I was terminated from my most recent employer in October 2025. My termination came two weeks after they laid off two VPs who had been with the company for over 10 years. They were let go for budgetary reasons. I was let go for “failure to disclose that I own and operate a bookkeeping business.” For context, I was working as a staff accountant for a student transportation company. My bookkeeping clients and target market are small businesses within my area. Company revenue is generated from contracts between the bus companies that the company owns/acquires and local school districts. Since I didn’t disclose, HR was not able to assess if there was a conflict of interest. This was all stated in my termination letter. I then filed to collect unemployment which was held up by said company saying I voluntarily resigned. After providing unemployment with my termination letter, they determined there was no misconduct on my part and that I was eligible to draw my unemployment benefits for the two weeks I did not work. As of November 17, I have been performing contract work through a local staffing agency. My goal has been to secure another full time job.
However, the agency called me Monday morning to let me know the client I was performing work for paused my contract due to the short week with the holidays. There is a good chance the contract will resume after the holidays. After much thought and consideration, I am entertaining the idea of collecting unemployment benefits and going all in on getting more clients for my bookkeeping business to generate a livable income.
To all of my fellow entrepreneurs who have transitioned from employee to business owner – please your share insights (the good, the bad, and the ugly.)
Posted by Quietstorm_2394
5 Comments
This sounds like a math problem. How much money do you make from the number of clients you have and how much would you make if you had X more clients. It also sounds like a control thing, and clearly you’re more in control if you’re running a business. But back to math, can you get more clients before the unemployment runs out? Can you get yourself health insurance or whatever that a regular job has that you want? It sounds like you should go all in, but this is a highly personal question so my real answer is this: trust your gut. My follow up advice is this: niches are generally good, so if you’re already working for people in a specific industry, that’s bonus points for your all in plan, IMO.
Thank you for your feedback! I have $20k left to collect in unemployment benefits, so about 6 months or so. Health insurance is a big factor for wanting full time employment. Having an entrepreneurial spirit, I do desire control of my time and finances. I would say 4 or 5 additional clients should replace my monthly salary. I price clients uniquely based on their bookkeeping needs (transaction volume, profit margin, number of bank and credit card accounts, etc.)
Sorry to hear the separation happened to you but if you believe in your bookkeeping business then maybe going all in is a smart call! Let’s assume you go all in. The number 1 piece of advice I can give you is get a simple website together, set aside 1,000 of your savings to generate leads from Google search pay per click or instagram ads. Set the daily budget max very low and see if you can generate 1-3 good leads per 25 of spending. Buy very specific words let me Bookkeeoing – service – your city or state. *Do Not* buy general keywords like Bookkeeper as you will lose you money. Get good at cheap lead generation then wow the clients you have and new ones and you will be on your way!
This is tough because you have a relatively short period of time to bring on 5 new clients and generate livable revenue. Further, bookkeeping is a crowded market and you’re going up against many better established competitors. u/DuctTapeMakesUSmart makes a good point to specialize in serving a niche. That helps distinguish you and makes it easier to create messaging and content. Your advantage is that you’ll be operating with very low overhead and without the burden of loans to get started.
It sounds like you have the fire to face these challenges and I’m inclined to encourage that route. Just don’t underestimate how difficult it could be to reach a comfortable place with new clients you need.
That’s a tough spot but honestly sounds like a blessing in disguise. Getting fired for not disclosing a side hustle when there wasn’t even a real conflict is pretty ridiculous, especially right after they axed those VPs for “budget reasons”
If you’ve got some unemployment cushion and already have bookkeeping clients, this might be the universe telling you to just go for it. The worst that happens is you end up back in corporate accounting in a few months, but at least you’ll know you tried