Freelance & Contractor Finances

Managing Irregular Income and Self-Employment Taxes

If you run camps, clinics, private training, speaking gigs, online courses, or side projects…
you already know the truth:

Irregular income is normal - but it requires a different system.

Freelance and contractor money can be powerful for coaches, but only if you manage the cash flow, taxes, and pay structure intentionally.

Let’s build a simple game plan.

Last Time the Market Was This Expensive, Investors Waited 14 Years to Break Even

In 1999, the S&P 500 peaked. Then it took 14 years to gradually recover by 2013.

Today? Goldman Sachs sounds crazy forecasting 3% returns for 2024 to 2034.

But we’re currently seeing the highest price for the S&P 500 compared to earnings since the dot-com boom.

So, maybe that’s why they’re not alone; Vanguard projects about 5%.

In fact, now just about everything seems priced near all time highs. Equities, gold, crypto, etc.

But billionaires have long diversified a slice of their portfolios with one asset class that is poised to rebound.

It’s post war and contemporary art.

Sounds crazy, but over 70,000 investors have followed suit since 2019—with Masterworks.

You can invest in shares of artworks featuring Banksy, Basquiat, Picasso, and more.

24 exits later, results speak for themselves: net annualized returns like 14.6%, 17.6%, and 17.8%.*

My subscribers can skip the waitlist.

*Investing involves risk. Past performance is not indicative of future returns. Important Reg A disclosures: masterworks.com/cd.

1. The Reality of Irregular Income

Freelance income means:

  • Some months are great

  • Some months are quiet

  • Taxes aren’t withheld

  • Cash flow matters more than salary math

The mistake most coaches make is treating freelance income like a paycheck.

It’s not.
It’s business revenue.

2. Separate the Money (Non-Negotiable)

Before anything else, do this:

✔️ Business checking account
✔️ Business savings account (for taxes)

All freelance income flows into business checking first.

This creates:

  • Clean records

  • Less stress at tax time

  • A real business mindset

If it all lands in your personal account, chaos follows.

3. Smooth the Ups and Downs

With irregular income, your goal isn’t “max every month.”
Your goal is stability.

The Income Smoothing Rule:

  • In good months → save the surplus

  • In slow months → pay yourself from reserves

This keeps your lifestyle steady even when income isn’t.

Think of it like managing minutes across a long season - not one hot game.

4. Pay Yourself on Purpose

Instead of random transfers, use a system.

Two simple options:

Option A: Fixed Monthly Pay

  • Choose a conservative monthly amount

  • Pay yourself the same amount every month

  • Extra stays in the business

Option B: Percentage-Based Pay

  • Pay yourself 40–60% of net income

  • Rest stays for taxes, expenses, and growth

Consistency > guessing.

5. Self-Employment Taxes (The Part No One Likes)

When you’re self-employed, you pay:

  • Federal income tax

  • State income tax (if applicable)

  • Self-employment tax (~15.3%)

That 15.3% covers:

  • Social Security

  • Medicare

No one withholds this for you - so you must.

6. The “Set Aside for Taxes” Rule

A simple, safe rule for most coaches:

👉 Set aside 25–30% of freelance income for taxes

Put it into your business savings account immediately.

Out of sight = out of temptation.

If you don’t set it aside early, tax season becomes stressful fast.

7. Track Everything (Yes, Everything)

Freelancers win by tracking:

  • Income by source

  • Expenses

  • Mileage & travel

  • Software & subscriptions

  • Equipment & facility rentals

Simple tools:

  • Google Sheets

  • Wave (free)

  • QuickBooks

  • Notion

The best tool is the one you’ll actually use.

8. Build a Buffer Before You Build Bigger

Before expanding:
✔️ Build 3–6 months of business expenses
✔️ Cover personal expenses consistently
✔️ Stay current on taxes

Growth without a buffer = stress.

Final Whistle

Freelance income is powerful - but only if you run it like a system.

Here’s the simple playbook:
✔️ Separate business and personal money
✔️ Smooth income swings
✔️ Pay yourself consistently
✔️ Set aside taxes early
✔️ Track everything

When you do this, side income stops feeling risky…
and starts feeling reliable.

  Subscribe here → Wealth4Coaches Newsletter

Coach Mike Klinzing
Founder, Wealth4Coaches
"Coach smarter. Save better. Live freer."