Chicago Freelancer / Self-Employed Tax & Accounting Services
1099 Income, Quarterly Taxes, and Deductions, Handled, So Your First Big Tax Bill Isn’t a Shock
Going out on your own is exciting, right up until tax time. Suddenly there is no employer withholding taxes for you, no one tracking your deductions, and a stack of 1099s adding up to a bill you did not see coming. Self-employment tax, quarterly estimated payments, and Schedule C are a whole new world, and no one hands you a manual.
Heard & Associates LLC helps Chicago freelancers, contractors, and self-employed professionals take control of the tax side of working for themselves. We calculate your quarterly payments so there are no surprises, capture every deduction you are entitled to, keep your books clean, and tell you the moment it makes sense to save money with an S-Corp. You focus on the work. We handle the numbers.
📞 Call (312) 810-3603 or Book Your Consultation Online today.
Who We Help
If you earn income that no one withholds taxes from, this is for you:
- Freelancers and independent creatives
- 1099 contractors and gig workers
- Consultants and coaches
- Solo professionals and service providers
- Online sellers and content creators
- Anyone who left a W-2 job to work for themselves
Whether this is your first year with 1099 income or you have been self-employed for years and want to stop overpaying, we meet you where you are.
What Our Self-Employed Service Includes
We handle the full tax and financial side of working for yourself:
The Quarterly Tax Trap Nobody Warns You About
Here is what surprises almost every new freelancer. When you were a W-2 employee, taxes came out of every paycheck automatically. Self-employed, that job is now yours, and the IRS expects you to pay throughout the year, not just in April.
If you wait until tax time, you can face a large lump-sum bill plus underpayment penalties on top. The IRS generally wants estimated payments four times a year, based on what you are earning. We calculate those payments for you, remind you when they are due, and adjust them as your income changes, so you are never blindsided and never penalized.
You’re Probably Leaving Deductions on the Table
Self-employed people overpay taxes for one main reason: they do not track and claim everything they are allowed to. When you work for yourself, a surprising amount of what you spend is deductible, but only if it is documented.
Common deductions we make sure freelancers capture:
- Home office, if you work from home
- Mileage and vehicle costs for business travel
- Equipment, computers, and software subscriptions
- Phone and internet, business-use portion
- Professional development, courses, and certifications
- Marketing, website, and business tools
- Health insurance premiums, in many cases
- Retirement contributions through a SEP-IRA or Solo 401(k)
Clean books are what make these deductions stick. We keep your records organized through the year so nothing is missed and everything is defensible.
When Should a Freelancer Become an S-Corp?
This is the question that saves self-employed people the most money, and almost no one explains it clearly.
As a standard freelancer or sole proprietor, you pay 15.3% self-employment tax on all of your profit. Once you are earning enough, electing S-Corp status lets you split your income between a reasonable salary and distributions, and only the salary is hit with that tax. For many freelancers past a certain income level, that is thousands of dollars in annual savings.
It is not the right move for everyone, and doing it too early can cost more than it saves. We run your actual numbers, tell you honestly whether you are at the point where it pays off, and handle the setup and payroll if you are.
First Year on Your Own? Start Right
If you just started freelancing, the smartest thing you can do is set up the tax side correctly from the beginning, before the habits and the mess set in. That means separating business and personal finances, tracking income and expenses from day one, and knowing what to set aside for taxes.
We help new freelancers get organized early so the first tax season is smooth instead of stressful, and so you are not scrambling to reconstruct a year of records in April. If you are already deep in your first year with no system, we help you catch up too.
Why Chicago Freelancers Choose Heard & Associates LLC
Angell
2 weeks ago
Professional and excellent communication
Kiara Moore
4 weeks ago
Mr. Heard is amazing! He was extremely helpful and more than willing to jump in and help with the beginning steps of a NFP org that I am apart of. He answered whatever questions I had and alleviated so many of my concerns! I have no doubt that he will be beneficial for all future steps.
Randy Smith
2 months ago
I was very pleased with the process everything was done thoroughly and promptly. I look forward to continuing my business with Heard & Associates.
Nageeb Hasan
2 months ago
Quick initial response. Clear communication and proactive. Easy to work with.
Teanna Ramirez
2 months ago
Darrel has been amazing to work with. I brought him a mess and he was able to get things sorted out quickly. He was responsive and offered additional services to help my business! I appreciated his time and effort and how easy he made this process for me! I will continue using him for all of my business needs!
Whats The Word Media Inc.
3 months ago
Kendra Spearman
3 months ago
Mr. Heard is exceptional! His expertise and professionalism have really saved me tremendous time and stress, which is extremely important to me as a small business owner. I am so excited to have him on my team.
carla Dotson
3 months ago
Heard & Associates made the tax process simple, easy to follow, and easy to understand. Mr. Heard returned my phone calls promptly whenever I had questions regarding my tax return. I would definitely give this company a 10/10 rating!
Thank you, Heard & Associates, for handling my 2025 tax return with professionalism and care. I will definitely be a returning customer next tax season! ⭐⭐⭐⭐⭐
Thank you, Heard & Associates, for handling my 2025 tax return with professionalism and care. I will definitely be a returning customer next tax season! ⭐⭐⭐⭐⭐
Marcus Cruz
3 months ago
Darrell is by far the best CPA I’ve encountered. He performs his due diligence with urgency and perfection. If you want the best outcome for any tax problems or just routine things that may have to get taken care of, he’s definitely the one to get you together. I’ve had a lot of different CPA’s but he is bay far the best. Very knowledgeable and professional.
Valerie Bryant
4 months ago
Darrel was extremely helpful with my taxes. He made sure everything was handled correctly and worked to ensure i paid little to none to IRS. He was professional, knowledgeable, and easy to work with throughout the entire process. I highly recommend his services
Laura Corno
4 months ago
Roosevelt Lesley
4 months ago
Very legit and respectful
Toni Howard
4 months ago
Heard & Associates is extremely proficient.
dawana smelly
4 months ago
I would really like to thank Heard Associates for a wonderful job on my taxes. I’ve been filing with them for 2 years and there’s never a disappointment. Thanks again.
Javana White
5 months ago
Heard & Associates is a business that exemplifies stellar professionalism and integrity. I have been entrusting Mr. Heard with my taxes for 4 consecutive years and counting. My results are always consistent, and I have recommended many close family and friends to Heard & Associates, where friendly and efficient service is at the forefront.
Kiarra Lee
5 months ago
I always have a great experience working with Darryl. He’s professional, responsive, and knowledgeable. He gets things done accurately and on time. Even when I have a tight deadline, he was able to deliver quickly. I appreciate his reliability and I would recommend Heard & Associates services to anyone looking for a trustworthy and efficient accountant.
Donald Olson
5 months ago
I was searching for firm in the area to handle the taxes for an elderly friend (93) in memory care. (I am her power of attorney) I looked online for places with great reviews and ran across Heard and Associates. Every interaction I had with Darryl was efficient, friendly and painless. Communication was excellent and the process of loading the tax documents to the portal and signing the return was very straightforward. Darryl was kind enough to give us an extra discount for the elderly based on my friend’s age and ended up doing the return for free! Five stars for Heard and Associates!! Would recommend Darryl to anyone.
Stephanie McBay
5 months ago
I found Darrell Heard of Heard & Associates by doing a search of the top 10 tax filing companies in the southwest suburbs and he had a 4.5 star review. Mr. Heard is attentive, fast and thorough. I forgot my property tax documents and he was patient while I yelled at my phone because I forgot my password. If you're looking for a true professional, Mr. Heard is the person you should call.
nikhil sampat
5 months ago
Darryl is amazing! Extremely knowledgeable and on top of his game! He takes the the time to explain everything properly and then executes! Highly recommended!
Tasha A.
5 months ago
I have been getting my taxes a little over three years. Darrel has been amazing and I wouldn’t get my taxes done by anyone else.
I always seem to have so many questions and Darrel always seems to have the answers.
If you are looking for a company and person that will be honest and get your taxes completed in a timely manner… he is it.
I always seem to have so many questions and Darrel always seems to have the answers.
If you are looking for a company and person that will be honest and get your taxes completed in a timely manner… he is it.
Muriel Mapp
6 months ago
Daryl is amazing! Finding a new accountant online can be a scary process, but I was blown away by his professionalism, tax knowledge, quick response time and attention to detail. I will be using him for years to come for tax preparation!
J. Murphy
6 months ago
My go to specialist for all my tax and accounting needs! Highly recommend Heard and associates!
Nitwa Ronah
6 months ago
I had an excellent experience with Heard Associates this year for my taxes 2025. They were extremely knowledgeable, patient, and professional throughout the entire process. Every question I had was answered clearly, and they made sure I understood my options to maximize my return. The process was smooth, organized, and stress-free. I truly appreciate their attention to detail and dedication to helping their clients. I highly recommend their services to anyone looking for a trustworthy and reliable tax professional.
Elilian Cooper
6 months ago
This is my 5 year and he never disappoints me 🥰 great service
Lazy Mobandz
6 months ago
Mr heard is some one I would say is a high level professional and absolutely excellent at what he does his communication skills are outstanding and he always has a smile on his face just a great individual to work with his customer service skills made me double take at my customer service skill for my own business
Angelo Jr. Simonelli
6 months ago
This was out first time filing taxes with anyone other than turbo tax and it went great. Darryl was extremely helpful and quick when it came to filing. He was also quick to respond to any questions. If you are looking for someone to file your taxes Id highly recommend!
Key Brown
6 months ago
Going on my third consistent year with Darryl Heard and his services. He is very professional and precise with all of your documents. He is very informative and knowledgeable about what steps you should take. He provides education in every step of the process. Thank you for being an outstanding accountant, tax associate, and professional at all times.
Kyra Lane
6 months ago
I was recommended this tax person from my good friend Dena. I have used his services for the last two years so far. I haven’t had any issues. He was very professional and answered my questions in a timely manner. I will be continuing to use his services.
Jason Wiley
6 months ago
Very precise, business oriented, kind, and handled every aspect of business in a timely fashion, and communication was over the top.
johnesha Phillips
6 months ago
I have experienced exceptional customer service for the third consecutive year with Darrel handling my taxes. Darrel ensured I was updated throughout the entire process. My inquiries about taxes were met with prompt and professional responses. Overall, my experience with Heard's was outstanding, and I highly recommend his services.
Omari Howard
6 months ago
Good business as usual
Omari Howard
6 months ago
Great customer service as usual
Mary Chandler
6 months ago
Very professional. Great customer service. Always answers all my tax questions throughout the entire year. Fees are reasonable.
niya rayford
6 months ago
I’ve been a client for a few years & each year the experience gets better. The service is fast & convenient. He’s always there if you have questions & also gives the best financial advice. If I could give 10 stars I would!
Chelsea Denise
7 months ago
Very professional, efficient, and knowledgeable. Made tax season simple and stress-free. Highly recommend!
McKayla Shepherd
7 months ago
I will probably never file my taxes with anyone else but this company! They make everything so easy and convenient and the process takes no time! Thanks so much Daryl!
Antwon Williams
7 months ago
I’ve had an excellent experience working with Heard & Associates . He’s extremely knowledgeable, professional, and takes the time to explain everything clearly, which makes the entire process stress-free. He’s thorough, detail-oriented, and always make sure I’m getting the best possible outcome. Communication is quick and reliable, and I never feel rushed or confused. I highly recommend him to anyone looking for a trustworthy and efficient tax professional.
Carmecia Mcknight
7 months ago
Darryl is very professional and prompt.
He was thorough and extremely knowledgeable. All questions were answered clearly, deadlines were met, and the entire process was seamless. I felt confident knowing my finances were handled with accuracy and care. I highly recommend his services.
He was thorough and extremely knowledgeable. All questions were answered clearly, deadlines were met, and the entire process was seamless. I felt confident knowing my finances were handled with accuracy and care. I highly recommend his services.
Leann Solorio
7 months ago
Just did my taxes with Mr. Heard and he was kind and educational as well. Very nice office as well. Highly recommend going to him.
Martin vOJTEK
7 months ago
Darryl is amazing. He got me the best return I’ve ever had. He’s also so patient and kind and he will go out of his way to help with any issues that arise. I tell everyone I know to go to Darryl and sing his praises.
Gabrielle Benson
7 months ago
I found Darryl via online research with no referrals and I'm so glad I went with him! I needed to find someone who could handle my yearly tax preparation, but was also interested in future tax planning as I continue to grow financially. His team was super responsive, I got a response the same day and we scheduled a meeting for the next week. He was able to give me a price estimate and expected turnaround and my taxes were completed that day. He was knowledgable about any additional questions I had and communication was quick and thorough. I look forward to continue working with him!
Qinah S.
7 months ago
My people, my people! After being guided by Yah to "do something different this year", He led me to Heard & Associates. Darryl is accurate, efficient, responsive and pleasant, just to name a few of the key words when describing my experience with filing with this firm. Look no further! I encourage anyone who seeks a tax professional to connect with H&A asap. He was great!
nikhil sampat
7 months ago
Great experience! Very knowledgeable and helped out a lot! highly recommend
Soulful Mama
7 months ago
Heard & Associates is a great tax and accounting company. Professional and personalized. Stellar service!
Najala Watson
8 months ago
Excellent service from start to finish. Darrel truly cares about his clients and goes above and beyond to make sure everything is done right. The process was stress-free, organized, and very thorough. It’s clear he’s passionate about helping individuals and small businesses succeed. I would definitely recommend him to anyone needing tax or accounting guidance.
Najala Watson
8 months ago
I’ve had a great experience working with Darrel and his team. They are professional, knowledgeable, and always take the time to explain things clearly. I felt confident knowing my taxes were handled accurately and efficiently. Communication was smooth, and any questions I had were answered promptly. I highly recommend this business to anyone looking for reliable tax and accounting services.
Q
8 months ago
Effective, trustworthy and consistent organization. I've been using this firm for my tax preparation needs for the past couple of years and it has provided me with a peace of mind during the busy tax season. I would/have recommend tax services to anyone in my network!
Jason Wiley
8 months ago
Very professional, helped with all of concerns and needs, I felt very comfortable, learned new information, had a very positive impacting experience! Thank you so much!!!!
Laquitta Williams
8 months ago
I had an excellent experience with Darrel Heard & Associates. From the moment I connected with them, I felt comfortable and confident that I was in good hands. They were patient, professional, and took the time to truly explain everything to me in a way that made sense. I never felt rushed or overlooked.
They were extremely thorough and detail-oriented, making sure everything was accurate and done in my best interest. What I appreciated most was how stress-free they made the entire process — that alone is priceless. I walked away feeling relieved, informed, and confident about my finances.
I highly recommend Darrel Heard & Associates to anyone looking for an accountant they can truly trust.
They were extremely thorough and detail-oriented, making sure everything was accurate and done in my best interest. What I appreciated most was how stress-free they made the entire process — that alone is priceless. I walked away feeling relieved, informed, and confident about my finances.
I highly recommend Darrel Heard & Associates to anyone looking for an accountant they can truly trust.
Brandon Atkins
8 months ago
I’ve had an excellent experience working with Heard and Associates for both my personal and business taxes. They are knowledgeable, professional, and extremely thorough. They take the time to explain everything clearly and make sure nothing is overlooked. Tax season is stress-free knowing I’m in good hands. I highly recommend Heard and Associates to anyone looking for a reliable and honest accounting firm.
Marilyn Lee
8 months ago
Mr. Heard was very professional and knowledgeable about his services he provided. The location was very easy to find as well. He gives great detail with various options to help suit your needs. I would definitely be recommending him to my colleagues, family, and friends. Thanks Again.
Dantoinne Williams Jr.
8 months ago
I was in a panic because the person who originally did my taxes wasn't available. I reached out to Heard & Associates and all of my stress went away. We sat down discussed my situation for my business and my taxes were taken care of in that moment! I'm forever grateful and extremely pleased with the customer service.
James Watson
8 months ago
Heard & Associates has been excellent to work with for my small business taxes. Mr. Heard knowledgeable, professional, and extremely detail-oriented, which gives me real peace of mind. He took the time to explain everything clearly, stayed on top of deadlines, and made what’s usually a stressful process feel easy. Communication was smooth and timely throughout, and I always felt confident that my business was in good hands. I highly recommend Heard & Associates to any small business owner looking for a dependable and trustworthy accounting firm.
James Watson
8 months ago
I’ve had a great experience working with Mr. Heard. He’s knowledgeable, thorough, and made the entire process stress-free from start to finish. Everything was explained clearly, all deadlines were handled on time, and I felt confident knowing my return was done accurately. Communication was easy and professional, and he was always quick to answer any questions I had. I highly recommend him to anyone looking for a reliable and trustworthy accountant.
JUANJOSE CINTRON
9 months ago
Excellent professional, quick to reply and very helpful and thorough advice.
A 143
9 months ago
Professional!
Issa Salat
9 months ago
Very professional.
Yore Omerey
9 months ago
I was really stressed as a small business owner in this financial climate especially with the intense work I do. Mr. Heard respected me as a small business owner and created a business model to get me back on track.
He brilliantly solved long and short term issues with immense professionalism. I felt heard, I felt protected, and educated in the process. He was generous with his time and genuinely cared about the success of my company. The service was thorough and cost effective, he has my gratitude. I highly recommend them!
He brilliantly solved long and short term issues with immense professionalism. I felt heard, I felt protected, and educated in the process. He was generous with his time and genuinely cared about the success of my company. The service was thorough and cost effective, he has my gratitude. I highly recommend them!
Julian Howard
10 months ago
Extremely knowledgeable and professional — they made the entire tax process smooth and stress-free.
Always available to answer questions and explain everything clearly.
I highly recommend them for anyone looking for accurate, efficient, and trustworthy tax services.
Always available to answer questions and explain everything clearly.
I highly recommend them for anyone looking for accurate, efficient, and trustworthy tax services.
Demetria Dotson
10 months ago
Heard & Associates have always been top tier!
I had such a great experience with Heard & Associates! Mr. Heard was professional, patient, and really took the time to explain everything in a way I could understand. The company made filing my taxes so easy and even helped me get my finances more organized for the future. You can tell they truly care about their clients. I’ll definitely be coming back every year and recommending them to my friends and family!
I had such a great experience with Heard & Associates! Mr. Heard was professional, patient, and really took the time to explain everything in a way I could understand. The company made filing my taxes so easy and even helped me get my finances more organized for the future. You can tell they truly care about their clients. I’ll definitely be coming back every year and recommending them to my friends and family!
Brandon Atkins
10 months ago
I’ve been working with Heard and Associates for both my personal and business tax preparation and consulting, and I couldn’t be more satisfied. They’re professional, knowledgeable, and always take the time to explain everything clearly.
They helped me organize my business finances, maximize deductions, and develop a tax strategy that truly fits my goals. I really appreciate their attention to detail, quick communication, and how they make what could be a stressful process feel easy and efficient.
They helped me organize my business finances, maximize deductions, and develop a tax strategy that truly fits my goals. I really appreciate their attention to detail, quick communication, and how they make what could be a stressful process feel easy and efficient.
Whats The Word Media Inc.
10 months ago
Working with Heard & Associates has been one of the best business decisions I’ve made. Their professionalism, attention to detail, and commitment to accuracy truly stand out. From day one, their team made it easy to get organized and stay on top of everything — especially when it comes to bookkeeping.
They’ve completely transformed how my business handles its financial records. Every transaction is tracked, categorized, and explained clearly, so I always know where my money is going and what my cash flow looks like. Their bookkeeping services are not only thorough but also easy to understand — they take the time to explain reports and help identify opportunities to save or scale.
What I appreciate most is their consistency and communication. They respond quickly, provide monthly updates without being asked, and make sure all my accounts are clean and compliant come tax time. It’s rare to find a team that combines deep expertise with such genuine care for their clients’ success.
If you’re looking for an accounting firm that truly treats your business like their own — especially when it comes to keeping your books in order — I highly recommend Heard & Associates. They’re reliable, transparent, and simply excellent at what they do.
They’ve completely transformed how my business handles its financial records. Every transaction is tracked, categorized, and explained clearly, so I always know where my money is going and what my cash flow looks like. Their bookkeeping services are not only thorough but also easy to understand — they take the time to explain reports and help identify opportunities to save or scale.
What I appreciate most is their consistency and communication. They respond quickly, provide monthly updates without being asked, and make sure all my accounts are clean and compliant come tax time. It’s rare to find a team that combines deep expertise with such genuine care for their clients’ success.
If you’re looking for an accounting firm that truly treats your business like their own — especially when it comes to keeping your books in order — I highly recommend Heard & Associates. They’re reliable, transparent, and simply excellent at what they do.
david mason
11 months ago
I can’t say enough great things about Heard & Associates! They handle all of my business bookkeeping and S-Corp taxes for my heating and cooling company, and the experience has been outstanding. Their team is professional, reliable, and truly cares about helping my business succeed. I’m beyond grateful to have found such a knowledgeable CPA firm, and I look forward to continuing to grow my business with their support. Highly recommend them to any business owner looking for trusted financial guidance!
Take the Stress Out of Self-Employed Taxes
Whether you are new to freelancing or ready to stop overpaying, Heard & Associates LLC handles your quarterly taxes, deductions, bookkeeping, and filings, so you keep more of what you earn and lose the tax-season dread.