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.



60 replies
  1. Aldo Ag
    Aldo Ag says:

    The Startup Lifestyle is so exhilerating even when you don’t actually have ALL the risks that you once had in one of your first startups.

    Great post, PT.

  2. Drew Tewell
    Drew Tewell says:

    Congratulations, Penelope, on your new (ad)venture! New challenges are exciting. By the way, guess who I’m interviewing today for my blog? Dan Pink! He reminds me a lot of you. Both of you seem to know what’s next when it comes to work. :)

    Have a good one,


  3. Tina Dietz
    Tina Dietz says:

    I could feel the startup energy all the way over here–total exhilaration despite all the uncertainty. I always tell people that being an entrepreneur is a chronic condition. Once you have it, you can’t recover from it. You can only hope to manage it.

    I like managing it. Looking forward to more posts-thanks for sharing the roller coaster!

  4. Jen
    Jen says:

    Thanks for this post – just what I needed today.

    It’s time for me to make a career change, but I’m paralyzed with fear and anxiety. The reminders to take risks and choose a meaningful life couldn’t have come at a better time.

    Congratulations, too, on your latest adventure!

  5. Angele Style
    Angele Style says:

    Totally agree seeking “happiness” will get nowhere seeking “meaning” in life is key. Wish in my younger days as a chronc risk taker I had been smart like you and invested in business ventures instead of romanitc adventures.

  6. MABEL
    MABEL says:

    Wow, what can I tell you Penelope, you are great and I am never tired of reading your stories. … your new adventures, your daily reactions,…. don’t change!

    Take care =)

    • Penelope Trunk
      Penelope Trunk says:

      You know what? Comments like this mean so much to me. I feel like my life doesn’t happen unless I write it here. So thank you so much for being there to read.


  7. Caitlin McCabe
    Caitlin McCabe says:

    Congrats Penelope! Seems like you’re back in the swing of things and Ian sounds great too!
    Can’t wait to hear more about the startup.

  8. Harriet May
    Harriet May says:

    I went to visit friends in NYC, Israel, and London for two weeks and came back having decided to go live in London. And last night I had a big heart-to-heart with my mother– over wine, of course– who said, “I was a little sad when you first told me but I think you need to go.” And now it feels obvious, if for no other reason than because it’s different; it’s a risk. I’m glad you’re doing a startup, and I’m glad I’m going to London.

  9. Rebecca@MidCenturyModernRemodel
    Rebecca@MidCenturyModernRemodel says:

    I don’t get why reference checking is a transgression? I guess maybe because he didn’t tell you he would check your references… or you didn’t provide the references previously? It seems smart to check references. But in your case kind of unnecessary because it is all out there on the blog.

  10. Melissa
    Melissa says:

    OK so how about calling someone and telling them that you were in love with them 20 years ago. Risky or reckless?? And if you received a call like that would you just think the person was a nutcase?

    I love that you took him to Target for clothes. That’s an awesome way to start a business meeting!

    • Harriet May
      Harriet May says:

      I think that could be really romantic (of course, it depends where he is in his life now, too). But it depends how you tell him. I love love letters, for example. When I like a guy, I *have* to write to him. Proper, through-the-post letters. And my friends think I’m crazy every time, but it works.

  11. Mark W.
    Mark W. says:

    Love love this exchange –

    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.”

  12. Razwana
    Razwana says:

    “Taking risks is an important factor in your happiness levels”

    Does this not depend on what personality type you are? For me, taking risks (however small) has become an essential part of living.

    For some, it’s just not part of who they are, and they’re miserable when they DO take risks, right?

    – Razwana

    • Cristen H
      Cristen H says:

      Not necessarily. I am an ISTJ, and a stay at home mom. In the last six months or so we have added a 3rd child, left a very comfortable corporate job for entrepreneur life, moved, explored Central America with 3 kids 5 and under for 6 weeks, and now looking to invest all our savings in a remote company in an industry in which my husband has no experience. I have championed every one of these ventures. With my type, the risks need to start small and feel manageable. I need to see how we all fare and respond so I know how what to anticipate and how to relax for the next one. I do not love the ride as much as my ENTP does, but I am much happier than I was stuck in suburban corporate hell.

  13. Chelsea
    Chelsea says:

    I love this post. While I might not be working on a startup, focusing on what I want and doing the things that seem important to me, rather than what I “think” I should be doing, sure seems like one hell of a risk. Even though I hold my breath and am scared out of my wits everyday, taking this risk to do what I want with my life sure does make life more fulfilling. Thanks for this post, Penelope. You are doing amazing things.

  14. Lisa Gulli Popkins
    Lisa Gulli Popkins says:

    I love this post- I am the Daughter of a Business Risk taker and a hater of risk- I am a Business/Career Risk Taker now married to a Risk Hater; and there is conflict but I feel like I am dead if I live any other life; I have tried twice and am so happy its over- Be true to yourself Penelope it is the only way to keep breathing every day!

  15. me
    me says:

    Ian sounds like a great partner & a good counterbalance for this kind of project. Be nice/fair to him: it’s not easy to find a competent co-pilot.

    P.S. Hey Ian: nice socks(!)

  16. Jill
    Jill says:

    Wow, I forgot this for over two months and I spent those two months feeling sad and hopeless. Last week it started coming back to me — sex with a complete stranger was surprisingly helpful.

    I spend all winter taking (fairly small) physical risks while skiing, but in the summer I have to make an effort to seek out ways to make myself uncomfortable enough to grow.

    • Penelope Trunk
      Penelope Trunk says:

      The idea of seasonal risk is so interesting. Like seasonal disorder or whatever that’s called – where winter makes you depressed. But it’s not depression, maybe, it’s winter risk-taking craziness, and summer stability or something like that. I wonder if we each have a season where we do our best risk-taking.


      • channa
        channa says:

        Yes – for me it is summertime – never outgrew the rhythm of school. The smell of late summer (which is blackberries and dry grass where I live) makes me crave life changes and new clothes.

        • Elizabeth
          Elizabeth says:

          Wow! For me it’s late spring. That’s when I make all the crazy decisions that sometimes pay off. It takes the rest of the year to actually make the things happen. Without fail, for years now.

      • Jill
        Jill says:

        It’s also connected to happiness for me: skiing makes me happy every single time, and being happy makes it easier for me to takes risks.

        However, taking those risks increases my happiness, something I need to keep in mind when I can’t ski every day.

  17. GingerR
    GingerR says:

    Glad you took some business to Penny’s. I knew they were going to can the fellow from Apple, he moved fast and upset all the middle-aged bargain hunters who love nothing more than clipping coupons and hunting down the cheapest junk they can find.

    Why anybody thinks those are the customers you want to attract I don’t know. They may still go under, the competition in that range is fierce and they let themselves slide.

    Good luck!

  18. Becky Eastham
    Becky Eastham says:

    I love that it’s about the process and not the end results, I adore your prescriptive and find myself dealing with situations and think, what would Penelope do?


  19. Braden Jageman
    Braden Jageman says:

    Your posts always seem to be just what I need at my stage in life. Just when I was worried about quitting my job and starting my own startup you come along and assure me that I’m making the right decision. Thank you!

  20. jessa
    jessa says:

    I have a question. You have stated that start ups can end a marriage. You have also said that you do not want your marriage to end, and that you are willing to make sacrifices to keep your marriage because divorce has a very negative affect on kids. You have also stated that your marriage is rocky, and this new start up is not helping the situation. So my question is: Why are you starting a new start up knowing that there is a risk you might get a divorce?

    • Juan
      Juan says:

      We tend to think that people are rational actors; that they pursue rational outcomes. I tend to think that people rationally pursue their emotional goals. So while it may be foolish to put her current situation at risk, I think Penelope is pursuing her emotional goals of creative destruction and change. I think it probably seems crazy to risk-averse people, but I get it.

  21. Pooja
    Pooja says:

    Hi Penelope,
    I love the way you’ve put together some of the risks you take, from your rich looking sunglasses to the green t-shirt, and your start-up. I can identify because I took a career switch risk some time back. Life can be awesome when you’re doing what gives meaning to your life!

  22. Laura
    Laura says:

    Hi Penelope,
    Amazing links from Psychology Today. You are in pursuit of happiness which to me is actual happiness. And you sound happy! Keep taking those fashion risks and business risks — it suits you.

    • Penelope Trunk
      Penelope Trunk says:

      I know! I loved the Psychology Today article, too. Actually, I bought the whole issue at a newsstand, and the whole issue is amazing. Like, another tidbit in there was about Tavi Gevinson. She launched a blog when she was in grade school and she became huge in the fashion industry and then dumped it all to launch a new business in high school. Career change in high school! It blew me away.


  23. Gary
    Gary says:

    So far, so good on cell, P. my wifi may be the culprit, will test when I get home. I’m trying to keep up, but the last two blogs haven’t been applicable to me… NOW. I’m wondering how many years I can save them, but ha, they’ll be obsolete by then, anyway. You just keep on keeping on, and have a wonderful Independence Day! G

  24. Michele
    Michele says:

    Thank you for this post. I am terrified of stepping out of my comfort zone but after reading this post yesterday I decided I needed to take a chance on myself. I hope it all works out for the best but if not, at least I am proud of myself for taking the risk. Thank you for the inspiration to try!

  25. Heather Sanders
    Heather Sanders says:

    I think it says something about me that of everything you wrote in this post, my favorite line was “Maybe I’m like those people who wear clothes that are not appropriate for their age.”

    Maybe it says I would suck at a start-up.

  26. pfj
    pfj says:

    Penelope, you’re an adrenaline junkie. When you say, “I want my days to be more interesting” . . . that means you want that rush that people get when they’re falling off the roof. How much pain will there be when you hit the ground?

  27. Jake Bauer
    Jake Bauer says:

    Hi Penelope. I just wanted to say that this is the first post of yours that I’ve ever read and it was definitely different, interesting, and entertaining. It read more like a short story than a blog post. I’ll continue reading. I’m interested to see what you’re all about and if all of your posts are like this.

    • Gary
      Gary says:

      I’m addicted to P’s blog, Jake, and I can tell you, what you see is what you get. So welcome aboard, and please buckle up!

  28. Rita
    Rita says:

    You two look like brother and sister, it’s uncanny! Makes me think it’ll all work out ok.

  29. Chiara
    Chiara says:

    “how people need meaning in their lives, not happiness”

    What a wonderful read. I love how you made it sound almost like a romantic relationship. For entrepreneurs, partnering up with someone can make you just as vulnerable..

    My first stop here and definitely not my last. This is great!

  30. Dems
    Dems says:

    Hmmm… startups! Love them but really there is a lot of work involved. I told myself a few years back that having a start up when you already have a good cash flow is going to be so much more fun that start broke! This is my first time here…I’m reading through..

  31. Nanny Peta
    Nanny Peta says:

    Hi Penelope,

    I visited your blog as there was a link to you from another blogger, having just read your Start Ups post l am hooked and look forward to reading many more of your posts. Love your use of the English language…lol.. Not that l say those kinds of words myself… (well not very often). But yes an interesting story and Ian sounds like a real good fellow who would provide many laughs.

    Pitty l must head out now, l want to read more of your posts asap, but will have to wait until l get back home tomorrow.

  32. lakisha jones
    lakisha jones says:

    Hi Penelope, I met you at the Berkeley flea market Pride weekend. I just wanted to thank you for all your inspiring words.I made my way to pride that day and I sold not one pair of my earring. .I was a little wounded but eventually I got over it..however; I did sell a few while I was at the Berkeley flea market. .That was kool.I didn’t truly flop..anywho now I’m still pushing and from tym to tym I have thought about you and here I am saying hello..Hope you had a great 4th..
    Peace and Blessing…

  33. Angie
    Angie says:

    Ian’s handsome. And I can’t wait to hear more about this new venture. When will it stop being super secret?

  34. Lori
    Lori says:

    I followed your blog back when you met the farmer, and then when you couldn’t believe you were living out there on the farm. I loved it but I started a new chapter in my own life and couldn’t be a regular reader any more so I dropped my email subscription. I started following again a few days or a week ago and I’m so glad to be back. I think I’ve read 20 posts tonight. This is a great one to end with. Great post. And some good lessons for me. Thanks for sharing, as usual.

  35. Ann Hooker
    Ann Hooker says:

    Do you know some things about the economy? You used the word implode when referring to it. I have been reading some strange stuff about large stockholders selling large amounts off. Just curious as to what you know….

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