Relationship Startup

It’s always worse than it is and better than it seems to be. Even when you’re cruel and it hurts, I know things will improve soon.

When you say I think I’m too good for a normal corporate job and that’s why I started a company, you make me feel arrogant and lazy. But I know I can still convince you to trust me. Maybe if I got some investment, or made progress on the product, you wouldn’t say I’m only doing this because I had a bad experience with a boss. I wince when you say, “You don’t think I’ve ever had a bad boss? I’ve been working for eight years. Why can’t you just pay your dues like everyone else?” 

I need to succeed to save the relationship. There’d be less tension between us if the air was less thick with the noise of all the conversations we weren’t having about money. 

I am always silently asking you as loud as I can why we’re so stressed about money with the assets we have. Our assets, if I can call them ours, total over $100k, and that’s including my debt. And isn’t that what being engaged to be married means, that I can say “our assets?” 

And if I listen closely to the words you’re not saying, I can sometimes hear you telling me to call it quits. “You gave it the old college try” is the phrase I remember assigning to the untold voices radiating from you. 

It would all be better if we had more money. If I got some investment and could pay back my debt, you’d feel less guilty asking me to go out with you to a nice restaurant, and I’d feel less stressed about saying yes. 

I know you have good taste, and I can’t blame you. It’s called nice stuff for a reason. But I don’t see an issue eating cheap junk food to save money and time. I want to give you nice things. I want to enjoy nice things with you. 

And hopefully soon my fortune will change and things will get better. 

I would later recognize this as a turning point in our relationship. This moment would live in my mind next to when we met, our first kiss, the moment we decided to move in together, and when we decided to move to Las Vegas when you bought your house. (Notable absences from this list include when you proposed to me). This was the last moment I still believed, truly believed, that it would work out. Something changed for me then even if I wasn’t fully aware of it yet. 

This was the last time hope outmatched despair in the quiet fights of my mind. 

My dreams were the first hint that something was off. I would wake up in a cold sweat at 5:30am with a deep anxiety about my debt/savings/income ratio. Sometimes it felt like being jolted awake by a phone call from an angry creditor looking for their money. 

But you were my only creditor outside the usual institutions like banks and credit cards. And you were always fast asleep when this happened, and I never wanted to wake you up. 

I would lay there in the dark, my heart racing, refreshing my bank statements looking for a miracle. 

This was before you made me promise to take three months off work while we were traveling. 

Your trip, the one you’d been dreaming of for six years, was the only reason we were worried about money. We both knew that’s what was going on, but we had never really talked about it. 

The closest we got to saying the words was right after I took out the loan. You came upstairs and sat next to me on the couch. You opened your laptop, looked at me, and sighed loudly. 

“What?” I asked. 

“We don’t have the same priorities.” 

I looked at you and froze. 

“You said you were on the same page about living abroad.” She took a few breaths. “Don’t just sit there. Say something.” 

“I know how important this trip is to you. It’s important to me too.” 

“If it was important to you, you wouldn’t have taken out that loan.” 

“We talked about it. I asked you about it before I did it.” 

“You asked me about 30,000 and then took out 50,000. We didn’t go through it in detail. I want to be clear, David. I am going to live abroad before I’m 30. I’m not going to put it on hold for you.” 

“I’ve already paid off 12,500.” 

“Because I’m paying all the bills.” 

“I promise you this –– the loan, my company, none of it will interfere with your trip.” 

The only time I ever lied to your face was later, when you asked me that impossible question.

How could I say no when you said, “I want to enjoy the trip with you. Come on, this is the only time in our lives we can do something like this.” 

It seemed like a silly thing to fight about. When I said my finances might not allow me to take 3 months off work, you said you’d pay for me. Who could refuse that? 

But I knew if the company was still running, I’d never be able to take three months off. No board of directors would sign off on the CEO taking a three-month sabbatical. Not at my stage of business. 

And if the company failed, I knew I’d be too anxious about paying off my debt to take a three-month vacation.

To this day, I still don’t fully understand why I lied to you then. Maybe I could sense an ultimatum coming. Maybe part of me wanted it to be true so it didn’t feel like a lie. But I knew it would never happen. 

“I promise you. I’ll take three months off.” 

“I know startup founders, David. I don’t think you’ll be able to.” 

“I’ll find a way,” I lied. “Nobody wants a nutcase running a company, huh? It’ll be a mental health thing.” Your smile widened when I said, “Or an extended honeymoon.” 

The last time I saw you, we were both wearing purple.

When you walked into the counselor’s room an hour late, the first thing I noticed was your hair –– a new, brighter shade of blue. You put the wrong time in your calendar, having mistook a conversation about scheduling for concrete plans. 

Even though I’ve made the same mistake a dozen times, it felt like a personal insult. Or like a microcosm of everything that had gone wrong in the relationship distilled into a single moment. 

The couch fibers dug into my skin in a rough way that wasn’t entirely unpleasant. Any excuse to escape from my mind into my body was a welcome distraction. Otherwise, I might have run out, slamming the door behind me. 

When you said, “You broke up with me when you read me that letter asking for a break,” my goal shifted. I no longer had any hope of understanding you or feeling understood. The goal was now to move my body through time. I would buy coffee after this. I would listen to my favorite playlist on the drive home. But the taste of coffee faded, and I was brought back into myself. 

“David? Are you even listening?” 

We were speaking different languages, the counselor an ill-equipped translator on a doomed diplomatic mission. Had we been asked about the nature of the mission, our answers would have diverged greatly. We didn’t know why we were there, not in any real way we could articulate to ourselves. 

I couldn’t possibly communicate how small I felt in the relationship, especially not after you said you felt like my goals took priority over yours. 

What’s in the space between two people who are together and both feel small? 

You were focused on your goal to travel and take time off work. I was focused on my goal to build something so I could permanently divorce my time from my money. 

In the quietest hour of the night, when it’s dark and I’m alone, I admit to myself that I think you should have delayed your trip. In those moments, I think that our goals were a lot alike and that the only reason there was all the pressure on money was because of this artificial deadline you gave yourself to live abroad for a year and take time off work before 30. 

I never asked you to delay your dream so I could pursue mine first. I don’t know if that’s ever a fair question to ask anyone. In those moments, I know my dream was time-bound in a way yours never was. If I had delayed too long, there would have been too many competitors for the opportunity to make sense.

I wouldn’t have hesitated to delay a non-timebound goal so you could pursue a timebound goal. And the person I’m looking for wouldn’t hesitate to do the same for me. 

Every relationship will have trade-offs like this, just like every choice limits the option pool. A career change to something less lucrative but more meaningful; a dream to move to a particular city; the decision to start a company. Some of these decisions become regrets. I would want a partner who would see it from the same perspective I saw it with you –– over the course of a lifetime, partners will take turns steering the ship, and the important thing to keep in mind is the lifetime proportion of steering the ship, not the local proportion of steering the ship. 

I can understand how, without thinking about it over the long term, it could feel like I was cutting the line to steer the ship. I wonder if there’s anything I could have said or done to help you consider the long-term perspective, and I wonder when exactly your heart had hardened past the point of no return.

It always felt like you resented me for cutting the line. Sometimes it felt like you were jealous of my courage to pursue my dream quickly when it took you years to finally make it happen, and even as late as July (the flights to Colombia had been booked for October), you asked me, “Am I making the right choice quitting my job to go abroad?” 

I was worried you’d resent my decision if the company failed, and it almost always felt like you were confident the company would fail. With decisions as major as these, and when failure is always a possible outcome, the most important thing should be the effort and the attempt, not the outcome. And that pressure to succeed probably fed into a vicious cycle where I put more of my attention into the company and less into the relationship.

It often felt like you saw my childlike wonder and naive optimism as weaknesses, vulnerabilities that could be taken advantage of. I'm starting to realize they are my superpowers. Like the guy in Slumdog Millionaire, I believe, "Everything always works out in the end. And if it hasn't worked out yet, it's not the end."

I'm still a little sad that you won't be a part of my "end."

I hope you can find a little optimism in your travels. Sometimes good things happen. Bad things happen too, but they're not some sort of punishment or karmic retribution for the good things.

I hope you can give yourself permission to be happy without waiting for the other shoe to drop.