Stop Making Financial Decisions
Based on How You Feel

A husband and wife. A piece of property they were about to sell. And a decision they couldn’t seem to make.

Do they do a 1031 exchange to defer the taxes? Do they pay down debt? Do they take the proceeds, pay what they owe, and reinvest the rest? It seemed like it should have a clear answer. But every time William Bissett thought they were getting close to one in a recent phone call with the prospective clients, the husband would shift direction.

One minute he was tired of owing people money and wanted to eliminate the debt. The next minute the tax bill felt unbearable and the 1031 made more sense. His wife put it plainly during the call. She couldn’t get a straight answer out of him.

It Wasn’t Indecision. It Was Invisibility.

William’s read on the situation was immediate. The husband wasn’t being difficult or inconsistent. He was making decisions the only way he could given what he had in front of him, which was nothing. No projections. No side by side comparison of outcomes. No visibility into what either path actually looked like a year, five years, or ten years down the road.

Without that visibility, every decision defaults to feeling. And feelings shift. One moment the emotional weight of owing money is loudest. The next moment the thought of writing a large check to the IRS takes over. Neither feeling is wrong. But neither one is a financial plan.

What Planning Actually Does

This is the gap that a real financial planning conversation is designed to close. Not to make the decision for the client, but to replace the back and forth with something concrete. What happens if you do the 1031? What does that look like in year three, year five, year ten? What happens if you pay down the debt instead? What does cash flow look like, what does the balance sheet look like, and how does that affect everything else you are trying to accomplish?

When you can see the outcomes side by side, the decision stops being about which feeling is loudest in the room. It becomes about which path actually lines up with where you want to go.

Feeling vs. Knowing

William describes this as the difference between feeling and knowing. Feeling is what you are left with when the picture isn’t clear. Knowing is what becomes possible when a plan gives you the vision to see what’s actually ahead.

That distinction matters for business owners and non-business owners alike. Major financial decisions, whether they involve real estate, business capital, tax strategy, or retirement planning, deserve more than a gut reaction. They deserve a framework that lets you see the future clearly enough to move toward it with confidence.

If you have ever found yourself going back and forth on a financial decision without being able to land anywhere, chances are the problem isn’t the decision itself. It’s that you don’t yet have the visibility you need to make it.

That’s exactly what the planning process is for.

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Stop Making Financial Decisions Based on How You Feel  | Portus Perspectives

 [00:00:00] 

So I had a meeting last week with a prospective client. It’s a couple. Um, it was actually a phone call and successful business owner, um, up in Blowing Rock area, accumulated a nice net worth. Uh, mainly what they’ve done is accumulated most of it in rental real estate. And so much like most of our potential clients that came to us as, uh, with kind of a burning question, which is we’re about to sell a, a nice piece of property and we don’t know what to do with it.

Do we do a 1031 because we’re trying to defer delay taxes? Do we pay down debt? Do we just take the proceeds, pay taxes, and invest it into, you know, something else? You know, what should we end up doing with it? It’s a great conversation. Husband, wife, um, husband and I, [00:01:00] or wife and I talk for a few minutes about, you know, the future and planning around the future and understanding this, that and the other thing.

And then the husband. You know, started asking a couple questions about tax deferral paying down debt, and he mentioned a couple times that he was tired of owing people money and you know, the wife jumped back into the conversation. At that point in time, she was like, she’s like, I just can’t get an answer from him.

He keeps going back and forth. One minute he wants to pay down the debt and another minute he wants to do the 1031 because he doesn’t want to pay income taxes. And it caused me to kind of pause and think, and I was like, this is a great point. I was like, what you’re getting is you’re getting somebody that’s going off of feeling, how does he feel at that moment in time?

Does he not want to owe somebody money? Um, or does he not want to pay taxes? And I was like, he doesn’t, he keeps going back and forth in, in this instance because. Um, [00:02:00] he doesn’t have any visibility. He doesn’t have a vision. He doesn’t know what happens if he does X versus what happens if he does Y. And so, you know, for them that that potential planning conversation that we can have with them starts to help to answer that question, right?

What happens if, what happens? What happens if you do this? What happens if you do that? And then starting to put the plan around, around those scenarios so they can see and understand and, and really get beyond the feel and, and actually truly know and understand what direction they want to take in it.

And you know, that’s, again, it’s just part of the planning conversation. Business owner, non-business owner, it doesn’t matter. Being able to see it is so much better than, than being able, than having to. Feel it, right? So you’re dealing with two different senses and I’m a huge advocate of the planning process because I believe it gives that vision into what the future might look like.

So, uh, [00:03:00] don’t shy away from planning.​ 

ORIGINAL MEDIA SOURCE(S):

William Bissett: Feeling vs. Knowing: Why Vision Is the Missing Piece in Your Financial Plan | Portus Perspectives

Originally Recorded on May 3, 2026

Portus Perspectives: Episode 14

By /Published On: May 8, 2026/