Making an annual plan

Critical for freelancers, useful for everyone else

I’ve been running my own business for a long time. Even in the years when I had full- or part-time employment, I kept my writing business going on the side. Early on, I decided that if I had my own business, I needed to have a business plan. And so, every year, I write a new annual plan. It’s usually short and mostly a list of things I want to do because, well, I love lists. The process changes a lot, and the biggest change I made in recent years was to think of it as a life plan rather than a business plan.

Here’s my current process. First, I like to read a book about writing or business to inspire me. This year, it was Our Endless and Proper Work, by Ron Hogan (Amazon affiliate link), about the importance of having a regular writing practice regardless of whether anything gets published.

Then, I think about a few big goals—Objectives and Key Results, or OKRs, in current business-speak—to guide everything. I have four for 2024: growing my business, maintaining my health, improving my sailing skills, and rebuilding my savings after a year that included a wedding, a funeral, lots of travel, and a new central air conditioner. Then, I list specific things that I will do each quarter toward each OKR, such as giving up sweets for Lent, sending queries to three new-to-me editors, or going to the library instead of buying books. Every quarter, I revise the list as the year plays out.

Finally, I go through my massive to-do list, kept on Dynalist, and remove old items, re-arrange things so that they make more sense, and add things that I want to do in the new year.

I go through this even though I know that the plan will be obsolete as it’s typed up. Last year, I had a 9 to 5 job, and my plan reflected that. By February, the firm had layoffs, and I was among those getting the axe. The OKRs related to that job immediately expired.

The overall plan still had value, though. I changed my work-related OKRs, one of which was to start this newsletter. Much of my plan had nothing to do with work, so that part didn’t change.

The value of an annual plan has nothing to do with the plan itself. Rather, it’s the time committed to pulling it together. It gives me a place to start and a way to respond to everything that happens.

Man plans, and God laughs. Maybe the world would be better if God laughed more.

Do you make a plan? Tell us about it in the comments.