I have a confession that probably won’t surprise anyone who grew up in the era of Trapper Keepers, Lisa Frank folders, and freshly sharpened No. 2 pencils:
I still love back-to-school supplies.
I don’t need a locker combination anymore. Nobody is handing me a class schedule. And there is absolutely no reason I need a new notebook simply because the calendar says September.
And yet …
Put me anywhere near a display of fresh notebooks, smooth-writing pens, colorful folders, and brand-new planners this time of year, and apparently my inner 12-year-old still has purchasing authority.
There was always something about those supplies, wasn’t there?
A fresh notebook held possibility. (It still does, if the truth be told!)
Nothing had been crossed out yet. No assignments were late. There were no coffee stains on the cover or mysterious notes scribbled in the margin that made perfect sense when you wrote them but became completely indecipherable three weeks later.
Everything felt possible.
Maybe this was the year you’d keep your binder organized.
Maybe this was the year you wouldn’t wait until Sunday night to start the project due Monday morning.
Or just maybe, this was the year you’d finally become one of those people whose notes looked effortlessly neat and color-coded.
Some of us are still waiting on that last one.
I’ve realized lately that perhaps our September fresh-start feeling was never really about the school supplies.
It was about possibility.
September marked the beginning of a new season, and with it came an unspoken question:
Who do I want to be in this one?
For work-from-home entrepreneurs, I think September still gives us an opportunity to ask that question.
In fact, I’d argue that September may be a better “new year” for your business than January.
Not because you need another round of resolutions.
Because you have something in September that you didn’t have in January: eight months of information about the year you’re actually living.
🌿 The YOU, Inc. Series
This article is part of our ongoing YOU, Inc. conversation about running your business like a CEO while remembering that the most important company you lead is yourself.
Your business has clients, projects, revenue, goals, and responsibilities.
YOU, Inc. has energy, relationships, health, creativity, confidence, boundaries, learning, joy, and a future.
The business is something you run.
YOU, Inc. is something you lead.
And as a new season begins, there’s one question worth bringing with you:
What would the CEO of YOU, Inc. choose?
✨ In This Article
If you tend to reach September already looking toward the holidays and wondering where the year went, you don’t need to cram more goals into the remaining months. You’ll discover how to use this natural seasonal transition to choose your direction, identify what matters now, and enter fall with greater clarity and confidence — so the season doesn’t get decided for you.
September Gives Us Something January Can’t
January asks us to imagine.
September lets us know.
In January, we make plans based largely on what we think the coming year will look like.
But by September?
We have receipts.
We know which clients require more energy than expected. And we know which projects gained momentum and which ideas never quite made it off the runway.
We know whether that schedule we created in January survived contact with actual life. And we know more about our families’ needs, our own capacity, our businesses, and ourselves.
And now, because we know more, we can make different decisions.
That’s why I don’t think September needs to be another “start over” moment.
You are not standing at the beginning of the year with an empty notebook. You are standing eight months into it with experience.
That matters.
You’ve learned things. Changed things. You’ve handled things you couldn’t have anticipated in January.
You’ve probably also discovered that some things you thought would matter this year … don’t matter nearly as much anymore.
That isn’t evidence that you wandered off course.
It’s information a good CEO can use.
September isn’t asking you to erase everything and begin again. It’s inviting you to choose forward from where you actually are.
A New Season Does Not Require a New You
Fresh-start culture loves reinvention.
New year. New habits. New routine. New goals. New you!
But I don’t think most women I know need to become entirely new people every few months.
Frankly, that sounds exhausting.
You don’t need to become CEO Barbie by October, armed with a color-coded strategic plan and a suddenly inexplicable enthusiasm for quarterly spreadsheets.
You just need to lead the woman who is already here.
The one who has been building this business. Who has figured things out as she went.
The one who has juggled client calls with family responsibilities, walked the dogs between deadlines, changed plans when life changed, learned new technology she never asked to learn, and kept coming back to her work.
She doesn’t need to be replaced.
She needs direction.
There’s a big difference.
Starting over says, “What should I change about myself?”
Choosing direction asks, “Given what I know now, where do I want to go next?”
That second question is much more interesting to me.
And much more useful.
Before You Choose Goals, Choose a Direction
New seasons can be where we entrepreneurs get ourselves into trouble. We feel the fresh-start energy and immediately make a list …
Launch this.
Finish that.
Increase revenue.
Post more consistently.
Clean up the website.
Start the podcast.
Revive the abandoned project.
Organize the office.
And perhaps alphabetize the spice cabinet while we’re at it.
Suddenly our “fresh start” feels suspiciously like a heavier backpack.
But what if you didn’t begin with goals?
What if you began with direction?
That’s one reason I chose compass imagery for this month’s Mini Power Tool, the Tenacious WFH CEO Vision Brief (available now for Insider and VIP subscribers).
A compass doesn’t tell you exactly what you’ll encounter along the way. It doesn’t promise smooth terrain or prevent the weather from changing. It doesn’t yell at you because you had to take a detour.
A compass simply keeps you pointed in the right direction ─ the direction you chose.
That is the kind of planning I find most useful for real life.
So before deciding what you want to accomplish this fall, ask yourself:
What do I want my business to look like at the end of this season?
Then ask:
What do I want my life to feel like?
And finally:
Who do I want to become as I lead both?
Notice that those are not all business questions.
That’s intentional.
Because a business goal that moves Company #1 forward while making YOU, Inc. miserable isn’t automatically a good goal.
Your business and your life aren’t operating in separate buildings. Especially when you work from home. They share the same hallways. Sometimes they share the same kitchen table.
So the direction you choose must accommodate both.
Fall Has a Way of Filling Itself
There’s another reason September is such a useful leadership moment …
We can see Q4 from here.
October will arrive. Then November. Then December will somehow contain 73 obligations despite still having only 31 days.
Client deadlines may tighten.
Holiday plans will appear.
Family calendars will fill.
Business opportunities will arrive.
There will be things you genuinely want to do and things you somehow find yourself doing because you said yes before checking whether you actually wanted to.
That’s why choosing your direction before the season fills up matters.
When you know what matters, you have something against which to evaluate what comes next.
Instead of asking only, “Can I fit this in?
You can ask:
Does this belong in the season I’m trying to create?
That’s a very different question.
Capacity asks whether there is an empty square on the calendar.
Leadership asks whether the thing deserves the square.
Pick Three Things That Deserve Your Leadership
If you want a practical way to do this without the Mini Power Tool, start by choosing three priorities for the season ahead.
Not three business goals. Three leadership priorities in three different areas.
- Choose one thing that matters for your business. Maybe you want to deepen relationships with existing clients rather than constantly pursuing new ones.
- Choose one thing that matters for YOU, Inc. Maybe you want to protect your evenings, return to regular movement, make space for a hobby, or simply stop treating lunch as an optional workplace benefit.
- Then choose one thing that matters for your leadership. Maybe you want to become more decisive. More visible. More willing to ask for help. Better at trusting your own judgment.
Limit yourself to just three priorities. Not 17. Because if everything is a priority, nothing really is.
If everything is a priority, nothing really is.
Once you know your three, they become part of your compass.
Then, when something new arrives, you can ask:
Does this support what I’ve already decided matters?
Sometimes the answer will be yes. Sometimes it will be no. And sometimes it will be, “That’s a good idea — just not for this season.”
That last answer deserves far more respect than we usually give it.
Don’t Forget to Ask What the CEO Needs
There’s one more question I want you to consider before you enthusiastically charge into fall:
What do you need in order to lead this season well?
Not what does the business need. What do you need?
Maybe there’s something you want to learn. Maybe you need more support.
Perhaps you need to protect your swimming mornings, dog walks, Friday afternoons, date nights, or weekends. Maybe you need a boundary around when clients can reach you.
Maybe the CEO of YOU, Inc. needs a better benefits package.
We tend to think of those things as separate from strategic planning.
I don’t.
If the person responsible for leading the business is depleted, distracted, resentful, or running on fumes, that’s not merely a personal issue.
It’s a leadership issue.
Investing in yourself is part of the recovery plan. And it also can be how you avoid getting to where you need the recovery plan in the future.
Your Fresh Notebook Already Has Writing in It
The thing I appreciate most about a September fresh start is that it isn’t actually a blank page. And I don’t want it to be.
You’re bringing eight months of scribbles into this year’s notebook.
Some pages are beautiful. Others are messy. Some contain things you’re proud of. And some have arrows pointing everywhere because apparently Past You thought Future You would understand what they meant.
There may be a few pages you’d happily tear out.
But all of it belongs to the story of the year you’ve been living.
You don’t need to throw that notebook away.
Just turn the page. Bring forward what you’ve learned.
And before you begin writing the next chapter, decide what you want it to be about.
That is the opportunity September gives us.
Not a new year.
Not a new you.
A new season — and the chance to choose how you’ll lead it.
🌱 Action Step This Week
Before you make another fall to-do list, give yourself 10 quiet minutes to reflect.
At the top of a blank page, write:
By the end of this season, I want …
And then write down what you want. Don’t overthink it. Keep writing until you’ve captured what you want for your business, your life, or yourself as a leader.
Then ask one more question:
Are my current choices taking me in that direction?
If yes, wonderful. Keep going.
If not, don’t turn the answer into criticism. Turn it into information.
Choose one small adjustment you can make this week that points you toward the season you actually want.
You don’t need the entire route mapped out.
You just need to know which way you’re heading so your compass can lead you there.
🌿 Your Next Leadership Step
If you’d like more structure for this process, September’s Mini Power Tool is The Tenacious WFH CEO Vision Brief: Strategic Direction for YOU, Inc. in the Season Ahead.
It walks you through your CEO North Star, Leadership Compass, Next-Season Vision, CEO Investment, Big 3 Priorities, decision filter, and CEO Declarations — giving you a practical place to work out your direction on paper before the season gets busy.
The Vision Brief is available to Tenacious WFH Insiders and VIPs, along with access to the growing archive of previous Mini Power Tools. If you’re ready for practical resources that help you lead your business — and yourself — with more clarity, confidence, and sustainability, upgrading gives you the tools to put these ideas into practice.
No hustle required. Just a favorite pen, a little thinking space, and perhaps a brand-new notebook.
I won’t tell anyone you bought another one.
FAQs
Treating September as a fresh start means using the seasonal transition as a deliberate point to reassess your direction — not erasing what happened earlier in the year. You use what you’ve learned so far to decide what matters for the months ahead.
Seasonal strategic planning is a shorter, more flexible approach to setting direction based on your current business priorities, personal capacity, values, and life circumstances. Rather than planning as though conditions won’t change, you choose what matters for the next meaningful season and adjust as necessary.
Start by describing what you want your business and life to look or feel like at the end of the season. Then choose three priorities: one for your business, one for yourself, and one for your leadership growth. Use those priorities to evaluate new opportunities and commitments.
Instead of asking which tasks are urgent, ask which areas most deserve your leadership. Choose a small number of priorities that support the direction you want to travel. Other worthwhile ideas can be postponed without being abandoned.
By September, you have months of real-world information about your business, capacity, commitments, and changing circumstances. That makes September an opportunity to choose your next direction based on experience rather than January’s predictions about how the year might unfold.
For a solo or micro-business owner, the business depends heavily on its leader’s energy, health, creativity, relationships, confidence, and capacity. Planning that consistently benefits the business while depleting the person running it is difficult to sustain.
You begin making choices based on values and priorities rather than reacting to every demand. You consider what both your business and your life need, invest in your own growth and well-being, and adjust your route when circumstances change without surrendering your overall direction. That’s self-leadership. And that’s the work of the CEO of YOU, Inc. 🧭