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Meg Daday

@megchicago

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Helping women design authentic lives, starting with where they live
📍Chicago + Boulder | @heyday.homes
🍾 Alcohol-free 1.1.23

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Entrepreneurs, do you have your people?

The ones you can share a big idea with without immediately hearing all the reasons it won’t work?

Wanting to create something, build a business, and work on your own terms can look a little crazy to people who want a more traditional path. They might see an unreasonable risk where you see possibility.

And when you keep having to explain yourself, it can get lonely.

That’s why it matters to have people who let you finish explaining the vision before picking it apart. People who challenge your thinking, but also understand why you want to try. You can bounce ideas around, ask “what if,” and feel understood instead of judged or shut down.

My walk with Meg this morning reminded me how much I appreciate having that kind of friend.

And Austin put on a SHOW for us. ☀️ The sunrise over the skyline, the reflections on the water… a pretty inspiring place to walk and talk about what’s possible.

Who’s in your corner when you start dreaming out loud? by @megchicago

I bought my Lincoln Park townhouse last September . . . and a lot has changed since then. (1640 N Bissell - check out the link in bio for the full rental listing.)

I paid $440,000 (above the list price of $400,000 to beat out other offers).

My monthly payments are $3,014 including mortgage + taxes, thanks to a 5-year arm with 5% interest rate.

There isn’t an HOA, so no additional fees + no rules against short term rentals, which is a big reason I bought it.

I ended up blowing past the initial renovation $200,000 budget and spent over $270,000, including replacing all the plumbing, windows and HVAC.

After months of debate, I’m experimenting with medium-term rentals (30-90+ days). My first guests were there for 6 weeks this summer and paid $8500 total.

The current tenants are there through Halloween and paid $15,626 to Airbnb. After 15% host fees (insane), I should net $13,203 for a two-month stay.

But here’s the part of real estate investing no one talks about: while I’ve made about $24k from tenants so far, I’ve also spent more than $25k on things I wouldn’t have bought for myself or done now, just to get it guest-ready: a king-size bed ($5k), front pavers ($5k), a front fence ($5500), other furniture, final contractor touch-ups and a coffee maker.

Is all of this worth it? I’m honestly still not sure, but I’m committed to the experiment.

Know anyone looking for a few months in Lincoln Park this winter? Send them my way. I’m motivated. 😆 by @megchicago

We’ve helped 40 families buy + sell so far in 2026.

One thing all 20 sellers had in common: they had interest rates under 4% (or no mortgage at all). Almost all of them bought their places between 2020-2022, but their lives now look nothing like they did back then.

On paper, giving up a rate that low feels irresponsible. You feel like you’re crazy for even considering it, right?!

But here’s what I’ve learned: although it doesn’t make sense on paper, a higher rate might be exactly what you need to move forward.

Because 3-5 years later, it’s normal to need more space, a backyard for the dog or a whole new city.

Our client Cristen is a great example: she bought her Lincoln Park condo in 2021 for $635,000. When she was working crazy hours in consulting, it was the perfect oasis. But as she explored less soul-sucking jobs, she realized her best options were outside Chicago. We helped her weigh the pros and cons between renting it out and selling.

She realized even if she eventually came back to Chicago, it wouldn’t be to this place, so she sold it for $925,000, a 45% increase and a huge amount of equity to invest elsewhere.

On paper, walking away from her insanely low payments didn’t feel like a smart move. But her life doesn’t look like it did in 2021 and it was time to invest in her future, not her past.

How much is your 3% rate actually costing you? DM us to talk it through. #heydayhomes #chicagorealestate #moveforward #homeselling by @megchicago

At 36, I left law behind and started my career in real estate. (Wild that it’s been 10 years!)

At 43, I experimented with 30 days alcohol-free and ultimately closed my 25-year chapter with alcohol

At 46, I’m splitting my time between Chicago + Boulder and designing a life that has room for both.

None of those changes meant the life before was wrong.

I spent years becoming a lawyer and built a career I was proud of.

I honestly would not be where I am without the experiences (good and bad) I had with alcohol.

And after 20 years in Chicago, I still love the city, my business, my community and the life I built there.

But I’ve learned that you can love your life and still feel like it’s time for some fresh energy.

You can be grateful for what got you here and admit that it doesn’t spark joy in quite the same way anymore.

You can honor who you’ve been and get curious about who you’re becoming.

You don’t have to blow it all up.

Sometimes you just follow the threads of joy, start with a micro move and see where it takes you.

A fresh start doesn’t mean starting over. Sometimes it’s just starting again. by @megchicago

At 46, I’m following the threads of joy.✨

When I went alcohol-free in 2023, I started to realize how much the life I had built over the last 20 years didn’t fit who I am now.

So, over the last 3.5 years, I’ve been quietly experimenting: working remotely from Austin, Barbados and Palm Springs, buying and renovating a Lincoln Park townhouse and building a team to support our Chicago clients at the highest level.

Lately, I’ve been splitting my time between Boulder + Chicago and realizing that all the micro moves I’ve made along the way are adding up to a life that feels much more aligned.

In Chicago, the @heyday.homes team is having our best year yet because clients feel *more* supported than when it was just me, trying to do everything.

Meanwhile, in Boulder, I’m experimenting with dating, building community around the things I love and finding joy in sunrise hikes.

I’ve realized just how much✨movement creates momentum ✨and I can’t wait to see where this journey leads.

#womenover40 #alcoholfreeliving #midlifereinvention by @megchicago

The biggest fear going into color analysis? “Please don’t tell me I can’t wear black anymore.” 🖤

The biggest plot twist? Black was only in my season (deep winter). 😂

Watching everyone’s reactions as they found their colors was the best part. Thanks to everyone who came out for a fun night with @yourcoloranalysis and to our co-hosts, @sarahmontgkmeryinteriors and @emmabutlergroup

#HeydayHomes #MicroEvents #ChicagoCommunity by @megchicago

Grateful for everyone who trusted us so far this year. 💕

This year’s spring market was incredibly competitive. Almost all of our listings so far this year have sold above asking, with two going $160k above list price (and one much higher than that yet to close).

Buyers dealt with 70+ groups at open houses and 10+ offers on places that were priced right.

The clients that closed in June:
✅ started the process in January / February (or last year — it takes longer than most people think!)
✅ wrote offers on multiple places before locking in “the one”
✅ moved to be closer to family and grandchildren
✅ need more space for their 1st . . . or 4th baby!
✅ sold an estate and made strategic updates to get more interest

The good news for both buyers and sellers: July is bringing a bit more balance.

Buyers are still out looking, so homes are still moving quickly but there is a lot less competition.

So, for anyone thinking about making a move, the next 6 months offer something that’s been missing for a while: a bit more breathing room to make a thoughtful decision.

Right now, we’re working with anyone thinking about moving in the next 12 months to start prepping their homes and honing in on what makes sense for their next chapter.

Moving is not an easy decision or a fast process. We’re here for the journey . . . as long as it takes.✨ by @megchicago

The only time I really miss drinking 👀

You know when you meet someone new, have a few drinks and suddenly it’s the best night ever?

That’s what I miss about drinking: the feeling of connection that comes with 2-3 glasses of wine.

Being alcohol-free adds a whole new layer to dating - one I haven’t faced since high school (and let’s be honest, I wasn’t dating then).

So yeah, dating . . . and socializing in general . . . without alcohol is different.

But I realized recently that, like most things about going alcohol-free, it’s actually much better.

Without the buzz, I’m aware much earlier when someone doesn’t share my values and I don’t stay out late (and regret it the next day) simply because the drinks take over.

Instead of “let’s grab a drink,” I find more creative activities that I actually want to do.

While I really miss the past version of me who was “fun” and up for anything, I actually like this version much better.

#womenover40 #alcoholfreeliving #healthandwellnessjourney #midlifeawakening #midlifemagic by @megchicago

I’m 46. And this is my re-defining decade.✨

Have you seen @drmegjay’s TED talk and book, The Defining Decade? She says your 20s set you up for the rest of your life.

In my 20s, I thought I was doing everything right: top 20 law school, big firm life and eventually Associate General Counsel at a really cool start-up. All of that layered with travel, parties, friends and a cute apartment in a fun city. On social media, it looked great.

Now, at 46, I’m realizing I did a lot of those things based on social expectations I never stopped to question.

It turns out, my 40s are my re-defining decade.

Through small and steady micro moves, I’ve paid off $172k in debt (2020); gone alcohol-free (2023); helped 50-60 families buy + sell real estate each year; and set up my business and team to allow me to work semi-remotely.

The vision for what I actually want is finally beginning to take shape. So now, my focus is on finding who/what/where truly sparks joy and using that as a compass for how I spend my time and energy.

And I’m leaning into connecting with more women on the path toward a more authentic, zero f*s given, joy-filled life.

Anyone else ready to move forward? by @megchicago

From the moment I took my first sip of alcohol, I was the girl who was up for anything.

If a friend needed a buddy for a concert, street fest, workout, race or trip, I willingly went along (and convinced at least part of the crew to stay out much later than necessary.)

My biggest fear going alcohol-free was losing that fun, free-spirited identity. And saying good-bye to parts of that girl was hard. (Much more difficult than the act of not drinking.)

Three years later, instead of going along with anything and everything because I’m scared of feeling left out, I’ve tuned back into the things that I actually want to do.

Meeting at 4:15a for a sunrise hike? *So much better* than anything that used to happen in the early hours.

Turns out, I’m still up for (almost) anything . . . as long as I’m in bed by 9. 😆 by @megchicago

Back to the beginning 🏊‍♀️

With the exception of a few months in 2023, I haven’t swam consistently since college water polo.

I spent about 20 years swimming . . . So I’m not exactly a beginner, but I have a longgggg way to go to get in swimming shape. (And I actually have no idea what that even looks like in my mid-40s.)

Something about the sun, pool and great weather is calling me back . . . And I’m even considering working up to joining a swim team that practices at lunch.

The best part? There’s no real goal. I’m not focused on an outcome or training for a race. (Except holding my own in lane 2 lol. I don’t want to be in the slowest lane.)

For maybe the first time ever, I’m simply enjoying being in the pool and seeing what happens when I commit to the process.

The hip/glute injury that’s been nagging me for 3.5 years was almost completely gone after a 20 min swim.

Of course, the one thing I’ve been avoiding turned out to be the solution all along. 🤦🏻‍♀️

Turns out, the joy is in the process.✨ by @megchicago