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643: Is It Time To Hire A Bookkeeper Or Keep Doing It Yourself

Contractor Success Map with Randal DeHart | Contractor Bookkeeping And Accounting Services

Release Date: 08/29/2025

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This Podcast Is Episode 643, And It's About Is It Time To Hire A Bookkeeper Or Keep Doing It Yourself

A Real-World Guide for Small Construction Business Owners

If you run a small construction business, you've probably worn every hat—from estimator and foreman to project manager and, yes, bookkeeper. Initially, doing the books yourself may have seemed manageable. But now, as you grow, you might be asking:

"Do I need a bookkeeper, or can I keep doing this myself?"

It's a valid question—and the answer depends on where your business is, where it's going, and how you manage your time and money.

As construction bookkeeping specialists, we've worked with both first-time business owners and seasoned contractors. We've seen the difference it makes when you stop guessing at your finances and start getting reliable, real-time information from a professional.

This post will break down the pros and cons of DIY versus hiring a bookkeeper, helping you determine which option is right for your business at this time.

DIY Bookkeeping: The Pros

Let's start with what's great about doing it yourself, because yes, it can make sense for some businesses in the early stages.

1. It's Low Cost (on the Surface)

When money is tight, it's tempting to save every dollar. Doing the books yourself means you don't have to pay a monthly fee or hourly rate.

2. You Learn the Basics

By managing your books, you get hands-on experience:

  • How income and expenses are tracked
  • What reports matter
  • How invoices, payments, and taxes work

That knowledge helps you communicate more effectively with professionals in the future.

3. You Stay Closely Involved

No one knows your business like you do. DIY bookkeeping keeps you aware of every transaction, which can be helpful when you're building habits and financial awareness.

DIY Bookkeeping: The Cons

While DIY works in the beginning, it often becomes a liability as your business grows.

1. It's Time-Consuming

Your evenings and weekends should be spent resting or planning, not catching up on receipts, reconciling bank accounts, or fixing errors from two months ago.

Time spent doing books is time not spent building, selling, or strategizing.

2. Mistakes Are Easy to Make

Without training, it's easy to:

  • Misclassify expenses
  • Forgot to reconcile accounts
  • Lose track of job costs
  • Miss important deadlines (like sales tax or quarterly estimates)

These errors can result in IRS penalties, underpricing, or inaccurate reporting, which can harm your business.

3. Poor Financial Visibility

Most DIY systems don't provide accurate job costing, cash flow forecasting, or profit tracking.

If you don't know:

  • How much are you really making per job
  • When you can afford to hire or buy equipment
  • Whether your prices cover your overhead

…then you're not making informed decisions—you're guessing.

4. It Adds to Your Stress

Let's be real: most contractors don't enjoy bookkeeping. It's one more task in an already overloaded day. That constant "I still need to do my books" feeling adds unnecessary pressure.

When to Consider Hiring a Bookkeeper

Hiring a bookkeeper isn't just about outsourcing busywork—it's about buying clarity, control, and peace of mind.

Here's how to know it might be time.

1. You're Consistently Behind

If you're weeks or months behind on categorizing expenses, reconciling bank accounts, or sending invoices, it's time for support.

A good bookkeeper will not only clean up your books but also keep them up to date moving forward.

2. You're Making More Than $100K in Revenue

Once your business is generating six figures or more, your financial picture becomes more complex:

  • Job costing becomes essential
  • Overhead needs to be tracked properly
  • Taxes become more critical (and riskier to ignore)

That's where a bookkeeper helps you protect what you're building.

3. You Want to Grow (Or Work Less)

Whether your goal is to scale, take on larger jobs, or finally reclaim some weekends, hiring a bookkeeper frees up your time and mental space to make that happen.

4. You're Not Sure What Your Numbers Mean

If you've ever looked at a Profit & Loss report and thought, "What am I supposed to do with this?"that's your cue.

A good bookkeeper doesn't just send you reports—they help you understand them and use them to improve your business.

DIY vs. Hiring a Construction Bookkeeper: Side-by-Side Comparison

Feature DIY Bookkeeping Hiring/Outsourcing
1. Cost Low upfront Monthly fee (varies)
2. Time required High Low (with some client input)
3. Accuracy Varies (risk of errors) High (with checks and clean records)
4. Stress level Often high Much lower
5. Job Costing & Profitability Often missing or incomplete Built-in and consistent
6. Tax readiness Risk of scrambling at year-end Clean books, ready for CPA
7. Scalability Harder to grow confidently Easier to plan and expand

Common Concerns About Hiring a Bookkeeper (And the Truth)

"Can I afford it?"

Hiring a bookkeeper isn't an expense—it's an investment.

Most of our clients save money long-term because:

  • Their invoices go out on time
  • They stop underpricing jobs
  • They avoid late fees and missed tax deductions

"What if I'm too disorganized?"

That's precisely why you need a bookkeeper. A good one will help you build systems that work for you, not shame you for being behind.

"Will they understand construction?"

Not all bookkeepers do—but we do. We specialize in construction businesses and know how to track labor, materials, subcontractors, job profitability, and project phases accurately.

How a Bookkeeper Helps You Grow

Once your books are in order, you can:

  • See which jobs are most profitable
  • Adjust your pricing based on real data
  • Budget for slow seasons
  • Plan for hiring or equipment purchases
  • Sleep better knowing your business is financially healthy
  • You stop reacting and start leading.

Final Thoughts:

Don't Wait Until It's a Mess

Suppose you're spending hours each month on books, avoiding financial check-ins, or unsure whether your job is making money. In that case, it's probably time to stop doing it yourself and outsource it to us.

Hiring a bookkeeper is like hiring a subcontractor—you could do the work yourself. Still, someone with more experience and tools will do it faster, cleaner, and with fewer mistakes.

You build homes. We'll help you build a business that lasts.

Ready to Explore Bookkeeping Support?

If you're ready to free up your time, reduce financial stress, and finally understand what your numbers are telling you, let's talk.

We can go over:

  • Where your books stand now
  • What kind of support makes sense for your business
  • How to set up a system that works (without drowning in spreadsheets)

Your time is too valuable to spend chasing receipts and guessing at job costs. Let's fix that.


About The Author:

Norhalma_VerzosaNorhalma Verzosa is a Certified Construction Marketing Professional and serves as the Web Administrator of Fast Easy Accounting, located in Lynnwood, WA. She holds a Bachelor's Degree in Psychology and is a Certified Internet Web Professional, with certifications in Site Development Associate, Google AdWords Search Advertising, and HubSpot Academy. She manages the entire web presence of Fast Easy Accounting using a variety of SaaS tools, including HubSpot, Teachable, Shopify, and WordPress.