Make the decisions now that will protect what matters in the season ahead.
Recently, I took two sick days.
To be clear, these weren’t “I’ll work from the couch instead of my desk” sick days. Not “I’ll just answer the important emails” sick days. And not that entrepreneurial classic: “I’ll rest as soon as I finish these three things” sick days.
Actual sick days.
I had severe sinus pain and congestion, a headache, and a brain that seemed to be processing information through dial-up internet.
Nothing alarming. Nothing that sent me to the doctor. Just miserable enough that trying to do meaningful work had become an uphill battle I clearly wasn’t winning.
So I did something that can be surprisingly difficult when you work for yourself:
I gave myself permission to be sick.
I took some over-the-counter medicine, retreated to a darkened room, and spent two days resting and watching mindless reality television.
Employee Michele was fully on board with this plan.
CEO Michele apparently needed a little convincing.
But somewhere in those two days — possibly between episodes of other people making highly questionable life choices for my entertainment — I realized something:
Why did I need permission in the first place?
If I worked for a company with a sick-leave policy, I wouldn’t wake up feeling awful and convene an emergency board meeting to determine whether employees were allowed to be sick.
The policy would already exist.
I might still need to decide whether I was sick enough to use it. But I wouldn’t have to renegotiate the company’s entire position on illness while my head hurt.
The leadership decision would already have been made.
And that got me thinking about how many things we WFH entrepreneurs repeatedly give ourselves permission to do that might work better as policies.
Key Takeaway
HR policies aren’t just for companies with employees. Solo entrepreneurs can use simple policies to make recurring decisions about working hours, time off, availability, well-being, professional development, and personal priorities. Instead of repeatedly asking yourself for permission, decide in advance how YOU, Inc. will operate.
🌿 YOU, Inc. Series: Permission Is Helpful. Policy Is Stronger.
Back in August, when we first opened the HR Department of YOU, Inc., I asked you to think about how you protect, develop, and retain your company’s greatest asset: you.
And your Action Step was intentionally small.
Write one HR policy.
Maybe yours involved lunch, vacation, email, movement, professional development, or something entirely different.
That first policy was an experiment in being a responsible employer of yourself. But now this month, we’re doing something different. September is about choosing your next season.
Last week, I asked you to think about where you want your business, your life, and your leadership to go from here. You chose a direction for what comes next.
Now we need to make it easier to keep choosing it. Because vision without anything supporting it can remain just a lovely idea on a piece of paper.
You can say your health matters.
Your family matters.
Your relationships matter.
Learning matters.
Rest matters.
Having a life outside your business matters.
But then Tuesday happens …
A client needs something. Your inbox fills up. An opportunity appears. A deadline shifts. You get sick.
And suddenly the things you said mattered are back at the negotiating table.
That’s where policy becomes powerful.
Vision tells you what matters.
Permission lets you honor it occasionally.
Policy helps you honor it consistently.
The CEO Doesn’t Need Another Permission Slip
Let me be clear: permission isn’t a bad thing. Giving myself permission to stop working and rest when I was sick was exactly what I needed to do.
In fact, sometimes permission is how we begin changing an old pattern.
For example, permission to take the afternoon off. Permission to say no. To close the laptop. To take the trip. To spend money on something that develops us. Permission to take care of ourselves before everything else is finished.
But permission has a weakness.
You have to keep granting it.
And every new situation becomes another little internal negotiation.
Can I really stop now?
Is it okay to take Friday off?
Should I answer this email tonight?
Can I justify spending money on that conference?
Am I really sick enough to rest?
Is going for a walk irresponsible when there’s work waiting?
Can I take an actual vacation when clients might need me?
And when you’re both the person requesting permission and the person granting it, the business has a sneaky advantage.
Business needs are immediate. Visible. Often attached to money or deadlines.
The needs of YOU, Inc., on the other hand, are easier to postpone.
So perhaps it’s time to stop relying on permission and start putting policies in place.
The CEO of YOU, Inc. doesn’t need another permission slip. She needs a policy.
A Policy Is a Decision You Don’t Have to Keep Making
Think about why companies create policies in the first place …
It’s not because every employee needs a giant binder of rules telling her how to exist.
It’s because policies make recurring situations easier to navigate.

Someone has already considered the issue, decided what the organization believes, and established how it will generally respond. That means every situation doesn’t have to begin at zero.
A solo business can benefit from the same thing.
An HR policy for a solo entrepreneur is simply a leadership decision made in advance about how your business will operate in a way that supports both the work and the person doing it.
That’s it.
We’re not inviting Corporate America into your home office. There will be no 84-page PDF. No mandatory webinar. No signature confirming that you understand the refrigerator-cleanout schedule.
We’re simply making some decisions before the emotionally loaded moment arrives.
For example, instead of deciding at 7:13 p.m. whether you should answer another email, you’ve already decided when YOU, Inc. closes up shop for the day.
Instead of deciding during vacation whether you should “just check in,” you’ve already established what vacation means.
Instead of debating whether movement is worth taking time away from your desk, you’ve already decided that physical well-being is something YOU, Inc. supports.
And instead of waiting until your calendar is completely full to decide whether professional development deserves time, you’ve already made it part of the company’s investment in its CEO.
The question changes from:
Am I allowed to do this?
to:
What’s our policy?
And that’s a very different conversation. Even, perhaps, an easier one.
Policy Doesn’t Mean Giving Up Flexibility
Now, if you’ve spent years building a business because you wanted more freedom and flexibility, the word policy may make you twitch a little.
I understand.
You did not leave traditional employment so you could recreate a corporate policy manual in your spare bedroom.
But a policy doesn’t have to eliminate flexibility.
In fact, a good YOU, Inc. policy can protect the flexibility you built your business to provide.
Your policy doesn’t have to say, “Lunch shall occur from precisely 12:00 to 1:00 p.m.” It might say, “At YOU, Inc., we step away from work for a real meal during the workday.”
It doesn’t have to say, “Exercise shall occur Mondays, Wednesdays, and Fridays at 7:00 a.m.” It could say, “At YOU, Inc., movement gets legitimate space on the workweek calendar.”
And a working-hours policy doesn’t mean you can never choose to work late.
Maybe you’re in the middle of a launch. Maybe inspiration strikes. Or maybe you took Tuesday afternoon off and genuinely want to work for a few extra hours Thursday evening.
The CEO still has discretion.
Policy provides a default, not a prison.
That’s particularly important for WFH entrepreneurs, because flexibility may be one of the reasons we built these businesses in the first place.
The goal isn’t to replace freedom with rules. It’s to stop letting the absence of rules quietly take away the freedom.
Where Are You Still Renegotiating With Yourself?
So how do you know which HR policies YOU, Inc. needs?
Don’t start by searching for somebody else’s employee handbook. Start by noticing your own recurring negotiations.
Ask yourself:
What do I repeatedly have to give myself permission to do?
Then:
What do I regularly feel guilty about doing even though I know it supports the life and business I want?
And perhaps most revealing:
Where does the business keep winning a negotiation I wish YOU, Inc. would win occasionally?
Your answers are clues.
Maybe you’re constantly renegotiating when the workday ends. Or maybe clients have slowly gained more access to your evenings than you intended.
Perhaps vacation is technically available but never completely work-free. Maybe you keep postponing medical appointments, movement, or mental-health breaks until there’s a more convenient time.
Maybe you’d love to invest in coaching, a class, a conference, better technology, or a more comfortable workspace — but you keep treating anything spent on you differently from anything spent directly on the business.
Or perhaps the people and activities you built your business to have more time for are consistently receiving whatever scraps remain after work takes its share.
Those aren’t necessarily signs that you’re doing entrepreneurship wrong.
They may simply be places where YOU, Inc. hasn’t established a policy yet.
Five Places to Look for Your HR Policies
You don’t need my five policies. Your business and your life aren’t identical to mine.
But if you’re wondering where your recurring negotiations might be hiding, I’d look in these five places:
1. Time
When does work generally begin and end?
What does a weekend mean at YOU, Inc.?
What counts as a real day off?
What happens when you’re sick?
How does vacation work?
You don’t need to account for every possible circumstance. You’re simply establishing your normal working conditions.
2. Access
Who gets access to you — and when?
How quickly do you expect yourself to respond to email?
Do clients have access to evenings or weekends simply because you happen to see their messages?
Does your phone get to interrupt anything it wants?
Working from home can make the boundary between reachable and available especially fuzzy. A policy can clarify it.
3. Well-Being
What does YOU, Inc. protect because a human body and brain are doing the work? That might include:
- Movement
- Mental health
- Medical appointments
- Rest
- Meals
- Recovery
Maybe even two days in a dark room watching reality television when your sinuses stage a hostile takeover.
These things don’t have to be justified by how much more productive they make you afterward.
Your well-being matters because you matter.
That’s self-respect, not a productivity hack.
4. Investment
What benefits does YOU, Inc. provide? This one can be fun.
Traditional companies understand that compensation isn’t the only investment they make in people. So what’s in your benefits package?
Professional development?
Books?
Coaching?
Conferences?
A good office chair?
Technology that makes your work easier?
Time for creative experimentation?
Maybe there should even be a line item for the occasional CEO lunch somewhere that doesn’t involve leftovers and a laptop.
What would change if investing in yourself became company policy instead of something you consider only when there’s money, time, and energy left over?
5. Life
Finally, what parts of your life are not routinely available for the business to consume? Some things to consider are:
- Relationships
- Family commitments
- Hobbies
- Travel
- Community
- Quiet
- Joy
- Whatever matters to you
This may be the most important category of all because your business is something you run. YOU, Inc. is something you lead.
The business exists inside your life. Not the other way around.
Connect the Policy to the Vision
Here’s where I want to bring us back to last week’s conversation.
Don’t create policies merely because they sound like things a responsible entrepreneur is supposed to have. Connect them to the upcoming season you’ve chosen for yourself.

If you said you want to feel healthier and more energetic by the end of this season, perhaps a movement or working-hours policy supports that vision.
Or if you want deeper connection with your family, perhaps there’s a policy about when the office closes.
If you want to become a more confident leader, perhaps professional development becomes part of the benefits package.
If you want more spaciousness in your life, perhaps every empty square on the calendar stops being automatically available to the business.
Try this sentence:
At YOU, Inc., we __________ because __________ matters to the season we’re intentionally building.
That second blank matters. It turns policy into something more than a rule. It connects the everyday decision to the bigger vision.
Here are some examples:
- At YOU, Inc., we don’t answer routine business email after 6 p.m. because being present for our relationships matters.
- At YOU, Inc., we budget for professional development because continued growth matters.
- At YOU, Inc., vacation means work-free time because having a life outside the business matters.
- At YOU, Inc., illness gets recovery time because health matters more than squeezing out a few sluggish hours of mediocre work.
The policy isn’t there to control you.
The policy is there to protect something you’ve already decided matters.
And that’s the difference.
🌱 Action Step This Week: Put Five HR Policies in Place
This week, I want you to take the one-policy experiment we began in August and build on it.
Start by identifying five recurring negotiations in your work or life.
Places where you keep asking:
Can I?
Should I?
Am I allowed?
Can I justify it?
Maybe just this once?
Then decide what CEO You wants the answer to be before the next negotiation happens.
And then, using that decision, write five simple HR policies for YOU, Inc.
You can use this formula:
At YOU, Inc., we _________ because __________.
Don’t try to anticipate every exception. Don’t write legal language. Don’t create a 47-page employee handbook — we’ll have plenty more to say about that next week. 😉
Just make five leadership decisions.
Then put them somewhere you’ll see them.
Because the goal isn’t merely to write five policies.
The goal is to put HR policies in place so that you can finally stop renegotiating with yourself.
Try them. Honor them. Notice where they make decisions easier. Adjust them when reality teaches you something.
A good policy doesn’t remove your judgment as CEO.
It gives your judgment somewhere to begin.
🌿 Your Next Leadership Step
If you already completed September’s Tenacious WFH CEO Vision Brief, pull it back out this week. (It’s one of the monthly Mini Power Tools available with a premium subscription to The Tenacious WFH Entrepreneur newsletter. You can upgrade your experience by enrolling here for just $7.)
Look especially at what you said you wanted for your business, your life, and yourself as a leader — and at what you identified under My CEO Investment.
What did you say you wanted to learn or strengthen?
What did you want to protect or prioritize?
Where did you need support?
Now ask:
Would an HR policy help turn any of those intentions into the way YOU, Inc. actually operates?
That’s how vision becomes more than something we write during a quiet planning session.
We build decisions around it. We protect it. We practice it on ordinary Tuesdays.
And yes, sometimes we discover its value while lying in a dark room watching mindless television and realizing that the world — and the business — kept turning without us for two days.
I was glad I gave myself permission to rest.
But the next time Employee Michele wakes up clearly unable to do good work, I hope CEO Michele has less negotiating to do.
Because some things shouldn’t require a new permission slip every time. Some things deserve to become company policy.
And you’re the CEO.
You get to put it in place.
FAQs
HR policies for a solo entrepreneur are decisions made in advance about how the business will operate in ways that support both the work and the person doing it. They can cover working hours, time off, availability, well-being, professional development, and other recurring situations that would otherwise require repeated decisions.
Useful HR policy areas for a WFH entrepreneur include time, access, well-being, investment, and life outside the business. The best policies are the ones that address situations you find yourself repeatedly renegotiating.
Start by noticing where you repeatedly ask yourself for permission, feel guilty about protecting something important, or keep making the same decision over and over. Then decide in advance how you want YOU, Inc. to handle that situation and turn the decision into a simple policy you can realistically honor.
HR policies create clear defaults for recurring situations such as when the workday ends, how quickly you respond to messages, what vacation means, and which personal commitments stay protected. That makes it easier to maintain boundaries without having to renegotiate them every time work competes for your attention.
Permission can be helpful, but it is usually situational and has to be granted again and again. A policy turns a recurring permission request into a leadership decision made in advance, making it easier to consistently protect something you’ve already decided matters.
Because the business operates inside your larger life. Policies that protect health, relationships, learning, rest, and other personal priorities help ensure the business supports the life you want instead of gradually consuming it.
Look for the decisions you keep renegotiating with yourself. If you repeatedly wonder whether you’re allowed to stop working, take time off, invest in yourself, protect a personal commitment, or care for your well-being, that recurring negotiation may be a sign that YOU, Inc. needs a policy.