September 2025 Progress Report

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I’m not the swiftest. It can take me a while to really understand something. Maybe even longer to be able to put it in words. This particular post is about small business generally, and some may even classify it as a rant. Either way, it is a valuable lesson I’ve recently been able to put words to, that applies to all small and micro business.

Once upon a time, I had a job at a micro-business. Low key office admin stuff.

My boss had mutually exclusive objectives that he didn’t seem to realize created conflict in his business plan. For years, I covered his ass, or bailed him out of problems he created because of a phrase he constantly used:

“I shouldn’t have to-” insert line item here.

That phrase drove me crazy. “I shouldn’t have to do -x- to -make this work-” I heard more often than not from my boss;

“I shouldn’t have to provide step by step directions for how to get here to a potential client”– While he lectured me that anything less than a 4star rating is an injury the business could never bounce back from.

“I shouldn’t have to do any of the admin work” While quoting the Ferengi Rules of Acquisition as how the business should be run.

“I shouldn’t have to supply paper/pens/etc” because the instructors are contractors, and if they need something, they should supply it themselves.

“I shouldn’t have to discount a client’s bill because they can’t show up to their own appointment on time” While having him undermine my work of upholding his billing policies whenever a client so much as squeakex to him about how they don’t like it.

“I shouldn’t have to train you, because you’re an adult and should be capable of figuring it out on your own” While being micromanaged, yet set adrift to essentially to create solutions on my own, without his input.

Even down to the lightbulbs: “I pay the lease on this suite. I shouldn’t have to buy lightbulbs when the ceiling florescents burn out.”

I learned through observation, through covering his ass, that capable small business owners say things like “how do I fix -line item;” how do I do -line item;” “how do I improve -line item.”

They do not say “I shouldn’t have to.”

You don’t have to have the answer right away, but you do have to accept responsibility for asking the question. You must be willing to research the answer, implement a solution, and learn from the mistakes you make along the way.

Some mistakes will be expensive. Others will be a minor inconvenience. Some solutions will have cheap work-arounds, others you won’t have any choice but to bite the bullet and suck it up.

Either way, the only reason you, as a small or micro-business owner should be saying “I shouldn’t have to -x-” is when you’re being charged taxes for a liquor license when you’re running a children’s daycare (an extreme example, but you get the point).

I learned this particular lesson well. I’ve observed what happens when that’s the mantra you run your business by. “I shouldn’t have to-x-” may get you sympathy in the beginning. Band-aids, and even a small bail out or 12.

But Real Business owners, people who are serious about bootstrapping a business because there are no other options, say “How can I do/fix/improve -x.”

Real business owners take responsibility. Real business owners step up. Real business owners understand if they’re only willing to put in 75% effort to make their business successful, they can’t reasonably expect any employee to be willing to put in more than 50% effort on their dream.

Yes, real business owners get tired, they get beat down, they get frustrated about the lack of profits, or about the employees who are more a drain than a help. Real business owners question if the migraines are worth it. They may even fantasize about how much easier it was to just work for someone else, because then you could say “I shouldn’t have to do -x- because that is Not my job.”

Being a business owner is messy. It’s unfair. It’s exhausting and confusing.

Real business owners don’t say “I shouldn’t have to,” because they’re already too busy working on solutions to the problem.

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