Hi! We're Jason and Caroline, a husband and wife creative team taking you behind-the-scenes of building our new business from scratch. Poke around and watch us figure it out as we go!

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Business Part 1: Working Together As A Creative Husband and Wife Duo

Business Part 1: Working Together As A Creative Husband and Wife Duo


We aren’t going to sugarcoat it, working together as husband and wife is HARD WORK.

Figured out the best way to collaborate so we a) create an awesome final product and b) don't kill each other in the process is... a challenge.

However, over the years we’ve realized one important thing, and it’s the singular thought that convinced us to commit to working together indefinitely through Wandering Aimfully. The thought was... that LaCroix and biscuits are a suitable entrepreneurial diet. (Just kidding. But ugh, don't we wish that was true.) No, the thought was:

We are better together.

We know that our skills compliment one another. We know that we can get twice as much done together. We know that we make up for one another's weaknesses. And we know that approaching our lifestyle as a team with one common goal is more effective. 

But again, that doesn't mean it's easy.

While I’d like to tell you we have this whole working together thing 100% figured out, the reality is, it ain’t all sunshine and rainbows round here. That being said, we’ve been working side-by-side for nearly seven years and we’ve learned a thing or two along the way that helps us keep this ship sailing (mostly) smoothly.

So... how do we keep your relationship intact, while also trying to work together as a couple?

It wasn’t totally intentional that I came up with five steps to answer my own hypothetical question (because, no thanks listicles, and there are probably way more things than the five I’m listing here), but alas, it helps organize my/our thoughts, so here we go…


Over-communicate, over-communicate... did I mention that you should over-communicate?


What does over-communicating even mean? Because it’s certainly not just continuing to talk forever, not giving your significant other a chance to reply, therefore winning every argument ever (note to self: try this?). Nay, friends...

Over-communication means clearly explaining the thought that’s bouncing around in your head more than you think you need to explain it.

Sounds trivial? Super basic? Like a no-brainer? Well then, you’re a relationship-communication-savant and we bow down to your greatness. But for us normal people, it can be really difficult, especially in unchartered-hazy-business-conversations, to clearly and effectively try to make your point—especially without letting messy emotional stuff charge whatever you're saying.

This usually comes up for us in business conversations where we both have a unique vision and the other person is having trouble seeing or understanding that vision so we get visibly frustrated. We've learned that the heated emotions we feel in most of those situations actually have little to do with the other person and everything to do with the fact that we can’t articulate our thoughts/feelings clearly enough to be understood and we’re mad at our own feeble brains.

The other situation we run into often when it comes to communicating, is that one of us will have an idea of how we see something going and we expect the other person to see it the same way without much explanation needed. Here’s a written dramatization from a real conversation Caroline and I had just the other day:

Caroline - So I’m writing up this doc for our developer, how did you see it going?  

Jason - I figured you’d write a thorough explanation of every pixel in the design, starting from the top left, and including every interaction a user may have, along with 16 color variations for each and every pixel. Also, a cat GIF should appear randomly.

Caroline - Ummm…. I thought I was just writing a few bullets?

Okay, obviously I was stretching the truth a bit there, but this situation is something we run into fairly often. I had thoughts in my head about how detailed I thought Caroline was going to be in a Google Doc we were creating for our developer. She had her own thoughts of how that was going to go. We didn’t communicate our thoughts thoroughly to each other, and it led to a conversation that was a bit more heated than intended because we each had a different expectation of what that task would entail. Had we over-communicated our thoughts to each other from the beginning, we’d have saved 20-30 minutes going back and forth.

Over-communication is never a checkbox that gets marked as completed. It’s something we have to work on daily and continuously, no matter how painful it may be to our brains.

Lesson 2:

Be willing to actively listen and fully commit to hearing your partner.

We've learned that there's a big difference between hearing what your partner is saying with your ears and then actually hearing what your partner is saying with your head and your heart. 

Caroline and I have been in many a conversation lately and she’ll say something to me and whether I want to or not, I barely listened to what she actually said (it really wasn’t intentional, I swear!).

Then, she’ll get frustrated because she wanted to be heard and validated with her thoughts (as anyone would), and instead I just nodded along like a stupid bobblehead doll… maybe grunting or something as well. She’ll get frustrated. I’ll get defensive. And then all the sudden we’ve been transported from Happy-Conversation-Town to Holy-Crap-This-Escalated-Quickly-Land. 

What we’ve found that helps in these moments is rather than getting upset, letting the other person know: Hey, I was really hoping you’d hear  what I was trying to convey to you and validate that I’m not off-base here. (If this sounds like an example of over-communication to you dear reader, you’ve earned yourself three gold stars and an all-expenses paid trip to Happy-Conversation-Town! Congrats to you!)

the right frame of mind to actively listen

One additional trick we’ve learned over the years to avoid trips to Holy-Crap-This-Escalated-Quickly-Land is to make sure the other person is in the right frame of mind to be able to hear you. Before I ask Caroline a question, I almost always ask Caroline, “Are you in the middle of a thought?” If she’s busy, I’ll wait until she’s done. This helps ensure I can be heard and that I'm not setting her up to fail (and vice versa, of course.)

lesson 3:

Daily meetings are CRUCIAL!

We have a standing meeting every morning on our calendar. We mentioned this in our productivity tools post, but I wanted to elaborate a bit further here. Especially now that we’re in the thick of building Wandering Aimfully, our daily morning meetings are huuuuugely important.

During this 10 am meeting, we try to go over a couple things together:

  1. What life stuff do we need to take care of that day or that week (this goes with our #WorkingToLive mindset and gets planned first)
  2. What are the big buckets of things we’re working on (Example: we know we need the website design to be done by Friday)
  3. What is the highest priority task we need to get done that day (and sometimes there are more than one)
  4. Then we look at the calendar and block off chunks of time for each thing we’re working on (all while discussing if we need help or are stuck)
  5. We try to have a moment of gratitude for each other each day too (but I’d be lying if I said we managed to squeeze it in every single day, #fulltransparency!)

Does that sound like overkill? To have that type of meeting every damn morning?

Well guess what... that’s how things get done and how you stay sane working as a husband and wife team. Heck, it’s how companies all over the world start their days (I first saw it at a Rails Development company back when I was just out of college).

While these morning meetings are pretty packed right now and can take 30-60 minutes each morning, when we’re not in the thick of building a business these meetings can take all of 5 minutes.

(Even more gold stars if you saw this as another example of over-communicating!)

Step 4:

Prioritize non-work tasks, even if they’re small things.

Here’s the truth: These past couple weeks and these next couple weeks are jam-packed with to-dos. Our Google Calendars are overflowing at the moment. It’s stressful. But, there’s a reason why we’re choosing for this to happen…

We’re willing to sacrifice free-time right now so we can build a business we love operating and have a lot more free time down the road.

That being said, sacrificing free-time is not the same thing as sacrificing the things that allow you to thrive.

We’re still prioritizing time for walks, trips to our favorite coffee shops, and even some Netflixing here and there. It takes prioritization and planning to carve out this time, otherwise we’d continue chopping away at our to-do lists from sunrise to sunset like beavers chewing down trees.

During our small breaks we try to not talk business if we can and just be present in that moment together. It's important to step out of hyper-focused work mode to enjoy each other and re-connect apart from what we're building. (Sometimes I’ll even make the effort to hold Caroline’s hand… ack, the insanity! I hate holding hands. I’m weird.)


Step 5:

Embrace the other person for who they are and what they bring to the table.

Let’s start with me (because, obviously). I’m the:

  • Analytical planner obsessed with efficiency
  • Future-thinker (looking a ways down the road from where we are)
  • Complete weirdo and jokester
  • Person who needs less sleep
  • Master-task-switcher (can jump from writing to customer service to whatever at the drop of a hat)
  • Huswife (yes, the person who does the laundry, cooks, etc - I’m cool with this!)
  • OCD one (noooo way, you never saw that coming did you?)

Now let’s look at my lovely wife, Caroline. She’s the:

  • Creative executor (writing, design, content, I mean just look at the Wandering Aimfully branding!)
  • Idea wrangler
  • Compassionate and emotionally in-tune one of us
  • Person who needs 8-10 hours of sleep (and a nice slow morning without me pestering her like I do every morning)
  • Laser-focused worker (she goes deep on one task and has longer switching time - which is okay!)
  • Somewhat analytical planner (when using the right tool, a la Airtable, Asana, etc)
  • Messy one? (Who said that??! ...But really, she’s “normal” and I’m just OCD.)

We can look at these lists of differences as pros or cons, and I bet you can already guess which lens you should use to view these bullet points? Yeah, as pros!

All of these things can and are pros to use. As Caroline says, there's a "flipside to every flaw" -- something that might first appear as a weakness that shows up in another way equally as a strength. What allows Caroline to be creative and laser-focused is also what probably makes her a little bit messy. What makes me OCD and sometimes stuck on efficiency is what makes me a great action-taker. 

It’s about acknowledging who we are and how we view our partner and their strengths. Sure, I’d love Caroline to always hang her clothes back up in our closet… BUT… I’ll trade a clothes pile or two for being emotionally well-adjusted and insanely good at tying all our ideas together.

There are frustrating moments that pop-up when our idiosyncrasies bother one another, but that’s just life. Instead of focusing on those things as shortcomings, we embrace them. We use our complimentary skillset to get as much done with as little friction as possible.

We over-communicate. We may disagree or get frustrated but we never yell out of mutual respect for each other. We stay "at the table" as long as it takes to resolve an issue or air out our feelings. And we laugh... a LOT.  

Communication, humor, and respect. That's the formula. Because...

We are better together.

It all comes back around to those four words. It’s the simple truth we’ve come to embrace and use to our advantage.

We were going to film a video about working together as husband and wife...

But THIS is what happened instead:

Hope you're enjoying us sharing the REAL ups and downs of building a big project. If you like what you see/read, please consider sharing this site with a friend using the buttons below! 

Business Part 2: Choosing A Business Model That Supports The Lifestyle You Want

Business Part 2: Choosing A Business Model That Supports The Lifestyle You Want

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