Decisions are not binary: Why I joined a startup even though my wife said NO

Photo by Stillness InMotion on Unsplash

How it started

It was September 25th, 2020, the year of the pandemic. An intense year, confined to our home with 2 young children and an infant. It felt like we cried as often as the baby! However, there was one area that was going well, work. I had a string of successes, built 3 new teams, and grew my pet project, Happy and Successful, to 50 engineers.

That day I received a message that caught my full attention. Jennifer Dulski, former head of Facebook Groups, COO of Change.org before that, bestselling author, kickass leader, that Jennifer Dulski, had messaged me.

“Hi! Hope you are doing well amidst all that is happening. I would love to catch up and wanted to see if you had some time next week.”

My wife predicts the future

That night I mentioned it to my wife: “Guess what? I got a message from Jennifer Dulski, she used to lead Groups... I think she’s doing a startup now.”

I thought I would get a “that’s nice” or maybe even an “oh cool”.

Instead she said one word: “NO”.

“??? Umm... what? What do you mean by that? That’s an odd response.”

She sighed, “I already know what’s going to happen. You’re going to leave your great job with all the great benefits and join the startup.”

I laughed to hide my shock. “Ha, that’s a bit premature isn’t it? I haven’t even talked to her yet. I have no idea what the startup is. Plus, I’m happy where I am.”

She took a deep breath. “Doesn’t matter. It’s going to happen. There’s nothing I can do about it, but I just wanted you to hear that I’m saying no.”

😅  (hint: my wife knows me better than I do)

A painful past

I was hurt. I told my coach, “My wife basically said that I’m going to ignore her. Why does she think that? That’s not what I want. I should just forget about the startup.”

Why did she think that? My wife and I made all of our decisions together... right? I reviewed a few of the past decisions my wife and I made together.

• Buying our first house. We bought it together. But I decided I wanted the house with the yard, which grew 5 foot tall weeds because we didn’t maintain it.

• Deciding to stay in LA. My wife wanted to move out of LA, after our street had a triple shooting and after she had been mugged on a walk with the baby. But I decided to get a new job, forcing us to stay in LA.

“Am I a terrible person, always steamrolling my wife’s opinions?”, I asked.

“Let’s review some more decisions”, my coach prodded.

I reflected on a few decisions that had a different outcome.

• Attending grandma’s funeral. After my grandmother passed, I really wanted to attend the funeral on the other side of the country. At that time, we were new parents overwhelmed with our 1st child. I knew my wife didn’t want me to leave her alone with our daughter and so I never seriously considered the trip.

• Pursuing my interests. My wife does a lot and I really appreciate that. I never felt comfortable asking for time to explore my own interests or to make my own friends because I worried it would add even more to her plate. I resigned myself to the idea that the only world I would know was work and family.

This was our dynamic. It was always either my way or her way. We kept hurting each other.

My coach said, “I want you to know that this is not your fault and it’s certainly not her fault. But now that you know, you can do better”.

Writing it down

Determined to change, we listened to each other’s concerns about the startup and wrote them down:

• Money: It’s a 50% pay cut! Are we going to run out of money? Can we afford our house?

• Quality of Life: We’ve been working on being less frugal and we’re finally starting to enjoy focusing on quality of life and value rather than money. Are we going back to being frugal?

• Hours and flexibility: Are you going to work crazy hours? Is it going to be hard to change your schedule if I need your help with something?

• Career and job risk: You’re doing so well at your current job, are you going to throw it all away? How will this affect your career? Startups are risky, what if this fails?

• Startup after startup: If this fails are you going to go to another startup? Is our life just going to be an endless cycle of startup after startup where we’re always struggling?

• It’s 2020, are you sure about this? We are in the middle of a pandemic, we have a clingy newborn child who screams all the time, we need to help the 2 older kids who are struggling with virtual school, and now you want to add a startup to the mix? WTF?!?!?

• Fulfillment: This is a huge opportunity for me to grow, learn, and do something fulfilling. I don’t want to feel like I missed my chance.

Win-win: Breaking out of the pattern

Writing down each concern made us realize that the decision was not all or nothing! We could address each item individually. Our mindset was: How can we make this work?

Risk: I was confident that I could always go back to my old job. We agreed on evaluating after 2 years. It was a risk free 2 year learning experience that I was being paid for! We added one more condition: My next job would be back at a more secure big tech company.

Money: We decided there would be no cutbacks on quality of life. No crazy hours. We calculated out the financial numbers and decided on a minimum compensation.

Fulfillment: We talked about why I wanted to do this. I saw it as a huge opportunity. The company’s vision resonated with me deeply and was exactly what I was working to start at my current job. Jennifer is a leader I’ve always admired and now I had a chance to work with and learn from her. Finally, I love building and what’s more exciting than building a completely new market, product, team, and company?

I did join the startup. In the end, while my wife didn’t agree with my decision, she felt that her concerns were addressed and she was no longer worried about our family. If we had repeated history, either she would have gone along with it only to end up feeling stressed and unhappy, or I would have given up on the startup only to end up feeling resentful. Instead, we worked together and brainstormed solutions we were both happy with. I’m so grateful that my wife supports me even when she doesn’t agree with me.

It’s been a little over a year since I joined. Every month that goes by I feel even more sure that we made the right decision. I’m happier and more fulfilled than I’ve ever been at work.

Takeaways

• Decisions aren’t binary! List out your reasons and concerns and address them individually.

• Work together to find the win-win. Don’t settle for win-lose.

What decisions do you want to re-examine?

Acknowledgements

Thanks to Jennifer Lin, Quratul-Ann Malik, Dustin Spencer, Gary Yuen, John Absher, Yao Cheng, and Sharon Kam for reading my drafts and giving me feedback!

Updates (4/18/2022):

• Edits for clarity

• Added a note about how I feel about the decision now.

• Added Acknowledgements!