How to have faith in yourself

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Sunday nights at our house are dinner with me, the kids, the Farmer and the Ex. They are always fun dinners, and I always feel very lucky for that.

My six-year-old talked about his new baby cousin, Eva (who is pictured, in utero, above). “She has a terrible name,” he said, “for Pig Latin. Its Vaeay. It doesn’t work.”

We all do the vowel arranging in our heads and agree, Eva is not a good Pig Latin name.

“Mom has a great name! It’s Enelopepay.”

The Farmer says, “It sounds like it could be the name of her next company.”

The Ex says, “Yeah, emphasis on the pay.”

The three adults laugh.

And then I get nervous. About what I’m going to do next. If you have had three companies, people assume you will have a fourth. So I assume that, too. Which makes me nervous.

When I was in the doctor’s office with my son, he was playing his DS and I was looking for something to read to distract myself from the urge to rein in his video game time (I decided that parents who limit video games are delusional.) And I saw this pamphlet that looked like a food pyramid so I grabbed it to get some insight into how to use the food pyramid to make myself not want to eat and lose weight overnight.

What I thought was a food pyramid pamphlet was actually a mental health pamphlet. It was a pyramid that had taking care of life goals and meaning of life stuff on the bottom, and the middle part was daily routine mental health stuff like exercise and talking to friends—the stuff you already know you should do every day. And the top was the immediate stuff. Ways to calm yourself down in the moment. For the most part, the top part was positive self-talk.

I am good at the first two, but the immediate stuff I’m not good at. In fact, I eat when I am anxious. I found, actually, that drinking is more calming when I’m anxious, but eating is more socially acceptable. Xanax is always good, but only if I can sleep the rest of the day. And really, if I have a day where I can sleep then I’m probably not anxious. Not that I would ever know. Because I haven’t had a day where I can sleep the whole day since I became a mother.

Anyway, I am trying to find good ways to calm myself down when I’m nervous. And I took the pamphlet home to make myself more conscious of what I do in the moment when anxiety arises. Mostly this means that I’ve started to tell myself, “Oh, look. I must be upset becacause I’m eating.” But in this moment, at the dining room table, while the kids talked to the dads, I went into the kitchen to calm myself down. And I didn’t eat. I practiced positive self-talk.

I had rehearsed it before, which is how to prepare for the moment of huge self-doubt. Here are the five points I’ve come up with:

1. Stay confident that I am making good choices based on good data.
When I started having kids I dropped out of the software industry and the startup world.

The moment was similar to me deciding that homeschooling is a non-negotiable. Everyone told me not to drop out and that I was crazy.

But I had read a lot about attachment theory—that kids need one, single primary caregiver for the first two years. I realized that it’s common knowledge among child development experts that kids need a single caregiver for the first two years, but no one wants to be the bearer of this bad news. Because daycare means there are two primary caregivers, at least, which jeopardizes a baby’s ability to attach. So sending a kid to daycare was out of the question for me.

And that’s how I feel now, about homeschooling. Even though it’s wreaking havoc on my career.

2. Remember the times I felt like a failure when it was not true at all.
This research made me intensely committed to finding work I could do from home to support the family. Which lead to temporary financial ruin. And I felt like a failure.

All my friends in the software industry disappeared because we had nothing to talk about. The writers I met earned so little money that I worried hanging out with them was bad for my career.

After a few years, I launched this blog. It got big enough that people who make a lot of money started paying attention to me again. And I didn’t feel like a failure anymore.

If I could go back to that time, I’d tell myself to stop worrying about failure. The worry just makes the change harder, and no one is a failure in the middle of a big change. You can’t fail if you’re moving toward something. You fail only if you stop.

3. During big transitions, be clear on priorities.
I have a startup right now. I started pitching some top-tier VCs I’d like to work with and they said the business idea would not grow big enough. So I showed how I can win at the whole online food business because the barrier to entry for selling meat and cheese online is huge and I have a way to get around that.

Everyone loved my marketing plan. Except that the business was too small to be funded. There would not be a big enough exit and I can’t get great business partners if I don’t have huge exit potential.

That’s a problem because I want to work only with hotshots. I don’t want to work with moms who want jobs on the side. Please God do not strike me down for saying this, but as a mom who is trying to have a really exciting career, I don’t want to work with other moms. I want to work with twenty-something men who have no kids and have endless time to address their endless curiosity.

So I worked with an angel investor to craft a business plan that moves quickly from online food to online everything. I talk about the future of shopping . It used to be that shopping was exciting because you could find different stuff in different cities. Discovery and exploration are part of shopping. But online, everything is a commodity. People want discovery and they want to feel that what they are buying is special.

I say all this to show how my online food business will transform the consumer experience. You need to say that kind of stuff to get A-list partners and A-list funding.

4. Getting what you want means deciding what you’ll give up.
So last month I got a great developer to agree to move forward with me. Last week there was no barrier to me launching my goat cheese business as step one to transforming the American consumer experience.

Except that I don’t think I can handle talking like this every day for five years. Which is what a startup is: talking like a manic dreamer with crazy ambitions that no one thinks you can really pull off, but some people will take a wild bet on. That’s what it would be.

It’s so fun. But not with kids. It’s so great to have an amazing business partner, but not if they have to chase you down in between playdates. They start to hate you.

So I have this business I’m not doing. And I’m banking on the advice I tell other people, that admitting what won’t work to do right now is a step toward figure out what will work to do right now.

5. Keep moving forward and believe you’ll go somewhere good.
I am at an in-between stage, and I’ve been here before, so I am going to have faith that I’ll come out okay. I am going to have faith that I am not going to wither away and lose my ability to earn a lot of money. I am going to have faith that when I am done with my current identity crisis there will be top-performers all around me.

I coach so many people in their 20s who are lost, and they are worried that their feeling lost will never end. And I tell them to just keep trying jobs until one sticks. Have patience and believe that you’ll figure things out. This is true for me, too. Right now. The more times you live through that feeling of being lost, the more faith you have that you’ll keep moving forward and come out fine.

You know what makes me happy right now? My sister-in-law had a baby after losing her first one. I’m really happy for her. And my small, odd family has fun dinners together. And focusing on the stuff that definitely feels good gives me faith to trust that eventually I can put the pay in Enelopepay.




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  1. Jane
    Jane says:

    Another great post. I suffered a lot of self-doubt and this post was very insightful.

    Also, who produced the pamphlet? I’d love to find it online.

  2. karelys
    karelys says:

    “Please God do not strike me down for saying this, but as a mom who is trying to have a really exciting career, I don't want to work with other moms. I want to work with twenty-something men who have no kids and have endless time to address their endless curiosity.”

    I doubt God will strike you down. I love that your passion will revolutionize what we currently know. it’s just a matter of time and funding.

    I love the whole of this post because i sort of feel the same way in different areas. i’m not lost but actually in transition.

    when i thought i was lost is because i was refusing to give up something for another and that made me stuck, i couldn’t move forward. but now i know.

    on the subject of faith, i went to bed late yesterday researching info on launching an idea my husband and i have. i am so nervous. but excited. and more and more i feel like if i don’t do it i will feel like i gave up, like i failed to fear.

    i prayed to God: “Is this what you want? am I just being stubborn?”

    then i find this. i think it’s an answer. not just a yes but a yes with wisdom and information. more than i asked for.

    i’m so happy.

    and more focused :)

    best to you. by the way time your co. launches i will be not pregnant anymore and as a lover of goat cheese…..i can’t wait!!!

  3. Susan Rubinsky
    Susan Rubinsky says:

    Just wait until your kids a bit older and it will all work out. I started by biz when my son was in second grade and he’s a a high school sophomore now.

    But I didn’t home school — he went to: inner city public then inner city charter then suburban private. Schools are awesome, it’s just about finding the right ones for your kid (sometimes what you want is different than what is good for your kid). I never could have done what I’ve done if I home schooled. And therein lies the question: what are your priorities? What are the best priorities for your kids? Personally, I was driven to see my company become a viable reality? Just the idea of it made me happy. A happy Mom is always better than an unhappy Mom doing what she thinks she “should” do.

  4. Genelia Santanelli
    Genelia Santanelli says:

    I am glad I stopped to read your post today… It was shaping up to be a bad day and as soon as I began to read your words, it began to magically slow down here are the office… Thank you! ;)

    I enjoyed your post. I especially smiled at the end… When you acknowledged and took in what brought you happiness [now]. And it something that many of us are not fortunate to make a practice of through life. Going through my father’s recent diagnose of stomach cancer (and my life being turned and held upside down) and having to manage working for a hedge fund and raising two boys (one heading for college this year!)… Well, my saving grace has been focusing on [now]. What fills my heart and energizes me [now]. What means most to me [now]. And this practice really has helped me to have more faith in myself and has helped me to begin the trials of learning to balance this big thing we call LIFE. Thank you for your thoughts Enelopepay! ;)

  5. Gus
    Gus says:

    Penelope, you know what makes me happy right now? Your words. Your thoughts couldn’t of come at a better time since today, I turn 27.

    Thanks for creating and sharing your art with the world. Greatest birthday gift, ever.

  6. Diane Dolinsky-Pickar
    Diane Dolinsky-Pickar says:

    Penelope, if I had your cell # I would just call you up and so you go gal! Because I can so relate and corroborate every point you’ve made here. You may think that I can kissing up on this, but honestly, I am not that kind of person. Here are the points of intersection: 1-I also eat when I am anxious. To witness, the 30 extra pounds I carry around, not all of which are due to tiramisu for lunch from time-to-time; 2-I also sacrificed a ton when trying to come to grips with my priority to raise kids. In my case, three; 3-I also heard back from the merchant bankers (when they received my business plan) that I was off by one or two zeros. Yeah, like I could just quicktime go find 3/4 of a million dollars, but I am not deterred because I just know that I can build this engine; 4-I want to work with the A-listers and not those Moms who are pussyfooting around. The “why” of this is only available to those in my personal network; 5-Indeed, I am going into it with my eyes wide open. Thank goodness that you point that out so clearly in your blog post. That kind of tough love is something you so excel at, and many folks don’t want to hear it so I’m glad you harp on it again and again. This crazy entrepreneurial-work-and-life-simultaneously is only for those who want in an interesting life, not those seeking happiness; 6-I’ve been many times to dial back my passion, but I’m not taking that advice.

    So, once again, you go gal!

  7. lynne whiteside
    lynne whiteside says:

    regarding the anxiety – I’m in a constant state of anxiety, and the best thing I do for myself that works Immediately, is the yoga breath – not the deep breath, but the short, forced breath thru the nose, do 100 at a time, 300 in all. sounds like a lot but it works. I do this first thing in the am when I walk the dog. my brain gets focused and I get rid of the anxiety till next time. I also do this breathing, the deep breathing throughout the day. keep it simple, your body will respond.

    • sf
      sf says:

      that particular yoga breathing technique is called pranayam and if done regularly and properly keeps you physically, mentally and emotionally fit which is what yoga is all about. good luck.

  8. Lesa
    Lesa says:

    I’ve had my share of in-between stages and the self doubt that comes along with that. Love this “…no one is a failure in the middle of a big change. You can’t fail if you’re moving toward something. You fail only if you stop.” and wish I had heard it back when I needed to hear it the most.

    Oh, and I’m so glad to hear that you are working on figuring out how to sell food online and make it work. I’ve recently learned much more about how our pork is raised and I’d was just lamenting the other day that I wish I lived closer to your farm so I could easily buy from you. Should have figured you were working on a way to make your farm products available globally.

  9. Amy Parmenter
    Amy Parmenter says:

    So here’s my question… How long is too long to be at an in-between stage?

    I’m at an in-between stage, even though I’m blogging and still working as a reporter…and I feel like I’m headed somewhere but I just can’t really tell yet where that is…and it’s been a while. From the outside, it doesn’t look like I’m moving forward but, on the inside, it feels like I am.

    So…how long is too long to be ‘in-between’?

    My answer — I don’t know, but I know I’m not there yet. Maybe life is just one big ‘in-between’ experiment?

    Amy Parmenter

    • Penelope Trunk
      Penelope Trunk says:

      It’s a good question. You make me think that really everything is in between — in between birth and death. And all the rest is moving forward. So we should think about process — how we feel about how we’re moving — as opposed to how we feel about where we are. Since where we are is always just temporary, even if it’s a great place to be.


  10. Kate
    Kate says:

    I’ve been reading your posts for a while now and I like most of them a lot. You write in a raw and sort of ‘naked’ way that really shows the point you want to make.
    I can relate to your constant struggle between kids and career. I have the same struggle at the moment thinking whether I should cut down on work and care for my kid (with special needs) or just continue with my career and pay other people to care for my kid. I’m trying an in-between way now but that’s very stressy. I don’t have the guts to go all the way like you did in choosing the radical situation (homeschooling in your case).

  11. Alexa
    Alexa says:

    Today I needed faith that karma is real and that if I focus on what I need to be doing (rather than getting swept up in melodrama) then things will work out. Keeping my fingers crossed for you and for me.

  12. Carla
    Carla says:

    I saw the photo and thought you were going to confess to being pregnant. Given all the turmoil, I’m glad to have reached the end of the post and learned the tummy shot was about your sister-in-law. Congrats to her and the auntie.

  13. Melissa
    Melissa says:

    “The worry just makes the change harder, and no one is a failure in the middle of a big change. You can’t fail if you’re moving toward something. You fail only if you stop.”

    Loved that post. Just what I needed right now.

  14. Eva
    Eva says:

    Saay aay uentflay eakerspay foay igpay atinlay orfay ecadesday, Iay avehay otay isagreeday ithway ouryay onsay’s pinionoay. Vaeay siay niay actfay ethay estbay ossiblepay amenay otay orkway ithway saay tiay siay ompletelycay nidentifyableuay, ichwhay siay fteraay ethay ointpay.

    Sincerely, Eva.
    PS Good luck with finding your way

    • jacqui
      jacqui says:

      You’d probably have to do this with the farmer.
      It’s more of a lifestyle choice than a startup. Probably more fun than counseling though xxxx

  15. Another Andrea
    Another Andrea says:

    Can you go on goat farm field trips? Maybe one or two would let you tour and you would get more ideas from there.

    Boa sorte.

  16. JessicaA
    JessicaA says:

    I’m curious to know why you’re seeking VC funding for such an early stage idea. Is it because you need significant capital to launch? I’m curious because, based on my (quite limited) understanding of VC, it’s in an entrepreneur’s best interest to bootstrap for as long as possible, get initial funds from angels, and prove the concept before moving toward VCs, so you can get better terms.

  17. sandyb
    sandyb says:

    I will remember this, in the near future, when I feel like a failure myself, so thank you for writing it, Penelope: “If I could go back to that time, I’d tell myself to stop worrying about failure. The worry just makes the change harder, and no one is a failure in the middle of a big change. You can’t fail if you’re moving toward something. You fail only if you stop.”

  18. ReportingLife
    ReportingLife says:

    I feel your energy should be spent on focusing on your beliefs. What guides you are your values, principles and what you believe and know about yourself. You apply those beliefs to any endeavor you choose to take up, whether it’s a job or parenting or relationships. You could be a writer, a pilot or a bartender, but your life purpose is still the same. You decide your own purpose, and that is how you decide to interact with others. It’s based on what you know about yourself and your natural gifts and talents. Your job and relationships are simply a vehicle to practice using those gifts and talents and benefiting others in some way. If you’re true to yourself and are aligned with your beliefs, the opportunities present themselves professionally and personally. Everything will flow naturally, and the money is just a bonus to an already great life.

  19. jjoyce
    jjoyce says:

    Great post — BUT I sense a bit more focus on high earning and top performers and momentum in this post that seems somehow at odds with some previous posts about balance…and the faith in future high earnings seems in direct conflict with the statement just before that one must decide what to give up whilst deciding what to pursue (or something like that). Obviously, these ideas swirl around and everyone has internal conflict — go back and read some of your earlier posts, take your own advice and you may find your faith in current and future prospects relies on restated objectives, and not necessarily an eventual return to the specific success model you have patterned on previous experiences.

  20. Ginny
    Ginny says:

    As a longtime supporter, a couple of stand outs. #1, it bugs the shit out of me when you say things like you’ll never work with other Moms. For goodness sake, how many uber talented women have you come across? How many that juggle a million balls successfully every single day? You’ve met incredibly successful working Moms, because you’ve met me! You should know better. The second thing, when something REALLY stresses me out. I have a trick that never fails. I think of what is the worst possible thing that could happen, and then how I would deal with it, and then the anxiety goes away.

  21. Grace
    Grace says:

    I think I’ve come to the conclusion that those days gone by, those moments when I felt confident and at the top of my games, were mythical. I may have been happy, but I was still unsettled. I’m in a pretty good situation right now, but I still often feel anxious and lost. Searching is just a part of the human experience. And knowing that is calming.

  22. Janet
    Janet says:

    Before I read this I was thinking about all the years I’ve been reading your blog. How I’ve learned from you, your courage and resilence. Through so much. I got those things back by reading your stories when I was newly divorced and completely terrified at my future.

    I remembered lines from a song from Evita. She is thrown out by another lover and asks, “where am I going to?” The guys answer,”You’ll get by you always have before.” Then I read this post and it seems to fit.

  23. Yuliana
    Yuliana says:

    Thank you for an encouraging and a very timely post. I am also at an in-between stage in my life and it was a great reminder to focus on my priorities instead of sweating the small stuff. This indeed means clearing up my life to make room for the things that matter most.
    Also reading other reader’s comments and seeing that so many others are going through similar transitional periods in their lives, makes me feel less lonely in my quest for getting unlost. Perhaps life really is one big in-between experiment. And even though we strive to control our experiment conditions, as any good scientist we should be prepared for a surprise.
    Last night I devoured your “Brazen Careerist” book. What an interesting, informational, and fun read! I love your writing style, it feels as if you were talking to the reader directly. Thank you so much for all the great advice and insights into the life of corporate America. I didn’t not grow up in this culture, so reading about navigating American professional world was like learning a new language (and thank god I am good at languages :). But I am determined to make something good out of myself. With your help, I have faith in myself to make things happen, so I keep on moving forward, experimenting along the way.
    Thank you.

  24. downfromtheledge
    downfromtheledge says:

    “I am a failure.” This is what I was thinking as I lay in bed last night, right before I chastised myself for useless self-flagellation.

    “Positive affirmations are what you *wish* you could believe about yourself, but know internally is bullsh*t.” That was my next thought.

    I know better, but I think I will start a new trend of negative affirmations. “Yep, you’re a dumb piece of sh*t; keep up the good work.” Why not do something I know I can be good at…

  25. Ashley
    Ashley says:

    How can you sit around the dinner table with your small children with a man that physically abuses you? What kind of example is that setting for them about independence and self respect?

    I’m stunned your ex is willing to “make nice” at sit at a dinner table with a man that physically harms you. His children LIVE with this man.

    Penelope, you neeed to leave your husband. He is abusive, and a terrible role model to your children. And you have become complicit in his abuse by continuing to stay.

  26. Dennis
    Dennis says:

    Sometimes one just needs to soak in life in order to to have the ability/experience to find/see that next opportunity. Time is equally your Ally!

  27. Dennis
    Dennis says:

    ometimesSay oneway ustjay eedsnay otay oaksay inway ifelay inway orderway otay otay avehay ethay ability/experienceway otay ind/seefay atthay extnay opportunityway. imeTay isway equallyway ouryay Ally!

  28. TT
    TT says:

    Ashley, the people at the Sunday dinner table know the truth. Simple as that. Currently we’re in the post-drama dormant period, where a series of lucid posts re-establishes credibility before the next bombshell crisis. During this time, comments on past dramas are ignored.

  29. Mariana
    Mariana says:

    I know the topic of homeschooling and attachment parenting was discussed –at length– in other posts but its mention here again made me jump.

    @Penelope: from all those links on the topic, how many are based on true empirical evidence as opposed to psychobabble? I’ve read the links you’ve posted and don’t see any science behind them. There are serious studies out there, and they show the benefits of a stay-at-home parent peaking at around 9 months. No need for the mother to sacrifice her career for years on end.

    And please note that I’m not writing this from a place of defensiveness. I’m lucky enough to live in Germany, where staying home for the child’s first year is the norm and not a (big) hindrance to one’s career. It’s just that this current of thought of “a child needs his mother 24/7 for the first 3 years of his life or he will be asocial” irks me to no end. It’s always espoused by conservative wackos without any reliable evidence to back it up.

  30. Brooke Farmer
    Brooke Farmer says:

    “You can’t fail if you’re moving towards something. You only fail if you stop.”

    That line has the potential to change lives, Penelope. I wrote it down so that I have a reminder any time I feel like giving up. Thank you.

    • Helen Wolwyn
      Helen Wolwyn says:

      I love this too. Boy, Penelope knows just what to say to a new entrepreneur! It is faith in myself that has led me down this path, and one can lose sight of this when things do not go as expected. Good reminder that really everything turns out ok if you just keep on keepin on and go with the flow (cliches much?)

  31. Elle
    Elle says:

    Very timely! Interesting perspectives and inspiration for women with drive. I’m struggling with returning to work at the moment and I’m actually excited to use childcare again. LOVE having my own time!

  32. Kris Costello
    Kris Costello says:

    Penelope, Have you read Barbara Sher’s stuff on scanners? Scanners have trouble seeing how they can get everything done. I’m a scanner and things have changed a lot since I started focusing on structure and boundaries. Interesting stuff.

  33. Emily
    Emily says:

    Penelope – what a great post! What about launching a company about 40-something Gen X’ers trying to make heads or tails of career ambitions while juggling the commitment to family as well. You know something for those of us who somehow believe that we are able to have both a family and stimulating career somehow, someway, however daunting or unrealistic?

  34. Nina
    Nina says:

    Work or stay at home; its the moments and what we draw from them that matters isn’t it? It should not be a need to spend hours and hours to create moments that matters with the once we spend them with, should it?

  35. nyx
    nyx says:

    Thank you, this post comes at a great time. Love what you said: “Getting what you want means deciding what you’ll give up.”

    Wishing you the best :)

  36. Meg
    Meg says:

    Once, at a personal crossroads, I felt as if I were in professional, personal, emotional freefall. Your post resonates with me on the nature of freefall, with its terrifying yet liberating repercussions. Homeschooling now, is like freefall, especially as I approach 40 with a dearth of cultural cohorts in my area. What I learned to embrace at that time, was the concept of immediacy. If you can determine that the next step you take is a good one, it doesn’t matter whether you can see past that single step. What matters is that you find your footing in the moment, and trust that any outcome from one right step, holds good, rather than bad, possibilities. So only focus on the 1 square foot step in front of you. Only 1 decision at a time. Hard to do for NTJ people, but possible to train up to.

  37. Geeske
    Geeske says:

    Thank you very much for this post! I’m so glad I read it today. I’m at an in-between-stage myself right now as I am looking for a neu carreer. Today didn’t start that great, but I feel a little better after reading your post. Greetings from Holland from a stay-at-home-mom.

  38. Havaladırma
    Havaladırma says:

    I’ve recently learned much more about how our pork is raised and I’d was just lamenting the other day that I wish I lived closer to your farm so I could easily buy from you. Should have figured you were working on a way to make your farm products available globally.

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