So, those of you who follow along with this publication know that this year I accepted a position as an assistant school softball coach to stand up the first team softball team for our middle school.
Who in the world am I to have accepted this (volunteer but very serious) role? Nothing about my recent history would let any outside observer think “Yep, she should be a middle softball coach”.
I haven’t played a game of softball in over 20 years.
We haven’t pursued that sport for our kids.
I haven’t seen good softball coaching in 2 decades.
I haven’t been around the game’s culture.
I don’t know how to run a softball practice.
Y’all, I don’t even have a child on the roster! My daughter is technically not old enough to play, but I convinced the school to let her be the “manager” so she can be with me and the team and learn to play during practices (because, fun fact, she is not actually a softball player…yet). And so by making her the manager,, I am not completely neglecting my entire family just to have a lot of fun for myself.
All this to say, I am wildly unqualified for this job.
I knew it would be so hard.
I knew I would feel like a huge dummy, but was ready for the “I am such a dummy” feeling so I can hopefully get to the “look at me doing a good job” feeling.
But I have a vision of what things could look like if I put in the hard work (by my calculations, we should be state champions by daughter’s sophomore year).
And I consciously thought about what qualifications I did bring:
I still know the basic rules.
I can still hit, catch, and throw which is kinda necessary to demonstrate skills and to lead a practice.
I am good at showing up prepared when I really care about something (Our team Google Drive situation is top notch).
I am really good at watching and noticing excellence and saying “I want to be around that”. The 2 other coaches are amazing humans and softball coaches.
Because I was particularly unqualified to be a coach, I have had to work harder than some other more qualified new coaches might have to work.
I have had to listen to a lot of podcasts and YouTube about drills and strategy, etc.
I had to really study the rule books for our league.
I made sure I was under the influence of 2 much more experienced coaches.
I admitted my limitations to the other 2 coaches and asked them to be extra patient with me.
I had to tell the other coaches that I couldn’t write any practice plans until I watched several practices that they organized and ran.
All this reminds me of exactly how I felt when I started my bookkeeping business 7 years ago.
So it begs the question…Should we do things that we know we are not qualified to do or not?
Y’all know I preach that aspiring bookkeepers have to know what they are doing before taking on the responsibility of managing a client’s books. I hate when I see gurus selling courses talking about how easy it is to make 6-figures while nursing your baby or sitting on the beach.
But it is a Catch 22. Because I also don’t think that anyone ever feels qualified when they start their bookkeeping business. Just like I’m guessing all serious 1st year softball coaches (even the ones that brought a lot more qualifications than I did) feel pretty unqualified, too.
So where does that leave those of us who dream of doing that hard bookkeeping thing?
Write out what you bring to each of the 4 steps of building a bookkeeping business.
Know accounting fundamentals (This is soooo critical, y’all!!)
Know a bookkeeping software
Set up a business
Get clients
If your 4 lists are short, but you are motivated and smart and willing to study hard and work hard and learn all sorts of new things, well, get ready to put in the blood, sweat and tears to keep increasing your qualifications.
If your list is pretty long because you have a lot of qualifications, well what are you waiting for?!?. There is someone out there (like me) with less qualifications that is getting a jump on the same dream you have.
As you think about that Step 2, you might consider learning a bookkeeping software that not all of your competition is using. 👀👀👀
Our sponsor Puzzle is an up-an-coming AI powered software that is inviting all bookkeepers to see what they are all about. Go grab a time slot for a demo and see if you like what they’ve built. Then become the #1 Puzzle bookkeeper in the world! Learn every single button. Every single quirk. Every single keyboard short cut and hack.
Bang that graphic to sign up for a demo.
💰 Puzzle is offering anyone who books a demo a $100 Amazon gift card.
💰 The Ambitious Bookkeeper, Serena Shoup is offering $200 off her signature Elevate program with code REVAMP*. Elevate your skills & client experience in just 4 weeks to become the collaborative controller or CFO that your clients need. Payment plans available.
💰 Bookkeeper Launch is having a 30% off sale with code spring30*. This is the course I took to get started. I love that is has lifetime access to the program. They also are having an additional 75% off sale on their Pain Points Bundle with code nopain75. That would be for folks who already have an established business but are feeling a lot of pain that comes with managing their business.
💰 Regretting not getting in in the spring sale deals from Veronica Wasek’s 5MB Academy?* Well I got you! You can still use code BSH15OFF for 15% off.
Please always send me any news of deals that you hear of that others might benefit from.
Items with a “+” are hosted by me. All these events can be viewed and registered for in the DESCRIPTIONS of each event on the Bookkeeping Side Hustle Calendar.
📅 +April 29: Puzzle Demo. Join me in my conversation with the founder of Puzzle and determine if this bookkeeping software would be a good fit for you. You can also book your own demo HERE.
📅+April 30: Behind The Hustle: Ryan Perch. SUBSCRIBE to the YouTube channel so you don’t miss it!
📅 May 12, 28, and June 3: Three-part webinar series covering durable AI-skills, firm-wide adoption strategy, and hands on GPT-training
May 13 | Upskilling AI: durable skills for an evolving profession
May 28 | From testing to standard practice: AI adoption for firm leaders
June 3 | Building your first custom GPT: a hands-on training session
📅+May 21: RESCHEDULED Digits Demo with 2026 Updates. Digits will be sharing new updates and giving us a live demo.
Subscribe to the YouTube Channel
🌶️A member (who wished to remain anonymous and I posted for her) asked if bookkeeping is boring? Gotta admit that I have often wondered the same! Even after doing this for 7 years! 😂 I certainly wondered the same at the very beginning before I started my business. Though, I needed to earn income for my family and asking myself “but what if it is boring” wasn’t really a luxury I could afford. This discussion is top notch. So insightful. And yes, I find bookkeeping a bit boring, so that is why I only do certain flavors of it.
🌶️ What do you do if you have a client that has 2 businesses but does not want to pay for 2 subscriptions to a bookkeeping software. The seasoned veterans had some words to share about this.
💪 Amy Loveland joined us on the Behind The Hustle show last week. Great interview! She brought in some interesting apps in her tech stack that have not been mentioned on the show before. She also shared an online accounting course that I had never heard of that taught her the Debits & Credits when she was starting on this journey
💪 You probably just received the email from Intuit announcing the 2026 QBO ProAdvisor Recertification. Akadian has the only program that I know of that has a formal instructional resource for helping you study for the QBO recertification exam*. And every year, I get to ask myself the question “Should I keep my QBO ProAdvisor certification since I only work with FreshBooks clients now”?
💪 For $39 a month you get to put yourself around the Hi-Tech Smarties in our industry. There was a post on LinkedIn by Chad Davis that caught my eye. He is one of the biggest brained accounting business owners out there. He runs AutomationTown, a community for accountants who build with AI (or who want to). The landing page says there was a Claude cohort starting in May. But there appears to be a lot happening for just $39 per month.
💼 The Job Guide had a few jobs added to it! Be sure to check it out - especially if you live in the DFW area!
Don’t forget the standing opps on my Find A Freelance Job article. 1099 and W-2 opps.
🎪I recently added another $31.19 monthly recurring expense to our family budget. That is how much it cost to get another $1,000,000, 10-year term life insurance policy on my husband.
We are less than 15 months out until he retires from the Navy with a military pension (yes, he is counting the days).
If you had asked me a couple years ago I would have thought we had sufficient life insurance coverage. We both have 20-year policies in place that will last until our youngest child is out of the house. And in the meantime we are deliberately building our personal balance sheet so that we will be “self-insured” by the time those 20-year policies expire.
But it hit me that part of my “self-insured” calculation counts on us getting that pension he worked hard for.
So I started to get very nervous about him dying before June 1, 2027 when the pension kicks in.
That risk exposure of losing out on the pension was way too high for my conservative self. It felt like a really bad gamble and started keeping me up at night.
I’ve always estimated his stream of pension payments would have a Net Present Value of ~$1,000,000 (very conservative estimate).
Would I pay $31 per month for the next 15 months to guarantee that I was eligible for someone to pay me an NPV of $1,000,000? Absolutely!
So I told my husband that I was nervous that he was going to get hit by a bus and thought we need just take a look at what another $1,000,000 in coverage would cost.
The process to get life insurance quotes is really quite easy, y’all. I just called a friend who is in that business and he shopped quotes for us after filling out some questionnaires. My husband didn’t even have to get a nurse visit for this policy (we did have to have nurse visits for our older policies).
I was prepared to spend a LOT more per month because I thought we’d just have the expense until June 2027. But now I’m thinking we might just keep the policy for 10 years it since it is so cheap.
I hope, hope, hope you have life insurance (even if it is more expensive for you for some unfortunate health reason).
I hope you talk about it with your family. Talk about how it is cheaper when you are younger. Talk about why the price goes up if you wait until you get sick. Talk about other ways to mitigate risks if you do have conditions that make you uninsurable.
In my family, we even briefly talked about how this term life insurance policy is void if the insured commits suicide in the first 2 yeas of the policy and why that makes sense if you think about it from the POV of an insurance company.
Get all those conversations about death out in the open.
🎢 Tonight I will be looking absolutely killer at our school’s auction. The theme is Saddle Up and I treated myself to a concho belt and a pair of jeans that I actually like (jeans shopping is the woorrrrssssttt!).
My bookkeeping business, Heritage Business Services bought a table for 10. My logo (that I made in Canva 5 years ago) will be on all the signage. I feel very grown up. And after our giving to our church, the school gets most of our charitable giving for the foreseeable future. I lam pretty proud of this sponsorship that also comes with a little extra kick of the advertising for my business.
🎢 After my FreshBooks tutorials on YouTube, my 2nd main marketing strategy has been to host a free monthly Q&A for FreshBooks users. And it is really going downhill. I’ve been doing this open meeting for close to 3 years. There have been months where I’ve had upwards of 15 people on those calls. But in March 2026, I only had 4.
And last week for the April meeting, I only had 1 person on the call. 😭
It felt like such a gut punch. Humiliating, actually. And she was an accounting professional asking me questions about her own client. I stayed on the call for the full hour it is scheduled for. That attendee hit the lottery with me giving her personalized advice for free for a full hour!
I’m feeling really whiny about it all. I don’t want to change marketing strategies. I just want my regular ideas to work. Hmmmph.
Oh wait…as a business owner, I might have to try new things. Adapt. Continually learn new and better methods. Again…hmmmph. Do I have the stamina? That is the question.
⚡Some of you will be happy with keeping your bookkeeping business small (a side hustle, if you will). But here is my advice to someone who wants to build a million dollar bookkeeping business.
✉️So grateful to Julie C. for this comment. And YES, to leave comments on YouTube videos. It is free for you and really helps me! Also, you could always email or DM me if you ever buy any courses or Apps and ask if I have a referral link. I probably do!
I love these interviews! I’m grateful for you hosting and all the work that goes into that, and those who openly share- it’s what draws me to this community as a whole! What do you need from us? YouTube comments? Happy to do so- you’re always bringing value!
The Behind The Hustle stories are helping me figure out what is possible at the moment as I continue to work on building things out. It’s giving me peace and confidence to keep going!
Keep hustling!
Kate
-Chief Hustler-
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I am down right rabid about transparency and full disclosure. If a link, including Amazon Links, has a * beside it, it means it is either an affiliate link where I might receive compensation if you make a purchase, at no additional charge to you. Or it could be a tracking link that another business provided me to see how many readers click on that link.
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