Lifestyle Freedom Solopreneur Strategies

How I Plan My Year as a Solopreneur Who Takes Two Months Off

With Lydia Lee

What does it actually look like to plan your year as a solopreneur when your life doesn’t move in flat monthly increments?

Most planning advice assumes you have the same energy in March as you do in October, and that’s just not how being a human works.

For a long time I tried to run my business that way.

With the same goals every quarter and the same expected output every month. And I’d hit a wall around the same point every single year without understanding why.

What I eventually had to admit is that I’m not built to work the same way 365 days a year. Nobody is. Our energy isn’t flat. Our lives aren’t flat. There are months I have more capacity and months I have a lot less, and that’s just what being a human is.

Most of us run our businesses as if none of that is true. I did too, for years. So I stopped, the same year I decided to keep things small.


Build your year around the life you actually want. Not the one your calendar defaulted into.

I put together the exact set of prompts and reflections I walk myself through every December, the same ones I use for my own year-end reset. Works for a full year review or a mid-year check-in.


Quarters never quite fit me. Seasons did.

I still think in four parts of the year, the way most people plan with quarters. I just stopped expecting each one to look and feel the same.

Here’s an example of what my solopreneur business seasons look like:

How I plan my year as a solopreneur: my four business seasons, spring, summer, fall, winter

Spring is my season for creativity. New content, new ideas, the stuff I’m planting for later. It’s high energy, it’s outward facing, it’s the season for sowing.

Summer is for relationships. This is when I’m building new connections, following up with people I met months ago, guest podcasting, actually talking to the community I already have instead of putting my head down to create something new. It usually overlaps with travel for me, which works out, because I’m already out meeting people and being present in places.

Fall is for projects. I come back from a summer break with the capacity for the bigger things, launching something, running a workshop, doing the market research I do every year so I actually know what my clients need instead of assuming I still do.

And then winter is the Marie Kondo season. Cleaning up the backend, improving the client experience, planning the next year without a single client call on the calendar to distract me from it.

None of this needs to map onto your calendar the way it maps onto mine. What matters is knowing what each season is actually for, so you stop trying to do everything in every quarter, and stop feeling like you’re failing every time one quarter doesn’t look like the last one.

The December reset is what makes the rest of it possible

Of the four, winter is the one that changes everything else. I call it my Marie Kondo season, and it’s not a vacation. It’s more like opening up the hood of the business and looking at what’s actually in there. It’s the one practice I’d keep if I had to give up all the others.

What I actually do is simple. Three or four days alone, somewhere quiet, away from my usual workspace. I sit with what felt aligned this year and what didn’t. What offers I loved delivering and which ones I dreaded. What content I made that I was actually proud of. What I want to leave behind before I start fresh.

It’s not flashy work. But it’s the difference between starting January already worn out from finishing the year before, setting goals from a tired brain, and starting January rested and clear on what I’m doing. That’s not a small difference. It’s the reason Q1 is consistently my strongest quarter.

I do a smaller version of this every quarter too. A day or two somewhere that isn’t my desk, a hotel lobby, a quiet café, wherever lets me actually think. You don’t need a whole month for any of this. Even two weeks of an intentional reset before a new year will change how the next twelve feel.

None of this works without a few deliberate choices

Here’s the part most planning advice skips over. A seasonal business isn’t just a mindset shift (FYI this episode on the Small on Purpose podcast talks about how I take a month off my business a couple of times each year).

It takes some specific decisions, and I want to be honest about what they are.

The first is pricing. Higher price points, fewer clients. I can’t run a business built around seasons if I’m also trying to keep a high volume coaching practice full. The math doesn’t work.

The second is building things that keep working when I’m not. My weekly newsletter, my YouTube channel, the videos and worksheets that support my clients without me answering the same question five times a week. These do the job of staying in front of people even in the months I’ve gone quieter.

The third is knowing my minimum viable presence. When I’m traveling or in a low season, I know exactly what stays on, my newsletter, occasional LinkedIn, videos I filmed ahead of time, and what goes fully dark, new content production, discovery calls, pitching anything.

And I picked one or two channels to actually go deep on instead of spreading myself across eight. For me that’s email and YouTube. Everything else is secondary.

Your business already has seasons, whether you plan for them or not

Life is going to interrupt you. Your energy is going to shift whether or not you’ve built room for it. The only real choice is whether you design around that or keep fighting it.

You don’t need to take two months off. You don’t need to run your business the way I run mine. But you can borrow the principle.

Your year has shape. Each part of it can have a purpose. And planning it is less about hitting output targets and more about designing something you can actually live inside of.

Read Next: How to Run a Business in 25 Hours a Week.

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