Runner-Up on Our First Try: What Best of the Best Taught Me About Small Firms, Big Rooms, and Year Five
You didn't start your business to be a bookkeeper. We did. $ You didn't start your business to be a bookkeeper. We did. $ You didn't start your business to be a bookkeeper. We did. $ You didn't start your business to be a bookkeeper. We did. $ You didn't start your business to be a bookkeeper. We did. $ You didn't start your business to be a bookkeeper. We did. $ You didn't start your business to be a bookkeeper. We did. $ You didn't start your business to be a bookkeeper. We did. $
I knew before I walked in the door.
Lookout Bookkeeping was named runner-up in the Bookkeeping & Payroll category of the 2026 Chattanooga Times Free Press Best of the Best awards. I found out the result before the gala on September 17.
And I didn’t tell my team.
Not one word. On purpose. (You can thank me for my crazy.)
Because here’s the thing. Watching my team sit in that room, waiting to hear who won our category, was one of the best parts of the whole night. The nerves. The side-eye glances. The “do you think we got it?” whispers. I sat there holding a secret and loving every second of it.
[PHOTO: Team at the gala table]
The Night Itself
The gala was at the Chattanooga Convention Center. It was fancy. It was a blast.
My good friend Ashley did my hair and makeup (and joined us for the evening), and she knocked it out of the park. Getting glam with a friend before a big night? Highly recommend.
The whole Lookout team showed up, minus Samantha, who couldn’t make the trip. After the awards, we stayed an extra hour to hang out and dance.
Yes, bookkeepers dance. No, you can’t see the video.
[PHOTO: Melissa and Ashley, glam-ready]
The Moment That Actually Mattered
The award was great. But it wasn’t the highlight.
During the evening, I had a moment with a team member who has been with me for five years. She told me she always has my back, and that she knows I’m doing the best I can with everything.
I don’t know how to put a dollar amount on that. I’m a bookkeeper, and I still can’t.
Running a business means you carry a lot that nobody sees. Hearing someone who’s been there from the early days say I see you, and I’ve got you? That hit harder than any placement on a winners list.
Who nominated us?
When we first got nominated, I had zero clue who put our name in. I didn’t nominate us. I’d never nominated us for anything.
Then, during voting, I asked one of our clients to vote for us.
Her answer: “I nominated you.” It was fun to hear & know at least one person who put our name out there for best bookkeeper.
Second Place, First Try. Here’s What That Proves.
This was our first nomination ever. We came in second.
We’re not a giant firm. We don’t have a marble lobby or a billboard on the interstate. We’re a small, remote team of bookkeepers who know our clients by name, and try to answer their questions in a timely manner.
Firm size does not equal quality. It never has. ***Link to my previous blog post on this topic? https://lktbook.com/2026/09/02/how-to-choose-a-bookkeeper-size-doesnt-matter/*** Well, maybe not since LI doesn’t like links in posts? I don’t know…
And here’s the part I want every small business owner to hear: once you make the top five, it’s a popularity contest. That’s not a knock. It’s the truth. If you’re willing to put yourself out there and ask for support, you can win.
It wasn’t that hard. It meant being willing to ask. Clients, referral partners, friends, family. Most people want to support you. They’re waiting for you to tell them how.
So if you’ve been sitting on the sidelines thinking awards are for the “big guys”? They’re not. Anyone can be nominated. Anyone can win.
Oh, and We Turned Five This Year
Lookout Bookkeeping opened on February 7, 2021. That means 2026 is our fifth year in business.
Five years ago, I decided to start a business doing what I had done for three years for another business; learning it on the job there, because as you know, I didn’t go to school to be a bookkeeper. I spent over 20 years working as an athletic trainer. And this year, I watched my team get dressed up and sit amongst giants as one of the top bookkeeping firms in Chattanooga.
Not a bad way to celebrate year five.
Congrats to Our People Who Took Home the Win
Some of the businesses I voted for (and told you to vote for) won their categories. Huge congratulations to:
- HHM, winner in the accountant category. We love it when clients work with them – they’re one of our favorite firms in town.
- Jelks Law, winner in the estate planning attorney category. No one else I would trust to put together an estate plan!
- TVFCU, winner in the credit union category. And we love them for their support of small businesses with their Idea Leap Grants each year (applications are open for 2027)!
Chattanooga has some great businesses, and I’m proud to work alongside these folks.
See all the 2026 winners here: https://winners.bestofchatt.com/
Thank You. All of You.
To my team: you are the reason any of this happened. Thank you for showing up, every day and on gala night.
To our clients: thank you for trusting us with your books; for voting, sharing, and nominating us especially (because we didn’t even nominate ourselves).
To our supporters, referral partners, and friends: thank you for every vote, share, and “you’ve got this” text.
And to my family: thank you most of all. You carry more of this than anyone sees.
We’re Coming Back Next Year
We’ll be asking for your nomination and your votes again in 2027. No paid ads. No billboards. Us, asking you.
Second place on the first try is a great start. We’re going for the top spot.
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