This is the Back Office
A Place for Bookkeepers, by a Bookkeeper
The part of the business no one sees
Most people only see the end result. A business that looks successful. A bookkeeper who seems established. Someone confidently taking on new clients. What they do not see are the systems, decisions, processes, and years of learning that made that possible.
The Back Office exists for that unseen work.
This is a space for bookkeepers, and aspiring bookkeepers, created by someone who is actively doing the work. The wins, the mistakes, the systems that helped, and the ones that did not.
When I started my bookkeeping journey, I consumed everything I could. Thousands of YouTube videos. TikToks. Instagram Reels. Facebook groups filled with advice.
Some of it was helpful. A lot of it was surface level.
It was often the bare minimum and rarely addressed the situations that actually come up once you are inside the work.
How I ended up here
During this journey, I had several people ask me the same questions.
“How did you do it?”
“What made you start?”
Their curiosity always stood out to me.
At the time, I was living a stable, comfortable life. I am a mom with two wild and active boys under three. I was not chasing chaos or trying to escape something.
Hi, I am Jessie Brundage, the owner of Oak and Ledger. I run a bookkeeping firm, I am exploring selling Squarespace websites, and now I am sharing my bookkeeping journey here in The Back Office.
It has officially been a year since I first felt the itch to start a bookkeeping business. Next month marks one full year since Oak and Ledger was legally formed, and today I want to acknowledge that.
This space is part of that celebration.
What I was doing before Oak and Ledger
If we go way back, I grew up in a small town in North Florida with fewer than 4,000 people. It was not overrun with franchises or chains. It was a community built by small businesses.
My father owned his own company, and watching him build it shaped me more than I realized at the time.
He worked long hours growing his business while also being present for his four daughters. He worked from home. He made it to our events. He showed me that entrepreneurship could support both work and family.
I wanted that life, even though I did not take that path right away.
Sports became my world. Soccer and softball, with softball taking the lead. That path took me to Stetson University on a Division 1 softball scholarship, where I was later inducted into the Hall of Fame.
Eventually, that chapter ended, and the next one began.
I earned my Master of Accountancy from Stetson University and accepted an audit position at Ernst and Young. It was not something I dreamed about as a kid, but it made sense for the path I was on.
And I liked it. I did not leave because of the hours, the intensity, or the corporate environment.
I left because something was missing.
What was missing
I loved audit. I was a high performer, and my decision to leave surprised a lot of people.
What I missed was connection.
My roots were in a small town where business was personal. Where relationships mattered. Where you knew the people behind the numbers. Around that same time, my boyfriend, now my husband, was living in three hours away. We had been together for years, and I knew I wanted to build a life closer to him.
At the same time, my grandmother, who handled the bookkeeping for my father’s business, could no longer keep up. My father needed help.
Moving from Big 4 public accounting to small business bookkeeping was humbling. But it was also grounding.
Looking back, it was the best decision I ever made.
The moment I pulled the trigger
Starting a bookkeeping business was not a dramatic leap. It was a slow, intentional decision.
I was doing bookkeeping for my father’s business. I was raising two young boys. I was running a household. I was doing a lot.
But I was missing the drive. The energy. The sense of purpose I used to feel when I played competitive sports.
That realization pushed me to build something of my own.
That is where Oak and Ledger began.
Why The Back Office exists
Bookkeepers need systems and support just as much as their clients do.
There are not enough honest conversations about operations, complexity, and what this work actually looks like behind the scenes without paying over $1000 to gain that access.
Not every client is a good fit, especially early on. Some businesses are simple. A service based solopreneur invoicing through QuickBooks Online can be a dream client.
Others have multiple point of sale systems, no internal processes, and no structure. That level of complexity can overwhelm a new bookkeeper quickly if you do not know what you are walking into.
The Back Office exists to talk about those realities.
What to expect here
This space will evolve, but at its core, it will focus on the behind-the-scenes work.
That includes networking, systems, client stories, challenges, decisions, trade-offs, and the things you only learn by doing the work.
Right now, I simply wanted a space to share this journey without managing another social media account or trying to explain complex ideas in a fifteen second clip.
If this resonates with you, I would love for you to follow along and subscribe.
A grounded invitation
This is not a place for shortcuts or overnight success stories.
It is a space for thoughtful work, strong systems, and bookkeeping businesses built to last.
If that resonates, you are welcome here.