Vineyard Vines No-Wrinkle Travel Shirt c/o (Also here in a darker blue!)

Mitch here!

This past September, I left teaching to run my small business and help Kelly manage hers.

It’s been six months. So… how’s it going?

Here are answers to some questions we get about our new lives!

What’s this small business you speak of?

I went a bit more in depth about my business here, but basically, I sell stuff online and use the profits to make investments. I started it with $100 five years ago, and it’s big enough now to require my full attention. In the past six months, I’ve (1) seen its true potential, (2) realized I have no idea what I’m doing, and (3) worked as hard as possible to learn how run a successful company.

Since leaving teaching, I’ve launched my most ambitious product to date, and I’m currently in the process of deploying it worldwide. More to come on this, as I’m very excited. But in short, I work on this for roughly half the day because it takes a good deal of time.

What would you say you do here on the blog?

The other half is spent helping Kelly. This isn’t exactly a new thing; I’ve had this role (in some capacity) since Kelly first mentioned that she wanted to start a blog. One day, upon leaving the Bronx, Kelly was being super quiet. This rarely happened, so I inquired.

Mitch: What’s wrong?

Kelly: I think I want to start a fashion blog.

Mitch: What’s a fashion blog?

Kelly: It’d be a website with fashion and photogra…

Mitch: We’ll call it ‘Kelly in the City’!

(It’s true. I named this site.)

A week later, she put this post up, and five years following that, she’s still chuggin’ along.

Before I left teaching, I functioned mostly as a sounding board, photographer, and occasional rambling writer. Now, though, I’m able to be help way more. Kelly loves the editorial and creative parts of blogging, but she dislikes the business and backend parts of it. Luckily, I love that stuff… so I’ve been able to take some more off her plate. Today, I also get to play the role of an agent, bookkeeper, accountant, producer, and developer of sorts. Sometimes I even get to model clothes. Which, yes, is weird for everyone.

The cool thing is that since our businesses have many similarities, I’ve been able to streamline significant portions of our day-to-day workflows vis-a-vis strategic synergistic simplifications. (Now that’s some business jargon I can get behind!) Kelly focuses on creating content; Mitch focuses on maximizing efficiency.

I’m unsure how I–an unlikely candidate for this job–ended up in this position. But I really like it. And I’m learning a lot.

So what have you learned?

I’ve been in school either as a student or teacher since I was something like three years old, and it feels very strange to start my work day without a bell going off. My workflow has always been laid out before me, chopped up into tidy block periods and chunked into precise piles of standard numbered lesson planned paperwork. Things are totally different now.

Over the last six months, I’ve learned that I love the freedom that comes along with working for myself. I like being able to take a phone call, work remotely and during weird hours, and use the rest room whenever I need to. (#teachingprobs) And I love knowing that I’m building something for myself and my family.

But working for myself isn’t necessarily easier than having a more traditional job. My “workflow” is unpredictable at best, and I probably put in longer hours than I did before. While we lead happier and far more balanced lives than we did last year, we still pull the occasional all-nighter, and there are times when we’re so tired that we think we might die, haha.

But it’s also SO exciting. Every day is different, and every day brings fun opportunities and crazy adventures.

So I guess I’d say that while this new lifestyle isn’t as glamorous as I thought it would be, I’m really enjoying it, and have zero regrets!

What’s it like to not have a boss?

I’ve had some strict bosses in my day, but it turns out that old Mitch Larkin is the toughest boss of ’em all. Since I took over my own employment, all frivolity went out the window. My days are spent frantically swiping between tabs and tasks before Emma’s daycare timer “runs out” or she wakes up from her nap. Most of our work gets done late at night, and the slightest hiccup can send the whole thing spiraling off into catastrophe.

Yes, it’s very nice to not have someone directly “over me,” but at the end of the day, I answer to myself… and I can be a tough one to answer to.

(Something else I’ve learned: Kelly is a straight-up productivity phenomenon. Yesterday, I fell asleep on the living room floor and while I was snoring, she posted on social about a dozen times, edited two photoshoots, and planned two more–all while snuggling with our sick daughter who was also in and out of dreamland. Kelly runs circles around me.)

What’s working with your spouse like?

I wish I had a more interesting answer for this one, but this is it: It’s the same as it’s always been! We like it!

I spoke about this here, but Kelly and I have always worked together. We met at work and started our first business about a month after we got together. She was there when I launched my thing–for the record, she didn’t want me to make the $100 investment–and we tried about a dozen ideas before Kelly in the City came about.

Even when we didn’t technically work together, we basically did. I was always there to take blog photos, and she was always there when I was stuck on a lesson plan or needed design help. Long story short, working together seems like the most natural thing in the world.

Do we always agree on things? No! Our biggest disagreement, right now, is how to back up our files. Kelly wants them on a physical hard drive; I want them on a cloud-based server. We’re compromising and doing both, in case you’re wondering. ;)

But in general, I think this improves things. Two viewpoints are better than one, and we push each other to try new things.

So where is this heading? Are you going back to teaching? What the heck is going on over there?

We had big goals for my first six months. Podcasts; videos; travel blogging; sleep. And while we’ve dipped our toes in some of that–shout out to Naptimes with Kelly and Mitch and our efforts to travel more wooooo!–we have a long way to go. It turns out the Dunning-Kruger effect is real. I mean, what we’re doing is terrifying. We’ve sacrificed a lot to get to where we are and, honestly, we’re loving it. As I write this sentence, though, it’s 1:15 a.m., and I finished about 10 percent of what I needed to get done tonight.

But I can’t wait to get back to it tomorrow.

The answer to the above questions, for now, is that I’m not sure. I hope that we’ll continue with this, and get better and better at what we do… but we’ll see!

I am, however, going to use this post as a reference for the year-end roundup that I hope to publish six months from now. Mitch, are you getting more sleep? How long has it been since you picked up your guitar? Do you currently have a frozen pizza in the oven? Is tomorrow’s post done? Are you happy?!

All good questions, and I can’t wait to answer ’em.

Mitch. Out.