Seven Signs for When a Small Business or Entrepreneur Should Hire a Bookkeeper

When you’re building a business from the ground up, it’s easy to fall into the “do it all” trap. You're the marketer, the sales team, the customer service rep—and yes, the bookkeeper too. But there comes a point where doing everything yourself stops being a smart hustle and starts costing you in ways you might not realize.

Recently, I came across a concept that completely shifted my perspective: your Freedom Figure. It’s the dollar value of your time. To calculate it, take your annual income and divide it by 2,080—the number of work hours in a year based on a 40-hour work week. For example, if your business earns $150,000 per year, your Freedom Figure is about $72/hour.

That means any task you can outsource for less than $72/hour is costing you money if you choose to do it yourself. And that includes bookkeeping.

Here are seven signs that it’s time to bring in a bookkeeper and free yourself up to focus on what really drives growth:

1. You’re Spending More Than a Few Hours a Month on Books

Bookkeeping can easily eat up 5–10 hours a month—or more if you’re not experienced. If your time is worth $72/hour, that’s up to $720 per month you could be putting toward higher-value activities like landing new clients or developing new products.

2. Tax Season Gives You Nightmares

If you're scrambling every April to pull receipts, categorize expenses, and pray you didn’t miss a deduction, it's time. A bookkeeper keeps your financials organized year-round, making tax prep smoother and potentially saving you money through accurate reporting and better deduction tracking.

3. You’ve Made Mistakes in the Past

Misclassified expenses, forgotten invoices, duplicate charges—sound familiar? Bookkeeping errors can lead to poor financial decisions, cash flow issues, and even IRS trouble. A bookkeeper brings accuracy and peace of mind.

4. You’re Avoiding Financial Reports

If you don’t know your profit margins, burn rate, or which of your products are most profitable, you're flying blind. A bookkeeper provides up-to-date reports so you can make strategic decisions based on real data—not gut feeling.

5. You Want to Grow, But You’re Stuck in the Weeds

You can’t scale if you’re buried in spreadsheets. Whether you're planning to hire, launch a new offer, or secure funding, having clean financials and someone to help you interpret them is essential.

6. Cash Flow Is a Mystery

If you’re wondering why your bank account feels tighter than your sales say it should be, a bookkeeper can help you get clarity. They track cash in and out, flag issues, and keep your operations smooth.

7. You Recognize the Opportunity Cost

Every hour you spend bookkeeping is an hour you're not growing your business. Ask yourself: what would be a better use of your time—reconciling your bank accounts or signing a new client worth thousands? If someone else can handle the task for less than your Freedom Figure, it’s not an expense—it’s an investment.

Final Thoughts

Hiring a bookkeeper might feel like a luxury, but for most entrepreneurs, it’s a smart business move—especially once you start thinking in terms of opportunity cost and your time’s actual value.

If your business is making $150,000 or more annually, it’s likely costing you more to not hire a bookkeeper. So the next time you’re knee-deep in expense reports, remember: your time is worth too much to spend it on something someone else can do more efficiently.

Business owner using calculator, phone, and laptop to do their own bookkeeping

Set up a call with me today to find out how affordable outsourcing bookkeeping actually is!

Spoiler Alert: The rates for Easy Seasons Bookkeeping start at $300 a month. I offer free consultations to discuss what your needs are and what your actual rate would be. Use my Calendly link now to be immediately scheduled.

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