Why Every Small Business Owner Should Outsource Bookkeeping (And How to Do It Right)

Introduction: Are You Trying to Do It All Yourself?

Do you run your own small business and try to handle every single task personally?

If so, you are not alone. Millions of entrepreneurs fall into the trap of believing that doing everything themselves is the only way to maintain control, save money, or ensure quality.

But here is a critical question you need to ask yourself: Why?

The Core Mistake: Ignoring Your True Strengths

Shouldn’t you be spending your precious working hours doing what you do best?

For most business owners, that means focusing on:

Selling and marketing to attract new customers
Delivering exceptional customer service to retain them
Making strategic decisions on how to grow your business

Instead, countless entrepreneurs waste their days wrestling with tasks they are ill-suited for—especially bookkeeping and financial record-keeping.

The Entrepreneur’s Dilemma: Too Many Balls in the Air

Every entrepreneur tries to juggle many balls each day. Sales, operations, customer support, inventory, payroll, marketing, and yes, bookkeeping.

Something Will Eventually Drop

The laws of physics—and business—are unforgiving. Sooner or later, one of those balls is going to be dropped.

You might miss a tax deadline. You could lose track of an important invoice. You might misclassify an expense. Any of these errors can cost you time, money, and peace of mind.

The 24-Hour Problem

A smart business owner eventually realizes a fundamental truth: you cannot do everything because there are only 24 hours in a day.

No amount of caffeine, late nights, or motivational podcast listening can change that simple fact.

When to Outsource: A Self-Assessment

Unless you are extremely organized AND genuinely enjoy working with numbers, you probably need to outsource this job.

The Cost of Doing What You’re Bad At

Too many business owners spend their days doing what they are not very good at—simply because they do not know how to find someone else to take over that responsibility.

This is not stubbornness. It is a lack of knowledge about the hiring and outsourcing process. But that can be fixed.

Where to Start: Finding Your Ideal Bookkeeper

So, how do you begin your search for a qualified part-time bookkeeper?

Step 1: Ask Your Accountant for Referrals

Your accountant is already familiar with your business finances. They almost certainly know trustworthy bookkeeping professionals in your area.

Why this works: Accountants refer only to people they trust, because your accountant’s reputation is also on the line.

Step 2: Target Moonlighters and Independent Professionals

You obviously do not need a full-time employee to do your books. A full-time hire would be expensive and unnecessary for most small businesses.

Your best bet is to look for someone who wants to moonlight at a part-time job—perhaps a trained bookkeeper looking for evening or weekend work.

Step 3: Consider Bookkeepers Who Run Their Own Small Businesses

There are also many independent bookkeepers with their own small businesses who are actively looking for new clients.

These professionals are ideal because:

They are already self-employed
They understand small business challenges
They bring experience from multiple clients

The Subcontractor Advantage (Vs. Full-Time Employee)

If you do not have any other employees, this arrangement works especially well for you.

Why Subcontracting Makes Sense

You can pay your bookkeeper as a subcontractor rather than as an employee on payroll. This saves you from:

Payroll tax filings
Workers’ compensation insurance
Paid time off and benefits
Employment law compliance

Tax Considerations: The Form 1099

At the end of the year, you will need to provide your bookkeeper with a Form 1099 for tax purposes.

However, here is an added benefit: since they are accounting experts, they can actually help you complete that task correctly. Most independent bookkeepers will guide you through the 1099 process as part of their service.

How to Interview a Prospective Bookkeeper

You should interview your prospective bookkeeper just as thoroughly as you would if you were hiring them as a full-time employee.

Request a Resume and References

Do not skip this step. Ask for a professional resume detailing their experience and qualifications. Also request at least three professional references.

Check Those References

Take the time to actually call and check references. Ask previous or current clients:

Was the bookkeeper reliable and punctual?
Did they make costly errors?
Were they easy to communicate with?
Would you hire them again?

Prioritize Trustworthiness

Since this person will be handling your confidential financial records—including bank accounts, credit cards, payroll, and tax information—you need someone who is absolutely trustworthy.

A single dishonest bookkeeper can destroy years of hard work.

What to Expect: Hourly Rates for Bookkeepers

Depending on your geographic location and the bookkeeper’s experience level, you should expect to pay between $15 and $50 per hour.

Low Rates Are Not Always a Bargain

Do not automatically hire the candidate who offers the lowest rate.

Remember: You generally get what you pay for.

A very cheap bookkeeper may lack experience, make frequent errors, or fail to meet deadlines. Correcting those mistakes will cost you far more than you saved on the hourly rate.

The Value of Experience

The more experienced person will cost you more per hour—perhaps $40–$50 instead of $15–$20.

However, that experienced professional will provide:

Valuable input and suggestions to streamline your financial processes
Proactive advice on tax savings and expense tracking
Time-saving systems that reduce your administrative burden

In the long run, a skilled bookkeeper will wind up saving you money—often far more than their invoice amount.

The Importance of Personal Chemistry

Since this person will be working closely with you in your business, you should feel comfortable with them on a personal level.

Trust Your Gut

You will be sharing sensitive information and communicating regularly. If you have any reservations about a candidate—even if you cannot articulate exactly why—politely decline and move on to the next candidate.

Go to the Next Candidate

Do not settle. There are many qualified bookkeepers available. Keep interviewing until you find someone who checks every box:

✅ Proven experience and references
✅ Fair and transparent pricing
✅ Trustworthy and discreet
✅ Good personal chemistry with you

Patience Pays Off: The Selection Process

While the selection process may take a while, it will be worth it later.

Short-Term Effort for Long-Term Gain

Spending several weeks to find the perfect bookkeeper might feel frustrating when you are already overwhelmed. However, this is an investment in your business’s future.

A Few Months from Now…

Take your time to find the right match. Then, after a few months of working with a skilled part-time bookkeeper, you will wonder:

“How did I ever manage to run my business before I hired one?”

You will have:

More free time to focus on high-value activities
Accurate, organized financial records
Less stress around tax time
Better data for making growth decisions

Conclusion: Stop Doing Everything Yourself

If you run a small business, your job is to work on the business—not just in it. Bookkeeping, while essential, is a task that can and should be delegated.

Key Takeaways

Outsourcing bookkeeping frees you to focus on sales, marketing, and strategy
Look for part-time or moonlighting bookkeepers to avoid full-time costs
Hire as a subcontractor (not employee) whenever possible
Expect to pay $15–$50 per hour depending on experience
Trust and personal chemistry are as important as technical skill
Take your time—the right hire pays dividends for years

Your Next Step

Stop juggling tasks you are not equipped for. Start your search for a qualified, trustworthy, part-time bookkeeper today. Your future self—and your growing business—will thank you.