Take more risks to make life more fulfilling

Take more risks to make life more fulfilling Im driving to the Madison airport to pick up Ian, my new partner in my new secret startup. Im wearing the sunglasses that Melissas 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 womens fashion and alienated all the loyal customers? This makes me think its okay that I like the shirts they sell. (Or used to sellsince 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 dont tell me its terrible. Its 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 havent had to meet a business associate in person in a long time. I do everything online. And I wonder if Ive 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 doesnt 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 cant 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 dont tell him that if I owned a house Id 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, its 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 its 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,  Im worried that its hard to be professional and be with a family in the same place. Im worried that people who are older are worse at taking risks and maybe I am too old for this. Maybe Im 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 cant keep your guard up when youre 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 everyones 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 Ive 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 dont 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 were a solid team. 3. Know the difference between risky and reckless. Until I get a call from Ryan Paugh,  a week later. Ryans 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? Thats 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? Hes a close friend. What could he possibly tell you that would make you stop working with me now? Its already been a month of working together. Ian says that hes sorry, that he hears me, that it will not happen again. I say, Fuck you you fucking asshole youre a jerk. I dont 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 were doing but having to move fast anyway. Ian is good for me. He is very good with people, and calm when Im 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 its hurtful to him. Okay. Fine. It turns out that Im 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 Im on the phone. Lets 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 youre a really good guy and that I need to get over my trust issues and stop having a fit when someone does something I dont like. Ian says, Thats 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 werent for you. Both of them said you were extremely loyal and caring. I am surprised. And so happy that I leave with no plants. Im saving my money for when the startup runs out of funding and I have to live off of savings. Not that Ill have savings. Its not my style. So I use the money for the weeks groceries instead, and Ive settled into the startup trenches.