Take more risks to make life more fulfilling

I’m driving to the Madison airport to pick up Ian, my new partner in my new secret startup. I’m wearing the sunglasses that Melissa’s boyfriend said make her look too rich and too Type-A. The glasses are perfect for today.

I am also wearing a new, green shirt that I got at JC Penney. Did you read about how the new CEO overhauled women’s fashion and alienated all the loyal customers? This makes me think it’s okay that I like the shirts they sell. (Or used to sell—since he just got fired for selling clothes I like.)

I email Melissa a picture of me driving with the shirt on. Then I call her.

“I forgot to get approval for this outfit before I left for the airport,” I tell her. “So don’t tell me it’s terrible.”

“It’s okay. Where did you buy it?”

“Forever 21.”

“Oh, I love everything at Forever 21.”

“I know.”

1. Taking risks is an important factor in your happiness levels.
I am nervous that I haven’t had to meet a business associate in person in a long time. I do everything online. And I wonder if I’ve lost my zing since I started living on the farm. Everyone I called for advice told me not to do another startup. They reminded me, “You have what you need. You earn a good living from your blog. All startups are a mess.”

When my brother told me I was going to get myself into financial trouble again I told him about the article that I read in the Atlantic about how people need meaning in their lives, not happiness, and while setback doesn’t make our lives more happy, it does give our lives more meaning.

My brother said, “Tell me that when you run out of money and you can’t get funding.” My brother buys startups for a huge rich company. He is blown away by how many entrepreneurs put their house on the line to build their company. I don’t tell him that if I owned a house I’d borrow against it in a minute.

I tell myself that I am smart to mess up my life because people who are happy expose themselves to the possibility of huge loss and disappointment. I tell myself that if I have to do this, it’s better to do this with my career than my personal life.

2. Process matters more than results.
Ian sees my car and walks toward me. He is tall which is good because tall people make more money and we are making money together. He is also Irish Catholic, which is comforting because the kids I grew up with were from large, boisterous Irish Catholic families that took me to church on Christmas and let me stay seated when they ate a wafer.

Ian dressed down for the farm, but it’s still too dressed up. So I take him to Target to buy farm clothes.

On the drive home we talk about our life stories like we are on a date and I thank God I am not dating anymore because I have heard my story so many times that I bore myself.

At the farm, I’m worried that it’s hard to be professional and be with a family in the same place. I’m worried that people who are older are worse at taking risks and maybe I am too old for this. Maybe I’m like those people who wear clothes that are not appropriate for their age.

Ian puts on his Target clothes, I put on my going-out-to-the-pasture clothes. Then we go out to the pasture with Matthew and the boys. You can’t keep your guard up when you’re dressed for the farm.

Ian is almost my opposite: friendly and easy-going. He talks to Matthew about cattle, he treks through tall grass that scratches his legs, and he laughs when he steps in cow poop, though the boys laugh harder.

I want to spend my days with my sons and have a startup, too. I think I want this more than I want a lot of money from a startup. I want the process to be good. I want my days to be interesting. Ian strikes me as the type of founder who succeeds because so much of his definition of success is about process. Process over outcome. Essential to everyone’s happiness, but especially everyone in a startup.

We eat dinner and Matthew puts the kids to bed so Ian and I can work. I have a weird faith that I will be able to handle the extra workload because I’ve done it so many times before. In Psychology Today I read that  the best way to create happiness in your life is to take risks. And the more risks you take the more risk-tolerant you become. Doing another risky startup is almost low risk for me, because I know, even if I crash and burn, it will make me happy. Crash and burn is interesting.

Ian is an ex-finance guy. His spreadsheets are gorgeous with no broken formulas and fonts that don’t vary, even from tab to tab. I am happy that I will never be the person to manage the spreadsheets in this company, which is a big deal because in a startup, there are no right answers for financial projections, so they change every day.

The next morning, the boys go into Madison with the nanny and Ian settles in for a long day of work.

I am back in startup land so easily. The rhythms of founders searching for a business model feel like intellectual home base for me. Ian leaves and we’re a solid team.

3. Know the difference between risky and reckless.
Until I get a call from Ryan Paugh, a week later. Ryan’s one of my co-founders at Brazen Careerist, and  Ian called him to get a reference.

“What? When? Are you fucking kidding me?”

“Relax,” Ryan says, “It was a few days ago.”

“What? That’s ridiculous. He already committed to me way before that. He already had me pitch to his investors.”

I hang up. I call Ian. “How could you call Ryan without asking me? He’s a close friend. What could he possibly tell you that would make you stop working with me now? It’s already been a month of working together.”

Ian says that he’s sorry, that he hears me, that it will not happen again.

I say, “Fuck you you fucking asshole you’re a jerk.”

I don’t call him for two days, but I miss him. I love working on a new idea. I love the urgency of having to get money right now before everything implodes. I love not knowing what we’re doing but having to move fast anyway.

Ian is good for me. He is very good with people, and calm when I’m screaming. He never screams. He never gets side-tracked by irrelevant topics. He told me “no name calling” because it hurts his feelings so I can choose to do it, but he wants me to know that it’s hurtful to him.

Okay. Fine. It turns out that I’m the only person who thinks his furtive reference check was a huge transgression.

I call Ian from the garden center at Home Depot. Perennials are half off and the only way I can do a startup and homeschooling is if I buy perennials while I’m on the phone.

“Let’s just move on,” I tell him. I pause at the bedraggled daylilies that are not even worth 50%. I tell him, “Also, I want you to know that Ryan said you’re a really good guy and that I need to get over my trust issues and stop having a fit when someone does something I don’t like.”

Ian says, “That’s nice. And I want you to know I learned a lot from calling those two.”

“You called two? You called the other Ryan also?”

“Yeah. They both said that you did so much for them. One of them said that he would not be where he is today if it weren’t for you. Both of them said you were extremely loyal and caring.”

I am surprised. And so happy that I leave with no plants. I’m saving my money for when the startup runs out of funding and I have to live off of savings. Not that I’ll have savings. It’s not my style. So I use the money for the week’s groceries instead, and I’ve settled into the startup trenches.