Issue #148 How Building My Business Almost Cost My Marriage

Seven years ago this month, Kelly and I gathered with our children, family and close friends to celebrate our twenty-fifth wedding anniversary by renewing our wedding vows.

The picture above was taken that day. It was one of those rare late-summer afternoons that seemed almost too beautiful to be real. Standing on a rooftop overlooking the spectacular Okanagan Valley, we found ourselves surrounded by clear blue skies, calm water and the mountain landscape that had recently become our new home. It was one of those moments when everything seemed to align, making it difficult to imagine a more fitting place to celebrate the journey we had shared together.

The timing couldn’t have been more meaningful. Only months earlier we had exited the toy business after nearly three decades. Although I knew I would continue building businesses, I had already decided my next chapter would be different. 

For much of my adult life, my business plan had shaped my life plan. This season became an opportunity to reverse that equation. 

In many ways, it felt as though we were beginning again. We had a new community to call home, a new chapter in business and, perhaps most importantly, a new way of thinking about our future together. 

At the time, it would seem that we were simply celebrating twenty-five years of marriage. The truth is we were doing something much more significant. We were choosing one another again, this time with a depth of understanding that only twenty-five years of shared life could provide.

What the people attending the ceremony didn’t know was that only a few years earlier Kelly and I had come dangerously close to losing the very relationship we had gathered to celebrate. It wasn’t because we had stopped loving one another, it was something far more subtle than that.

Somewhere along the way I had begun taking our marriage for granted.

Almost losing my marriage became a crucial inflection point in my life, forcing me to confront a difficult truth: I hadn’t misunderstood the importance of marriage; I had misunderstood the ongoing investment it required.

My pursuit of achievement had helped me build a significant life and business. However, left unchecked, it had also almost cost me my marriage.

The Cost of Assumption

Looking back, I can now see how deeply achievement shaped the way I viewed the world. I have always been goal-oriented. I loved imagining what was possible, creating a plan and then striving tirelessly to make it a reality.

I had spent years intentionally investing in building myself, my community and my businesses, yet somehow overlooked the fact that my most important relationship would require the same effort and intention.

Like many entrepreneurs, I naturally measured progress through milestones. Starting a business, buying a first car, purchasing a new home and celebrating our first million dollars in sales. Each of these felt like meaningful markers along the road, with every accomplishment representing another step toward the life I imagined we would one day enjoy.

Without ever consciously intending to, I quietly placed my relationships into that same framework.

Marry the beautiful girl.

Check.

Have children.

Check.

And with those milestones accomplished, I naturally turned my attention toward building everything else in the pursuit of fulfilling my goals and dreams.

I have been surrounded by entrepreneurs my entire life and I am convinced that this is a very common pattern. Founders are wired to pursue goals, solve problems and move toward measurable outcomes. We naturally gravitate toward things that can be built, completed and improved. 

Knowing that then why would we expect that we would think about relationships any differently? After all, there is nothing about a wedding ceremony or the birth of a child that suggests the greatest work is only just beginning. If anything, those moments feel like the successful completion of another important milestone.

And that is where the misunderstanding begins.

The problem wasn’t that I lacked commitment. I loved Kelly deeply and never questioned my desire to spend my life with her. The problem was that I misunderstood what commitment actually meant.

In business, we celebrate completion. We launch the company. We close the acquisition. We ring the bell. Achievement has a series of progressing finish lines.

Marriage is different.

The wedding day isn’t the completion of the work.

It is the commencement of it.

I falsely assumed that the effort I had invested in pursuing, attracting and eventually marrying my wife was complete and that our relationship would continue to flourish on those initial investments. Somewhere along the way, I had unconsciously begun treating marriage as something I had achieved rather than something I needed to continually cultivate. I assumed that because I had exchanged the rings and spoken the vows, the relationship itself would just naturally continue growing. It was an assumption I didn’t even realize I was making until it was almost too late.

Yesterday’s Investment

I have often asked myself how two people who genuinely love one another can come so close to losing the relationship they once believed would last forever.

Looking back now, I can see that commitment alone doesn’t sustain a marriage.

Investment does.

When Kelly and I were first married, conversation seemed effortless. We talked about everything. We imagined the future together, dreamed about the family we hoped to build, the businesses we might one day create and the kind of life we wanted to share. Those conversations weren’t scheduled. They simply emerged because we had time, curiosity and a genuine desire to understand one another.

As the years passed, however, life became fuller. Business demanded more. Children arrived and responsibilities multiplied. Without ever deciding to, we slowly found ourselves talking less about the things that were shaping us and more about the things that needed to get done. 

Our conversations became increasingly practical. Calendars replaced curiosity and logistics replaced dreaming together. We became remarkably good at managing our life together while becoming less intentional about continuing to grow together.

None of those conversations were unimportant; they were simply insufficient. I have come to believe that our marriage wasn’t weakened by one dramatic failure, rather it was weakened by a thousand small assumptions.

I assumed tomorrow would provide another opportunity to reconnect.

I assumed unspoken disappointments would simply fade away.

I assumed yesterday’s investment would be enough to sustain tomorrow’s relationship.

It wasn’t.

Relationships are living things. They cannot survive indefinitely on yesterday’s investment any more than a garden can flourish on last year’s rain. They require continual attention, continual care and continual renewal.

Looking back now, I don’t believe Kelly and I came close to losing our marriage because we lacked love.

We came close because we assumed our love could flourish without our continual investment..

From Good Intentions to Intentional Practices

If there is one lesson I have carried forward, it is this: healthy relationships are not sustained by good intentions; they are sustained by intentional practices.

We realized that if we wanted our marriage to continue growing, we couldn’t simply hope for meaningful conversations to happen. We had to create the space for that to happen.

That is when we began establishing a simple weekly rhythm. Not because something was wrong, but because our relationship had become too valuable to leave to chance.

It has become part of our commitment to continue our “fifty-year conversation.” Not because every conversation solves every problem, but because it creates the space for the conversations that keep our relationship alive. It moves us beyond the logistics of everyday life and back into the curiosity, vulnerability and shared dreams that first brought us together.

We have learned to talk not only about our calendars, but also about our hearts. We celebrate what is bringing us joy, acknowledge what is weighing us down, speak honestly about where we are struggling and encourage one another toward the people we hope to become. Our conversations are no longer simply about what we are doing. They are about who we are becoming.

I don’t believe our weekly rhythm has saved our marriage however I believe it continually renews it.

Reflect & Align

For most of my life, I believed the greatest investment I could make was in the businesses I was building. Today I no longer believe that. The greatest investment I have ever made isn’t about business; it was in choosing the person with whom I would build my life. Every meaningful achievement that followed has rested upon that foundation.

By renewing our vows, it wasn’t simply an opportunity to celebrate the previous twenty-five years. It was an opportunity to enter the next twenty-five differently.

At twenty-five years old, I thought marriage was something I had achieved.

By forty-five, I had come to understand it was something I needed to continually invest in.

Something I needed to keep cultivating.

Something worthy of my very best.

I have come to believe there is no stasis in life. We are either green and growing or ripe and rotting. Relationships are no exception. They are living things. Left unattended, they don’t remain healthy; they slowly begin to wither. Like a well-tended garden, they flourish through consistent cultivation rather than waiting until the vines have begun to die.

Last week I shared the simple GARDEN Framework we use to guide those weekly conversations. If you missed it, or would like a complimentary copy, simply leave a comment or send me a direct message with the word GARDEN, and I’d be happy to send it to you.

As you reflect this week, perhaps these questions are worth considering:

• Have I unintentionally treated my closest relationships as achievements rather than investments?
• How have I assumed that the health of our marriage would simply take care of itself?
• Am I giving my best energy to what matters most, or merely to what is demanding my attention today?

Achievement taught me how to build a business.

Marriage taught me what was truly worth building.

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