year. Instead, the author argues, a solo business should work in shorter increments.

What a 90-day cycle actually contains

A 90-day roadmap planning cycle is simple enough to start immediately. The author breaks it into four components:

• A theme. The specific steps being worked on toward one of the larger goals.
• Milestones every week or two. If the roadmap starts slipping, the operator notices right away.
• Time elapsed tracked next to progress. If 45 days into the 90-day cycle have passed, is the operator 50% done with the action items on the roadmap?
• A specific outcome. What should be accomplished by the end of the 90 days?

At the start of each planning cycle, the author recommends asking how the roadmap for the next 90 days rolls up to the larger goals for the year. It also pays to think about what the next building block will be in the following 90 days — though planning for that next cycle doesn't need to start yet.

The review at the end of the cycle

Without a scheduled review, 90-day planning doesn't help build over the course of the year, the author writes. Reviewing and reflecting on results is what sets up the next cycle.

The practical advice: put the review on the calendar as a recurring event, and don't let it get scheduled over or moved. The author blocks roughly half a day, a few days after the end of each quarter.

During the review, the operator compares what they said they would get done with what they actually got done, then looks at what worked and what didn't. The author follows a template each time, writing down observations. Claude, the AI assistant, gathers information in the background so the author doesn't spend time compiling data.

Ninety days is long enough to gain traction and assess, the author writes. At that point, the questions become: is something new working, does it need more time, or does the course need to change?

Planning for a business that keeps changing

A company with hundreds of employees has resources a solo operator doesn't have. But it also has hundreds of people working from the same roadmap, which makes it hard to change direction when something drastic comes up. In a one-person business, that type of change can happen whenever it's necessary.

The 90-day roadmap is the means to reach annual goals — and if a cycle or two reveals that an annual goal is out of reach, the author says it's okay to make an adjustment.

The system ends at the monitor. The author keeps big-picture goals on a sticky note on the screen. The details, projects, and plans live within the 90-day roadmap. That, the author writes, is where the work happens.