Should I Hire a Tax Professional—or Just Do It Myself?

Financial Horizons: Insights for Building Wealth and Securing Your Legacy

By Dr. Jose G. Cardenas, Chief Tax Strategist at The C & R Group, LLC

Let’s be honest—between “free” tax software, DIY videos, and social media tax gurus, it’s easy to think:

“Why would I pay someone to do my taxes when I can just click through a program myself?”

Fair question.

But here’s the part most people miss:
You’re not just paying for someone to enter numbers into a form. You’re paying for strategy, protection, and peace of mind—things that software alone simply can’t deliver.

The real question isn’t “Can I do this myself?”
The real question is:

“What is it costing me—today and in the future—to keep doing this myself?”

Let’s break down when DIY might be okay, when hiring a professional is a smart power move, and how the right tax advisor can actually help you build wealth, not just file a return.

When DIY Might Be Enough (For Now)

I’ll give it to you straight—there are situations where DIY tax prep might be workable, at least for a season of life.

You might be okay on your own if:

• You have one W-2 job, no side hustle, no business
• You don’t own property or rental real estate
• You don’t have significant investments outside a basic retirement account
• You haven’t moved states, separated, divorced, or had other major life changes
• You’re not getting scary letters from the IRS or your state

If that’s you, a simple software solution can get the job done—as long as you’re careful and honest, and you’re not leaving money on the table.

But here’s the catch: most people don’t stay in that “simple” category for long.

When Hiring a Tax Professional Is a Smart, Strategic Move

As soon as life gets even slightly more complex, DIY taxes start becoming more like DIY surgery. You can try—but you probably shouldn’t.

You absolutely should consider hiring a tax professional if any of these sound familiar:

1. You Own a Business or Have a Side Hustle

Freelancer, consultant, rideshare, coach, online shop, landlord, truck driver, nurse doing PRN, contractor—whatever your title, once you’re self-employed, the game changes.

Now we’re dealing with:

• Business income & expenses
• Home office, vehicle, equipment, and other deductions
• Self-employment tax
• Possible entity choices (LLC, S corp, partnership)

Done right, this is where major tax savings live. Done wrong, it’s where audits and big surprise bills come from.

2. You Have Rental Property or Multiple Homes

Renting out a home, room, or Airbnb brings in income—but also opens the door to:

• Depreciation
• Repairs vs. improvements
• Travel, supplies, and other deductible expenses
• Passive vs. active activity rules

If you own real estate and you’re guessing on these things, you’re gambling with some of the most powerful (and complex) tax rules available.

3. You Have Significant Investments or Multiple Income Streams

If you’re dealing with:

• Capital gains and losses
• Stock options or RSUs
• Crypto trades
• Multiple 1099s from different platforms

…you’re now in territory where coordination and planning matter more than just “plugging in numbers.”

4. You’ve Had a Major Life Change

• Marriage or divorce
• New baby
• Caring for aging parents
• Inheritance
• Big move to a new state

All of these can change your tax picture—and the way you file and plan going forward.

5. You’re Receiving IRS or State Letters

If notices are piling up and you’re letting them sit unopened, it’s time to bring in backup. A professional can:

• Decode what the IRS is actually saying
• Respond properly and on time
• Help you avoid making things worse by guessing

At that point, a tax pro isn’t a luxury. It’s protection.

What a Tax Professional Does That Software Doesn’t

Let’s answer the real question: What are you actually paying for?

A strong tax professional doesn’t just “do taxes.” They:

1. Look for Deductions and Credits You Don’t Know Exist

Software only asks questions programmed into it. A professional asks questions based on:

• Your work
• Your family
• Your business
• Your goals

That’s how we uncover things like:

• Missed business deductions
• Overlooked credits
• Smarter ways to time income and expenses

One good discovery can pay for the entire fee (and then some).

2. Turn Your Taxes Into a Year-Round Plan

Tax software is reactive—“What happened last year?”

A strategist is proactive—“How can we change what your next return looks like?”

That can include:

• Adjusting your withholdings or estimated payments
• Choosing or optimizing an entity structure
• Mapping out retirement contributions
• Planning for big events (sale of a business, property, or investments)

This is where tax planning turns into wealth building.

3. Help You Stay on the Right Side of the IRS

Most people don’t intend to cheat. They just don’t know the rules.

A tax professional helps you:

• Stay compliant
• Keep clean, defendable records
• Avoid risky positions that look fine in software but ugly in an audit

You’re not paying just for the return—you’re paying to reduce future problems.

4. Give You Confidence and Clarity

You shouldn’t be losing sleep wondering:

• “Did I miss something?”
• “Did I overpay?”
• “If I get audited, am I dead in the water?”

A good advisor gives you confidence that:

• Your return was prepared with your situation in mind
• You understand the big picture
• You have someone in your corner if questions ever come up

“But Isn’t Hiring a Pro Expensive?”

The better question is:

“What’s the cost of not getting this right?”

If a professional helps you:

• Avoid a penalty
• Capture deductions you were missing
• Structure your business more efficiently
• Prevent a bad mistake that could trigger years of problems

…then their fee isn’t just an expense—it’s an investment in protection and profit.

Try thinking of it this way: if you’re serious about earning more, keeping more, and building a legacy, does it really make sense to treat your tax strategy like a $49 afterthought?

What to Look For in a Tax Professional

Not all tax preparers are created equal. When you’re evaluating who to work with, consider:

• Experience with your type of situation
  Self-employed? Rentals? Multiple states? Make sure they’ve seen it before.
• Credentials & ongoing education
  Are they staying up to date as the tax code changes?
• Year-round availability
  Can you reach them outside of March–April, or do they disappear until next tax season?
• Strategic mindset
  Do they just key in your numbers, or do they talk about planning, goals, and long-term strategy?

You want someone who sees beyond the form—and helps you build a future.

How The C & R Group, LLC Can Help

At The C & R Group, LLC, we don’t just “do returns.” We:

• Analyze your full financial picture
• Look for missed opportunities and hidden risks
• Help you align your tax strategy with your business and personal goals
• Provide ongoing guidance so tax season stops being a crisis and becomes a checkpoint

Whether you’re:

• A W-2 earner with growing investments
• A self-employed professional or business owner
• A landlord, truck driver, nurse, consultant, or entrepreneur

…we help you move from reactive filing to proactive planning.

Final Thoughts: Don’t Go It Alone When the Stakes Are High

Could you keep doing your taxes yourself? Sure.

But ask yourself:

• Are you confident you’re not overpaying?
• Are you sure you’re not missing deductions, credits, or smarter structures?
• Do you have a plan—or just a filing habit?

If you’re serious about building wealth, protecting your family, and creating a legacy, hiring a tax professional isn’t a luxury. It’s a smart, leveraged decision.

You focus on creating income.
Let a strategist help you keep more of it.

🔗 Read more at: www.thecrgroupllc.com/blog

📅 Ready to see what a strategic tax partnership looks like?
Book a consultation with Dr. Cardenas

About the Author

Dr. Jose G. Cardenas is a retired U.S. Army Finance Officer and the Chief Tax Strategist at The C & R Group, LLC. With a Doctorate in Business Administration and over 20 years of experience in financial strategy and tax planning, Dr. Cardenas helps individuals and business owners reduce taxes legally, protect their wealth, and build a lasting legacy. Learn more at www.thecrgroupllc.com

📌 Disclosure

This article is for educational and informational purposes only and is not intended to serve as personalized legal, tax, or investment advice. Tax strategies and filing decisions should be evaluated in light of your specific circumstances, and tax laws are subject to change. You should consult with a qualified tax professional before making any decisions. Dr. Jose G. Cardenas, DBA, provides tax advisory services through The C & R Group, LLC. Insurance and investment strategies may be offered through his role as a licensed financial professional affiliated with Experior Financial Group.

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