Just Because You CAN Doesn’t Mean You SHOULD

The last time I moved myself was the LAST time I’ll do it. I’ve hired movers since, because I learned this lesson the hard way — I thought I was being smart.

Rented a U-Haul. Recruited some friends. Figured I’d save a few hundred bucks and get it done in a day.

What actually happened? Parking violations because I couldn’t find a legal spot for the truck. A borrowed van from a friend because one load wasn’t enough. More trips than planned because of friend availability. More hours than planned. More money than planned.

By the time it was over, I probably spent more money and I definitely spent more in time than if I had just hired movers from the start.

I was chasing pennies and tripping over dollars.

Here’s the thing about DIY. We do it for a lot of reasons. To save money. To stay in control. To enjoy the process, and sometimes just for fun.  SOMETIMES, however, just out of pride. And for a lot of things in life? It works great.

But there’s a version of DIY that costs you more than you bargained for. You’re smart. You’re capable. You just didn’t know what you needed to be saved from.

That’s the part nobody tells you upfront.

I recently worked with a client on a big-ticket deal. Sharp guy. Sophisticated. Does deals for a living in his industry and knows how to negotiate.

He initially wanted to handle it himself.

I told him: it’s about your position, not your skill.

Think about it this way. If you walk into an art gallery and say you don’t love the color blue, the artist might take it personally. But the gallery manager? They just walk you over to something green. Same gallery. Same artist, even. But a completely different outcome, because one person has the emotional distance to create space, and the other doesn’t.

When you’re the owner, every comment a prospect makes about your property lands differently. What someone else hears as honest feedback or personal preference, you hear as criticism. That closes you off. It stiffens the negotiation before it even starts. OR- the prospect knows you are the owner and never opens up about how they truly feel. If you can’t put your finger on what doesn’t work, its harder to find a solution.

And it gets deeper than that.

Once we found a better offer for my client, he was genuinely anxious about running into his original contact. Worried about the social pressure. Worried about disappointing someone he knew casually.

That anxiety? That’s not a negotiation. That’s a trap. And he walked right into it the moment he tried to do the deal himself.

My team stepped in, took over the negotiations, and got him top dollar from a willing buyer. It only happened once he let go.

I know how to sweat pipes. That is the activity of soldering copper pipes and fittings together to form a permanent bond so that liquid can pass through the pipes. These pipes provide water to your sinks, tubs, showers, etc.  I learned it years ago for some projects I was working on. 

But when I more recently needed a water shut-off valve installed in my condo — perched above other units — I hired a plumber without hesitation.

Not because I couldn’t do it. Because I’m not licensed here for that work. I don’t carry the insurance for it. And if something went wrong, it wasn’t just my home at risk. It was my neighbors’ homes too.

Knowing how to do something in one context doesn’t make it the right call in every context.

The same logic applies to taxes. If your return is simple, DIY tax software is probably fine. But the moment complexity enters the picture — changes in tax law, multiple income streams, investment properties — the cost of what you miss far outweighs the cost of hiring someone who does this every day. I started saving more money the moment I stopped trying to do my own taxes. Happy to introduce you to my guy, btw!

Real estate is no different.

We work in these markets every single day. We help people position their properties. We help people position their goals. We help people understand where they stand in the context of current trends so they can execute a strategy that actually works in their favor.

That’s not something you pick up on a weekend. It’s not something a quick Google search covers. And it’s definitely not something pride should get in the way of.

You might be the smartest person in the room. You might know how to negotiate. You might even know how to sweat pipes.

But just because you CAN do something doesn’t mean you SHOULD.

Sometimes the most sophisticated move you can make is knowing exactly when to hand it off.