You hover the mouse over the tab, the one labeled “Business Banking Portal.” You’ve already logged in-that’s the easy part, the mechanical compliance of the modern broker who knows the password by heart. The hard part is looking at the actual balance, and harder still, scrolling to see the transaction history. Before the page even fully renders the five-figure number you instinctively know is incorrect, you hit Command+W.

We confuse complexity with messiness. Messiness we can fix. Complexity takes expertise, but first, you have to admit the mess exists. I do this too. Not with bank accounts, but with the small, insidious things that accumulate. I checked the fridge three times this morning, convinced that if I stared long enough, a new container of hummus would materialize. It’s the same logic: avoidance leads to magical thinking. If I ignore the business P&L long enough, perhaps the $3,095 expense from five months ago will have politely identified itself.

It won’t. It never does. And every transaction you ignore, every receipt you fail to reconcile, adds a tiny, imperceptible weight to your shoulders. We call this ‘financial anxiety,’ but that term is too soft. This is an unreconciled debt to self-a debt that makes every decision feel heavy, murky, and ultimately, risky.

The real weight isn’t the tax bill. It’s the constant low-level thrumming of uncertainty, the suspicion that the number in the bank account is a lie. You might have $22,675 in operating cash, but if $1,555 of that is money belonging to a client trust account or an undisbursed commission, then you don’t actually know what you can spend. That lack of clarity is a form of paralysis.

This paralysis is why I had such an intense conversation with my friend Liam K., a dedicated grief counselor. I know, a grief counselor talking about accrual accounting sounds like a terrible party joke, but hear me out. Liam specializes in something he calls “unidentified grief.” He says it’s the kind that settles in when the loss isn’t officially named-the job you didn’t get, the friendship that faded without a fight, the business metric that died quietly and wasn’t officially audited or mourned.

Financial avoidance is precisely this [unidentified grief]. You’re grieving the loss of control, the loss of clarity, and the loss of wasted time trying to figure out what happened in Quarter 2. The fear isn’t of the number itself; it’s the fear of what the number implies about your competence, or worse, the fear that fixing it will take 45 hours of agonizing manual labor.

And here is the contradiction I live with: I know better. I’ve written extensively about operational excellence. I tell people to face their demons, yet I also understand that the moment the chaos becomes overwhelming, the brain flips a switch. It opts for predictable anxiety over the sudden, sharp pain of reality. Predictable anxiety is a dull anchor, but at least you know its shape. Reality is a tidal wave.

This is where the ‘yes, and’ principle comes into play. Yes, you are overwhelmed, and yes, the mess is probably worse than you imagine. But the realization that this specific problem-the messy books, the unreconciled accounts, the lack of a proper general ledger-is a solvable, systemizable problem is the great relief. This isn’t a strategy problem, or a sales problem; it is a foundational hygiene problem. Hygiene can be outsourced.

If you find yourself opening the bank tab only to slam it shut immediately-if you look at your quarterly reports and immediately feel a spike of nausea that you medicate with another coffee or another sales call-that is your soul telling you that you need operational clarity, not just another piece of business. You need a trusted third party to look at the books and tell you the truth, without judgment.

For insurance brokers, this feeling is exacerbated by the complexity of commissions, carrier payables, and the strict compliance needed for trust accounting. You need someone who speaks the specific language of your industry, someone who recognizes a direct bill commission payment versus an agency bill receivable immediately. That specialized knowledge immediately cuts down the 45 hours of manual labor to… well, a few simple conversations.

This is why I advocate so strongly for specialized help. We hire experts for legal counsel… Why do we assume we can run the operational backbone of a multimillion-dollar agency based on an incomplete QuickBooks file and sheer willpower? It’s hubris dressed up as bootstrapping.

I’ve seen firsthand the radical transformation that happens when an agency owner delegates this anchor. It’s not just financial relief; it’s mental bandwidth returned. Suddenly, the owner can think about scaling, product development, and staff retention-the things that actually move the business forward-instead of trying to find that one specific $5 transaction receipt from February 2015. They stop operating in defense mode.

For those who feel that acute, physical dread whenever ‘quarterly review’ is mentioned, I suggest looking for specific solutions engineered for your niche. You need partners who don’t just process transactions but understand the unique rhythms and regulatory pressure points of brokerage accounts. Finding that focused support is non-negotiable for scaling safely. It removes the emotional weight, turning the terrifying black box of your finances into a predictable, boring, and actionable dashboard. It allows you to finally mourn the time you lost worrying, and start planning for the future.