Kelly’s Suede Leggings (Also: favorite skinny jeans and white jeans on sale!), Leopard Pumps, and Navy Top c/o
Emma’s Leggings & Top and Mary Jane Sneakers
Mitch’s Loafers (also here on sale and here), Bonobos Blazer c/o, JeansGingham Shirt and Maxwell Scott Briefcase c/o

Mitch here!

So this is that “big Mitch post” that some of you probably saw coming, on account of my recent daytime activity on Instagram Stories. We meant to get this up in September, but a few things set us back. In any case, here’s the big news:

I’m taking a break from teaching.

Before I explain, though, a few things you should know:

  1. I’ll likely teach again.
  2. This past year was awesome but also very tough, and my family needs me to do this. It makes the most sense for us, both financially and happiness-wise.
  3. This is a great thing, and I’m really excited about it.

A decade in the classroom

I should start by saying that for a long time, I’ve wanted to be two very different people: a teacher and an entrepreneur.

I decided to be a teacher first. I moved to New York fresh out of college looking like this, and I took a job at the lowest performing school in the poorest community in the country–where I met Kelly, who decided to do the same thing. I taught all day, juggled grad school at night, and planned lessons and graded papers whenever and wherever I could: usually at weird hours, between classes, on the subway, or in bed.

I imagined myself being that cool teacher who walks out of school feeling fulfilled, high-fiving students along the way.

“Great lesson today, Mr. L.! You’ve really made a positive impact on my life!”

“Think nothing of it, Students. Changing lives is what I do!”

The problem was that teaching in the inner city was, in reality, far more challenging than I expected it would be. If you know a teacher, do me a favor and hug him or her the next time the opportunity presents itself. Because it’s tough.

Imagine this: You have to give a presentation to 33 of your coworkers tomorrow. The presentation must be informative, thought-provoking and entertaining–and it needs be packed with engaging activities… and it must last for exactly an hour and a half. And it has to go perfectly, otherwise you’ll face some very serious consequences. After you get through that, you’ll have to give three new 1.5-hour presentations… every day for the next 180 days. Oh, and instead of professional co-workers, your audience is 12- and 13-year-old kids. And those kids are all woefully under-serviced and under-privelidged. And most have some pretty serious behavioral issues. Also, in this scenario, your office has cut all budgets to zero, so you’re personally financially responsible for the materials you’ll need to pull this off. (Shoutout to all of the generous Kelly in the City readers who made donations to my classroom via Donors Choose over the years!) Similarly, the budget doesn’t allow for appropriate preparation time, so you’ll need to do most of this work at home–when you normally spend time with your significant other, family or friends–because you’re too busy during the day preparing for and giving those presentations… and fulfilling a ton of other professional responsibilities.

…and imagine doing that for 10 years straight.

Still, I freakin’ loved teaching. My job was important, and I carried extraordinary reverence for the objectives that needed to be achieved each day. For many of my students, the classroom was the only stable element in their lives. I lived for those special moments when I could guide students through difficult spots or help them achieve their goals. During any given school day, it was my knowledge, experience, creativity and personality that made lessons work in my classroom. And that was pretty cool.

But teaching is this slow, barefaced life lesson that things don’t work like they should. I mean, there’s a reason that inner city schools have been in crisis for decades. It seems like the whole world is stacked against success in those classrooms. I can’t remember a situation over the last 10 years in which a budget situation improved or a class size diminished, for example. Politicians and public personalities earn points by railing against “money-hungry teachers,” and nearly every staff meeting begins with bad news. I remember one meeting in the Bronx–and this is true–when the principal stood up in front of the staff and said, “Listen. We all love Kelly. We don’t want to have to fire Kelly. So you all need to get those test scores up so I don’t have to fire Kelly. Last hired, first fired.” And that’s undoubtedly my least shocking teaching story. (Read Kelly’s post and you’ll get a better idea of what the job is like.) This kind of thing is just a standard part of any inner-city teacher’s workday. We’d leave these awful staff meetings with the weight of a whole neighborhood on our shoulders, and then limp off to teach for eight hours.

I’d like to think that over the course of last 10 years, I became the teacher I thought I could be. No, maybe I didn’t leave the building every single day feeling fulfilled, high-fiving students along the way. But I can finally say that I’m good in the classroom. I gained the skills and perspective necessary to provide each student and every class with the lessons they need and the instruction they deserve, while maintaining a safe and welcoming environment. I figure that over the last 10 years, I’ve had nearly a thousand students. I hope that I taught them half as much as I learned from them.

Tough decisions

If I loved teaching so much, then why did I leave? Good question! It wasn’t a rash decision. It took Kelly and me months and months of deliberation before we decided that hanging up my coffee-stained khakis and chalk-addled ties for a while was the right call for our family. Here’s why:

  1. Classroom teachers, unfortunately, do not make very much money (compared to other professionals with similar qualifications), and childcare in Chicago is expensive and paid for with after-tax dollars. We figured that as much as 60 percent of my take-home pay would go to daycare, which was simply too much. A nanny? Even more.
  2. The job of a teacher requires significant dedication to working long hours. As such, there were many days last year when I was only able to spend about an hour with Emma after I got home from school. It wasn’t enough.
  3. Life was simply way too crazy last year, and Kelly was drowning. She was a full-time stay-at-home mom, but she also worked full-time. Getting four or five hours of sleep every night had become the norm for her, and she was constantly exhausted and sick. It wasn’t a sustainable lifestyle, and it wasn’t good for anyone.
  4. I, too, was exhausted. While I probably didn’t get to the point that Kelly did when she decided to step away from the classroom, teaching in the inner city for 10 years certainly took its toll on me, and I was ready for a change.
  5. I found myself constantly daydreaming about entrepreneurialism. My business (which I talk about below) started demanding more of my time, and Kelly needed my help to keep her head above water. As you might imagine, I was really struggling to work three jobs and be a good dad all at the same time.
  6. My priorities shifted. Once I became a father, my #1 priority was my family, and making sure they were happy and healthy. I’d dedicated a decade to the less fortunate; it was time to dedicate myself to my family.

All of this became clear to us late one night at Kira and Tom’s lake house this past winter. Everyone else had gone to bed, and we stayed up talking. Kelly was in tears; she said she had too much on her plate and needed help. She wanted more quality time with our daughter, and with me. I felt the same.

After much deliberation, we decided that I needed to leave my job. The moment we made the decision, it felt like a huge weight had been lifted off our shoulders. We told our families and a few friends–and while there was certainly some apprehension about the less-than-traditional route we were taking, everyone was supportive and excited for us. Yes, we had many more months to get through until school let out. But there was a light at the end of the tunnel.

Our dream

At heart, I’m an entrepreneur. Or, I consider myself to be an entrepreneur, at least. I’ve started companies and launched products with my best friend/business partner since I was 12 years old: First there was Mike’s Mowing (my real name is Michael, FYI); then there was DJ Shawnee Video Productions. Then came Middle Illinois Land Ventures, and PassingPeriod.com followed. After that, we created TopHat Technologies, under which we launched Couch Clamp, Table Tablet, Freezer Meter, Dress Anchor, and ColdTI .

We started TopHat Technologies with $100, and now sell tens of thousands of products a year all around the world. Today, our free time is filled with design work, materials sourcing, marketing strategies, packaging and eventually shipping products… and we also manage a good number of investments.

And I absolutely love it.

When Kelly and I started dating, we instantly became entrepreneurial together as well. We launched Kelly Sheehan Photography, and when Kelly determined that her heart wasn’t in wedding photography, we turned the business into Larkin Printing Company–which eventually became Kelly in the City. My role with this blog has been fairly consistent since day one: help Kelly to create great content. At first, I was just the photographer. Now, though, I manage the backend and business side of the site. Kelly hates that part of blogging, and I, coincidentally, can’t get enough of it. Besides being the business manager, I’m also a part-time childcare provider, guest blogger, travel agent, videographer, communications director, and accountant. It’s great.

When Kelly and I first moved to Chicago, we’d walk around Lincoln Park and admire all the beautiful houses, and there was this one very modest house down the street from our dumpy apartment that always caught our eye. It had a home office with a big bay window, and inside, you could make out two desks that faced each other, with two big desktop computers on ’em. And every time we passed that house, we couldn’t help but stop and smile. And I couldn’t help but hope that one day, I’d be able to step away from teaching and try my hand at entrepreneurialism.

We don’t have that single-family home with home office today. We work at our kitchen table, and someone else owns the other half of our house. Our businesses are just getting started, but we love thinking that if we continue working hard, we might be able to have something like that one day.

One month later

We’re happy. While things aren’t perfect–there’s still too much work to complete and not enough hours in the day–we’re figuring it out, and life has improved dramatically since the big change.

Kelly and I now go on dates. We can take Emma to the park without freaking out about deadlines. We have work-free weekends. We go to bed before 3 a.m.!

In case you’re wondering what our days are like, they’re anything but traditional. My mom comes up two days per week and Kelly and I work at a coffee shop while she’s with Emma. On the other three days, we utilize the daycare services our gym offers. We work for two hours in the morning, an hour during nap time, and then two hours in the afternoon. We also clock a couple of hours after Emma goes to bed. I think we’ll likely hire a part-time nanny at some point, but for now, this is working.

I love actually having time to work on my business and help Kelly manage hers. I love the flexibility that comes along with working for ourselves and the excitement that each day brings… and I can’t wait to see what the future holds for us.

Will I teach again? I think I will. Maybe when our kids are in school and I have more time on my hands. Or maybe our businesses flop, and it’s a necessity. Or maybe we decide that entrepreneurialism isn’t for us, and we both go back to more traditional jobs. Who knows? We’re just takin’ it one day at a time… and for now, things are good.

Before I jet, I’d like to thank you for your support as I’ve started to play a more significant role with this site. I’m having a blast and I’m learning a ton. Who knew that there’s a difference between dresses and skirts?! (Apparently everyone.) But thanks for accepting me with open arms. You guys are fun, and I can’t wait to share more of this adventure with you.

Mitch in?

Shop the post:

Kelly’s Suede Leggings (Also: favorite skinny jeans and white jeans on sale!), Leopard Pumps, and Navy Top c/o
Emma’s Leggings & Top and Mary Jane Sneakers
Mitch’s Loafers (also here on sale and here), Bonobos Blazer c/o, JeansGingham Shirt and Maxwell Scott Briefcase c/o