Brewed Awakenings - Built It, Lived It...Retired!

Jill’s entrepreneurial journey began twenty years ago. Having spent most of her adult life crunching numbers and doing what CPA’s do best, Jill’s ordinary workday took an unexpected detour. One of her longtime clients floated an idea about starting a payroll company. He would provide the capital; Jill would run the business. Same partnership, different investments. On paper, it made sense. With her strong management skills, a reputation for getting things done right, no conflict of interest since her current firm did not offer payroll services and knowing the business inside out, logic said it was time to take a chance; still Jill was hesitant. Although she was intrigued by the prospect of owning her own business, this was not a decision she could make lightly or on a whim. Running every aspect of a payroll service would be no small undertaking and she needed to carefully weigh the pros and cons before taking a leap of this magnitude.

Her client was convinced it was a great idea and gave Jill the time she needed to decide, although he was persistent in keeping the idea alive. Not once, not twice but for an entire year, he returned to the conversation. Finally, Jill decided it was time to embrace the challenge. “I am proof that the best business plans aren’t always mapped out step by step or drafted in a boardroom. Sometimes you just make the decision to jump in and figure it out as you go. Persistence, thy name is Payroll.”

Pay Day Payroll came to life with a simple name and a clear mission,” we do it all” from payroll to taxes and everything in between. Clients could trust our expertise and stop worrying about delays, deductions, inaccurate employee paychecks, or penalties for late tax penalties. The office was located upstairs above one of her partners businesses. “Definitely a prime location if you love the smell of ambition and fast food,” she laughed. “It was time to get to work and roll up my sleeves.”

Those first six months were a real learning curve with no paycheck and extreme exhaustion. Getting started meant having to purchase a state-of-the-art software system, necessary supplies and relying on a client list that consisted of her partner’s businesses and a couple of former CPA clients who needed payroll services. Not exactly a stampede, but it was a start. “Even though I knew it would be like this for a while, there were days I definitely wondered what I had gotten myself into.”

Building a business is anything but passive. The real work of connecting with new clients, ensuring financial stability, and making sure the whole operation stayed on track was critical for success. The hours were long and sleep was a luxury rarely afforded. Honestly, if I hadn’t been single and had set aside some savings, I’m not sure I could have kept going. I knew patience was key and I was confident the financial landscape would soon change and it did. By the end of the first year, we had about thirty clients and I was finally able to take a small paycheck.

Feeling grounded and optimistic, Jill knew it was time to take things to the next level. Help arrived when a former co-worker and friend joined her on the journey. Together they got to work building the business. Networking quickly became their new game. They joined just about every networking group throughout the Tri-State, and before long, new businesses hopped on board.

By the fifth year, business was booming, and it was time to add employees to the mix. That’s when things got really real. “Suddenly, I was the 'boss'". (Cue the existential dread.) “I quickly realized that being in charge isn’t easy; sometimes it felt like I was the villain of the story. Think about it, you interview someone, check their background, and then trust them with everything you’ve built, your clients, your reputation, and in a way, your future. One of the biggest lessons I learned was realizing that, while I was deeply passionate about the business, my employees often saw it simply as their job, even when they loved it. Expecting them to share my level of enthusiasm and perfectionism just wasn’t realistic or fair. It took time to understand that their perspective was different, and that was okay.

A few years later, she married Randy. It didn’t take long for Jill to realize she wanted and needed to spend less time at the office and more time at home. She shared a Facebook memory that really stuck with her, a picture of her three dogs, captioned, “I’ve seen my family about six hours this week.” That was when she began cutting back on hours and taking more time for herself and her family. She and Randy often spoke about retirement, but at that point, it was a distant dream. That is until 2020, when Covid turned the world upside down. She began to think more and more about retirement and began to plan for it. 2025 marked her twentieth anniversary as a business owner. She felt it was the perfect time to go ahead and take early retirement. 

These days, Pay Day Payroll continues to thrive, serve the community and provide outstanding options and services. As for Jill, she spends much of her time volunteering for her church, helping out friends and promoting local businesses.

It's difficult to capture twenty years of work, stress, and accomplishment into a brief article. To wrap up our time, I asked Jill if she would share her thoughts and advice about the realities of entrepreneurship:

“Well, let me say first and foremost, business ownership is not good for family life. The myths around business ownership suggest you can make your own hours, be your own boss, and make a lot of money." Jill then reflected on her experience and shared several hard truths she learned along the way:

• You're always on call.
• When something goes wrong, it’s on you.
• Realize that business needs come before your paycheck, personal life, and/or vacations.
• Make sure the business is something you know inside and out.
• Have at least a couple of years of income saved to live on.
• Expect long hours and forget about vacations.
• Have start-up capital.
• Find a location.
• Obtain necessary licenses, permits and insurance.
• Obtain a Federal ID# (IRS Form SS4).
• Register your business with the Secretary of State.
• Open a business checking account.
• Check with an attorney for business structure.
• Join networking groups to promote your business.
• Promote and build up other small businesses along the way.