Top 10 Challenges of Working With Your Spouse

by | Apr 27, 2015 | 13 comments

Anyone that has worked with family, whether it is simply trying to plan a vacation or actually partnering in business knows that there can be a lot of challenges.  In this post, Ariana and I each compiled our top 5 challenges that we face with the other.  We each introduce and describe our challenge, then together discuss how we have or will try to address it with each other going forward to improve our businesses and our relationships.

#1: Tom’s Challenge: Struggle To Get Consistent Time to Work Together on the Businesses

A challenge that we constantly face, especially with me working a full time job and us being parents, is finding dedicated time for us to work together to drive the businesses forward. For a while we did this on Sundays (which lead to our batching and Sunday review), but as Elena got older and began taking less naps, this time was lost. We then tried to find other times, but this was never consistent.  The struggle that I have with this is that without a consistent time and an agenda, we end up not always being aligned on what things we should be working on next to achieve our goals.

What We Will Try to Address This Challenge: We realized that part of our problem was not setting aside a consistent time each week, and putting it in the calendar.  Going forward, we have scheduled a one hour meeting on Fridays while Elena is sleeping.  After Ariana has our second child in June, we are going to switch Elena from her Tuesday/Thursday childcare/pre-school program to a Monday/Wednesday/Friday program.  This will give us more time on Fridays to focus on our work, freeing up more of our weekend.  We will also be looking for a family member/babysitter to watch the new baby during our designated work time.

#2: Ariana’s Challenge: I have a highly motivated spouse who keeps adding things to my list

I simply cannot keep up with with the sheer amount of ideas coming out of this man’s brain. And while I appreciate his ability to spout genius around every turn, I struggle to bring him down to a more practical level. Sometimes it is very difficult for me to be the voice of reason without squashing all of his newly hatched concepts. I walk a very fine line between supporting his plans, while also trying to keep myself sane.

What We Will Try to Address This Challenge: We realized that in order to manage all of our ideas, we need to focus.  We’ve always planned out our goals, but we have recently become a lot more specific.  We have created a new “goal wall” in our office that aligns our goals, the activities that we are pursuing to achieve them and the current progress towards each one visible.  We’ve agreed that all new ideas will go into an idea bucket.  From there, we will review each idea and decide if we should focus energy on them to achieve our goals.  This will make sure that new ideas aren’t dismissed, while also allowing us to focus our energy where needed.


Do you want to see the exact process that we recommend and get access to the templates that we use to build your own “goal wall”?  If so, be sure to check out our Roadmap for Life goal planning mini-course.

Roadmap for Life Covers - small



#3: Tom’s Challenge: Ariana Gets Stuck Working “In” the Business and Not “On” the Business

Micheal Gerber describes this concept in The E-Myth Revisited: Why Most Small Businesses Don’t Work and What to Do About It.  The basic concept that he introduces is that most “entrepreneurs” who start a business are not really entrepreneurs, but instead are technical people that are good at what they do, but not able to handle all of the additional aspects of running a business (ex. hiring, payroll, taxes, marketing, strategy, etc).

I’ll be the first to admit, this is largely my fault. When we first started each business, I worked in the business to get it going. Then our strategy for growth was to transition these items to Ariana, especially as she left her job and now stays home with Elena. So the only reason we have grown and why I have any free time is because Ariana has taken on the majority of the day to day work to run the businesses.  The problem is that it got stuck there and we didn’t do a great job of transitioning those items off of Ariana’s plate and off to someone else.  This means that as am off trying to create a new business or grow an existing business and partnering with Ariana to do so, she gets frustrated with me because she is trying to work in the existing businesses and keep them running.

What We Will Try to Address This Challenge: Our focus as of late has been on analyzing everything that Ariana has to do to support our businesses.  After we made a list, we’ve been working step-by-step to create procedures and outsource each activity that Ariana does.  For example, each week she was doing the ordering for Warsaw Wine & Spirits, which took several hours.  She has since created a procedure guide that walks through the process.

Wine and Liquor Store Inventory Reordering Procedures

We then trained one of our employees on the process, and now he is doing the reordering each week.  This means one less thing for Ariana to do.  We’ve also done a similar thing with Sylvester Enterprises, our real estate investing business.  Ariana created procedures to outsource the process of showing and leasing out new apartments.

Real Estate Landlord Outsource Leasing Procedures


So we have now outsourced two of the major items that were taking Ariana’s time.  We are continuing to work through her list and freeing up her time so that we can together focus on other business ventures.  As a side benefit, we are using these procedures to create digital products to sell.  Last week we launched our first digital product, which was a collection of our forms and procedures that we use in our real estate investing business.

Landlord Real Estate Investing Forms, New Tenant Packet and Outsourcing Procedures

#4: Ariana’s Challenge: Time Splits-Business, Personal, Adult, Family

One of the hardest parts of running a business with your spouse is time management. We struggle with this on a daily basis, and have yet to come up with a complete working process. With me being a work-from-home mom, I constantly am trying to juggle time with Elena, time for myself, and time for work. On the weekends when Tom is home, we add even more onto our schedule: Family time as a unit, Daddy/Daughter time, Husband/Wife time and of course, team business time. So far, we have tackled this with a sort of nonchalant, we’ll plan a couple things and see how the rest fits in type of plan. Obviously, it has not worked very well. We need to figure out a better option, as bad time management can often lead to resentments when working with your spouse.

What We Will Try to Address This Challenge: One of the major things that we are doing for this is to really utilize our shared calendar.  We both use Google Calendar and sync it between all of our devices.  We’ve created a calendar for each business and type of time mentioned above.  We are being very explicit about scheduling our time so that we make sure we are focused and get time for everything that is important to us.  This not only includes work time, but also things like father/daughter time and couple time.  We also have made sure to schedule time for each of us to pursue our hobbies.  Ariana likes to sing, so she has joined a local choir and attends one night a week.  Tom enjoys playing video games, so we schedule some time on the weekend for Tom to destress.

#5: Tom’s Challenge: Ariana is Great and Doesn’t Realize Her Potential

Most people closely tie their worth to their career and how much money they make.  Ariana graduated with a degree in zoology but the closest job she had to that was a minimum wage job at a local animal shelter.  She then bounced around to various office jobs and is now “just” a stay at home mom.  She is a truly amazing woman and that is why I snatched her up quick (she was the first woman that I met at college)!  When we first discussed starting this blog, she didn’t think she would be able to write blogs or people would care what she had to say.  I see her often hesitate when we talk about things and don’t see the confidence/passion of what she can achieve as well as what we can achieve together.

How we have started to handle this is talking out our goals and how we can each contribute to those goals. That helps give her an identity.

What We Will Try to Address This Challenge: We are continuing to work on this.  Each success that we have with business helps her gain confidence.  Additionally, as we speak with other entrepreneur couples, she realizes that we are typically several steps ahead of them and we can help them in their journey.

#6: Ariana’s Challenge: Keeping Tom up to date without continually stressing him out

This one is a big one for me. Because Tom is away so much, I know he feels disconnected with a lot of what’s going on here at home. In my attempts to keep him updated, I feel I sometimes add more stress on top of all that he’ already dealing with. His job is very intense, and he deals with a lot of important people in high-pressure situations. When it comes to the businesses, I often hold information back because I don’t want to add more onto his already full plate. This means I have to take care of things on my own, and he frequently gets frustrated because he feels detached from what’s going on. When it comes to personal life, I try to keep him in the loop by sharing funny Elena stories and pictures whenever I can. Unfortunately, I think this often has a reverse affect. Instead of cheering him up, it makes him all the more sad for being away and missing it.

What We Will Try to Address This Challenge: We have decided to keep a list in Evernote of key activities that we need to discuss, but may not need to discuss right away.  We will review these items together at our weekly meeting.  If an item is urgent, then we will first discuss if this is a good time to talk about the item.  If it isn’t, then we will plan a time to discuss it.

#7: Tom’s Challenge: Not Focusing Too Much on the Ends

I am highly motivated to achieve our goals and retire early.  With that said, I have to constantly make sure that I am not too focused on the end goal that I miss living life.  My reason for wanting to have both Ariana and I retire early is to be able to enjoy life and spend time with our children.  Like many entrepreneurs, I have to make sure I am not missing out on my current life while working to achieve the life that Ariana and I want.

What We Will Try to Address This Challenge: Ariana is a huge help with me on this.  She makes sure to point out when I am getting to caught up in work and recommends time for us to spend together or a special day for me to spend with Elena, whether it be taking her to the museum or to the zoo.  It is also helping us to schedule all of these times in our calendar.

#8: Ariana’s Challenge: I feel I don’t always get as much done as I should

One of the hardest parts of having such a motivated spouse is comparing yourself next to them.  I know I am a pretty productive person. I know I could probably be more productive. When I look at all the things Tom gets done on a daily basis, I feel overwhelmed! Not only does he go to work all day, but then he works late into the night on our side businesses. Next to that, sometimes I find myself feeling guilty, and like I’m not contributing as much as I should. Often, that leads to me losing focus, as I feel that even the little things I get done each day aren’t enough in the grand scheme of things. An added challenge for me at the moment is the fact that I’m 7 months pregnant. With the exhaustion settling in during my 3rd trimester, I find myself putting things off that need to be done because I just don’t have the energy. Even though I know in my head that it’s necessary for me to take more breaks, it doesn’t help my reservations about my ever-growing list of things to do!

What We Will Try to Address This Challenge: One of the reasons that we don’t feel like we get as much done as we should is because we don’t really see all of the things that we do.  This became very apparent to us when we detailed our daily activities for an entire month.   Again going back to our weekly meeting, we are going to set specific tasks/goals to accomplish during the week.  During the meeting the following week, we will review each item that we completed.  We also agreed that we can shift/share tasks during the week.  So if one of us needs helps to complete something they signed up for, they should share that with the other.  Also, Ariana will not try to keep up or compare her productivity to Tom.  This is not a competition to see who can get the most done, it’s a partnership to achieve our goals, and we each contribute in different ways.

#9: Tom’s Challenge: Not As Aligned On Our Goals

It’s no secret that I am highly motivated.  Many people often think that I am a workaholic.  The truth is, I’m really not a workaholic.  What I am is clear on my/our goals and dedicated to achieving them.  I truly believe in the following quote:

“Entrepreneurship is living a few years of your life like most people won’t so you can spend the rest of your life like most people cant.” – Warren G. Tracy’s student

With this, I do work a lot.  My struggle comes when I put in this work and we are not progressing towards our goals, or we are but not as fast as I would like us to.  Often times, I feel like this is a result of me/us not being focused.  In the periods of intense focus (which I have had many more of lately), I see us making huge progress, but we are not as crisp with our goals and activities towards them as we could be.

What We Will Try to Address This Challenge: As mentioned previously, we took over one of the walls in our home office and created our goal wall.  This has made our goals very visible, and clearly linked them to the larger goal that they contribute to and the time period that we are targeting.  This then allows us to become laser focused in our weekly meeting to make sure the activities that we are doing are aligned towards our goals.

#10 Ariana’s Challenge: Talking to your spouse about your individual challenges without harboring resentment/jealousy

This challenge is by far one of the biggest, and also I think one of the most dangerous to those of us who work with our spouses. Tom & I pride ourselves on being able to communicate about everything and anything. It is the foundation of any happy, healthy relationship. However, when working with the one you love, the lines of communication can sometimes get crossed, or even dropped, due to the nature of the entreprenewlywed world. When you both take on different roles, it can be hard to talk to each other about your own personal challenges.

Example: Working from home with a small child can be both mentally & physically exhausting. With a husband who travels, it drives my challenges up a notch. I am responsible for all the household chores, child rearing and business running during the week, somewhat on my own.

What I want to do about it: Complain to my best friend, my husband. When Elena has an off day, I want to be able to vent about it to Tom, as he is her parent too. When things go wrong at home, I want to be able to run to him for consoling, or blame him for not being here to help me.

Now, because we are so open with our communication, I know that this is the absolute wrong thing to do. Tom is already jealous (without meaning to be) of the time I have at home with our daughter. I know it kills him that he misses out on the little things, and that he has to watch her grow up each week through pictures I send. So I try not to complain too much to him about these things he can’t control, because I don’t want our relationship to suffer. This often leaves me with my own resentment, because I then feel that I have no one to share these frustrations with. Sure, I know other stay at home moms, but I don’t know many who run their own businesses from home while their husbands travel for work each week. I’m sure he feels the same way about his situation, hence the need to address this challenge and find a solution.

What We Will Try to Address This Challenge: Obviously this is a very important one for us to address and work through.  We know and work with various other entreprenewlywed couples, so one option is to potentially meet and share successes/challenges with them.  We also have started to reserve time for us to specifically talk and share the struggles that we each face.  By specifically reserving time, we can both make sure we are ready to talk and support each other, instead of seeing the topics as complaints or becoming jealous.  We are also looking to strategies that are used in couples therapy, which not only can we use, but we can share these strategies with other entreprenewlyweds.  We are also really focused on working together and supporting each other to get to our goals, one of the first one being getting to a point where Tom does not have to travel so much, and eventually not at all. 


We strive to be transparent, not only with our businesses, but more importantly with our relationship.  Many entrepreneurs don’t ever share or discuss the relationship challenges of being a couple that works together, and it is hard work.  We don’t have it all figured out, but we work on getting better each day.


About 6 months after this post was originally published, we did a podcast episode where we reviewed these challenges and provided an update on how we have been able to improve them.  Check it out below.

Serial Startups Podcast Show 5 Challenges Working With Spouse

Are you a couple that works together?  If so, we’d love to hear the challenges that you face with your significant other, as well as any strategies that you use to manage them.