Don't Quit Before the Turn

Current Market Conditions

You ever want to give up on something?

Not because you stopped believing in the dream…
But because you’re tired of losing?

I graduated college in December of 2006.

I was 21. Licensed. Ambitious. Certain I was going to make it big.

I’ve always believed in visualization. If you want something, you need to see yourself having it. But I’m not one of those people who thinks you just visualize and wait. You visualize — and then you work for it.

So when I graduated, I was already licensed and jumped right in.

Commercial. Industrial. Residential. South Side. South suburbs.

And it didn’t work.

I thought if I worked hard enough, it wouldn’t be that hard. But I was 21 and stupid. I had to learn.

Heck, I lived at home until I was 27.

Every morning I’d wake up at my parents’ house and run through my neighborhood. I lived close to my old high school. Every single day I ran past it thinking, I don’t want to be the guy who never left. Still living by his old high school.

I watched my friends get jobs. Move out. Start making money.

Then the recession hit at the end of 2008.

Two years in. Nothing to show for it. And now I was in the business that helped crumble the economy. Real estate was the laughing stock of the world.

I had negative $5,500 in my bank account.

And I’m not ashamed to say it, there were nights I cried myself to sleep.

Not because of the money. But because I was disappointed in myself.

I expect a lot out of me. And even when I had no proof… no closings… no clients…

I still believed in me.

Even when no one else did.

At 23 years old, at the lowest point of my life, I almost walked away.

A friend lined up an interview for me downtown. I remember driving there with a pit in my stomach. My whole life I had dreamed of following my dad’s footsteps and taking this company to another level. Sitting in that car, I knew something clearly:

If I took that job, I wasn’t just changing careers.

I was giving up on my dream.

I walked into that building. Saw the people in suits. The structure. The security. And I thought, I guess this is my life now.

I did the interview. I held back. I don’t know why. Fear maybe. Doubt. Pride.

The next day they called.

I didn’t get it.

And I felt relieved.

Relieved because I didn’t quit on my dream.

But something else happened that day.

Driving downtown, I felt alive.

The energy. The skyline. The movement.

I realized if I was going to make it in this business, it wasn’t going to be where I started.

It was going to be there. Downtown. 

I had no money. No office. No connections.

But at my lowest moment, I made a decision:

I wasn’t going to give up on the dream.
I was just going to chase it differently.

And that’s where the market is right now.

We are in the peak of multiple-offer season.

From mid-February to the end of March is when offers get the craziest. April and May lease deadlines are approaching, and buyers have to decide, renew, or go all in.

So they’re pushing all their chips to the middle of the table.

And here’s the part people don’t understand:

Buyers aren’t making bad offers.

They’re making great offers.

And they’re still losing.

Submit. Lose.
Submit. Lose.
Submit. Lose.

It’s defeating.

Some of these buyers were casually looking in December. No lines. Easy showings. Now? Packed open houses. Ten offers. Escalations that feel insane.

This is the buyer fatigue phase.

This next 45 days is what makes someone a buyer… or makes them a renter for another year.

People start to question themselves.

“Maybe it’s not meant to be.”
“Maybe we should just wait.”
“Maybe we should give up.”

It feels a lot like sitting in that car downtown, wondering if you should walk away from the dream because the road got hard.

But here’s what I’ve learned, in business and in this market:

The moment you want to quit is usually the moment right before the shift.

Because fatigue sets in.

By June, the lines shorten. The casual buyers fall off. The desperate ones either win or leave. And what’s left is a different market, not easy, but different.

The buyers who win this year won’t be the ones who never lost.

They’ll be the ones who refused to give up when it got uncomfortable.

Because sometimes the dream doesn’t change.

The strategy does.

And in this market, just like in life

If you don’t quit in the hard season…

You’re usually a lot closer than you think.

Demand picked up this week, and you can feel it. April lease buyers are starting to panic, throwing everything at deals, and sometimes it is still not enough.

A wave of new inventory hit the market, giving buyers a renewed sense of hope that they might finally land something.

Rates dropped again this week.

Contract signings rose again, showing buyers are still stepping up and getting deals done.

Multiple offer are the norm on new listings.

The downtown high rise market in the $750K to $2M range saw another dip in demand, especially for dated units. The contrast is striking. In the outskirts, buyers are stretching hard and throwing money at properties to win. Downtown, every dollar is scrutinized. Buyers are cautious and analytical, particularly when a unit needs updates. Condition and pricing matter more here than anywhere else.

High HOAs are a major factor for buyers right now. Most are not dissecting what the dues cover such as gas, maintenance, AC, cable, or internet. They see a high number and move on. When you compare large versus small buildings, the true cost gap is often smaller than it appears. Still, if the HOA looks high, buyers are staying away. Payment sensitivity is driving decisions more than ever.

Offers are getting aggressive. Inventory remains very low, and buyers are feeling the pressure. We are seeing prices pushed well beyond ask with aggressive terms, and in many cases it is still not enough to win. Competition is extremely strong and this trend should continue through April and likely into May.

In the outskirts, the strategy is clear. Many new listings are limiting first showings to the open house, with highest and best due Monday. Some buyers try to get in early, but most sellers are not allowing it. Even those who claim they are out of town somehow make it to the open house. Agents understand the strategy, and most are sticking to it. Expect this pattern to continue throughout the spring.

Single Family Homes 
This remains the hottest and most sought after property type on the market, and demand picked up again this week. Buyers are feeling pressure as timelines shrink. Inventory has increased slightly but is still far below what buyers want. Bidding wars are standard, and it is less about list price and more about what buyers are willing to pay to win. This is a very strong seller’s market.

Lincoln Park, Lakeview, North Center, Roscoe Village
This is the hottest pocket of the market. Many sales are driven by urgency, not just value, as buyers tied to rental timelines compete for limited inventory. Emotions are elevated, and multiple offers are expected on nearly every well priced listing. Duplex downs and townhomes remain limited, though supply is ticking up slightly. This is a strong seller’s market.

West Town, Wicker Park, Bucktown, Logan Square, Avondale
Same as above.

West Loop
Momentum is building as activity increases heading into warmer months. Newer, high end, turnkey properties are moving quickly, while dated luxury units are sitting. The middle tier is feeling the most pressure, especially if updates are needed. Buyers want value and condition to align. For now, this is a balanced market.

Old Town
Old Town remains red hot. Well priced walk ups and townhomes are selling quickly, often within days, with multiple offers. Dated high rises are the only segment seeing resistance. Buyers continue to prioritize character, outdoor space, and move in ready condition. This is a seller’s market.

South Loop
The South Loop is still challenging overall, but entry level properties are beginning to move faster, which is an encouraging sign. The mid tier market, especially units with high HOA fees, remains slow as buyers are highly payment sensitive. Properly priced townhomes are moving, but strategy matters. Inventory is lower than last year, which supports stability. For now, this is a buyer’s market.

New East Side & The Loop
Activity picked up this week. More renters are transitioning into ownership, and there has been a slight increase in empty nesters buying entry level luxury units. Mid tier and dated luxury properties remain the most challenged. Buyers want value or turnkey condition. This market is significantly improved from 2023 but not fully back. For now, it remains a buyer’s market.

River North, Streeterville, Gold Coast
Confidence is returning. Renters are actively exploring purchases, and some buyers priced out of the outskirts are recognizing the value here. Entry level luxury saw a push this week, which is encouraging. However, aggressively priced or dated luxury properties are still sitting with extended market times. Momentum is improving, but the high end remains soft. For now, this is a buyer’s market.

The Big Picture:

• Outskirts: It remains a seller’s market across all categories, 

• Downtown Core: Is a buyer’s market.