The Question We Never Asked

Right now, we have a house sitting on the market. Three months. No offers. It's a buyer's market, prices are soft, and we listed in a window that has not been kind to us. We will probably lose a little money on this one. Not a disaster, but not nothing either.

We bought this house in a high market. We're selling in a low one. This isn't the first time this has happened to me. Years ago I bought a home and sold it at the right time, made a solid profit, felt like I had it figured out. Then I bought again, at a high, and now I'm selling at a low. Same person. Same intentions. Different point in the cycle.

That's the part that took me a long time to understand. Everyone tells you the housing market goes up. Nobody tells you it goes up and down on a cadence nobody can predict, and where you land in that cadence when you buy or sell can be the difference between a profit and a loss, with almost nothing to do with how smart you were going in.

Life works the same way. You have high years and low years. High months and low months. Some of that is market forces outside your control, and some of it is just the natural rhythm of things changing, your perspective shifting, your environment moving under your feet. Nobody talks about this enough either. High and low is normal. It doesn't mean something is wrong with you. It means you're a person living through time, and time is not a straight line.

I bring this up now because I'm sitting inside one of those low moments and it's forcing me to look at something I got wrong before the house ever hit the market.

When we listed, I brought in a realtor, we talked pricing, we talked strategy, and we went with it. Reasonable due diligence. But three months in, sitting with no offers, my wife has a list of fixes. Change this, remodel that, put more money into it. And I'm sitting here thinking maybe we should have priced it more aggressively out of the gate. Maybe one big reduction instead of the string of small ones we've done. Maybe if we drop again we're just bleeding leverage we won't get back.

Round and round. Everybody's got a theory about what we should do differently now. But that's not actually the problem.

The real question surfaced when I asked myself why we never talked about this before we listed. Not the pricing. The scenario planning. Nobody sat down and asked what happens if this doesn't sell quickly. Or what happens if it doesn't sell at all for six months. We never asked that question. We just had hope.

And when I really dig into why, the answer is almost embarrassingly simple. We were busy. Life was moving, work was moving, and we didn't dedicate the time to sit down and think it through. It wasn't that we're bad planners. It's that we never prioritized the conversation. Nobody blocked the time. The question of what do we do if this doesn't sell never even made it onto the agenda, because we never built an agenda in the first place.

This is the same failure I've watched happen on job sites for years, just wearing a different outfit. A project team does due diligence, builds a schedule, identifies some risks, and feels good walking into execution. But due diligence isn't the same as a management plan. Identifying a risk isn't the same as deciding, in advance, what you'll actually do if that risk shows up. The teams that recover fast from a setback aren't the ones who got lucky and avoided the setback. They're the ones who had already asked the uncomfortable "what if" question before the pressure was on, so when the setback landed, they weren't inventing a plan and managing their emotions at the same time.

That's the whole difference. Clarity doesn't stop the down cycle. Nothing does. The market moves, the schedule slips, the scope changes, the house sits. That's not a failure of planning. That's just what cycles do. What clarity actually buys you is speed getting out of it. If we had sat down before listing and asked what our threshold was for a price drop, what our timeline tolerance looked like, what we'd do at the 30 day mark versus the 90 day mark, we wouldn't be having a reactive, slightly tense conversation right now about remodeling versus repricing. We'd be executing a plan we already agreed to. Instead we're improvising under pressure, which is the most expensive way to make a decision.

I've noticed this pattern in my own life outside of houses too. I go through stretches of extreme growth and execution, followed by stretches where I have to rest, reflect, and do the front end thinking I skipped the first time around. I used to think the growth phase was the important one. Now I think the recovery and planning phase is where the actual leverage lives, because that's when you get to ask the questions you were too busy to ask while you were moving fast.

I'm not going to pretend I know how this house sale ends. I'm not a predictor of markets, and I suspect all of us have more high years and low years ahead, because that's simply how this works. But I do know what I'm taking from this one. The lesson isn't price the house better next time. The lesson is put the plan in place before you need it, so the low cycle doesn't catch you standing there with no answer, just hope.

Nothing worse than walking into a crisis with no plan. Talk about the risk before it's an emergency, not after.

Earn your success. Every day.