How Do I Know If I Can Afford to Pay Myself?

Paying yourself confidently as a Small Business Owner, Therapist, Counselor, or service-based solopreneur.

“How do I know if I can afford to pay myself?” is one of the most stressful questions a Small Business Owner can wrestle with. It’s not just about the number in your bank account — it’s about confidence. Many owners are either afraid to take money out because they’re worried it’ll sink them later, or they’re pulling money with no real plan.

Kim is the founder of BreezePoint, a remote bookkeeping service for Small Business Owners and mental health professionals. This article is part of a series answering the most common questions about bookkeeping, cash flow, and taxes for small businesses.

BreezePoint is an online done-for-you bookkeeping service for Women Business Ownerss, Therapists, Creatives service-based solopreneurs across the U.S..

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The Concept

• Why paying yourself feels so confusing for many Small Business Owners
• The most common mistakes that make owner pay feel risky or random
• A simple framework to decide if you can afford to pay yourself
• How clean bookkeeping supports confident, consistent owner pay

Why Paying Yourself Feels So Hard

If you’ve ever had a paycheck job, you know how simple it felt: money just showed up in your bank account every two weeks. Someone else did all the math.

When you become self-employed, everything changes. You’re the owner, the employee, sales, HR, and payroll.

A lot of Small Business Owners handle pay like this:

“I look at my business account. If there’s money, I transfer some.”

Then a big bill hits, or taxes come due, and suddenly that transfer doesn’t feel so smart. That guessing game creates stress. And that stress affects:

• How you show up in your business
• Whether you invest in growth
• The sense of stability at home

Good news: you don’t need a fancy formula to fix this. You need separation, tracking, and a plan.

Common Mistakes When Paying Yourself

Most of the pain comes from a few predictable mistakes.

Mixing business and personal money.
If your personal and business funds are all in the same pot, you’ll never know what truly belongs to the business vs. what’s safe to take home. That’s not strategy — that’s chaos.

Paying yourself “whatever’s left.”
Waiting until the end of the month, paying the bills, then grabbing what’s left feels logical… until you remember that tomorrow starts a whole new month of expenses. Owner pay stays inconsistent, which keeps you on edge.

Ignoring taxes.
Many owners forget that a chunk of that income is not theirs to keep. If you’re not setting aside money as you go — often 20–25% for many self-employed folks — the tax bill can wipe you out. The IRS’s Self-Employed Individuals Tax Center is full of people who learned this the hard way.

Not tracking income and expenses in real time.
If you don’t have bookkeeping, you’re flying blind. A healthy bank balance can make you feel profitable, but:

• You’re not seeing all the small expenses that trickle out
• You’re not thinking about upcoming or annual costs
• You’re not seeing the full picture, just today’s snapshot

Without that clarity, every owner draw feels like a gamble.

A Simple Framework to Pay Yourself with Confidence

You don’t need a complicated system. You need a few clear steps.

Separate your accounts.
One checking account for the business, one for personal. Designate one credit card for business only (even if it started as a personal card). Immediately, your tracking and decisions get cleaner.

Track your numbers monthly.
You need to know:

• What came in
• What went out
• What’s left after expenses

You can use a spreadsheet, software like QuickBooks Online or Xero, or hand it to a bookkeeper. That’s exactly what we handle in our done-for-you bookkeeping services.

Set aside money for taxes.
A simple rule: move 20–25% of your income into a separate tax savings account as it comes in. Don’t wait for April to figure it out.

Set a realistic, consistent owner pay.
Pick a number your business can handle after expenses and tax savings — even if it’s small at first. Maybe it’s $200, $500, or $1,000 a month. Pay yourself on a regular schedule (monthly or biweekly). The consistency builds confidence.

Review and adjust quarterly.
Once a quarter, look at your books:

• Is your revenue consistently covering expenses, taxes, and your current pay?
• Is there still a little cushion building in the business account?

If yes, you can consider a raise. If not, you adjust. Either way, you’re deciding based on facts, not fear.

The first time you pay yourself on purpose — not just because extra cash happened to be there — is the moment you start feeling like you’re running a real business.

A Quick Real-World Example

I worked with a photographer who was making decent money, but rarely paid herself. Every time she thought about transferring money, she hesitated — what if something big came up?

We:

• Cleaned up her books
• Set up a separate tax savings account
• Picked a starting owner draw she felt comfortable with

She began paying herself a fixed amount every month. When the numbers showed that the business could reliably support more, she gave herself a raise.

Nothing magical changed in her revenue. What changed was clarity — and that clarity gave her the confidence to finally pay herself like a real owner.

Bringing It All Together

So, how do you know if you can afford to pay yourself?

You start by knowing your numbers and using a simple system:

• Separate business and personal accounts
• Track income and expenses with basic bookkeeping
• Set aside money for taxes as you go
• Choose a realistic, consistent owner draw
• Review quarterly and adjust based on real data

It’s not about waiting until you’re “big enough.” It’s about building the habit now. The sooner you treat your business like a business, the sooner it can support your life.

If you’re still guessing, make today the day you stop. Put simple systems in place. Commit to a small, regular paycheck you can grow over time. Let your clarity drive your confidence.

If you need support, that’s exactly what we do for Small Business Owners, Therapists, and Counselors who don’t want to become part-time bookkeepers.

Key Takeaways for SMB Owners

• Guessing based on your bank balance is not a pay strategy
• Mixing personal and business money makes it impossible to know what’s safe to take
• Clean bookkeeping + tax savings + consistent owner draws = confidence
• Start small, pay yourself regularly, and adjust as profits grow
• Treating your business like a business is what allows it to reliably pay you

Frequently Asked Questions About Paying Yourself

How much should I pay myself as a Small Business Owner?
There’s no universal number. Start with a modest, predictable amount your business can handle after expenses and tax savings. Adjust as you see consistent profit. Once your business elects s-corp status, more guidance and oversight becomes necessary.

Do I need bookkeeping before I start paying myself regularly?
You don’t need perfect books, but you do need basic clarity. Over time, done-for-you bookkeeping gives you clean data and more confidence.

Watch the Video

Watch “How Do I Know If I Can Afford to Pay Myself?” on YouTube »

About BreezePoint

BreezePoint provides done-for-you small business bookkeeping for Women Business Owners, Therapists, Creatives, and Professional Service Solopreneurs—clean books, clear reports, zero jargon.

If you’re ready to stop guessing and start paying yourself with confidence, contact Kim about done-for-you bookkeeping support.

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