Some days I am gung ho about entrepreneurship and I’m spending the day with my kids while money comes in from my blog and my coaching and I think “I’m great, I’m living the 4-hour workweek,” and for one minute I forget that I hate Tim Ferriss.

I hate him for making people think that it is possible for anyone to make money without working hard. Because the next minute, I am telling my husband that I promise I’ll pay him back and I’m paying my developer for my startup with money earmarked for corn, and I’m in therapy from the stress of knowing that probably my last marriage fell apart because I used family finances to support my  startup.

And now it looks like I’m doing it again.

I see familiar signs: My husband in bed at night, unable to sleep because all he can think about is my startup’s insatiable need for cash.

For all you financial snobs I want you to know it is very common for startup founders to ruin their lives funding their company. It’s why I said I’ll never do another startup. I have online businesses that are stable and profitable. Why can’t I just leave well enough alone? I don’t know. But I know that’s why people say being a startup founder is tantamount to having a brain disorder.

My husband overhears me doing a coaching call where I say, “You can’t have an amazing career and be home at 3pm when your kids come back from school. There are no careers where everyone else puts in their full effort and they also want to work with someone who works part time.

“And besides that,” I say, in a speech I give at least once a week, “If you start a new career when you have a four-year-old kid, you are competing against 23 year olds who also are starting new careers but have no kids. That’s tough competition.”

Then the conversation goes like this: “Penelope, you’re doing it. You’re home with your kids and you have a great career.”

How can I explain to them that IT’S FUCKING TERRIBLE TO HAVE MY CAREER. No one would ever want it. I take insane risks that no one would want to take.

Today I got an email from Kiva. They do micro-financing for people in countries where you can buy a cow for three dollars.

I decided to put a little fund together and then my husband would help the kids go through the site to decide who to lend the money to; I’d rather the kids learn how to be investors than entrepreneurs.

So the kids sit down with my husband and read the descriptions of the businesses people want to launch.

My husband is partial to agriculture.

But the kids choose who to fund based on what they look like, which is probably closer to how real investors work.

My husband tells me, “This week three people from Kiva paid us back.”

I say, “I know. You’ve told me twice.”

“It’s bugging me.”

“Do you want to marry one of them?”

He is pissed. He doesn’t like that I make jokes about owing him money. He bounced a check and it’s the first check he’s ever bounced in his whole life.

It’s hard for me to get upset about bouncing a check because I bounced so many checks that I stopped writing them; if you have a hard time keeping track of checks, it’s really hard to keep track of bounced checks. You have this feeling like it’s raining bank statements.

I see, though, that I’m ruining his life. His life is about financial stability. He owns land. He is not liquid. And my financial life is so liquid it practically evaporates.

I kiss him.

Did you know the purpose of kisses is that women can tell how men feel by their kiss?
Men don’t need this because woman actually say how they feel.

Don’t tell me I’m sexist. When you are low on cash you have decision overload. There’s research. Click the link. It’s why people spend their food stamps on Ho-Hos. The blogger equivalent is irresponsible sexism.

So I kiss him and his kiss says fuck you I’m going to burn the house down if you don’t pay me back.

That’s what ISTPs do when they are under stress. They want to burn everything down.

As an ENTJ under stress I get too wound up in the details. So I wash dishes while he fumes.

We both know that good marriages require two people who are able to be kind to each other even if things are crumbling around us. I dry dishes and he eats chocolate from the hiding place where I make him keep the chocolate so that I don’t eat it.

“Can I have some?” I say.

He says, “No. It’s mine.”

I say, “Thank you. Thank you for caring so much about me.” And I kiss him a good soft kiss with a little chocolate chaser.

And I think that maybe at the end of our financial trouble I’ll have a stronger marriage and a thinner waist and a company that has made it to another round of funding.

58 replies
  1. Ann
    Ann says:

    I laughed with delight all the way through this post, especially the line about ISTPs wanting to burn things down. Brilliant writing. Have you ever thought about doing stand up comedy?

  2. Derek Scruggs
    Derek Scruggs says:

    “Men don’t need this because woman actually say how they feel.”

    Good one.

    “What’s wrong?”

    “Nothing.”

    “Wasn’t it obvious? I dropped hints…”

  3. Samantha Gluck
    Samantha Gluck says:

    Loved this post and your straight-forward advice wrapped in your personal experience. And, I don’t curse (out loud), but I curse A LOT in my head and when I see you let loose in your posts, it’s like I get to curse vicariously through you and vent my own frustrations by proxy, of sorts (especially when I share said posts).

  4. Jim B
    Jim B says:

    Love the post. Just when I think its only me going through a new existential crisis you put things into perspective…

    I also follow Tim Ferris closely and he seems to have become more authentic lately, but I still feel like he is running a highly engineered playbook for life which seems unreal.

  5. Cay
    Cay says:

    Since we like interesting here, it would be very interesting to read a clear blog post about where all the money you make actually goes.

  6. jestjack
    jestjack says:

    Your poor husband….holy crud…how much money did you borrow? And for the “uninformed” please explain why is it that “start-ups” eat so much cash . My thought is…you’ve done this before…so you’re smarter…know the short cuts, etc..

  7. ellen
    ellen says:

    Did you know the purpose of kisses is that women can tell how men feel by their kiss?
    Men don’t need this because woman actually say how they feel.

    Where did you learn this? I’ve never heard of this before…

  8. Savvy
    Savvy says:

    I’ve worked with a couple of women whose husbands had start-ups. Both talked about the financial stress, the second mortgages, the credit card debt and the sleepless nights. One gave her husband a two-year deadline to become profitable (his company imported electrical components from China for resale). He didn’t make it and went back to work for his old company. She switched to part-time. The other couple muddled through, but she said if he had stayed at GE he would be retired now with their friends. Instead he is still pleasing partners and investors and has no money. He told me once he will never retire. She retired at 62 to take care of her Grandkids and to sell their home – which was never completely finished inside because he ran out of time and money.

  9. Maria
    Maria says:

    Your post reminds me of a joke about a woman who had to choose between hell (which looked like a fun paradise) and heaven (which was what you’d typically expect). She chose hell and was sent to a desolate place with garbage everywhere and her coworkers were picking up garbage. When she asked why the difference between what she saw before which looked like paradise and now the devil put his arm around her and said “Yesterday we were recruiting you; today you’re staff.”

    http://www.ahajokes.com/hea26.html

    I think entrepreneurship is like that.

    I asked Penelope for advice and her advice was don’t work for yourself (I am great in sales for others but for myself I have the “deer in the headlights” anxiety attack and fail. The problem is when I work for others, my paycheck is almost always shorted or bounces. So I decided working for myself, at least I don’t have to worry about getting paid and in theory I should have multiple income streams.

    As for cost of running a business, my formula is simple, I do EVERYTHING myself (or learn how) until I have enough revenue to outsource different parts of the business. Then I try to do it in percentages. (20% of revenue goes to labor…etc)

    So I only have my living expenses. I live in an rv. It’s paid for (I paid $500 because the pipes had burst). I still went broke. I signed up for welfare and got a job. Within 3 months I will be back on my feet with my classes, my property taxes ( I own a 100 year old church in another province that’s paid for) and my old utility bill, rv insurance paid.

    IF I stay in my RV. It’s very cold, very uncomfortable, I’m parked in a church parking lot to save on camping fees, buy propane heat and pay $40/month for a gym membership for the showers. I walk everywhere to save on gas. I stocked up from the food bank before the job’s first check. (it’s prestigious but pays almost minimum wage-irony! But I’m keeping it because it’s great training for what I want to do).

    I know that sick feeling in the pit of your stomach as well as the farmer’s stomach. I lived through it when I was in real estate and a single mom paying rent (my baby is an adult). I would rather freeze my ass off in a 25 foot 30 year old motorhome with wall to wall tarps for insulation than ever feel that way again.

    I think the solution is “D. All of the above”. Work for someone else some, try launching your own low cost business some, raise your child some, rinse and repeat.

    • Dee
      Dee says:

      Thanks for this joke! It’s head on. The feeling that your boss bullshitted you at the beginning…
      It gave me perspective after a bad day.

  10. redrock
    redrock says:

    easy to be the far distance psychologist (and probably far off the mark…) is it possible that it is not only about all the money but about showing respect and valueing the needs of a farm and by proxy showing respect and value for the farmers profession and livelihood? I mean you have always moved around and had a zillion different things you did to make money, the farmer has one way to do this – farming is not just what he does but who he is.

    • Tracy
      Tracy says:

      So I reread this post today as it feels so relatable, and like redrock want to indulge in some armchair analysis.

      I’ve also been striving for the amazing career and being there for the kids. But in my case the checks I was writing cost time not money. And I bailed myself out time & time again by using up my husband’s time to work on my projects. Eventually he couldn’t meet his commitments as well as my own so massive stress ensued. So we’ve been working on it now for a few weeks – me by being realistic and cutting back, him by establishing better boundaries. We’ll see how it goes.

      So it would seem to me, that in your case your husband needs to figure out where to draw the line in a way that he can cope with the stress. Which at some point will mean saying no to you. And I’ll bet saying no to you is near on impossible – but it has to be done, he has to stick to his guns no matter how much you scream, throw things or whatever you’d do to get your way in a moment of weakness. Then the shoe will be on the other foot and you get to see how kind you will be when he comes to kiss you.

      And then you’ll figure out another way to do what you want to do, because that’s what entrepreneurs do, brain tumors & all. And the stakes are high: not just the marriage and family stability, but because otherwise you need to update your coaching advice to be ‘Yes you can have a great career & be with the kids, as long as you have a husband to use as a crutch and draw down on’.

      Anyway, here’s to sustainable family in the face of business. I love your openness.

  11. Diana
    Diana says:

    Thank you so much for this post. I am in the midst of growing a young business with my husband (not sure that was a wise choice :)) and homeschooling our kids. It’s been really tough at times, really really tough. It’s so incredibly refreshing to read honest stories about business, it’s ridiculously hard and I sometimes feel I am insane, but I take great comfort knowing I am not the only one out there feeling like this! Thank you! I LOVE your writing.

  12. Dani
    Dani says:

    This is my life. I feel like it’s groundhog day (year?)

    It’s like I go through cycles. Everyone wants to be me. But they really don’t want to be me, it’s tough.

    It’s just no one knows it.

  13. Priya N
    Priya N says:

    wow ….!!! You have written this post finally !!! great
    it is very tedious job to maintain balance between business and family.
    Love the way you write , your topics , your words amazing …!!!

  14. Patricia
    Patricia says:

    Found this post very engaging. It IS incredibly challenging to balance both personal and professional lives. Best of luck on your startup!

    I have an electronic version of Tim Ferriss’s book. Haven’t gotten around to reading it yet though. Hmm…

  15. Bando
    Bando says:

    It may be true that start-ups burn cash, but I think it is also true that to a frugal person your personal lifestyle seems like an exploding volcano of wastefulness. Have you considered whether living more simply might be the key to a peaceful life?

    • Bookish Jen
      Bookish Jen says:

      I agree. Penelope needs to cut back on the expenses. She doesn’t need to fly to California to get Botox. I’m sure Madison has doctors that will fill her face with botulism. Her kids can also take music lessons in Madison. And if I’m not mistaken, she also has a fridge that cost somewhere in the five figures. Penelope is just too much of a materialistic, high-maintenance, spoiled brat.

  16. Angela
    Angela says:

    Thanks for the honesty of your post, about what life as a woman/mom/wife is really like when trying to value oneself in the midst of meeting everyone else’s needs. On the outside, in social media, etc. it looks easy. I’m thankful to you for offering transparency and authenticity that most people don’t. And speaking of transparent, I was introduced to your blog by Jon Morrow, another writer with an immense spirit who doesn’t sugar coat life. By sharing your truths, we your readers, can all accept ourselves a little more, and create more light in the world. Thank you for making that happen.

  17. Nicholle
    Nicholle says:

    What a relief to see such a powerful, intelligent, strong woman wrestle with similar issues as myself. Thanks for your honesty. It’s inspired me to trade in some of the shame I carry around for a little more acceptance.

  18. Anthony
    Anthony says:

    My lovely wife Lehla reads bits and pieces of your blogs to me at random moments…….today is the moment I decided to jump in.
    I asked her how many men were commenting on this blog and it seems none?! So here I am. A bloke ( Brit for normal man) Anyway that’s an oxymoron I guess. Normal Man. Are any of us Normal? What does that mean anyway? My bit is that men are not usually decipherable via kissing. ( Not that I have kissed any in that way, being usually doing that Kissy Cheeky thing we Europeans like to do, men to men ) .
    I think what is going on Penelope is that when you get close you are quickly ( or your natural human sensing system is ) reading his breathing rate, skin temperature, muscle tone and scent ( yes fear has a smell) and quickly realising that he may be in Fight or Flight or both….
    This actually works the other way around as men do the same with women. Lip moistness, tension and yielding in either direction indicates all sorts of things……
    But contrary to your generalisation about men ( based I guess on your personal knowledge of them ) men do talk about their feelings. And most of the men I know ( ok we do all belong to men’s group thing and run around outside at night dressed in animal totems ) are quite happy to tell you how they are feeling.
    Actually your point may mean you have been hanging out with men who don’t like talking about their feelings. Which you could change by changing who you hang out with.

    Now to money and start-ups and…..well lots to say. Had many myself, some badly funded, some well funded. Some (the most recent one) have taken all the family cash and some silver ( and I may be selling myself in unsavoury ways if the glint in Lehla’s eye does not recede more in the next few months ) and it is unnerving and yet exhilarating all at the same time.
    Being an entrepreneur is about accepting and living with risk. Don’t we all live with risk anyway? The idea that we can live without risk is a self-deluding device to ty to grab some relief from fear. Living is risky right? I mean we areall gonna die. That’s risky.
    And please don’t tell me that having a job these days is more secure?

    I think enjoying it all is what it’s about. If you and husband can’t enjoy whatever you are up to then well what is the point? And what is the modelling to the kids? Risk = Misery? Start ups = parental tension and anxiety? = funny kissing?

    Start ups start up and then fail or succeed depending on so many factors outside your control its not funny. I know. I started an environmental project and launched it almost the very week in 2010 when the entire world temporarily forget that the natural environment was falling apart as they were all panicking about their jobs and you could get anyone to think green was remotely important.
    Now it’s back on track. Weirdly the investor who funded much of the project emailed me recently to ask if I thought we should try again on the grounds that it was a good idea but badly timed. I said no.

    So good luck with the startup. No doubt it will succeed or not according to factors you cannot predict or have control of. But either way enjoy it!

    • Elizabeth
      Elizabeth says:

      Thanks for sharing your thoughts Anthony. Like Lehla, I also share thoughts and comments from Penelope’s two blogs with my husband. He would never comment on this or any other blog but he is always interested in what I have to share with him.

      I agree with you about men and feelings, in my experience with having friendships with mostly men there are always more emotions with great intensity than I personally am comfortable dealing with. I hate seeing men cry because it is devastating to me, but I love it at the same time. Really I hate seeing anyone cry… I can count how many times I have cried in my life.

      My own spouse has a myriad of emotions that I had no clue even existed. It can be quite exhausting at times.

      Life without any risk-taking is not appealing to me. But there is a limit and I haven’t reached it yet.

  19. Tracy
    Tracy says:

    Haha (*nervous laughter* on behalf of the farmer) you make me feel better about my bank balance.

    Came across this line in a Philippa Gregory novel and thought it was meant for me, but you can have it :-)
    To be a good wife is to be a woman with a will of iron that you yourself have forged into a bridle to curb your own abilities

  20. Dave
    Dave says:

    I think Tim’s point about the 4-hour work week is that the reality of most mind-numbing corporate jobs is that it only takes about 4 hours of actual work to accomplish enough not to be fired. So if you can arrange to be working remotely so people are not looking into your cube to see you posting comments on Penelope Trunk’s blog, filling out timesheets for your side business, or sending emails to the people you manage in your other side business, then you can keep your job and your health insurance while you get your real business started.

  21. Rachel C.
    Rachel C. says:

    I’d love to see a post about why you decided to do another startup. There is a stress level difference between your startup related posts and the others that is so notable that I swear I can feel my blood pressure go up when I read these.

    But outside of the startup you seem to do well financially and are confident with your schooling decisions, so I’m just curious what is driving you into start ups over again?

  22. Katybeth Jensen Ruscitti
    Katybeth Jensen Ruscitti says:

    I want to learn from people who keep their word, operate with integrity, and mind their finances. This post is confusing. I’m not sure if you are sharing a mistake or how clever you are for deceiving your husband into thinking you’ll pay him back. More confusing is why I ever trusted you to coach my son. Through Chicago friends (after recommending you) I’ve learned more about your success at the expense of others than I care too. Maybe the farmer will stick around, but I think my time will be better spent elsewhere. Good luck to you and to everyone your life touches.

  23. Liobov Triufanova
    Liobov Triufanova says:

    Only a woman with Aspergers would claim that men don’t need to kiss women in order to know how they feel because women actually tell them how they feel. ;)

  24. Derek
    Derek says:

    Hi Penelope,

    I see a lot of people confusing “start up” with “new business”. A “start up” is a very specific, high risk (& stressful), high potential reward business model, that often requires significant cash burn in the early stages to fund development and the tech side, satisfy investors w speed of growth etc. Like Uber or AirBNB.

    For 99.99% of the readers of your blog (and you), there’s no reason an why you shouldn’t run your business in a cash flow positive manner from day 1. Online courses delivered through video and phone based consulting should not require large amounts of cash. It shouldn’t require a lot of staff either. It’s a business based around you, with low fixed costs and low incremental costs.

    I believe you used to do paid webinars, sold from this blog, that were quite well attended and cash flow positive, but then when you spun it off into a separate website and business and started calling it a “start up”, paying for developers etc now it’s burning cash?

    Am I missing something here? I am very curious as to why a change in business model (eg. close the other site and bring it back to the blog) couldn’t make dramatic changes to your cash flow position. You have already done the decades of hard working building such a large audience and reputation in your niche, so I don’t understand why you’re unable to monetize it better. Do you love stress for the sake of stress? Thanks.

    • Terry Vance
      Terry Vance says:

      Great point, great post. Apple was profitable on its first purchase order. The ideas that a business is supposed to take a long time to be profitable and that ruining your finances is a sign of confidence are pretty crazy. The question of true motivation is dead on.

  25. Mali
    Mali says:

    “I’d rather the kids learn how to be investors than entrepreneurs.” I think about this for myself every day.

  26. Karen
    Karen says:

    That kissing insight is hugely useful.
    Also I keep telling my daughter when she asks “What should I be when I grow up?” I say you want to be an owner.

  27. Nicole
    Nicole says:

    New reader here…great article! Thank you for your honesty. Balancing a career and family can be challenging at times. We have to find different ways to laugh at the various situations in both personal and family life.

  28. Alta
    Alta says:

    You told the exact story of mine. I started my website. I thought it’s easy and got an initial finance of $1000 from my husband. But, in last 4 months I spend more than that without getting any return. I spent hours behind it. I definitely put more hours than I envisaged. It’s not easy at all. But reading your story, I got the confidence that I’m not alone.

  29. Hammo
    Hammo says:

    Yikes, as cute and whimsical as you sound, it doesn’t look like you really learnt any lessons that first time around. You have a keeper there so why not take your own advice and work on it. I’m surprised you haven’t been the one bounced after that cheque incident.

  30. havalandırma
    havalandırma says:

    One gave her husband a two-year deadline to become profitable (his company imported electrical components from China for resale). He didn’t make it and went back to work for his old company.

  31. Kats
    Kats says:

    Penelope, Your writing is so true to those gut-wrenching places that everyone gets into and no one usually shares. It could be about education, money, almost anything. I thing everyone has a place of doubt and places of difference approaches with their spouse.

    While, given my nature, and who I am, I would have difficulty doing what you are doing and being in the place you are at, what you write is so universal, that it was easy for me to identify with you.

    Only you will know if this path is right for you, but it is great to read your honest posts, filled with truth, doubt, confidence and fear. I do have a suggestion–of bringing your husband to do some couples’ therapy, where you both can vent feelings and establish more ground rules.

    Thanks for your honesty and I wish you an eventual smooth going through your transition. Life so seems to be about change, whether or not I like it!

  32. Ravit
    Ravit says:

    Penelope, great post in regards that wanting to be successful is very hard in reality and that it can affect the closest people to you. I would highly recommend taking a look at Gile Cadman’s take on business and becoming a successful investor.

    What do you think?

  33. Pirate Jo
    Pirate Jo says:

    If your earlier startups are stable and profitable, why aren’t their cash flows funding your newest startup?

  34. Kris Costello
    Kris Costello says:

    Why not put a button on your website to help fund your start up? Rather than borrowing it? I’m sure your loyal readers ( Of which I am one…) would want to help support you. You’ve made me laugh so many times with your descriptions of life with an ENTJ and a ISTP, and homeschooling and working, all of which I am all too familiar with!

  35. zdravko
    zdravko says:

    That was a hard post actually… Hey, I’m nobody to give advice, but I’ll express my opinion anyway…

    I think we all come to a point in our lives (which are limited after all), where we need to make a decision what’s our biggest goal and purpose in life.

    I think if you see that your career is constantly causing you trouble in your personal and family life, that maybe it’s time to decide what’s more important for you?

    Why not to take this online business to a whole new level and put your startups on a standby for a while?

    I know people making great careers and millions of dollars by killing it online and still being able to be at home with their families.

    Of courses, none of this matters because you know your life situation the best…

    Anyway, thanks for sharing your story with the public, because I believe many of us can learn some lessons from your personal experience.

    I wish you a happy life, stable and loving family, and lots of success in your career. I hope you get to experience all three of them.

  36. Jeff Bronson *Kraven*
    Jeff Bronson *Kraven* says:

    I agree with zdravko that often it comes down to making a decision about what’s really important.

    Personally I’m trying to make a go of freelance at 40 while living in Asia and haven’t yet allowed myself a partner or home base. I often wonder how people can have a regular job, a side business, a family, hobbies, free time and time for exercise, seems impossible.

  37. Tony Husted
    Tony Husted says:

    I personally love Tim Ferris’s 4 Hour Workweek. I wasn’t the biggest fan, until I read the book again as a metaphor. If you take it literally, it is annoying as crap, but when read as a metaphor I realized that many of my day to day problems were created by me. One of the biggest areas of challenge for me was controlling my finances, which I am now focusing on finding avenues to create more passive income. Tim Ferris is a storyteller trying to see books. Some of what he says can be applied. I lost 40 pounds using 4 Hour Body!

  38. kamagra
    kamagra says:

    Its really tough to manage business and family, i am experiencing currently , i have just started my own small business of IT Services but i am not able to give the time to my daughter and wife as well.

  39. Giles Cadman
    Giles Cadman says:

    That you for the article, its very interesting. It never was easy to be successful in business and at home at the same time. Both take huge amount of time. You have to find a perfect balance to be happy.

  40. Michael Anthony
    Michael Anthony says:

    The struggle of a start up. If it were easy, everyone would do it. I often get discouraged too when I’m working towards my lofty goal that others don’t understand. You know what the stinker is too, that after all this hard work, once you do make it, people will never realize all the hard work that it took and they’ll act as though you “fell,” into success, etc. I think that’s why so many successful start up’ers are always encouraging other’s to give it a try. They just want them to have a taste and know what it really takes.

  41. Michael Anthony
    Michael Anthony says:

    I once had a writing teacher who told me that she thought she’d be a better writer if she didn’t have kids. She said it half jokingly, yet half seriously, too.

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