3 conversations you need to have with your partner if either of you are entrepreneurs

By Heather Wentler

My partner Chris and I have been together for 18 years. After college, I went into teaching and Chris immediately began to build what eventually became Sector67, a Madison community workspace, aka hackerspace. After about eight years in teaching, I left the stability of a 9-to-5 (let’s be real, teaching is more like 7 a.m. to 6 p.m.) to begin my entrepreneurial journey as well.

I’ve experienced both the role of the life partner who maintains a stable job while cheering on their entrepreneurial partner, and the role of the entrepreneur. Through the years, I’ve learned a lot about how to communicate and navigate the challenges of love in the pressure cooker that is entrepreneurship. 

Looking back, I believe our relationship has survived and thrived through the turmoil because we have gotten on the same page about three key things: the standard of living we both want, how we divide household duties, and how much advice we want from each other about our businesses. 

Of course, any relationship will benefit from these conversations, but entrepreneurship adds this layer of financial insecurity, unpredictable schedule, and fear/emotional overdrive that makes these conversations more important than ever. 

Question 1: What standard of living are we comfortable with? 

When you begin the path of entrepreneurship, you often forego a level of financial security that makes the “American dream” possible. 

When Chris moved Sector67 into its new location in 2018, the plans allowed for a Caretakers Quarters to be built within the space for Sector67 staff to live in, and we plan to live there when it’s finished in order to avoid the financial commitment of a home mortgage. For us, avoiding debt has been a great way to limit the external pressure to “make money or else”—pressure that can force you to give up on your venture before it matures. 

But this decision doesn’t make sense to many people. Both of our parents often wonder why we don’t both get full-time jobs and move back to the Janesville area where we could buy a house for one-third of the cost of a house in Madison.

We’ve found that we have to let go of other people’s expectations for what our lives will look like, and we have to stop comparing ourselves to other couples, especially our peers who have 9-to-5s. I’m not going to lie, it can be hard to listen to a friend talking about going to an all-inclusive resort for vacation when I know our next vacation will be spent in a tent in the woods, and instead of getting rubbed down with pampering massage oils, I’ll be getting rubbed down with bug spray. But I’m just thrilled that I get to take a vacation at all.

Question 2: How will we divide the household duties?

When Chris and I decided to get married we didn’t have a traditional engagement and wedding—if you haven’t noticed, we tend to buck tradition. Instead we made the decision and eloped within two weeks at 8 a.m. on a blizzarding Tuesday morning in February. But before we signed the legal documents pronouncing us “husband and wife” we spent those two weeks Googling every night, searching for all kinds of “things to talk about with your soon-to-be spouse before the wedding.” Household duties and financials were at the top of all of those lists we came across, and we spent lots of time discussing and “discussing” (read: arguing) our feelings and how we can compromise.

Again, these are conversations that every couple shoud have, especially if you’re in a heterosexual relationship, because it can be easy to fall into antiquated gender norms that shift the majority of the housework onto women. 

In the context of entrepreneurship, this conversation is especially important because the entrepreneur’s schedule can appear to be more flexible because they are free from the rigors of showing up somewhere at 8 a.m. everyday. It can be easy for the one with the more flexible schedule to end up taking on more of the housework. 

But as so many of our members know, being an entrepreneur does not necessarily mean that you have “more free time” or even more flexibility. When Chris first started Sector, he was working until 10 o’clock most nights. I felt like I never saw him, and I was disappointed that I couldn’t take my partner with me to social events. The inevitable “Where’s Chris?” question hurt and angered me because I would see our friends always with their partners.

When I made the transition to entrepreneurship, I started putting in those long days-into-nights, and I finally understood what he had been going through. I apologized for not being more supportive back in the beginning. We’ve now established a weekly “date night” policy, which means we eat a meal together and do something non-work related, even if that’s just grocery shopping or folding laundry...so sexy, I know.

I’ve also seen other couples where the entrepreneur in the partnership does have more flexibility, and uses it to manage more of the household duties by choice, but that’s a conversation that needs to be had, with both parties explicitly agreeing to that. Managing a household is a lot of work, and it can significantly eat away at the time and mental energy you have available to devote to your venture. 

And when you throw kids or a live-in parent or family member into the mix, or a pandemic, it’s all even more challenging. Entrepreneurial couples must talk about how to divide the burdens of childcare or eldercare, and return to that conversation often as their situations change. I’m thankful Chris and I don’t have to deal with either of those responsibilities right now. Not having kids is a hard choice, but it’s one we have made because we know we’re not ready to be the types of parents we would want to be while also getting our ventures to a point where they’re stable. 

How much advice about my business do I want from my partner? 

Chris and I have learned that it doesn’t work well for us to mix the roles of life partner and business coach. For me, I often need to hear advice from someone besides Chris to be able to evaluate it rationally. When I hear Chris giving advice to me, it triggers a defensive reaction in me. 

Of course, sometimes I do want advice, but I often need Chris to just listen for a while before I’m ready to hear advice. I often need to talk through situations out loud in order to wrap my head around them. So Chris and I have established which phrases mean I just want him to listen, and which ones mean I want advice. I will start conversations by saying, “I want to talk through something, can you just listen right now?” or “Let me get everything out first and then can you help me put the pieces together?” or sometimes he’ll say to me, “Do you want me to give feedback or just nod in agreement right now?” It’s taken practice and patience on both ends to be able to laugh with each other when we’re not at our best or after high stress situations. 

But ultimately, having a business coach has been a lifesaver for our relationship. If Chris and I talk about the business challenges we’re facing too much, then we both end up knowing too much about each other’s business, and it compounds the stress we are each facing. And we start to mix business financial conversations with personal financial conversations. I might begin to pressure Chris to make a particular decision in his business in order to achieve our shared financial goals, but it’s not my place to make those decisions for him, and the same goes with my business. 

Our solution is to communicate our shared financial goals as a couple, and then trust each other to make the decisions we need to make in our businesses to get us there. 

I also think this is another reason why it’s crucial to manage all of your own finances in your business. If you rely on your romantic partner to help you calculate crucial figures like your cash flow or your runway, it will be harder to maintain that separation between shared personal financial goals and business financial goals. 

I know that some couples find ways to work together on this, which is great and I give high praise to those couples. But in working with Doyenne entrepreneurs, I’ve also seen the flipside of this. I’ve had husbands tell me that their wives need to attend Doyenne programming. They have asked me to reach out to their wives encouraging them to attend, without mentioning that their husband has asked me to do so. If you listen closely to what the husbands have said during different conversations what I really hear from them is they’re trying to wear the hats of life partner, ad hoc business partner, and business coach to be supportive of their wives but also asking for a lifeline so they can get out of having to work within their spouse’s business and wanting them to seek support from others besides the husband. The husbands are at a point where they feel like they’ve given their all. They don’t know how to be supportive to help their wives get to the next stage, and they want to separate work from home in a supportive way that doesn’t damage their relationship in the process. 

Bonus question: Are we both all-in? 

Loving an entrepreneur is a wild ride. It will not work if the entrepreneur and the partner are not both absolutely committed to the entrepreneur’s dream. For Chris and I, as much stress as we face running two non-profit businesses, we’re still happier than we ever were or would be in the corporate world. I know Chris would be a shell of a person if he had taken the path of his peers to become an engineer in a big corporate setting. And most days, it’s awesome to be married to a fellow entrepreneur, because we both get it. The ups and downs, the crushing blows, and the ecstatic wins. 

But it’s also important to develop friendships with other entrepreneurial couples, because it helps decrease some of that unnecessary keeping-up-with-the-joneses stress. 

One of the biggest goals I had for Doyenne when I co-founded it eight years ago was to foster a community of women entrepreneurs who would relate to the choices that Chris and I have made about our standard of living. I now have a cohort of women, and some very close friends, who understand what I’m going through, and why I don’t feel like a loser for taking a vacation in a tent instead of an all-inclusive resort.

My last piece of advice is to remember that your life partner doesn’t have to be everything to you. It’s unrealistic to expect one person to be your romantic partner, your business coach, your best friend, and the person you go to business and social functions. It’s totally OK to look to other people to fill some of those roles, freeing up your romantic partner to be just that. 


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