The Deep Struggles, Great Joys, and Lessons Learned of Blending Entrepreneurship & Marriage

by Michael Simmons on Jul 11, 2013

“So this is how a marriage ends.”

That’s the thought that went through my mind as I hung up the phone in my hotel room after a lifeless conversation with my wife / business partner while I was traveling on business two years ago.

The idea that two people who were ‘meant for each other’ could just ‘grow apart’ never seemed like a suitable cause of separation. But, now I was living the possibility of it, and I understood.

At some level, I wished for the arguments of the past so I knew that we both still cared, but willpower no longer worked as a way to create emotion. I was losing hope for the first-time in our 13-year relationship. I was scared.

I wondered, “How have we gotten to this point!? How can I make sure this never happens again?”

The Story of Us

personal-sheena-michaelI met my wife, Sheena, during orientation our Freshman year in college. We spent almost every day at each other’s dorms and moved in together the summer before our Sophomore year. We talked for hours a day on our philosophies in life and our desire to make an impact. We envisioned an ideal lifestyle of being able to travel, meet incredible people, and make an impact. Through the realization of these conversations, the Extreme Entrepreneurship Tour was born. The tour has now been held nearly 400 times across the world with the mission of helping to spread the entrepreneurial mindset across the world.

Our daughter, Halle, was born when I was 27 and Sheena was 26. Although we were young, we had already been together 8 years, and we knew we were ready. Today, Halle is 4 and Jayden, our son, is 2. For the first 18 months of Halle’s life, we opted out of daycare and split our time watching her. One of us worked from 7:30am-1:30pm, and the other worked from 1:30pm-7:30pm. For the last two summers, we’ve followed the same routine.

business-sheena-michaelOur relationship is unique because we’ve blurred the traditional lines that people put up in their marriages between life, work, and parenthood. Instead, we’ve aligned everything under a shared purpose of each living to our full potential and having a positive impact on the world.

Blending is what has allowed us to grow together and to grow stronger. I used to think that marriage and life overall were fairytales where an amazing life just happens effortlessly after the right pieces are put in place.

What I now see is that where fairytales end; real life begins. Marriage begins when we see our partners’ imperfections, and, instead of running away to look for the next honeymoon, we still choose love. That is the kind of love that Sheena and I share.

Lesson One: Invest in the Relationship with Energy

The reality is that as business partners, parents, and husband/wife, every day is a serious struggle to rise up to competing demands while staying sane. As each day draws to a close, my mind is numb from going full force every single second. Switching between the highs and lows of parenting and entrepreneurship, all in one day, can be utterly exhausting. The thought of having a deep conversation on life or brainstorming how to improve the relationship after the children fall asleep often feels laughable.

For a period of a year, we only went on a handful of date nights and only one two-day vacation. When we did go on date nights, sometimes we’d literally drive somewhere to park and take a nap.

To thrive, a relationship needs more than time. It needs energy. That means spending time together when we aren’t about to break down from exhaustion. It requires having energy to truly listen, to take constructive feedback, to have real conversations, and to be intimate.

So, how can one have enough energy to invest in the relationship? This takes us to lesson two.

Lesson Two: Take Rest

It is often assumed that new parents and entrepreneurs should just accept that they will be sleep-deprived. Sleep deprivation was one of the worst decisions I ever made.

When one is tired, one’s willpower to deal with and contain stress dramatically goes down. Furthermore, one’s mood is dramatically altered.

The biggest challenge for me is having a lower breaking point. Little things that I’d normally brush off push me over the edge. It is like becoming a different person. I yell at the children for small things. I become passive aggressive. My logical mind shuts down.

Willpower is not a sustainable solution. Sleep and breaks throughout the day is.

When I made parenting and entrepreneurship the center of my life, I based my life on two of the most volatile things in the world. When I take the time to recharge, I have a reserve to enjoy life, and I don’t hit my breaking point.

Lesson Three: Invest In Your Soul

What makes our relationship work is our curiosity for life, our desire to live to our full potential, and our enjoyment of being on this journey together.

When we both became overworked, each of us stopped daily routines like journaling, meditation, and reading so we could rise to short-term demands. Interestingly, the body has a similar reaction to stress. When we continually activate the flight or fight response, the body diverts all of its energy to short-term performance and away from longer-term restorative processes that may prevent life-threatening diseases like cancer.

When stressed, instead of looking at challenges as signs that there was something for each of us to learn, we looked at them as signs that there was something wrong with the other person.

In the short-term, it is easy not to invest in oneself. There will not be an immediate negative consequence. However, the challenge is that by the time you notice something is wrong, it may be too late, or you will be in a hole that will take a lot of digging to get out of.

Lesson Four: Don’t Use Busy Periods As An Excuse to Not Do Lessons One, Two, and Three

We all hit busy periods in our lives. Those periods can last a few days, months, or even years. It is tempting to save time by not working on the relationship or investing in one’s self during busy periods. However, I’ve learned that a relationship can begin to unravel in just a few months or even weeks. One can become burned out in the same period of time.

It is so tempting to go all out in business and believe that doing so will take you over a hump that will change everything. My experience is that many of these busy periods are self-inflicted and the result of poor project management. Pushing through one busy period generally doesn’t take you to the promised land. It is about the long haul of showing up consistently.

It is hard to draw a strong line and keep investing in important things when things are tough, but there is no better long-term choice.

The End of the Honeymoon; The Beginning of the Lifelong Marriage

As entrepreneurs, our business is not just a different compartment of our life. It is an extension of who we are. Many of us start businesses to provide for our families, to live the lifestyle we want, to express ourselves, to challenge ourselves to become better people, and to have freedom. However, the dirty secret of entrepreneurship that few people talk about is that the exact opposite can and often does become a reality if we’re not careful.

I now understand that marriages challenge the core of who we are. Shortcomings in our character that no one else (sometimes including ourselves) sees are uncovered after years of marriage. As they’re uncovered, we can either hide from them or address them. Marriage can be the ultimate personal growth environment or its worst enemy.

Successful long-term marriages and personal lives don’t just happen. They require constant investment. But there is no better investment known on Earth.

I believe that our spouse is the most important person in our life. In the context of a lifetime, our children, parents, siblings, and business partners are our closest relationships for a only small period of time compared to our spouse. Over time, no single relationship has more of an impact on who we are as individuals, parents and entrepreneurs.


Ed. Note – Special thank you to my wife, Sheena Lindahl, for helping me write this post through 5+ revisions and lots of long conversations reflecting on our relationship.


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I'm the co-founder of Empact, one of the leading entrepreneurship education organizations in the world. I'm obsessed with understanding how we all can lead meaningful lives that have a positive social impact. I love probing into the truth of how we experience life. I believe that challenges are what make us grow the most, and I openly share my experiences. Continue reading…